74708-24-0

Basic information

• Product Name: (1S,2R)-(+)-trans-2-(Cyanomethyl)cyclohexanol
• Synonyms: (1S,2R)-(+)-trans-2-(Cyanomethyl)cyclohexanol
• CAS NO: 74708-24-0
• Molecular Weight: 139.197
• Mol File: 74708-24-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1S,2R)-(+)-trans-2-(Cyanomethyl)cyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-(+)-trans-2-(Cyanomethyl)cyclohexanol(74708-24-0)
• EPA Substance Registry System: (1S,2R)-(+)-trans-2-(Cyanomethyl)cyclohexanol(74708-24-0)

Safety Data

• Hazardous Substances Data: 74708-24-0(Hazardous Substances Data)

Usage

Description

(1S,2R)-(+)-trans-2-(Cyanomethyl)cyclohexanol is a chiral chemical compound with the molecular formula C9H15NO. It is a derivative of cyclohexanol, featuring a cyano group attached to the second carbon of the cyclohexane ring. (1S,2R)-(+)-trans-2-(Cyanomethyl)cyclohexanol exists in two enantiomeric forms, with the (1S,2R)-(+)-trans isomer being the specific form of interest.

Uses

Used in Pharmaceutical Industry:
(1S,2R)-(+)-trans-2-(Cyanomethyl)cyclohexanol is used as a building block for the preparation of various pharmaceuticals. Its unique structure and chirality make it a valuable component in the synthesis of complex organic molecules, contributing to the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical industry, (1S,2R)-(+)-trans-2-(Cyanomethyl)cyclohexanol is utilized as a precursor for the synthesis of various agrochemicals. Its properties allow for the creation of compounds that can be used in pest control and crop protection.
Used in Asymmetric Catalysis:
(1S,2R)-(+)-trans-2-(Cyanomethyl)cyclohexanol may have applications in asymmetric catalysis, where its chiral nature can be leveraged to produce enantioselective reactions, leading to the formation of desired enantiomers in an efficient and selective manner.
Used in Synthesis of Chiral Intermediates:
(1S,2R)-(+)-trans-2-(Cyanomethyl)cyclohexanol is also used in the synthesis of chiral intermediates, which are essential for the production of enantiomerically pure compounds. Chiral intermediates are crucial in various chemical processes, particularly in the pharmaceutical and agrochemical industries, where the purity and specificity of the final product are of utmost importance.

Upstream product

• 286-20-4 cyclohexane-1,2-epoxide 
• 75-05-8 acetonitrile 
• 99749-00-5 lithioacetonitrile 
• 74708-24-0 (1R*,2S*)-2-hydroxycyclohexane acetonitrile 
• 42185-27-3 2-(cyanomethyl)cyclohexanone 
• 765-87-7 cyclohexane-1,2-dione 
• 38461-13-1 2,2-dimethoxycyclohexanone 
• 173948-39-5 (E)-(2-Oxocyclohexylidene)ethanenitrile 
• 74708-29-5 (1S,2R,R)-trans-2-(Cyanomethyl)cyclohexyl N-<1-(1-Naphthyl)-ethyl>carbamate 

Downstream Products

• 90226-51-0 (+/-)-trans-2-(2-amino-ethyl)-cyclohexanol 
• 5426-58-4 trans-(2-hydroxy-cyclohexyl)acetic acid 
• 74629-91-7 (1R,2S,R)-trans-2-(Cyanomethyl)cyclohexyl N-<1-(1-Naphthyl)-ethyl>carbamate 
• 74708-29-5 (1S,2R,R)-trans-2-(Cyanomethyl)cyclohexyl N-<1-(1-Naphthyl)-ethyl>carbamate 
• 24871-12-3 trans-hexahydro-2(3H)-benzofuranone 
• 101859-26-1 (1R*,2S*)-((2-tert-butyldimethylsilyl)-oxy)cyclohexaneacetonitryle 
• 101859-27-2 (2-t-butyldimethylsiloxy)cyclohexylacetaldehyde 
• 101858-81-5 (1R,2S)-2-((E)-4-Benzyloxy-but-2-enyl)-cyclohexanol 
• 101859-31-8 (1R*,2S*,(2E))-2-((tert-butyldimethylsilyl)oxy)cyclohexane-3-methyl-2-buten-4-ol 
• 101858-82-6 (1R*,3S*,4R*,6S*)-3-((benzyloxy)methyl)-4-iodo-2-oxabicyclo<4.4.0.>decane 
• 101858-94-0 (1R*,3S*,4R*,6S*)-3-((benzyloxy)methyl)-2-oxabicyclo<4.4.0>dec-4-ol 
• 101859-57-8 (1S,2R)-2-((E)-4-Benzyloxy-3-methyl-but-2-enyl)-cyclohexanol 
• 101858-88-2 (1R*,6S*)-8-(2-(benzyloxy)-1-iodoethyl)-7-oxabicyclo<4.3.0>nonane 
• 101859-28-3 (E)-4-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-but-2-enoic acid methyl ester 

Relevant articles and documents

Biotransformation of αβ-unsaturated carbonyl compounds: sulfides, sulfoxides, sulfones, nitriles and esters by yeast species: carbonyl group and carbon-carbon double bond reduction

The reduction of αβ-unsaturated ketones with γ-sulfide, sulfoxide, sulfone, nitrile and ester functions has been investigated.Both C=O and C=C reduction was observed.In the sulfur series, C=O bond reduction was always observed, but significant C=C bond reduction was observed only with the sulfide.The unsaturated nitriles gave the corresponding alcohols as the major bioreduction product, with smaller but significant amounts of fully reduced product.A similar result was obtained with the ester substrate.Relative and absolute configurations of bioreduction products were determined.A comparison was made between reductions catalysed by bakers' yeast (Saccharomyces cerevisiae) and by other yeasts (Zygosaccharomyces rouxii, Pichia capsulata, P. farinosa, Candida chalmersi and C. diddensiae).The tendency of Z. rouxii to give products enantiomeric with thouse obtained using S. cerevisiae was noted.The relationship between substrate structure and the stereochemistry of C=C double bond reduction is discussed.

Enantiomerically Pure Lactones. 2. Approaches to Cis or Trans Multicyclic Lactones

Enantiomerically pure bicyclic lactones 1-3 and tricyclic lactones 4 and 5 have been prepared by either of two procedures, each hinging upon the liquid chromatographic seperation of rationally selected diastereomeric derivatives.After seperation, the diastereomers are converted by a simple high-yield reaction sequence to the enantiomeric multiring lactones, none of which has been previously reported in optically active form. The relative strengths and weaknesses of each approach are discussed.Lactones 4 and 5 were α-methylated, these derivatives being suitable for the determination of enantiomeric purity and absolute configuration using the chiral solvating agent (S)-(+)-2,2,2-trifluoro-1-(9-anthryl)ethanol.