74364-79-7

Basic information

• Product Name: (R)-1-HEXYN-3-OL
• Synonyms: (R)-1-HEXYN-3-OL
• CAS NO: 74364-79-7
• Molecular Formula: C₆H₁₀O
• Molecular Weight: 98.143
• Mol File: 74364-79-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-1-HEXYN-3-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-HEXYN-3-OL(74364-79-7)
• EPA Substance Registry System: (R)-1-HEXYN-3-OL(74364-79-7)

Safety Data

• Hazardous Substances Data: 74364-79-7(Hazardous Substances Data)

Usage

Uses

Used in Perfumery and Flavor Industry:
(R)-1-HEXYN-3-OL is used as a key component in the manufacturing of perfumes and flavorings, leveraging its distinctive sweet odor to enhance the fragrance and taste profiles of various products.
Used in Pharmaceutical and Medical Applications:
Due to its antimicrobial properties, (R)-1-HEXYN-3-OL is employed in certain medical and pharmaceutical applications, where it can contribute to the development of new treatments and therapies.
Used in Organic Synthesis:
(R)-1-HEXYN-3-OL serves as a building block in organic synthesis, allowing for the creation of a wide range of chemical products. Its unique structure and properties make it a valuable compound for research and development in the chemical industry.
Used in Research and Development:
(R)-1-HEXYN-3-OL's potential for future applications in various industries is being explored through ongoing research and development efforts, which may lead to new discoveries and innovations in fields such as materials science, pharmaceuticals, and more.

Upstream product

• 70095-35-1 (R)-hex-1-yn-3-yl acetate 
• 689-00-9 hex-1-yn-3-one 
• 108-22-5 Isopropenyl acetate 
• 105-31-7 1-hexyn-3-ol 
• 122-79-2 Phenyl acetate 
• 108-05-4 vinyl acetate 
• 141-78-6 ethyl acetate 
• 1384108-75-1 C₆H₉O₄S^(1-)*Na⁽¹⁺⁾ 
• 1384108-53-5 C₆H₉O₄S^(1-)*Na⁽¹⁺⁾ 
• 1219718-23-6 (2S,3R)-trans-3-propyloxiranemethylchloride 
• 111003-36-2 ((2R,3S)-3-propyloxiran-2-yl)methanol 
• 561321-79-7 1-(triisopropylsilyl)hex-1-yn-3-one 
• 56438-75-6 3-benzoyloxy-1-hexyne 
• 15352-99-5 (+/-)-hex-1-yn-3-yl acetate 

Downstream Products

• 821-74-9 (Sa)-nona-4,5-diene 
• 227951-93-1 (R)-1-(hex-1-en-3-yloxy)-4-methoxybenzene 
• 930608-59-6 1-((R)-hex-1-yn-3-yloxy)-4-methoxybenzene 
• 930608-62-1 4-((R)-hex-1-yn-3-yloxy)phenyl acetate 
• 930608-63-2 2-((R)-hex-1-yn-3-yloxy)phenyl acetate 
• 930608-61-0 1-((R)-hex-1-yn-3-yloxy)-2-bromobenzene 
• 930608-64-3 3-((R)-hex-1-yn-3-yloxy)phenyl acetate 
• 930608-58-5 1-((R)-hex-1-yn-3-yloxy)-4-methylbenzene 

Relevant articles and documents

Ester Synthesis in Water: Mycobacterium smegmatis Acyl Transferase for Kinetic Resolutions

The acyl transferase from Mycobacterium smegmatis (MsAcT) catalyses transesterification reactions in aqueous media because of its hydrophobic active site. Aliphatic cyanohydrin and alkyne esters can be synthesised in water with excellent and strikingly opposite enantioselectivity [(R);E>37 and (S);E>100, respectively]. When using this enzyme, the undesired hydrolysis of the acyl donor is an important factor to take into account. Finally, the choice of acyl donor can significantly influence the obtained enantiomeric excesses. (Figure presented.).

The substrate spectrum of the inverting sec-alkylsulfatase Pisa1

The substrate spectrum of the inverting alkylsulfatase Pisa1 was investigated using a range of sec-alkyl sulfate esters bearing aromatic, olefinic and acetylenic moieties. Perfect enantioselectivities were obtained for substrates bearing groups of different size adjacent to the sulfate ester moiety. Insufficient selectivities could be doubled by using dimethyl sulfoxide (DMSO) as co-solvent. Hydrolytically unstable benzylic sulfate esters could be sufficiently stabilised by introduction of electron-withdrawing substituents. Overall, Pisa1 appears to be a very useful inverting alkylsulfatase for the deracemisation of rac-sec-alcohols via enzymatic hydrolysis of their corresponding sulfate esters, which furnishes homochiral products possessing the 'anti-Kazlauskas' configuration. Copyright

First stereoselective total synthesis of (-)-stagonolide A

The first stereoselective total synthesis of the nonenolide (-)-stagonolide A is described. Olefin metathesis and epoxide opening reaction are the key steps involved.

