132617-15-3

Basic information

• Product Name: (1R,4S)-4-hydroxycyclohex-2-en-1-yl acetate
• Synonyms: (1R,4S)-4-hydroxycyclohex-2-en-1-yl acetate
• CAS NO: 132617-15-3
• Molecular Weight: 156.181
• Mol File: 132617-15-3.mol

Chemical Properties

• CAS DataBase Reference: (1R,4S)-4-hydroxycyclohex-2-en-1-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4S)-4-hydroxycyclohex-2-en-1-yl acetate(132617-15-3)
• EPA Substance Registry System: (1R,4S)-4-hydroxycyclohex-2-en-1-yl acetate(132617-15-3)

Safety Data

• Hazardous Substances Data: 132617-15-3(Hazardous Substances Data)

Upstream product

• 132513-00-9 (+/-)-1α,4α-diacetoxy-2β,3α-dibromocyclohexane 
• 78776-45-1 cis-2-cyclohexenyl-1,4-diacetate 
• 74293-60-0 (3aR,7R,7aS)-7-hydroxy-2,2-dimethyltetrahydrobenzo[d][1,3]dioxol-5(6H)-one 
• 121573-17-9 (3aR,7aS)-2,2-dimethyltetrahydrobenzo[d][1,3]dioxol-5(6H)-one 
• 697741-23-4 (1S,4S)-4-((tert-butyldimethylsilyl)oxy)cyclohex-2-enol 
• 942514-50-3 (1R,4S)-4-((tert-butyldimethylsilyl)oxy)cyclohex-2-enol 
• 32384-42-2 (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone 
• 108-22-5 Isopropenyl acetate 
• 53762-85-9 (1S,4R)-Cyclohex-2-ene-1,4-diol 
• 1165952-91-9 cyclohexa-1,3-diene 
• 108-24-7 acetic anhydride 
• 91923-19-2 1-acetoxy-4-trifluoroacetoxy-2-cyclohexene 
• 91923-19-2 trans-4-acetoxy-1-trifluoroacetoxy-cyclohex-2-ene 
• 142-71-2 copper diacetate 

Downstream Products

• 50557-37-4 4-(acetoxy)cyclohex-2-enone 
• 930-68-7 cyclohexenone 
• 96039-76-8 trans-4-chloro-2-cyclohexen-1-yl acetate 
• 705943-59-5 (1S,4S)-4-Butyl-cyclohex-2-enol 
• 114467-53-7 trans-2-phenylcyclohex-3-en-1-ol 
• 71911-76-7 1,2,3,4-tetrahydro-[1,1'-biphenyl]-4-ol 

Relevant articles and documents

Iron(II) Halide Promoted Cyclization of Cyclic 2-Enynamides: Stereoselective Synthesis of Halogenated Bicyclic γ-Lactams

A simple and mild process was developed for the highly stereoselective synthesis of halogenated bicyclic [4.3.0] and [3.3.0] γ-lactams, possessing four stereocenters, from easily available cyclic 2-enynamides. The reaction required only an inexpensive iron(II) halide under dry air and was tolerant of aryl, heteroaryl, and alkyl groups at the alkyne terminus.

Further study on synthesis of the cyclobakuchiols

Abstract Two results are described. First, quinic acid was transformed into the monoacetate of 2-cyclohexene-1,4-diol. The Ni-catalyzed allylic substitution of the monoacetate with CH2C(Me)MgBr/ZnCl2/TMEDA followed by oxidation of th

The thio-adduct facilitated, enzymatic kinetic resolution of 4-hydroxycyclopentenone and 4-hydroxycyclohexenone

The addition of 3,4-dimethoxybenzyl thiol 8, as a benzyl thiol surrogate, to racemic 4-hydroxycyclopent-2-enone 2 and 4-hydroxycyclohex-2-enone 15 gave the corresponding cis-adducts (±)-3-(3,4-dimethoxybenzylthio)-4- hydroxycyclopentanone 4b and (±)-3-(3,4-dimethoxybenzylthio)-4- hydroxycyclohexanone 16 with good diastereocontrol. In both cases, subsequent treatment with vinyl acetate, in the presence of a lipase enabled enantiomer resolution. Thus, (+)-16 and the acetate of its enantiomer, (-)-(1R,2S)-2-(3,4- dimethoxybenzylthio)-4-oxocyclohexyl acetate, (-)-17 were isolated in 98% enantiomeric excess. Based on the 1,4-dioxygenation pattern, (-)-17 can be used to prepare both enantiomers of 4-(tert-butyldimethylsilyloxy)cyclohex-2-enone 19. Firstly, saponification, with a sub-stoichiometric amount of NaOMe, followed by a one-pot silyl ether formation-sulfide elimination sequence gave (+)-19. Then using the same starting material a 6-step sequence, featuring a diastereoselective NaBH4 reduction and a Cope-type sulfoxide elimination, gave (-)-19.

