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
• Article Data: 20

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

• 74502-18-4 cyclohexa-1,3-dienyl acetate 
• 30182-12-8 4-hydroxy-2-cyclohexenone 
• 78776-45-1 cis-2-cyclohexenyl-1,4-diacetate 
• 77300-23-3 cyclohex-(±)-(1R*,4S*)-2-ene-1,4-diyl dibenzoate 
• 844638-47-7 7-(N-phenylaminooxy)-1,4-dioxa-spiro[4.5]decan-8-one 
• 626-02-8 3-Iodophenol 
• 1176877-26-1 (4R,5S)-4,5-dihydroxycyclohex-2-enone 
• 85808-18-0 βγ-epoxycyclohexanone 
• 132658-85-6 Acetic acid (7S,8R)-7-((R)-toluene-4-sulfinyl)-1,4-dioxa-spiro[4.5]dec-8-yl ester 
• 132658-83-4 (S)-7-((R)-Toluene-4-sulfinyl)-1,4-dioxa-spiro[4.5]decan-8-one 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 183252-96-2 (4aR,5aS,9aS,10aR)-5a,9a-Dimethoxy-4a,5a,6,7,8,9,9a,10a-octahydro-1H-dibenzo[1,4]dioxin-2-one 
• 331268-67-8 4,4-[(1R,2R)-(1,2-diphenylethylene)dioxy]-2-cyclohexenone 
• 331268-79-2 (1R,3R)-4,4-ethylenedioxy-3-phenylthiocyclohexanol 

Downstream Products

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

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.).

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.