132746-89-5

Basic information

• Product Name: 2-Cyclohexen-1-one, 4-hydroxy-, (R)-
• CAS NO: 132746-89-5
• Molecular Formula: C6H8O2
• Molecular Weight: 112.128
• Mol File: 132746-89-5.mol

Chemical Properties

• CAS DataBase Reference: 2-Cyclohexen-1-one, 4-hydroxy-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclohexen-1-one, 4-hydroxy-, (R)-(132746-89-5)
• EPA Substance Registry System: 2-Cyclohexen-1-one, 4-hydroxy-, (R)-(132746-89-5)

Safety Data

• Hazardous Substances Data: 132746-89-5(Hazardous Substances Data)

Upstream product

• 132658-89-0 (R)-4-acetoxy-2-cyclohexen-1-one 
• 119414-47-0 (+/-)-4-(tert-butyl(dimethyl)silyloxy)-2-cyclohexen-1-one 
• 334700-60-6 (4R,5R)-4,5-[(2S,3S)-2,3-Dimethoxybutane-2,3-diyldioxy]cyclohexan-1-one 
• 85808-18-0 βγ-epoxycyclohexanone 
• 844638-47-7 7-(N-phenylaminooxy)-1,4-dioxa-spiro[4.5]decan-8-one 
• 626-02-8 3-Iodophenol 
• 108-94-1 cyclohexanone 
• 1021418-48-3 8-hydroxy-1,4-dioxa-spiro[4,5]dec-6-ene 
• 13250-27-6 3-bromo-6,6-ethylenedioxycyclohexene 
• 1004-58-6 1,4-dioxa-spiro[4.5]dec-6-ene 
• 1728-15-0 (R,S)-6-bromo-1,4-dioxaspiro<4.5>decane 
• 77300-23-3 cyclohex-(±)-(1R*,4S*)-2-ene-1,4-diyl dibenzoate 
• 1176877-26-1 (4R,5S)-4,5-dihydroxycyclohex-2-enone 
• 132658-85-6 Acetic acid (7S,8R)-7-((R)-toluene-4-sulfinyl)-1,4-dioxa-spiro[4.5]dec-8-yl ester 

Downstream Products

• 142012-03-1 (R)-4-[(4-methoxyphenyl)oxy]cyclohex-2-en-1-one 
• 1303528-24-6 (4E,7S)-N-[(2Z)-((5R)-5-5-tert-butyldimethylsilyoxy-2-oxocyclohex-1-enyl)-2-chloromethyleneethyl]-7-methoxytetradec-4-enamide 
• 1303528-39-3 C₂₄H₃₈ClNO₄ 
• 1303528-22-4 (4E,7S)-N-[(2Z)-((5R)-5-allyloxy-2-oxocyclohex-1-enyl)-2-chloromethyleneethyl]-7-methoxytetradec-4-enamide 
• 1303528-07-5 (4R)-4-allyloxy-2-dihydroxyboryl-2-cyclohexen-1-one 

Relevant articles and documents

A practical synthesis of enantiopure (R)-4-hydroxy-2-cyclohexen-1-one

The title compound R-4a was prepared from (-)-quinic acid (1) in 6 steps in 18% overall yield (Scheme 3) and with 100% enantiomeric purity (Figure 1). The initiating step is the regio- and stereoselective acetalization of the trans-oriented vicinal OH groups of 1 (+ 5 → 8). Alcohol A-4a can be protected as the 2-ethoxyethyl ether A-4e (78%). VCH Verlagsgesellschaft mbH, 1996.

Total Synthesis of the Potent and Broad-Spectrum Antibiotics Amycolamicin and Kibdelomycin

The complex and intriguing structures of the antibiotics amycolamicin and kibdelomycin are herein confirmed through total synthesis. Careful titration of the synthetic products reveals that kibdelomycin is the salt form of amycolamicin. This synthesis emp

Enzyme-Catalysed Synthesis of Cyclohex-2-en-1-one cis-Diols from Substituted Phenols, Anilines and Derived 4-Hydroxycyclohex-2-en-1-ones

