2105-40-0

Usage

Uses

Used in Pharmaceutical Industry:
2-Methylcyclohexane-1-methanol is used as a reagent for the synthesis of N-substituted benzamides, which are important in the treatment of pain. These benzamides act as central analgesics, providing relief from moderate to severe pain by targeting specific receptors in the central nervous system.
The compound's unique structure allows it to be a versatile building block in the synthesis of various pharmaceuticals, making it a valuable asset in the development of new pain management medications. Its use in this application is due to its ability to form stable intermediates and final products with desired pharmacological properties.

Upstream product

• 2611-01-0 8-oxabicyclo[4,3,0]nonane-7-one 
• 89-94-1 6-methyl-3-cyclohexene-1-carbaldehyde 
• 53955-82-1 4-methyl-1-oxaspiro[2.5]octane 
• 78426-32-1 2-(hydroxymethyl)-1-methylenecyclohexane 
• 67-56-1 methanol 
• 82166-21-0 methyl cyclohexane 
• 50-00-0 formaldehyd 
• 28886-01-3 (2-methyl-cyclohex-3-enyl)-methanol 
• 13076-15-8 2-methylcyclohexyl carboxaldehyde 
• 496-14-0 1,3-dihydroisobenzofuran 
• 7077-04-5 2-methyl-1-cyclohexanecarboxylic acid 
• 928-40-5 hexane-1,5-diol 
• 18915-70-3 2-methyl-cyclohex-3-enecarboxylic acid methyl ester 
• 2004-70-8 1-methylbuta-1,3-diene 

Downstream Products

• 1073-27-4 1-chloromethyl-2-methyl-cyclohexane 
• 68996-12-3 1-bromomethyl-2-methyl-cyclohexane 
• 98551-93-0 1-iodomethyl-2-methyl-cyclohexane 
• 53075-45-9 2-methyl-cyclohexanemethanol, acetate 
• 875823-03-3 (2-methyl-cyclohexyl)-acetaldehyde 
• 2808-75-5 2-methyl-1-methylenecyclohexane 
• 13076-15-8 2-methylcyclohexyl carboxaldehyde 

Relevant academic research and scientific papers

Catalytic Asymmetric Synthesis of Cyclohexanes by Hydrogen Borrowing Annulations

Hydrogen borrowing catalysis serves as a powerful alternative to enolate alkylation, enabling the direct coupling of ketones with unactivated alcohols. However, to date, methods that enable control over the absolute stereochemical outcome of such a process have remained elusive. Here we report a catalytic asymmetric method for the synthesis of enantioenriched cyclohexanes from 1,5-diols via hydrogen borrowing catalysis. This reaction is mediated by the addition of a chiral iridium(I) complex, which is able to impart high levels of enantioselectivity upon the process. A series of enantioenriched cyclohexanes have been prepared and the mode of enantioinduction has been probed by a combination of experimental and DFT studies.

Synthesis of β-Chiral Amines by Dynamic Kinetic Resolution of α-Branched Aldehydes Applying Imine Reductases

Imine reductases (IREDs) allow the one-step preparation of optically active secondary and tertiary amines by reductive amination of ketones. Until now, mainly α-chiral amines have been prepared by this route. In this study, we explored the possibility of synthesizing β-chiral amines, a class of compounds which is also frequently found as structural motif in pharmaceuticals but much more challenging to prepare due to the following reasons: (i) The aldehyde substrate already contains the chiral center and needs to be racemized to enable full conversion. (ii) Because the intermediate imine bears the stereo center two carbon atoms remote to the imine nitrogen, it is more challenging to achieve high enantioselectivity compared to α-chiral amine synthesis. For investigating the proof of concept, we first confirmed that different IREDs are able to convert a variety of α-branched aldehydes when combined with five different amine substrates. The IRED from Streptomyces ipomoeae was a suitable enzyme facilitating the dynamic kinetic resolution of 2-phenylpropanal and a substituted 2-methyl-3-phenylpropanal: the corresponding N-methylated β-chiral amines were obtained with '95 % conversion and 78 and 95 %ee. Other amines were formed with low to moderate enantiomeric excess. This exemplifies the potential of IREDs for the one-step synthesis of secondary β-chiral amines, but also the challenge to identify highly selective enzymes for a desired amine product.

Directing abilities of alcohol-derived functional groups in the hydroformylation of olefins

The hydroformylation of allylic and homoallylic alcohols and their derivatives using cationic and neutral rhodium complexes has been examined. The highest diastereoselectivity (87:13) was observed in the reaction of 1-methoxymethoxy-2-methylenecyclohexane. Higher yields and similar selectivities were obtained in the reaction of the TBDMS-protected alcohol. The major diastereomer results from hydroformylation syn to the functional group, which would suggest a directing effect. However, hydroformylation of 3-methylene-1-cyclohexanol derivatives occurs on the face opposite to the directing group in the major isomer. These data, in addition to the results of hydroformylation of 1-methyl-2-methylenecyclohexane, suggest that inherent conformational preferences are of significant importance in determining the product distribution and that the directing power of simple alcohols and their derivatives is moderate at best under the conditions examined in this study.

Novel and facile selective reduction of carboxylic acid with a samarium diiodide-lanthanide triflate-methanol-base system

The facile selective reduction of carboxylic acids in the presence of an aldehyde or that bearing a formyl group proceeded smoothly with a samarium diiodide-lanthanide triflate-methanol-base system at room temperature to give the corresponding alcohols in good to almost quantitative yield.

Silica Gel-supported Zinc Borohydride. Part 3. Regioselective Reductive Cleavage of Methylenecycloalkane Oxides to the Less-substituted Alcohols

Highly selective reductive cleavage of methylenecycloalkane oxides to less-substituted alcohols has been achieved by a simple procedure using silica gel supported zinc borohydride in tetrahydrofuran.

Alkane Functionalization on a Preparative Scale by Mercury-Photosensitized Cross-Dehydrodimerization

Alkanes can be functionalized with high conversions and in high chemical and quantum yields on a multigram scale by mercury-photosensitized reaction between an alkane and alcohols, ethers, or silanes to give homodimers and cross-dehydrodimers.The separation of the product mixtures is often particulary easy because of a great difference in polarity of the homodimers and cross-dimers.It is also possible to bias the product composition when the ratio of the components in the vapor phase is adjusted by altering the liquid composition.This is useful either to maximize chemical yield or to ease separation by favoring the formation of the most easily separated pair of compounds.The mechanistic basis of the reaction is discussed and a number of specific types of syntheses, for example of 2,2-disubstituted carbinols, are described in detail.The selectivity of cross-dimerization is shown to exceed that for homodimerization and reasons are discussed.Relative reactivities of different compounds and classes of compound are MeOHp-dioxanecyclohexane1,3,5-trioxacyclohexaneethanolisobutaneTHFEt3SiH.The observed selectivities generally parallel those for homodimerization, reported in the preceding paper, but certain differences are noted, and reasons for the differences are proposed.The bond-dissociation energy of Et3SiH is estimated from the reactivity data to be 90 kcal/mol.Eleven new carbinols are synthesized.