27583-43-3

Usage

Uses

Used in Chemical Production:
2-Hydroxymethylcyclohexanol is used as a solvent for the production of other chemicals, facilitating the synthesis process and enhancing the efficiency of chemical reactions.
Used in Cosmetics and Personal Care Products:
In the cosmetics and personal care industry, 2-Hydroxymethylcyclohexanol is utilized as a fragrance ingredient, adding pleasant scents to various products while ensuring compatibility with other ingredients.
Used in Pharmaceutical Industry:
2-Hydroxymethylcyclohexanol is employed as an intermediate in the synthesis of various drugs and pharmaceutical compounds, contributing to the development of new medications and therapies.
It is crucial to handle 2-Hydroxymethylcyclohexanol with care due to its potential harmful effects if ingested or inhaled, and its ability to cause skin and eye irritation.

InChI:InChI=1/C7H14O2/c8-5-6-3-1-2-4-7(6)9/h6-9H,1-5H2

Upstream product

• 1188284-68-5 C₂₇H₃₈O₈ 
• 7639-12-5 trans-1-hydroxymethyl-2-chlorocyclohexane 
• 60-29-7 diethyl ether 
• 1193-63-1 Cyclohexanone-2-carbaldehyde 
• 53185-69-6 pimelaldehyde 
• 7639-16-9 di(trans-2-chlorocyclohexylmethyl)formal 
• 75909-39-6 Methoxy-phenyl-acetic acid 6-formyl-cyclohex-2-enyl ester 
• 936-03-8 trans-2-carbomethoxycyclohexan-1-ol 
• 833-72-7 (+/-)-trans-2-acetoxy-1-acetoxymethyl-cyclohexane 
• 5331-08-8 2-(hydroxymethyl)cyclohexanone 
• 286-20-4 cyclohexene oxide 
• 286-20-4 cyclohexane-1,2-epoxide 
• 50-00-0 formaldehyd 
• 110-83-8 cyclohexene 

Downstream Products

• 832131-69-8 (+/-)-cis/trans-2-{[(tert-butyl)(dimethyl)silyloxy]methyl}cyclohexanol 
• 5331-08-8 2-(hydroxymethyl)cyclohexanone 
• 38739-10-5 2-hydroxy-1-cyclohexene-1-carbaldehyde 
• 55309-53-0 2-hydroxycyclohexane-1-carbaldehyde 
• 71518-98-4 2-chloro-1-methylenecyclohexane 
• 115883-97-1 (2R,4aR,8aS)-2-(4-Octyloxy-phenyl)-hexahydro-benzo[1,3]dioxine 
• 104333-27-9 4-Pentyloxy-benzoic acid (2R,4aR,8aS)-4-(hexahydro-benzo[1,3]dioxin-2-yl)-phenyl ester 
• 104333-30-4 4-Nonyloxy-benzoic acid (2R,4aR,8aS)-4-(hexahydro-benzo[1,3]dioxin-2-yl)-phenyl ester 
• 104348-27-8 4-Decyloxy-benzoic acid (2R,4aR,8aS)-4-(hexahydro-benzo[1,3]dioxin-2-yl)-phenyl ester 
• 104333-17-7 4-Methyl-benzoic acid (2R,4aR,8aS)-4-(hexahydro-benzo[1,3]dioxin-2-yl)-phenyl ester 
• 104333-33-7 (2R,4aR,8aS)-4-(Hexahydro-benzo[1,3]dioxin-2-yl)-benzoic acid 4-pentyl-phenyl ester 
• 104333-35-9 (2R,4aR,8aS)-4-(Hexahydro-benzo[1,3]dioxin-2-yl)-benzoic acid 4-pentyloxy-phenyl ester 

Relevant academic research and scientific papers

1,2-Disubstituted cyclohexane nucleosides: Comparative study for the synthesis of cis and trans adenosine analogues

A new class of adenosine analogues with 1,2-disubstituted carbocycles (with cis and trans stereochemistry) have been synthesized. Construction of the base on the amino group of (±)-cis-(2-aminocyclohexyl)methanol was more efficient than the Mitsunobu cond

Selective Isomerization via Transient Thermodynamic Control: Dynamic Epimerization of trans to cis Diols

Traditional approaches to stereoselective synthesis require high levels of enantio- and diastereocontrol in every step that forms a new stereocenter. Here, we report an alternative approach, in which the stereochemistry of organic substrates is selectivel

X-ray Structure-Guided Discovery of a Potent, Orally Bioavailable, Dual Human Indoleamine/Tryptophan 2,3-Dioxygenase (hIDO/hTDO) Inhibitor That Shows Activity in a Mouse Model of Parkinson’s Disease

Human indoleamine 2,3-dioxygenase 1 (hIDO1) and tryptophan 2,3-dioxygenase (hTDO) have been closely linked to the pathogenesis of Parkinson’s disease (PD); nevertheless, development of dual hIDO1 and hTDO inhibitors to evaluate their potential efficacy against PD is still lacking. Here, we report biochemical, biophysical, and computational analyses revealing that 1H-indazole-4-amines inhibit both hIDO1 and hTDO by a mechanism involving direct coordination with the heme ferrous and ferric states. Crystal structure-guided optimization led to23, which manifested IC50values of 0.64 and 0.04 μM to hIDO1 and hTDO, respectively, and had good pharmacokinetic properties and brain penetration in mice.23showed efficacy against the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse motor coordination deficits, comparable to Madopar, an anti-PD medicine. Further studies revealed that different from Madopar,23likely has specific anti-PD mechanisms involving lowering IDO1 expression, alleviating dopaminergic neurodegeneration, reducing inflammatory cytokines and quinolinic acid in mouse brain, and increasing kynurenic acid in mouse blood.