Substrate-dependent stereochemical course of the (Z)-13-desaturation catalyzed by the processionary moth multifunctional desaturase

The stereochemical course of the Δ13 desaturation involved in the biosynthesis of Thaumetopoea pityocampa sex pheromone was studied using stereotopically labeled and tagged palmitic acids as metabolic probes. In the synthetic pathway, a functionalized acetylene common synthon was used for introducing the four deuterium tags. Further coupling of the tetradeuterated synthon to the appropriated alkynol and a double chemoenzymatic strategy to resolve the alcohol functionality allowed one to obtain the enantiomerically enriched probes used in the mechanistic studies. Mass spectrometric analyses of extracts from tissues cultured with each probe revealed that removal of the C13 and C14 hydrogens in 11-hexadecynoate and (Z)-11-hexadecenoate are pro-(R)- and pro-(S)-specific syn-dehydrogenation processes, respectively. This finding constitutes the first example in the literature of an enzymatic (Z)-desaturation exhibiting a substrate-dependent stereochemical course.

Catalytic asymmetric synthesis of allylic aryl ethers

(Chemical Equation Presented) The reaction of trichloroacetimidate derivatives of (Z)-2-alken-1-ols with phenol nucleophiles in the presence of the palladium(II) catalyst [COP-OAc]2 provides 3-aryloxy-1-alkenes in high yields and high enantiomeric purity (typically 63-90% yield and 90-97% ee). The reaction is exemplified by 20 examples. The method employs 1 mol % of the commercially available catalysts (S)- or (R)-[COPOAc]2, produces the branched isomer with unprecedented regioselectivity, and is compatible with the presence of base-labile functionality in either reactant.

Rearrangements and stereomutations of metallacycles derived from allenes and imidozirconium complexes

The mechanisms of the rearrangements and Stereoinversion of azametallacyclobutenes generated via [2+2] cycloaddition of allenes and imidozirconium complexes have been studied. Metallacycles derived from allenes bearing β-hydrogen atoms racemize at room temperature by reversible β-hydride elimination, a process which is also responsible for their eventual conversion to monoazadiene complexes. Metallacycles derived from diarylallenes racemize by reversible thermal bond homolysis at 95°C; racemization of these metallacycles is also catalyzed by mild oxidants.

Mechanisms of allene stereoinversion by imidozirconium complexes

The zirconium-mediated stereoinversion of allenes has been investigated by studying the stereochemical behavior of metallacycles derived from [2+2] cycloaddition of enantioenriched allenes with chiral and achiral imidozirconocene complexes. Relative rates of metallacycle racemization were measured by circular dichroism, and intermediates in the selective stereoinversion of diphenylallene with a chiral imidozirconium complex were observed by NMR spectroscopy. Metallacycles derived from dialkylallenes are proposed to racemize via reversible β-hydride elimination. Stereoinversion of diarylallene-derived metallacycles proceeds much more slowly and is thought to proceed through an η4-azatrimethylenemethane transition state. Copyright

The effect of catechin derivatives on the enantioselectivity of lipase-catalyzed hydrolyses of alkynol benzoate esters

Polyphenols, such as (+)-catechin and pyrogallol could be used to enhance stereochemical control in the lipase-catalyzed hydrolysis of alkynol benzoate esters, leading to increased enantioselectivities in the kinetic resolution of alkynols with lipase Amano AH.

Mutation of cysteine-295 to alanine in secondary alcohol dehydrogenase from thermoanaerobacter ethanolicus affects the enantioselectivity and substrate specificity of ketone reductions

The mutation of Cys-295 to alanine in Thermoanaerobacter ethanolicus secondary alcohol dehycrogenase (SADH) was performed to give C295A SADH, on the basis of molecular modeling studies utilizing the X-ray crystal structure coordinates of the highly homologous T. brockii secondary alcohol dehydrogenase (YKF.PDB). This mutant SADH has activity for 2-propanol comparable to wild-type SADH. However, the C295A mutation was found to cause a significant shift of enantioselectivity toward the (S)-configuration in the reduction of some ethynylketones to the corresponding chiral propargyl alcohols. This result confirms our prediction that Cys-295 is part of a small alkyl group binding pocket whose size determines the binding orientation of ketone substrates, and, hence, the stereochemical configuration of the product alcohol. Furthermore, C295A SADH has much higher actifity towards t-butyl and some α-branched ketones than does wild-type SADH. The C295A mutation does not affect the thioester reductase activity of SADH. The broader substrate specificity and altered stereoselectivity for C295A SADH make it a potentially useful tool for asymmetric reductions. Copyright

Enantioselective synthesis of both enantiomers of various propargylic alcohols by use of two oxidoreductases

The oxidoreductases Lactobacillus brevis alcohol dehydrogenase (LBADH) and Candida parapsilosis carbonyl reductase (CPCR) are suitable catalysts for the reduction of ketones to afford enantiopure sec. alcohols. A broad variety of alkynones (1, 3, and 5) are accepted as substrates and the corresponding propargylic alcohols (2, 4, and 6) are obtained in good yield and excellent enantiomeric excess. By changing the steric demand of the substituents the ee values can be adjusted and even the configurations of the products can be altered.