Pyrrolizidine alkaloids by intramolecular palladium-catalysed allylic alkylation: Synthesis of (±)-isoretronecanol

An efficient and stereoconvergent approach to 3-substituted hexahydroindol-2-one derivatives by palladium-catalysed intramolecular allylic alkylation has been developed. Subsequently, the straightforward conversion of the hexahydroindol-2-one 7d into the alkaloid (±)-isoretronecanol has been performed. The synthesis entails 11 steps starting from 1,3-cyclohexadiene, affording the final target in a 29% overall yield. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Palladium-catalysed enantiodivergent synthesis of cis- and trans-4-aminocyclohex-2-enols

Enantiomerically pure cis- and trans-4-aminocyclohex-2-enols are prepared from cyclohexa-1,3-diene via (-)-cis-(1R,4S)-4-acetoxycyclohex-2-enol (-)-2a using palladium(0) chemistry. Benzylamine and diethylamine are tested in the Pd0-catalysed allylic amination reactions. Since acetate is too slow as a leaving group and gave considerable amounts of side products, a number of leaving groups have been investigated. Of these phosphinate and 2,4-dichlorobenzoate are excellent leaving groups and result in efficient and highly stereoselective reactions; chloride as allylic leaving group also gives good results. By variation of the leaving group and proper choice of the protecting group it is possible to synthesise all four stereoisomers of 4-aminocyclohex-2-enol in good yield and high enantiomeric excess.

ENZYMATIC PREPARATION OF (3S,6R) AND (3R,6S)-3-HYDROXY-6-ACETOXYCYCLOHEX-1-ENE

Pseudomonas cepacia lipase-catalyzed enantioselective hydrolysis of 2 in water afforded (3S,6R)-3.The antipode (3R,6S)-3 was prepared by enantioselective acylation of 4 using the same enzyme.

A Rule To Predict Which Enantiomer of a Secondary Alcohol Reacts Faster in Reactions Catalyzed by Cholesterol Esterase, Lipase from Pseudomonas cepacia, and Lipase from Candida rugosa

The enantioselectivity of the title enzymes for more than 130 esters of secondary alcohols is correlated by a rule based on the sizes of the substituents at the stereocenter.This rule predicts which enantiomer of a racemic secondary alcohol reacts faster for 14 of 15 substrates of cholesterol esterase (CE), 63 of 64 substrates of lipase from Pseudomonas cepacia (PCL), and 51 of 55 cyclic substrates of lipase from Candida rugosa (CRL).The enantioselectivity of CRL for acyclic secondary alcohols is not reliably predicted by this rule.This rule implies that the most efficiently resolved substrates are those having substituents which differ significantly in size.This hypothesis was used to design syntheses of two chiral synthons: esters of (R)-lactic acid and (S)-(-)-4-acetoxy-2-cyclohexen-1-one, 70.As predicted, the acetate group of the methyl ester of lactyl acetate was hydrolyzed by PCL with low enantioselectivity because the two substituents, CH3 and C(O)OCH3, are similar in size.To improve enantioselectivity, the methyl ester was replaced by a t-butyl ester.The acetate group of the tert-butyl ester of lactyl acetate was hydrolyzed with high enantioselecticity (E > 50).Enantiomerically pure (R)-(+)-tert-butyl lactate (>98percent ee, 6.4 g) was prepared by kinetic resolution.For the second example, low enantioselectivity (E 65) using either CE or CRL.Enantiomerically pure 70 (98percent ee) was obtained after removal of the bromines with zinc and oxidation with CrO3/pyridine.

PALLADIUM-CATALYZED 1,4-ACETOXY-TRIFLUOROACETOXYLATION OF 1,3-DIENES

Palladium-catalyzed oxidation of conjugated dienes in acetic acid containing CF3COOH/LiOOCCF3 results in the formation of 1-acetoxy-4-trifluoroacetoxy-2-alkenes.

SYN-1,4-ADDITION OF CARBOXYLATE SALTS TO CYCLIC ALLYLIC EPOXIDES MEDIATED BY CUPROUS CHLORIDE

A mild method for the 1,4-syn opening of certain cyclic allylic epoxides has been found, using sodium carboxylates in the presence of cuprous chloride.