propargyl alcohol
1-hydroxy-2-propyne
Identification
| Name | propargyl alcohol |
| CAS Number | 107-19-7 |
| EINECS | 203-471-2 |
| FDA UNII | E920VF499L |
| Molecular Formula | C3 H4 O |
| Molecular Weight | 56.06408000 |
| MDL Number | MFCD00002912 |
| Nikkaji Number | J13B |
| Beilstein | 0506003 |
| XlogP3 | -0.40 (est) |
Regulatory
Physical Properties
| Appearance | colorless to pale yellow clear liquid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.96300 @ 25.00 °C. |
| Boiling Point | 113.60 °C. @ 760.00 mm Hg |
| Vapor Pressure | 10.556000 mmHg @ 25.00 °C. (est) |
| Flash Point | 97.00 °F. TCC ( 36.11 °C. ) |
| logP (o/w) | -0.380 |
| Soluble in | water, 9.355e+005 mg/L @ 25 °C (est) |
Organoleptic Properties
| Odor Description | at 100.00 %. |
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | oral-guinea pig LD50 60 mg/kg |
| Dermal Toxicity | skin-rabbit LD50 16 mg/kg |
| Inhalation Toxicity | inhalation-mammal (species unspecified) LC50 3000 mg/m3 |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | herbicides / pesticides |
| Recommendation for propargyl alcohol usage levels up to | not for fragrance use. |
| Recommendation for propargyl alcohol flavor usage levels up to | not for flavor use. |
Potential Uses
Natural Occurrence
Synonyms
acetylene carbinol
acetylenylcarbinol
agrisynth PA
ethynyl carbinol
ethynylcarbinol
3-
hydroxy-1-propyne
1-
hydroxy-2-propyne
methanol, ethynyl-
prop-2-in-1-ol
prop-2-yn-1-ol
prop-2-yne-1-ol
propargylalcohol
2-
propyn-1-ol
1-
propyn-3-ol
1-
propyn-3-yl alcohol
3-
propynol
propynyl alcohol
2-
propynyl alcohol
PubMed:
trans-Diborylation of Alkynes: pseudo-Intramolecular Strategy utilizing Propargylic Alcohol Unit.
PubMed:
Total Synthesis of the Biphenyl Alkaloid (-)-Lythranidine.
PubMed:
EGF Receptor-Targeting Peptide Conjugate Incorporating a Near-IR Fluorescent Dye and a Novel 1,4,7-Triazacyclononane-Based (64)Cu(II) Chelator Assembled via Click Chemistry.
PubMed:
6-Triazolyl-6-deoxy-β-cyclodextrin derivatives: synthesis, cellular toxicity, and phase-solubility study.
PubMed:
Construction of Divergent Fused Heterocycles via an Acid-Promoted Intramolecular ipso-Friedel-Crafts Alkylation of Phenol Derivatives.
PubMed:
Synthesis of novel 5-(3-alkylquinolin-2-yl)-3-aryl isoxazole derivatives and their cytotoxic activity.
PubMed:
Tandem Pd/Au-catalyzed route to α-sulfenylated carbonyl compounds from terminal propargylic alcohols and thiols.
PubMed:
First total synthesis of acetylenic alcohol 15-methyltricosa-2,4-diyne-1, 6-diol (strongylodiol-G) derived from marine sponge.
PubMed:
Linear propargylic alcohol functionality attached to the indazole-7-carboxamide as a JAK1-specific linear probe group.
PubMed:
Fluorescence sensor for Cu(II) in the serum sample based on click chemistry.
PubMed:
Rh(III)-catalyzed coupling of benzamides with propargyl alcohols via hydroarylation-lactonization.
PubMed:
Increasing the structural span of alkyne metathesis.
PubMed:
Evaluation of propargyl alcohol toxicity and carcinogenicity in F344/N rats and B6C3F1/N mice following whole-body inhalation exposure.
PubMed:
Rhodamine-propargylic esters for detection of mitochondrial hydrogen sulfide in living cells.
PubMed:
Lewis acid catalysis and ligand exchange in the asymmetric binaphthol-catalyzed propargylation of ketones.
PubMed:
Oxygenation of ruthenium carbene complexes containing naphthothiophene or naphthofuran: spectroscopic and DFT studies.
PubMed:
Gold meets rhodium: tandem one-pot synthesis of β-disubstituted ketones via Meyer-Schuster rearrangement and asymmetric 1,4-addition.
PubMed:
Benzyne cycloaddition onto carbon nanohorns.
PubMed:
Platinum catalysed hydrosilylation of propargylic alcohols.
PubMed:
New Ag(I)-iminophosphorane coordination polymers as efficient catalysts precursors for the MW-assisted Meyer-Schuster rearrangement of propargylic alcohols in water.
PubMed:
Lewis acid-catalyzed cyclization of enaminones with propargylic alcohols: regioselective synthesis of multisubstituted 1,2-dihydropyridines.
PubMed:
Trimerization of β-cyclodextrin through the click reaction.
