85711-13-3

Basic information

• Product Name: D-CYCLOHEXYLGLYCINOL
• Synonyms: (R)-CYCLOHEXYLGLYCINOL;R-2-AMINO-2-CYCLOHEXANEETHANOL;(R)-2-AMINO-2-CYCLOHEXYL-ETHANOL;H-D-CHG-OL;D-CYCLOHEXYLGLYCINOL;(R)-(-)-2-Amino-2-cyclohexylethan-1-ol;D-2-aMino-2-cyclohexyl-ethanol;(R)-b-AMino-cyclohexaneethanol HCl
• CAS NO: 85711-13-3
• Molecular Formula: C₈H₁₇NO
• Molecular Weight: 143.23
• Product Categories: pharmacetical;Peptide
• Mol File: 85711-13-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 72-74篊.°C
• Boiling Point: 274℃
• Flash Point: 119℃
• Appearance: /
• Density: 0.999
• Vapor Pressure: 0.000716mmHg at 25°C
• Refractive Index: 1.497
• Storage Temp.: Store at 0-5°C
• PKA: 12.85±0.10(Predicted)
• CAS DataBase Reference: D-CYCLOHEXYLGLYCINOL(CAS DataBase Reference)
• NIST Chemistry Reference: D-CYCLOHEXYLGLYCINOL(85711-13-3)
• EPA Substance Registry System: D-CYCLOHEXYLGLYCINOL(85711-13-3)

Safety Data

• Statements: 36
• Safety Statements: 26
• Hazardous Substances Data: 85711-13-3(Hazardous Substances Data)

Usage

General Description

D-Cyclohexylglycinol, also known as D-CHG, is a chemical compound with the chemical formula C8H15NO. It is a chiral amino alcohol, meaning it has a specific three-dimensional arrangement of atoms. D-CHG is used as a chiral building block in the synthesis of pharmaceuticals and agrochemicals, as well as a resolving agent in the production of optically pure compounds. It is also used as a chiral ligand in asymmetric catalysis, helping to facilitate the synthesis of enantiomerically pure substances. D-Cyclohexylglycinol is a valuable and versatile chemical in the field of chemical synthesis and manufacturing.

InChI:InChI=1/C8H17NO/c9-8(6-10)7-4-2-1-3-5-7/h7-8,10H,1-6,9H2/t8-/m0/s1

Upstream product

• 875-74-1 (R)-phenylglycine 
• 14328-52-0 (R)-2-amino-2-cyclohexyl acetic acid 

Downstream Products

• 1617545-77-3 4-[6-((R)-1-cyclohexyl-2-hydroxy-ethylamino)-pyrazin-2-yl]-3-fluoro-phenol 
• 1617545-72-8 (R)-2-[6-(5-chloro-2-fluoro-phenyl)-pyrazin-2-ylamino]-2-cyclohexyl-ethanol 
• 1617545-94-4 (R)-2-(6-chloro-pyrazin-2-ylamino)-2-cyclohexyl-ethanol 
• 1356453-48-9 3-[(2R,5R)-5-cyclohexyl-2-(2-hydroxyethyl)-3-oxomorpholin-4-yl]-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylic acid 
• 1356457-36-7 3-[(2R,5R)-5-cyclohexyl-2-(2-hydroxyethyl)-3-oxomorpholin-4-yl]-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylic acid methyl ester 
• 1356457-29-8 3-((2R,5R)-2-allyl-5-cyclohexyl-3-oxomorpholin-4-yl)-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylic acid methyl ester 
• 1356457-28-7 3-((2S,5R)-2-allyl-5-cyclohexyl-3-oxomorpholin-4-yl)-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylic acid methyl ester 
• 1356456-54-6 3-[(2R,5R)-5-cyclohexyl-2-(3-hydroxypropyl)-2-methyl-3-oxomorpholin-4-yl]-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylic acid 
• 1356457-27-6 3-[(2R,5R)-5-cyclohexyl-2-(3-hydroxypropyl)-2-methyl-3-oxomorpholin-4-yl]-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylic acid methyl ester 
• 1356457-26-5 (2R,5R)-5-cyclohexyl-2-(3-hydroxypropyl)-2-methylmorpholin-3-one 
• 1356457-23-2 (2S,5R)-2-[3-(tert-butyl(dimethyl)silanyloxy)propyl]-5-cyclohexyl-4-(4-methoxybenzyl)-2-methylmorpholin-3-one 
• 1356457-24-3 (2R,5R)-2-[3-(tert-butyl(dimethyl)silanyloxy)propyl]-5-cyclohexyl-4-(4-methoxybenzyl)-2-methylmorpholin-3-one 
• 1356456-36-4 3-[(R)-5-cyclohexyl-2-(3-hydroxypropyl)-3-oxomorpholin-4-yl]-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylic acid 
• 1356457-22-1 3-[(R)-5-cyclohexyl-2-(3-hydroxypropyl)-3-oxomorpholin-4-yl]-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylic acid methyl ester 

Relevant articles and documents

Palladium(0)-Catalyzed Enantioselective Intramolecular Arylation of Enantiotopic Secondary C?H Bonds

The enantioselective functionalization of nonactivated enantiotopic secondary C?H bonds is one of the greatest challenges in transition-metal-catalyzed C?H activation proceeding by an inner-sphere mechanism. Such reactions have remained elusive within the realm of Pd0 catalysis. Reported here is the unique reactivity profile of the IBiox ligand family in the Pd0-catalyzed intramolecular arylation of such nonactivated secondary C?H bonds. Chiral C2-symmetric IBiox ligands led to high enantioselectivities for a broad range of valuable indane products containing a tertiary stereocenter, as well as the arylation of secondary C?H bonds adjacent to amides. Depending on the amide substituents and upon control of reaction time, indanes containing labile tertiary stereocenters were also obtained with high enantioselectivities. Analysis of the steric maps of the IBiox ligands indicated that the level of enantioselectivity correlates with the difference between the two most occupied and the two less occupied space quadrants, and provided a blueprint for the design of even more efficient ligands.

Stereoselective Aldol Reaction with Chiral Secondary Acetamides

The deprotonated acetamides 4a - c and 5a - c are added to prochiral carbonyl compounds.The influence of the solvent, of the reaction temperature, and of the enolate gegenion on the ratio of the isomeric products 8/9, 18/19, and 26/27, respectively, are studied.The highest degree of diastereoselectivity are observed, when the titanium enolate of the acetamide 4a or the threefold deprotonated N-acetyl-α-phenylglycinol (5a) is used.The diastereomers 18a - d, formed in excess in the addition of 5a to aldehydes, are isolated in pure from by a single recrystallization, and afford the enantiomerically pure β-hydroxy carboxylic acids 3a - d.Thereby, the chiral auxiliary, α-phenylglycinol (14), is recovered.