121652-00-4

Basic information

• Product Name: 2-Cyclohexen-1-one, 4-hydroxy-, (S)-
• Synonyms: (S)-4-hydroxycyclohex-2-en-1-one;(4S)-4-hydroxy-2-cyclohexen-1-one;(S)-(-)-4-hydroxycyclohex-2-enone;(S)-(-)-4-hydroxycyclohex-2-en-1-one;4(S)-hydroxy-2-cyclohexen-1-one;(4S)-4-hydroxycyclohex-2-enone;4-Hydroxy-cyclohex-2-enone
• CAS NO: 121652-00-4
• Molecular Formula: C6H8O2
• Molecular Weight: 112.128
• Mol File: 121652-00-4.mol

Chemical Properties

• CAS DataBase Reference: 2-Cyclohexen-1-one, 4-hydroxy-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclohexen-1-one, 4-hydroxy-, (S)-(121652-00-4)
• EPA Substance Registry System: 2-Cyclohexen-1-one, 4-hydroxy-, (S)-(121652-00-4)

Safety Data

• Hazardous Substances Data: 121652-00-4(Hazardous Substances Data)

Upstream product

• 74502-18-4 cyclohexa-1,3-dienyl acetate 
• 132658-87-8 (S)-4-benzyloxy-2-cyclohexen-1-one 
• 132513-02-1 (S)-(-)-4-acetoxy-2-cyclohexen-1-one 
• 132746-90-8 (7S,8S)-7-((R)-Toluene-4-sulfinyl)-1,4-dioxa-spiro[4.5]decan-8-ol 
• 121573-17-9 (3aR,7aS)-2,2-dimethyltetrahydrobenzo[d][1,3]dioxol-5(6H)-one 
• 57466-29-2 (1S)-(-)-cis-1-acetoxy-4-hydroxy-2-cyclohexene 
• 134180-35-1 C₂₂H₂₆O₂ 
• 32061-93-1 endo-tricyclo[6.2.1.0^2,7]undec-9-ene-3,6-dione 
• 794526-34-4 (3R,4S)-3-benzylthio-4-hydroxycyclohexan-1-one 
• 443286-53-1 (S)-6-hydroxy-3-methoxycyclohex-2-en-1-one 
• 443286-54-2 (R)-6-acetoxy-3-methoxycyclohex-2-en-1-one 
• 682746-13-0 (R)-7-(N-phenyl-aminooxy)-2,3-dioxa-spiro[4.5]decan-8-one 
• 132513-00-9 (+/-)-1α,4α-diacetoxy-2β,3α-dibromocyclohexane 
• 132658-83-4 (S)-7-((R)-Toluene-4-sulfinyl)-1,4-dioxa-spiro[4.5]decan-8-one 

Downstream Products

• 1421312-82-4 N-((2aR,2a¹R,3R,3aS,6R,6aR)-3-methyl-4-((triisopropylsilyl)oxy)-2a,2a¹,3,3a,6,6a-hexahydro-2H-cyclobuta[cd]benzofuran-6-yl)-2-(phenylselenyl)acrylamide 
• 1421312-71-1 (S,E)-4-(but-2-en-1-yloxy)cyclohex-2-en-1-one 
• 118207-44-6 4(S)-<(4-methoxybenzyl)oxy>-2-cyclohexen-1-one 
• 221649-23-6 (1S,3R,4R)-3-(2-Chloro-5-pyridyl)-4-[(methylsulfonyl)oxy]cyclohexan-1-ol 
• 198407-83-9 (4S)-4-[(tert-Butyldimethylsilyl)oxy]-2-iodocyclohex-2-en-1-one 
• 119478-74-9 (S)-4-((tert-butyldimethylsilyl)oxy)cyclohex-2-enone 
• 132513-03-2 (S)-4-benzoyloxycyclohex-2-enone 

Relevant articles and documents

Improved synthesis of racemic and optically active 4-hydroxycyclohex-2-en-1-one

A simple and inexpensive synthetic route which affords S-(-)-4-hydroxycyclohex-2-en-1-one (1a) with high stereoselectivity and moderate enantioselectivity is reported. A key step in this procedure involves baker's yeast promoted reduction of 1α,4α,4aα,6,7,8aα-hexahydro-1,4-methanonaphthalene-5,8-dione (3), which affords optically active 8-hydroxy-1α,4α,4aα,8β,8aα-tetrahydro-1,4-methanonaphthalen-5(1H) -one (4a, 80% de, 67% ee) in 32% yield. The absolute configuration of the 3,5-dinitrobenzoate ester of 4a (i.e., 5a) was established unequivocally via single crystal X-ray structural analysis.

An efficient protocol for the enantioselective preparation of a key polyfunctionalized cyclohexane. New access to (R)- and (S)-4-hydroxy-2- cyclohexenone and (R)- and (S)-trans-cyclohex-2-ene-1,4-diol

(Chemical Equation Presented) Starting from very accessible raw materials such as p-methoxyphenol, ethylene glycol, and thiophenol, a protocol has been developed to prepare multigram quantities of the polyfunctionalized cyclohexane (±)-7. A highly efficie

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.

A New and Efficient Chemoenzymatic Route to Both Enantiomers of 4-Hydroxycyclohex-2-en-1 -one

(Matrix Presented) A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting 4-hydroxycyclohex-2-en-1-one in three steps starting from 3-methoxycyclohex-2-en-1-one is described. Manganese(III) acetate-mediated acetoxylation follo

New, highly efficient syntheses of rac-, (R)- and (S)-4-hydroxy-2-cyclohexenone

Both enantiomers of 4-hydroxy-2-cyclohexenone have been synthesised from chiral p-benzoquinone equivalents through very short and simple sequences in good overall yields.

The effect of DMSO on the borohydride reduction of a cyclohexanone: A formal enantioselective synthesis of (+)-epibatidine

An asymmetric synthesis of (+)-epibatidine is described which uses the increased stereoselectivity of a borohydride reduction induced by the presence of DMSO.

Mn-salen catalyzed asymmetric oxidation of enol derivatives

Mn-salen complex 1 was found to catalyze highly enantioselective oxidation of enol ethers with iodosylbenzene as a terminal oxidant giving the corresponding hydroxy acetals, when the reaction was carried out in an alcoholic solvent. The reactions in the u

Enantioselective epoxidation of cyclic 1,3-dienes catalyzed by a sterically and electronically optimized (salen)Mn complex

Chiral (salen)Mn(III)Cl complexes catalyze epoxidation of cyclic 1,3-dienes with moderate-to-good enantioselectivity. A new catalyst (2), bearing sterically hindered and electron donating (OSi(iPr)3 (OTIPS) substituents, induces up to 12% higher selectivity than the previously-reported tert-butyl substituted analog 1.