PubMed:
Skeletal diversification via heteroatom linkage control: preparation of bicyclic and spirocyclic scaffolds from N-substituted homopropargyl alcohols.
PubMed:
A novel convenient approach towards pyrrolo[1,2-b]pyridazines through a domino coupling-isomerization-condensation reaction.
PubMed:
One-pot synthesis of pyrazoles through a four-step cascade sequence.
PubMed:
Nucleophilic ortho-propargylation of aryl sulfoxides: an interrupted Pummerer/allenyl thio-Claisen rearrangement sequence.
PubMed:
Hydrophosphination of propargylic alcohols and amines with phosphine boranes.
PubMed:
Kinetic and dynamic kinetic resolution of secondary alcohols with ionic-surfactant-coated Burkholderia cepacia lipase: substrate scope and enantioselectivity.
PubMed:
Atom-economical chemoselective synthesis of 1,4-enynes from terminal alkenes and propargylic alcohols catalyzed by Cu(OTf)2.
PubMed:
Rhodium-catalyzed chemo- and regioselective cross-dimerization of two terminal alkynes.
PubMed:
Original TDAE strategy using propargylic chloride: rapid access to 1,4-diarylbut-3-ynol derivatives.
PubMed:
Synthesis of novel 2-alkyl triazole-3-alkyl substituted quinoline derivatives and their cytotoxic activity.
PubMed:
Catalytic asymmetric enyne addition to aldehdyes and Rh(I)-catalyzed stereoselective domino Pauson-Khand/[4 + 2] cycloaddition.
PubMed:
Synthesis of 9-alkylated calcitriol and two 1α,25-dihydroxy-9-methylene-10,19-dihydrovitamin D3 analogues with a non-natural triene system by thermal sigmatropic rearrangements.
PubMed:
Microwave spectroscopic and atoms in molecules theoretical investigations on the Ar···propargyl alcohol complex: Ar···H-O, Ar···Ï, and Ar···C interactions.
PubMed:
1-(2'-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis.
PubMed:
Synthesis of indeno[1,2-c]furans via a Pd-catalyzed bicyclization of 2-alkynyliodobenzene and propargylic alcohol.
PubMed:
Chemoselective synthesis of substituted pyrazoles through AgOTf-catalyzed cascade propargylic substitution-cyclization-aromatization.
PubMed:
Ruthenium-catalyzed reductive coupling of 1,3-enynes and aldehydes by transfer hydrogenation: anti-diastereoselective carbonyl propargylation.
PubMed:
Facile synthesis of fully substituted dihydro-β-carbolines via Brønsted acid promoted cascade reactions of α-indolyl propargylic alcohols with nitrones.
PubMed:
Propargyl hydrazides: synthesis and conversion into pyrazoles through hydroamination.
PubMed:
Development of Zn-ProPhenol-catalyzed asymmetric alkyne addition: synthesis of chiral propargylic alcohols.
PubMed:
Ruthenium-catalyzed allylation-cyclization reactions of cyclic 1,3-dicarbonyl compounds with 1-vinyl propargyl alcohols.
PubMed:
Hypoiodous acid initiated rearrangement of tertiary propargylic alcohols to α-iodoenones.
PubMed:
A novel fluorescent sensor for mutational p53 DNA sequence detection based on click chemistry.
PubMed:
Cobalt-mediated synthesis of the tricyclo[5.2.1.0(1,6)]decene framework in solanoeclepin A.
PubMed:
Regioselective catalytic hydroboration of propargylic species using Cu(I)-NHC complexes.
PubMed:
Scope and mechanistic analysis of the enantioselective synthesis of allenes by rhodium-catalyzed tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor carbenoids and propargylic alcohols.
PubMed:
Regioselectivity switch: gold(I)-catalyzed oxidative rearrangement of propargyl alcohols to 1,3-diketones.
PubMed:
Heteropolyacid-catalyzed direct deoxygenation of propargyl and allyl alcohols.
PubMed:
Sequential allenylidene/vinylidene cyclization for stereoselective construction of bicyclic carbocycles from propargyl alcohol.
PubMed:
Kinetic versus thermodynamic stereoselectivity in the hydrostannylation of propargylic alcohol derivatives using AIBN and Et3B as promotors.
PubMed:
Synthesis of α-allylated α,β-unsaturated carbonyl compounds using vanadium/palladium contemporaneous dual catalysis.
PubMed:
Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions.
PubMed:
Highly regioselective synthesis of polysubstituted tetrahydroquinolines by an iodine-induced tandem cyclization reaction from propargylic alcohols and amines.
PubMed:
Synthesis of electronically modified Ru-based neutral 16 VE allenylidene olefin metathesis precatalysts.
PubMed:
A gold(I)-catalyzed route to α-sulfenylated carbonyl compounds from propargylic alcohols and aryl thiols.
PubMed:
Synthesis of a heparan sulfate mimetic library targeting FGF and VEGF via click chemistry on a monosaccharide template.
PubMed:
Alkyl triazole glycosides (ATGs)--a new class of bio-related surfactants.
