220199-90-6

Basic information

• Product Name: (S)-2-HYDROXYMETHYLCYCLOHEXANONE
• Synonyms: (S)-2-HYDROXYMETHYLCYCLOHEXANONE
• CAS NO: 220199-90-6
• Molecular Formula: C₇H₁₂O₂
• Molecular Weight: 0
• Mol File: 220199-90-6.mol
• Article Data: 17

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-2-HYDROXYMETHYLCYCLOHEXANONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-HYDROXYMETHYLCYCLOHEXANONE(220199-90-6)
• EPA Substance Registry System: (S)-2-HYDROXYMETHYLCYCLOHEXANONE(220199-90-6)

Safety Data

• Hazardous Substances Data: 220199-90-6(Hazardous Substances Data)

Usage

Description

(S)-2-Hydroxymethylcyclohexanone, also known as (S)-cis-1-hydroxy-2-methylcyclohexanone, is a chiral cycloalkanone compound with a non-superimposable mirror image, existing as two enantiomers, (R) and (S). It is a versatile molecule with unique structure and reactivity, making it significant in the field of organic chemistry and drug discovery.

Uses

Used in Pharmaceutical Synthesis:
(S)-2-Hydroxymethylcyclohexanone is used as a building block for the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. Its application is due to its ability to undergo various reactions such as hydrogenation, acylation, and reduction, yielding different derivatives.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-2-hydroxymethylcyclohexanone is used as a key intermediate for creating a wide range of chemical compounds. Its application is attributed to its versatile reactivity and structural properties.
Used in Medicinal Chemistry:
(S)-2-Hydroxymethylcyclohexanone is being investigated for its potential as a therapeutic agent in the treatment of various diseases. Its application is due to its potential medicinal properties and the ongoing research into its therapeutic effects.
Used in Drug Discovery:
In the process of drug discovery, (S)-2-hydroxymethylcyclohexanone is used as an important molecule for identifying and developing new pharmaceutical agents. Its application is based on its unique structure and reactivity, which can lead to the creation of novel and effective drugs.

Upstream product

• 50-00-0 formaldehyd 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 108-94-1 cyclohexanone 
• 70254-36-3 (6-Methylene-cyclohex-1-enyl)-methanol 
• 64-18-6 formic acid 
• 75-07-0 acetaldehyde 
• 105956-40-9 2-(hydroxymethyl)cyclohex-2-en-1-one 

Downstream Products

• 1374119-02-4 (S)-2-((MOM)methyl)cyclohexanone 
• 1374119-14-8 (1R,2S)-2-((methoxymethoxy)methyl)-1-((trimethylsilyl)ethynyl)cyclohexanol 
• 1374119-05-7 (1S,2S)-2-((methoxymethoxy)methyl)-1-((trimethylsilyl)ethynyl)cyclohexanol 
• 175398-36-4 (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclohexanone 
• 29569-80-0 (1R,2S)-2-(hydroxymethyl)cyclohexanol 

Relevant articles and documents

Direct organocatalytic asymmetric α-hydroxymethylation of ketones and aldehydes

Direct organocatalytic asymmetric α-hydroxymethylation of ketones and aldehydes with formaldehyde has been developed, which furnished the corresponding α-hydroxymethylated adducts with high chemo- and enantioselectivity. The reaction is catalyzed by proline derivatives and is a simple method for the enantioselective synthesis of α-hydroxymethylated ketones and aldehydes, and C-2 symmetric diols.

Organocatalytic α-hydroxymethylation of cyclopentanone with aqueous formaldehyde: Easy access to chiral δ-lactones

Optically active lactones are important synthons in perfume and aroma manufacturing. Therefore, developments of efficient asymmetric syntheses are desired. Organocatalytic asymmetric α-hydroxymethylations of cyclopentanone with aqueous formaldehyde have b

Investigating: Saccharomyces cerevisiae alkene reductase OYE 3 by substrate profiling, X-ray crystallography and computational methods

Saccharomyces cerevisiae OYE 3 shares 80% sequence identity with the well-studied Saccharomyces pastorianus OYE 1; however, wild-type OYE 3 shows different stereoselectivities toward some alkene substrates. Site-saturation mutagenesis of Trp 116 in OYE 3 followed by substrate profiling showed that the mutations had relatively little effect, opposite to that observed previously for OYE 1. The X-ray crystal structures of unliganded and phenol-bound OYE 3 were solved to 1.8 and 1.9 ? resolution, respectively. Both structures were nearly identical to that of OYE 1, with only a single amino acid difference in the active site region (Ser 296 versus Phe 296, part of loop 6). Despite their essentially identical static X-ray structures, molecular dynamics (MD) simulations revealed that loop 6 conformations differed significantly in solution between OYE 3 and OYE 1. In OYE 3, loop 6 remained nearly as open as observed in the crystal structure; by contrast, loop 6 closed over the active site of OYE 1 by ca. 4 ?. Loop closure likely generates a greater number of active site protein contacts for substrate bound to OYE 1 as compared to OYE 3. These differences provide an explanation for the differing stereoselectivities of OYE 3 and OYE 1, despite their nearly identical X-ray crystal structures.

Chitosan aerogel beads as a heterogeneous organocatalyst for the asymmetric aldol reaction in the presence of water: An assessment of the effect of additives

The catalytic properties of chitosan aerogel for the direct asymmetric aldol reaction in water assisted by various surfactants and acid co-catalysts have been evaluated by employing a range of donor and acceptor systems. A beneficial effect on both the yi