Investigation of Electrostatic Interactions towards Controlling Silylation-Based Kinetic Resolutions

Electrostatic interactions between a silylated isothiourea intermediate and an ester π system were explored by determining how variations in sterics and electronics affect the selectivity of a silylation-based kinetic resolution. Sterics on the π systems affect the selectivity factors of alkyl 2-hydroxycyclohexanecarboxylates, resulting in a strong correlation of selectivity factors to Charton values. Induction effects of electron-withdrawing substituents on phenyl esters significantly enhance selectivity supporting an edge to face π–π interaction. The linear free energy relationships that were uncovered will aid in future incorporation of intermolecular electrostatic interactions towards controlling asymmetric reactions.

Chemoenzymatic approaches to the synthesis of the (1S,2R)-isomer of benzyl 2-hydroxycyclohexanecarboxylate

We examined ten strains of cultured whole-cell yeasts for the asymmetric reduction of commercially available ethyl 2-oxocyclohexanecarboxylate, and found that the (1S,2S)-stereoisomer of ethyl 2-hydroxycyclohexanecarboxylate was the major stereoisomer produced by Williopsis californica JCM 3600. The ethyl group of the ester was then substituted with a benzyl group with low volatility and increased hydrophobicity to facilitate the isolation of the expected product. Incubation with W. californica furnished benzyl (1S,2S)-2-hydroxycyclohexanecarboxylate (>99.9% ee) in 51.0% yield together with its (1R,2S)-isomer (>99.9% ee) in 35.4% yield. Upon treatment of the same substrate bearing the benzyl ester with a screening kit of purified overexpressed carbonyl reductases (Daicel Chiralscreen OH), two enzymes (E031, E078) furnished the (1R,2S)-isomer as the major product. With another enzyme (E007), the (1S,2R)-isomer was obtained, but its ee was very low (25.6%). The highly enantiomerically enriched (1S,2S)-isomer obtained by W. californica was transformed to the (1S,2R)-isomer (>99.9% ee), whose availability until now has been low, in 43.3% yield over two steps involving tosylation and subsequent inversive attack with tetrabutylammonium nitrite.

BIARYL PYRAZOLES AS NRF2 REGULATORS

The present invention relates to biaryl pyrazole compounds, methods of making them, pharmaceutical compositions containing them and their use as NRF2 regulators.

SN2 Reactions at Tertiary Carbon Centers in Epoxides

Described herein is a novel concept for SN2 reactions at tertiary carbon centers in epoxides without activation of the leaving group. Quantum chemical calculations show why SN2 reactions at tertiary carbon centers are proceeding in these systems. The reaction allows flexible synthesis of 1,3-diol building blocks for natural product synthesis with excellent control of the relative and absolute configurations.

ANTIDIABETIC SUBSTITUTED HETEROARYL COMPOUNDS

The present invention relates to a compound represented by formula I: and pharmaceutically acceptable salts thereof. The compounds of formula I are agonists of G-protein coupled receptor 40 (GPR40) and may be useful in the treatment, prevention and suppression of diseases mediated by the G-protein-coupled receptor 40. The compounds of the present invention may be useful in the treatment of Type 2 diabetes mellitus, and of conditions that are often associated with this disease, including obesity and lipid disorders, such as mixed or diabetic dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.

ANTIDIABETIC SUBSTITUTED HETEROARYL COMPOUNDS

The present invention relates to a compound represented by formula (I): and pharmaceutically acceptable salts thereof. The compounds of formula I are agonists of G-protein coupled receptor 40 (GPR40) and may be useful in the treatment, prevention and suppression of diseases mediated by the G-protein-coupled receptor 40. The compounds of the present invention may be useful in the treatment of Type 2 diabetes mellitus, and of conditions that are often associated with this disease, including obesity and lipid disorders, such as mixed or diabetic dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.

Regioselective mono-deprotection of di-ferf-butylsilylene acetal derived from 1,3-diol with ammonium fluoride

Here we report a novel and efficient method for the regioselective mono-deprotection of di-terf-butylsilylene acetals derived from 1,3-diols consisting of primary and secondary alcohols. The ammonium fluoride-mediated reactions of pyripyropene A derivative, thymidine and uridine derivatives, methyl β-D-glucofuranoside, and pyranoside derivatives each gave the corresponding primary alcohol with high regioselectivity.