PubMed:
Synthesis of 3,4-dihalogenated furan-2-(5H)-ones by electrophilic cyclization of 4-hydroxy-2-alkynoates.
PubMed:
Development of a method for the preparation of ruthenium indenylidene-ether olefin metathesis catalysts.
PubMed:
EXAFS and NRVS reveal a conformational distortion of the FeMo-cofactor in the MoFe nitrogenase propargyl alcohol complex.
PubMed:
1,2,3-triazole: unique ligand in promoting iron-catalyzed propargyl alcohol dehydration.
PubMed:
A convenient approach to β-heteroarylated (C-N bond) ketones from Cs2CO3 promoted reaction between propargyl alcohols and nitrogen-heterocycles.
PubMed:
Atom-economical synthesis of functionalized cycloalkanes via catalytic redox cycloisomerization of propargyl alcohols.
PubMed:
Synthesis of allene triazole through iron catalyzed regioselective addition to propargyl alcohols.
PubMed:
Highly chemoselective calcium-catalyzed propargylic deoxygenation.
PubMed:
Gold- and silver-catalyzed reactions of propargylic alcohols in the presence of protic additives.
PubMed:
Cyclization of aromatic propargyl alcohol with a thiophene group yielding naphthothiophene aldehyde induced by a ruthenium complex.
PubMed:
1,4-Diazaspiro[2.2]pentanes as a flexible platform for the synthesis of diamine-bearing stereotriads.
PubMed:
Kinetic resolution of secondary alcohols using amidine-based catalysts.
PubMed:
Synthesis of tetrasubstituted alkenes through a palladium-catalyzed domino carbopalladation/C-H-activation reaction.
PubMed:
Brønsted acid catalyzed asymmetric propargylation of aldehydes.
PubMed:
Convenient synthesis and biological evaluation of modafinil derivatives: benzhydrylsulfanyl and benzhydrylsulfinyl [1,2,3]triazol-4-yl-methyl esters.
PubMed:
Toxicity of propargylic alcohols on green alga--Pseudokirchneriella subcapitata.
PubMed:
[Development of environmentally benign transformations via 1,3-transposition of hydroxyl group].
PubMed:
Lewis acid-promoted three-component reactions of propargylic alcohols with 2-butynedioates and secondary amines.
PubMed:
Addition of arylboronic acids to arylpropargyl alcohols en route to indenes and quinolines.
PubMed:
Lewis acid-catalyzed propargylic etherification and sulfanylation from alcohols in MeNOâ-HâO.
PubMed:
Asymmetric synthesis and sensory evaluation of sedanenolide.
PubMed:
Expeditious entry to novel 2-methylene-2,3-dihydrofuro[3,2-c] chromen-2-ones from 6-chloro-4-hydroxychromen-2-one and propargylic alcohols.
PubMed:
Applications of propargyl esters of amino acids in solution-phase Peptide synthesis.
PubMed:
Chiral propargyl alcohols via the enantioselective addition of terminal di- and triynes to aldehydes.
PubMed:
Intramolecular OHÂ·Â·Â·Ï interactions in alkenols and alkynols.
PubMed:
Synthesis of iodo-indoloazepinones in an iodine-mediated three-component domino reaction via a regioselective 7-endo-dig iodo-cyclization pathway.
PubMed:
Contemporaneous dual catalysis: chemoselective cross-coupling of catalytic vanadium-allenoate and Ï-allylpalladium intermediates.
PubMed:
Tandem reaction of propargyl alcohol and N-sulfonylhydrazone: synthesis of dihydropyrazole and its utility in the preparation of 3,3-diarylacrylonitrile.
PubMed:
S(N)1-type reactions in the presence of water: indium(III)-promoted highly enantioselective organocatalytic propargylation of aldehydes.
PubMed:
Formal total synthesis of (+)-lysergic acid via zinc(II)-mediated regioselective ring-opening reduction of 2-alkynyl-3-indolyloxirane.
PubMed:
Preparation of Clickable Poly(3-hydroxyalkanoate) (PHA): Application to Poly(ethylene glycol) (PEG) Graft Copolymers Synthesis.
PubMed:
Highly selective methods for synthesis of internal (α-) vinylboronates through efficient NHC-Cu-catalyzed hydroboration of terminal alkynes. Utility in chemical synthesis and mechanistic basis for selectivity.
PubMed:
New quinolin-4-yl-1,2,3-triazoles carrying amides, sulphonamides and amidopiperazines as potential antitubercular agents.
PubMed:
Synthesis and anti-HIV-1 activity of new fluoro-HEPT analogues: an investigation on fluoro versus hydroxy substituents.
PubMed:
Propargyl alcohols as β-oxocarbenoid precursors for the ruthenium-catalyzed cyclopropanation of unactivated olefins by redox isomerization.
PubMed:
Facile oxygenation reactions of ruthenium acetylide complex containing substituted olefinic group.
PubMed:
Application of Mitsunobu reagents to redox isomerization of CF3-containing propargylic alcohols to (E)-α,β-enones.
PubMed:
A new and general one-pot synthesis of propargyl alcohols from esters.