Toluene dioxygenase-catalysed cis-dihydroxylations of substituted aniline and phenol substrates, with a Pseudomonas putida UV4 mutant strain and an Escherichia coli pCL-4t recombinant strain, yielded identical arene cis-dihydrodiols, which were isolated as the preferred cyclohex-2-en-1-one cis-diol tautomers. These cis-diol metabolites were predicted by preliminary molecular docking studies, of anilines and phenols, at the active site of toluene dioxygenase. Further biotransformations of cyclohex-2-en-1-one cis-diol and hydroquinone metabolites, using Pseudomonas putida UV4 whole cells, were found to yield 4-hydroxycyclohex-2-en-1-ones as a new type of phenol bioproduct. Multistep pathways, involving ene reductase- and carbonyl reductase-catalysed reactions, were proposed to account for the production of 4-hydroxycyclohex-2-en-1-one metabolites. Evidence for the phenol hydrate tautomers of 4-hydroxycyclohex-2-en-1-one metabolites was shown by formation of the corresponding trimethylsilyl ether derivatives. (Figure presented.).

An Enantioselective Approach to 4-O-Protected-2-cyclopentene-l,4-diol Derivatives via a Rhodium-Catalyzed Redox-Isomerization Reaction

Kinetic resolution of a series of cyclopentene-1,4-diol derivatives has been successfully achieved with enantiomeric excess up to 99.4% and a kf/ks ratio of 55 by a rhodium-catalyzed redox-isomerization reaction in a noncoordinating solvent.

Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis

The palladium-catalyzed oxidative desymmetrization of meso-dibenzoates yields γ-benzoyloxy cycloalkenones in good yields and with excellent levels of enantioselectivity. These compounds serve as precursors to a broad range of substituted cycloalkenones, including well-established synthetic building blocks and elaborated cycloalkanone derivatives. The ability to prepare both enantiomers of the oxidative desymmetrization products enables a unified strategy toward stereochemically diverse epoxyquinoid natural products.

Total synthesis of malyngamides K, L, and 5″-epi-C and absolute configuration of malyngamide L

An accelerated, enantioselective, and general synthetic route to a class of malyngamides, K (1), L (3), and 5″-epi-C (4), bearing a cyclohexenone ring or a heavily oxygenated six-membered ring and a vinyl chloride structural motif was developed. The key s

Dioxygenase-catalysed cis-dihydroxylation of meta-substituted phenols to yield cyclohexenone cis-diol and derived enantiopure cis-triol metabolites

cis-Dihydroxylation of meta-substituted phenol (m-phenol) substrates, to yield the corresponding cyclohexenone cis-diol metabolites, was catalysed by arene dioxygenases present in mutant and recombinant bacterial strains. The presence of cyclohexenone cis-diol metabolites and several of their cyclohexene and cyclohexane cis-triol derivatives was detected by LC-TOFMS analysis and confirmed by NMR spectroscopy. Structural and stereochemical analyses of chiral ketodiol bioproducts, was carried out using NMR and CD spectroscopy and stereochemical correlation methods. The formation of enantiopure cyclohexenone cis-diol metabolites is discussed in the context of postulated binding interactions of the m-phenol substrates at the active site of toluene dioxygenase (TDO). The Royal Society of Chemistry 2011.

New families of enantiopure cyclohexenone cis-diol, o-quinol dimer and hydrate metabolites from dioxygenase-catalysed dihydroxylation of phenols

Toluene dioxygenase-catalysed cis-dihydroxylation of phenols has led to the discovery of new enantiopure cyclohexenone cis-diol, o-quinol dimer and phenol hydrate metabolites having synthetic potential.

Novel preparation of (-)-4-hydroxycyclohex-2-enone: Reaction of 4-hydroxycyclohex-2-enone and 4-hydroxycyclopent-2-enone with some thiols

A new route to (R)-4-hydroxycyclohex-2-enone from cyclohexanedione monoketal (27% yield) commences with reaction of the ketal with nitrosobenzene catalysed by l-proline. 4-Hydroxycyclohex-2-enone and 4-hydroxycyclopent-2-enone react with thiols to afford

Facile biocatalytic syntheses of optically active 4-hydroxycyclohex-2-enone and 4-benzylthiacyclopent-2-enone

Novozyme 435 (Candida antarctica Lipase B) effects the kinetic resolution of both 3-benzylthia-4-hydroxycyclopentanone and its six-membered ring analogue, providing a novel route to both enantiomers of 4-benzylthiacyclopent-2-enone and the two enantiomers of 4-hydroxycyclohex-2- enone, all in a state of very high optical purity.