132921-97-2

Basic information

• Product Name: (R)-1-Cyclohexyl-propane-1,3-diol
• Synonyms: (R)-1-Cyclohexyl-propane-1,3-diol
• CAS NO: 132921-97-2
• Molecular Weight: 158.241
• Mol File: 132921-97-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (R)-1-Cyclohexyl-propane-1,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-Cyclohexyl-propane-1,3-diol(132921-97-2)
• EPA Substance Registry System: (R)-1-Cyclohexyl-propane-1,3-diol(132921-97-2)

Safety Data

• Hazardous Substances Data: 132921-97-2(Hazardous Substances Data)

Upstream product

• 1303556-21-9 (R)-(E)-ethyl 5-cyclohexyl-5-hydroxypent-2-enoate 
• 2043-61-0 cyclohexanecarbaldehyde 
• 135981-00-9 (2S,3S)-2-Bromo-3-cyclohexyl-3-hydroxy-propionic acid tert-butyl ester 
• 96854-34-1 (S)-3-phenyl-1,3-propanediol 
• 119638-96-9 (R)-3-Cyclohexyl-3-hydroxy-propionic acid tert-butyl ester 
• 115362-12-4 (-)-(2S,3S)-2,3-epoxy-3-cyclohexyl-1-propanol 

Downstream Products

• 1196532-14-5 (R)-3-(tert-butyldimethylsilyloxy)-1-cyclohexylpropan-1-ol 

Relevant articles and documents

Enantioselective iridium-catalyzed vinylogous reformatsky-aldol reaction from the alcohol oxidation level: Linear regioselectivity by way of carbon-bound enolates

Reformatsky reinvented: Highly enantioselective vinylogous Reformatsky-type addition has been achieved from the alcohol oxidation level with linear regioselectivity through carbon-bound enolates (see scheme; Boc=tert- butoxycarbonyl). Complete levels of c

Synthesis of trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine opioid antagonists: Application of the cis-thermal elimination of carbonates to alkaloid synthesis

Improved syntheses of two trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine opioid antagonists from 1,3-dimethyl-4-piperidinone are described. The 1,3-dimethyl-4-arylpiperidinol 23 was selectively dehydrated in a two step process to the 1,3-dimethyl-4-aryl-1,2,3,6-tetrahydropyridine 26 by the cis-thermal elimination of the corresponding alkyl carbonate derivative at 190°C. In the presence of a basic nitrogen, the success of the elimination was found to be critically dependent upon the nature of the carbonate alkyl group, with Et, i-Bu, and i-Pr being preferred (90% yield). Alkylation of the metalloenamine, formed by deprotonation of 26 with n-BuLi, proceeded regio- and stereospecifically to give the trans-3,4-dimethyl-4-aryl-1,2,3,4-tetrahydropyridine 27, which was converted in three steps to the common intermediate, (3R,4R)-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine. LY255582, a centrally-active opioid antagonist, and LY246736-dihydrate, a peripherally-active opioid antagonist, were prepared from 1,3-dimethyl-4-piperidinone in 11.8% yield (8 steps) and 6.2% yield (12 steps), respectively.

Regioselective reductive opening of 2,3-epoxy alcohol derivatives with lithium borohydride in a solid state

2,3-Epoxy alcohol derivatives were reduced regiospecifically with lithium borohydride in a solid state suspended in hexane to yield the corresponding C-3 opening products.