PubMed:
Tandem reaction of propargylic alcohol, sulfonamide, and N-iodosuccinimide: synthesis of N-(2-iodoinden-1-yl)arenesulfonamide.
PubMed:
A general procedure for the synthesis of enones via gold-catalyzed Meyer-Schuster rearrangement of propargylic alcohols at room temperature.
PubMed:
Palladium catalyzed bicyclization of 1,8-diiodonaphthalene and tertiary propargylic alcohols to phenalenones and their applications as fluorescent chemosensor for fluoride ions.
PubMed:
An atom-economical access to β-heteroarylated ketones from propargylic alcohols via tandem ruthenium/indium catalysis.
PubMed:
Optimization of a ligand immobilization and azide group endcapping concept via "Click-Chemistry" for the preparation of adsorbents for antibody purification.
PubMed:
Intramolecular Nicholas reactions in the synthesis of dibenzocycloheptanes. Synthesis of allocolchicine NSC 51046 and analogues and the formal synthesis of (-)-allocolchicine.
PubMed:
Cinchona alkaloid-catalyzed asymmetric trifluoromethylation of alkynyl ketones with trimethylsilyl trifluoromethane.
PubMed:
Ultrasonic assisted Fischer glycosylation: generating diversity for glycochemistry.
PubMed:
Catalytic asymmetric synthesis of chiral propargylic alcohols for the intramolecular Pauson-Khand cycloaddition.
PubMed:
Scandium-catalyzed propargylation of 1,3-diketones with propargyl alcohols bearing sulfur or selenium functional groups: useful transformation to furans and pyrans.
PubMed:
Brønsted acid catalyzed cyclization of propargylic alcohols with thioamides. Facile synthesis of di- and trisubstituted thiazoles.
PubMed:
Iron-catalyzed C-O bond activation for the synthesis of propargyl-1,2,3-triazoles and 1,1-bis-triazoles.
PubMed:
Gold-catalyzed one-step practical synthesis of oxetan-3-ones from readily available propargylic alcohols.
PubMed:
Facile one-pot synthesis of three different substituted thiazoles from propargylic alcohols.
PubMed:
Expeditious synthesis of highly substituted indolizinones via a palladium-catalyzed domino sequence.
PubMed:
Palladium-catalyzed [3,3]-rearrangement for the facile synthesis of allenamides.
PubMed:
Mitotic arrest induced by a novel family of DNA topoisomerase II inhibitors.
PubMed:
Diversity-oriented construction of highly substituted indolizinones.
PubMed:
Synthesis of polysubstituted furans based on a stepwise Sonogashira coupling of (Z)-3-iodoalk-2-en-1-ols with terminal propargylic alcohols and subsequent Au(I)- or Pd(II)-catalyzed cyclization-aromatization via elimination of H2O.
PubMed:
Highly diastereoselective zinc-catalyzed propargylation of tert-butanesulfinyl imines.
PubMed:
Improved synthesis of three methyl-branched pheromone components produced by the female lichen moth.
PubMed:
Photodissociation dynamics of propargyl alcohol at 212 nm: the OH production channel.
PubMed:
Alkyne- and 1,6-elimination- succinimidyl carbonate - terminated heterobifunctional poly(ethylene glycol) for reversible "Click" PEGylation.
PubMed:
A striking exception to the chelate model for acyclic diastereocontrol: efficient access to a versatile propargyl alcohol for chemical synthesis.
PubMed:
Synthesis of azide-alkyne fragments for "click" chemical applications. Part 2. Formation of oligomers from orthogonally protected chiral trialkylsilylhomopropargyl azides and homopropargyl alcohols.
PubMed:
Cooperativity of regiochemistry control strategies in reductive couplings of propargyl alcohols and aldehydes.
PubMed:
Synthesis of tetrahydropyrans from propargyl alcohols and 1,1-cyclopropanediesters: a one-pot ring-opening/Conia-ene protocol.
PubMed:
Preparation of Disubstituted Phenyl Propargyl Alcohols, their Use in Oxathiolene Oxide Synthesis, and Evaluation of the Oxathiolene Oxide Products as Anticarcinogenic Enzyme Inducers.
PubMed:
Ytterbium(III) triflate catalyzed tandem Friedel-Crafts alkylation/hydroarylation of propargylic alcohols with phenols as an expedient route to indenols.
PubMed:
Silver(I)-catalyzed dual activation of propargylic alcohol and aziridine/azetidine: triggering ring-opening and endo-selective ring-closing in a cascade.
PubMed:
Apparent copper(II)-accelerated azide-alkyne cycloaddition.
PubMed:
An extremely facile synthesis of furans, pyrroles, and thiophenes by the dehydrative cyclization of propargyl alcohols.
PubMed:
Syntheses of naturally occurring cytotoxic [7.7]paracyclophanes, (-)-cylindrocyclophane A and its enantiomer, and implications for biological activity.
PubMed:
Enantioselective nucleophilic addition of trimethylsilylacetylene to n-phosphinoylimines promoted by C(2)-symmetric proline-derived beta-amino alcohol.
PubMed:
Matching active site and substrate structures for an RNA editing reaction.
PubMed:
Stereospecific synthesis of beta3-amino acid derivatives from propargylic alcohols: efficient solution-phase synthesis of oligopeptides without coupling agents.
PubMed:
Novel carbon-carbon bond formation from propargylic alcohols and olefin toward five-membered heterocyclic rings catalyzed by AgSbF6.
PubMed:
Functional group compatibility. Propargyl alcohol reduction in the presence of a vinyl iodide.
PubMed:
Synthesis of functionalized indenes via cascade reaction of aziridines and propargyl alcohols.
PubMed:
A versatile route to (E)- and (Z)-2-hydroxy-3,4-unsaturated disubstituted sulfilimines and their haloamidation reaction.
PubMed:
'Clicking' on the nanoscale: 1,3-dipolar cycloaddition of terminal acetylenes on azide functionalized, nanometric surface templates with nanometer resolution.
PubMed:
A simple and versatile re-catalyzed Meyer-Schuster rearrangement of propargylic alcohols to alpha,beta-unsaturated carbonyl compounds.
PubMed:
Highly enantioselective zinc/amino alcohol-catalyzed alkynylation of aldehydes.
PubMed:
Tandem ring-opening/closing reactions of N-Ts aziridines and aryl propargyl alcohols promoted by t-BuOK.
PubMed:
Platinum-catalyzed cycloisomerization reaction of 1,6-enyne coupling with rearrangement of propargylic esters.
PubMed:
Highly regio- and stereoselective cyclic iodoetherification of 4,5-alkadienols. An efficient preparation of 2-(1'(Z)-iodoalkenyl)tetrahydrofurans.
PubMed:
A novel feature of intramolecular vibrational redistribution in propargyl alcohol and propargyl amine.
PubMed:
First synthesis of 1-chlorovinyl allenes via palladium-catalyzed allenylation of alkynoates with propargyl alcohols.
PubMed:
Toxicology and carcinogenesis studies of propargyl alcohol (CAS No. 107-19-7) in F344/N rats and B6C3F1 mice (inhalation studies).
PubMed:
Synthesis of naphthalenyl acetate by platinum-catalyzed [1,5]-sigmatropic hydrogen shift of propargylic esters.
PubMed:
A DFT study on the reaction pathways for carbon-carbon bond-forming reactions between propargylic alcohols and alkenes or ketones catalyzed by thiolate-bridged diruthenium complexes.
PubMed:
Cascade synthesis of 3-quinolinecarboxylic ester via benzylation/ propargylation-cyclization.
PubMed:
Gold mediated glycosylations: selective activation of propargyl 1,2-orthoesters in the presence of aglycones containing a propargyl moiety.
PubMed:
Rationalizing the formation of damascenone: synthesis and hydrolysis of damascenone precursors and their analogues, in both aglycone and glycoconjugate forms.
PubMed:
An atom-economic and selective ruthenium-catalyzed redox isomerization of propargylic alcohols. An efficient strategy for the synthesis of leukotrienes.
PubMed:
Controllable one-step synthesis of spirocycles, polycycles, and di- and tetrahydronaphthalenes from aryl-substituted propargylic alcohols.
PubMed:
Propargylation of 1,3-dicarbonyl compounds with 1,3-diarylpropynes via oxidative cross-coupling between sp3 C-H and sp3 C-H.
PubMed:
Direct and stereospecific synthesis of allenes via reduction of propargylic alcohols with Cp2Zr(H)Cl.
PubMed:
A gold(I)-catalyzed intramolecular reaction of propargylic/homopropargylic alcohols with oxirane.
PubMed:
Ruthenium/TFA-catalyzed coupling of activated secondary propargylic alcohols with cyclic 1,3-diones: furan versus pyran ring formation.
PubMed:
Efficient and selective syntheses of (all-E)- and (6E,10Z)-2'-O-methylmyxalamides D via Pd-catalyzed alkenylation--carbonyl olefination synergy.
PubMed:
Aluminum-catalyzed asymmetric alkylations of pyridyl-substituted alkynyl ketones with dialkylzinc reagents.
PubMed:
Self-assembled thermoreversible gels of nonpolar liquids by racemic propargylic alcohols with fluorinated and nonfluorinated aromatic rings.
PubMed:
Carbonyl propargylation from the alcohol or aldehyde oxidation level employing 1,3-enynes as surrogates to preformed allenylmetal reagents: a ruthenium-catalyzed C-C bond-forming transfer hydrogenation.
PubMed:
The proposal of architecture for chemical splitting to optimize QSAR models for aquatic toxicity.
PubMed:
Directed diastereoselectivity in the asymmetric claisen/metathesis reaction sequence.
PubMed:
Mo-Au combo catalysis for rapid 1,3-rearrangement of propargyl alcohols into alpha,beta-unsaturated carbonyl compounds.
PubMed:
Ring opening/fragmentation of dihydropyrones for the synthesis of homopropargyl alcohols.
PubMed:
Synthesis of 2,4,5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols.
PubMed:
Palladium-catalyzed synthesis of indene derivatives via propargylic carbonates with in situ generated organozinc compounds.
PubMed:
One-step synthesis of substituted dihydro- and tetrahydroisoquinolines by FeCl3.6H2O catalyzed intramolecular Friedel-Crafts reaction of benzylamino-substituted propargylic alcohols.
PubMed:
Zirconium-promoted epoxide rearrangement-alkynylation sequence.
PubMed:
Studies on the synthesis of apoptolidin A. 1. Synthesis of the C(1)-C(11) fragment.
PubMed:
Remarkable effect of N-substituent on enantioselective ruthenium-catalyzed propargylation of indoles with propargylic alcohols.
PubMed:
Addition of alkynes to aldehydes and activated ketones catalyzed by rhodium-phosphine complexes.
PubMed:
Synthesis of spirocyclic C-arylglycosides and -ribosides by ruthenium-catalyzed cycloaddition.
PubMed:
Directed hydrozirconation of propargylic alcohols.
PubMed:
Highly efficient synthesis of functionalized indolizines and indolizinones by copper-catalyzed cycloisomerizations of propargylic pyridines.
PubMed:
Lewis acid catalyzed propargylation of arenes with O-propargyl trichloroacetimidates: synthesis of 1,3-diarylpropynes.
PubMed:
Reductive cyclization of o-nitrophenyl propargyl alcohols: facile synthesis of substituted quinolines.
PubMed:
Lewis acid-catalyzed conjugate addition-cyclization reactions of ethenetricarboxylates with substituted propargyl alcohols: stereoselectivity in the efficient one-pot synthesis of methylenetetrahydrofurans.
PubMed:
Copper(I) alkoxide-catalyzed alkynylation of trifluoromethyl ketones.
PubMed:
Bistrimethylsilylpropargylic ether: a versatile ambident synthon to access substituted allenyne ethers and alpha-substituted bispropargylic alcohols.
PubMed:
Assembly of conjugated enynes and substituted indoles via CuI/amino acid-catalyzed coupling of 1-alkynes with vinyl iodides and 2-bromotrifluoroacetanilides.
PubMed:
One-pot synthesis of alpha-iodo-substituted alpha,beta-unsaturated aldehydes from propargylic alcohols.
PubMed:
Synthesis of terpene and steroid dimers and trimers having cyclobutadienyl-Co and aromatic tethers.
PubMed:
Chiral ruthenium-allenylidene complexes that bear a fullerene cyclopentadienyl ligand: synthesis, characterization, and remote chirality transfer.
PubMed:
Ruthenium-catalyzed cycloisomerization-6pi-cyclization: a novel route to pyridines.
PubMed:
Rhodium-catalyzed asymmetric one-pot transesterification and [2 + 2 + 2] cycloaddition leading to enantioenriched 3,3-disubstituted phthalides.
PubMed:
Pt-catalyzed cyclization/1,2-migration for the synthesis of indolizines, pyrrolones, and indolizinones.
PubMed:
Recent developments in the metal-catalyzed reactions of metallocarbenoids from propargylic esters.
PubMed:
Iron-catalyzed carbometalation of propargylic and homopropargylic alcohols.
PubMed:
A general and efficient FeCl3-catalyzed nucleophilic substitution of propargylic alcohols.
PubMed:
Mono- and dinuclear oxovanadium(V)calixarene complexes and their activity as oxidation catalysts.
PubMed:
Coupling-isomerization synthesis of chalcones.
PubMed:
B-allenyl- and B-(gamma-trimethylsilylpropargyl)-10-phenyl-9-borabicyclo[3.3.2]decanes: asymmetric synthesis of propargyl and alpha-allenyl 3-degree-carbinols from ketones.
PubMed:
trans-hydroalumination/alkylation: one-pot synthesis of trisubstituted allylic alcohols.
PubMed:
Vanadium-catalyzed addition of propargyl alcohols and imines.
PubMed:
Synthesis of spirocyclic C-arylribosides via cyclotrimerization.
PubMed:
Supramolecular assemblies of chiral propargylic alcohols.
PubMed:
A highly efficient preparative method of alpha-ylidene-beta-diketones via Au(III)-catalyzed acyl migration of propargylic esters.
PubMed:
The nicholas approach to natural product hybrids.
PubMed:
Zinc- and indium-promoted conjugate addition-cyclization reactions of ethenetricarboxylates with propargylamines and alcohol: novel methylenepyrrolidine and methylenetetrahydrofuran syntheses.
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Enhanced diastereoselectivity in beta-mannopyranosylation through the use of sterically minimal propargyl ether protecting groups.
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Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates.
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Synthesis of a NO-releasing prodrug of rofecoxib.
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[1,3]-Transfer of chirality during the Nicholas reaction in gamma-benzyloxy propargylic alcohols.
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Alkyne hydrosilylation catalyzed by a cationic ruthenium complex: efficient and general trans addition.
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Carbon 1s excitation spectroscopy of propyne, trifluoropropyne, and propargyl alcohol.
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Electron inventory, kinetic assignment (E(n)), structure, and bonding of nitrogenase turnover intermediates with C2H2 and CO.
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Gold(III)-catalyzed nucleophilic substitution of propargylic alcohols.
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Reactivity of alkynes containing alpha-hydrogen atoms with a triruthenium hydrido carbonyl cluster: alkenyl versus allyl cluster derivatives.
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Phototransformation of clodinafop-propargyl.
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Synergistic dimetallic effects in propargylic substitution reaction catalyzed by thiolate-bridged diruthenium complex.
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Highly stereoselective one-pot procedure to prepare bis- and tris-chalcogenide alkenes via addition of disulfides and diselenides to terminal alkynes.
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Ruthenium-catalyzed cycloisomerizations of diynols.
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Substrate interactions with the nitrogenase active site.
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Synthesis of diindeno-fused 4H-cyclopenta[def]phenanthren-4-ones and related compounds via benzannulated enediynyl propargylic alcohols.
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Reaction of alpha-(N-carbamoyl)alkylcuprates with propargyl substrates: synthetic route to alpha-amino allenes and delta3-pyrrolines.
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Antinociceptive properties of acetylenic thiophene and furan derivatives: evidence for the mechanism of action.
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Oxathiolene oxide synthesis via chelation-controlled addition of organometallic reagents to alkynols followed by addition of sulfur electrophiles and evaluation of oxathiolene oxides as anticarcinogenic enzyme inducers.
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Aryl annulation of cyclic ketones via a magnesium carbometalation-6-pi- electrocyclization protocol.
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Meerwein-Ponndorf-Verley alkynylation of aldehydes: essential modification of aluminium alkoxides for rate acceleration and asymmetric synthesis.
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Regioselectivity control in a ruthenium-catalyzed cycloisomerization of diyne-ols.
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Silicon-assisted propargylic transfer to aldehydes.
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Substrate interaction at an iron-sulfur face of the FeMo-cofactor during nitrogenase catalysis.
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The mechanism of nitrogenase. Computed details of the site and geometry of binding of alkyne and alkene substrates and intermediates.
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Synthesis of deuterated fatty acids to investigate the biosynthetic pathway of disparlure, the sex pheromone of the gypsy moth, Lymantria dispar.
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An organometallic intermediate during alkyne reduction by nitrogenase.
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(+)-3-{(4S,5S)-5-[1,1-Dimethyl-2-(phenylthio)ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}prop-2-yn-1-ol.
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Localization of a catalytic intermediate bound to the FeMo-cofactor of nitrogenase.
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Zn(II)/amine-catalyzed coupling reaction of alkylidenemalonates with propargyl alcohol: a one-pot synthesis of methylenetetrahydrofurans.
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B(C6F5)3-catalyzed allylation of propargyl acetates with allylsilanes.
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Rhenium-catalyzed aromatic propargylation.
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Coupling-isomerization-coupling sequences switched on by propargyl alcohol-enone-isomerization.
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Construction of azacycles based on endo-mode cyclization of allenes.
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Ru(II)-catalyzed chemo- and regioselective cyclotrimerization of three unsymmetrical alkynes through boron temporary tether. One-pot four-component coupling via cyclotrimerization/Suzuki-Miyaura coupling.
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Phosphorylated 1,6-diphenyl-1,3,5-hexatriene.
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Rhenium-catalyzed coupling of propargyl alcohols and allyl silanes.
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Facile one-pot synthesis of photochromic pyrans.
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A mechanistic dichotomy in ruthenium-catalyzed propargyl alcohol reactivity: a novel hydrative diyne cyclization.
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Localization of a substrate binding site on the FeMo-cofactor in nitrogenase: trapping propargyl alcohol with an alpha-70-substituted MoFe protein.
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Clotrimazole, ketoconazole, and clodinafop-propargyl as potent growth inhibitors of equine Babesia parasites during in vitro culture.
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Application of selectively acylated glycosides for the alpha-galactosidase-catalyzed synthesis of disaccharides.
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A Rh(I)-catalyzed cycloisomerization of homo- and bis-homopropargylic alcohols.
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A mild C-O bond formation catalyzed by a rhenium-oxo complex.
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Ruthenium-catalyzed alkyne-propargyl alcohol addition. An asymmetric total synthesis of (+)-alpha-kainic acid.
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A mechanism for the formation of bis-glutathione conjugates of propargyl alcohol.
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Characterization of propargyl bromide transformation in soil.
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Total synthesis of rhizoxin D, a potent antimitotic agent from the fungus Rhizopus chinensis.
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Steric control of organic transformation by a dendrimer cage: organocobalt dendrimer porphyrins as novel coenzyme B(12) mimics.
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Asymmetric synthesis of anti-homopropargylic alcohols from aldehydes and chiral sulfonimidoyl substituted bis(allyl)titanium complexes through generation and elimination of novel chiral alkylidenecarbene (dimethylamino)sulfoxonium ylides.
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Propargyloxycarbonyl (Poc) amino acid chlorides as efficient coupling reagents for the synthesis of 100% diastereopure peptides and resin bound tetrathiomolybdate as an effective deblocking agent for the Poc group.
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Asymmetric total synthesis of 11-deoxytetrodotoxin, a naturally occurring congener.
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An unusual ruthenium-catalyzed cycloisomerization of alkynes and propargyl alcohols.
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A Ru catalyzed divergence: oxidative cyclization vs cycloisomerization of bis-homopropargylic alcohols.
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A Highly diastereoselective synthesis of (1R)-(+)-camphor-based chiral allenes and their asymmetric hydroboration-oxidation reactions.
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Indenylidene complexes of ruthenium: optimized synthesis, structure elucidation, and performance as catalysts for olefin metathesis--application to the synthesis of the ADE-ring system of nakadomarin A.
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Coupling of alkynylTMS derivatives with vinylic iodides. An efficient route to 1,3-enynes and dienes.
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Lipase-mediated resolution of 4-TMS-3-butyn-2-ol and use of the mesylate derivatives as a precursor to a highly stereoselective chiral allenylindium reagent.
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A novel one-pot pyrrole synthesis via a coupling-isomerization-Stetter-Paal-Knorr sequence.
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Highly diastereoselective synthesis of propargylic 1,2-anti-diol derivatives using alpha-alkoxypropargylstannanes.
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Disposition of propargyl alcohol in rat and mouse after intravenous, oral, dermal and inhalation exposure.
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Reactions of first-row transition metal ions with propargyl alcohol in the gas phase.
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Atom economy: aldol-type products by vanadium-catalyzed additions of propargyl alcohols and aldehydes.
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Total synthesis of epothilone B, epothilone D, and cis- and trans-9,10-dehydroepothilone D.
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Cytochrome P450 2E1 metabolically activates propargyl alcohol: propiolaldehyde-induced hepatocyte cytotoxicity.
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A novel 1,5-benzoheteroazepine synthesis via a one-Pot coupling-isomerization-cyclocondensation sequence
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Identification of metabolites of [1,2,3-(13)C]Propargyl alcohol in mouse urine by (13)C NMR and mass spectrometry and comparison to rat.
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A novel three-component one-pot pyrimidine synthesis based upon a coupling-isomerization sequence.
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Mechanism-based inactivation of thymidylate synthase by 5-(3-fluoropropyn-1-yl)-2'-deoxyuridine 5'-phosphate.
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Identification of metabolites of [1,2,3-(13)C]Propargyl alcohol in rat urine by (13)C NMR and mass spectrometry.
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Unusual propargylic oxidations catalyzed by chloroperoxidase.
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Sex attractants of geometrid and noctuid moths: Chemical characterization and field test of monoepoxides of 6,9-dienes and related compounds.
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Hybrid molecules containing propargylic sulfones and DNA minor groove-binding lexitropsins: synthesis, sequence specificity of reaction with DNA and biological evaluation.
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Comparative oxidation of 2-propyn-1-ol with other low molecular weight unsaturated and saturated primary alcohols by bovine liver catalase in vitro.
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Mutagenic activity of 3 industrial chemicals in a battery of in vitro and in vivo tests.
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Vinylstannylated alkylating agents as prosthetic groups for radioiodination of small molecules: design, synthesis, and application to iodoallyl analogues of spiperone and diprenorphine.
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Zinc-activated alcohols in ternary complexes of liver alcohol dehydrogenase.
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Evidence that enzyme-generated aromatic Michael acceptors covalently modify the nucleotide-binding site of 3 alpha-hydroxysteroid dehydrogenase.
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Fluorinated androgens and progestins: molecular probes for androgen and progesterone receptors with potential use in positron emission tomography.
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Flavin-dependent alcohol oxidase from yeast. Studies on the catalytic mechanism and inactivation during turnover.
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Role of propiolaldehyde and other metabolites in the pargyline inhibition of rat liver aldehyde dehydrogenase.
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Two geometrical isomers of linoleic acid: improved total syntheses.
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Acute oral toxicity as LD50 (mg/kg) of propargyl alcohol to male and female rats.
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Penitricin, a new class of antibiotic produced by Penicillium aculeatum. III. Structural confirmation by chemical synthesis and biological activity.
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Sex pheromone of the European grapevine moth,Lobesia botrana Schiff. (Lepidoptera: Tortricidae): Synthesis and effect of isomeric purity on biological activity.
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Irreversible inactivation of the flavoenzyme alcohol, oxidase with acetylenic alcohols.
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Inhibition of aldehyde dehydrogenase by propiolaldehyde, a possible metabolite of pargyline.
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An approach to the synthesis of C18 tri-insaturated fatty acids.
PubMed:
C-nucleoside studies. Part 6. Synthesis of 3-[2,3,5-tri-O-benzyl-beta-(and alpha)-D-ribofuranosyl]prop-2-yn-1-ol and related compounds; a new synthesis of 3(5)-(2,3,5-tri-O-benzyl-beta-D-ribofuranosyl)pyrazole.
PubMed:
[Synthesis of sulfazine from propargyl alcohol].