76686-09-4

Basic information

• Product Name: 2-Cyclohexen-1-one, 4-hydroxy-2,6,6-trimethyl-, (R)-
• CAS NO: 76686-09-4
• Molecular Formula: C9H14O2
• Molecular Weight: 154.209
• Mol File: 76686-09-4.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 2-Cyclohexen-1-one, 4-hydroxy-2,6,6-trimethyl-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclohexen-1-one, 4-hydroxy-2,6,6-trimethyl-, (R)-(76686-09-4)
• EPA Substance Registry System: 2-Cyclohexen-1-one, 4-hydroxy-2,6,6-trimethyl-, (R)-(76686-09-4)

Safety Data

• Hazardous Substances Data: 76686-09-4(Hazardous Substances Data)

Upstream product

• 123196-48-5 (S)-2,2-Dimethyl-4-(tetrahydro-pyran-2-yloxy)-cyclohexanone 
• 123196-48-5 (+/-)-2,2-Dimethyl-4-tetrahydropyranyloxy-1-cyclohexanone 
• 131319-94-3 (-)-(S)-4-Hydroxy-2,2-dimethyl-1-cyclohexanone 
• 123214-39-1 (+/-)-4-Hydroxy-2,2-dimethyl-1-cyclohexanone 
• 76451-81-5 (+/-)-2,2-Dimethyl-4,4-ethylenedioxy-1-cyclohexanol 
• 131206-75-2 3,3-Dimethyl-4,4-ethylenedioxy-1-cyclohexanone 
• 1193-47-1 2,2-dimethyl-cyclohexanone 
• 76686-18-5 Methanesulfonic acid (S)-3,5,5-trimethyl-4-oxo-cyclohex-2-enyl ester 
• 64809-50-3 (4S)-4-hydroxy-2,6,6-trimethyl-cyclohex-2-en-one 
• 254963-54-7 (+/-)-4-oxo-3,5,5-trimethyl-2-cyclohexenyl chloroacetate 
• 19620-37-2 (+/-)-4-hydroxy-2,6,6-trimethyl-2-cyclohexenone 
• 1125-21-9 2,6,6-trimethyl-2-cyclohexene-1,4-dione 
• 254963-55-8 (R)-4-oxo-3,5,5-trimethyl-2-cyclohexenyl chloroacetate 
• 76739-79-2 Acetic acid (R)-3,5,5-trimethyl-4-oxo-cyclohex-2-enyl ester 

Downstream Products

• 80736-98-7 (2R,3S,4R)-2,3-Dibrom-4-hydroxy-2,6,6-trimethylcyclohexanon 
• 76686-12-9 (1R,4R)-4-(1-Methoxy-1-methyl-ethoxy)-2,6,6-trimethyl-cyclohex-2-enecarbaldehyde 
• 80713-71-9 (R)-3-Brom-4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-on 

Relevant articles and documents

β-hydroxysulfoxides as chiral cyclic ketone equivalents: Enantioselective synthesis of polysubstituted cyclohexanones, cyclohexenones and cyclohexenediones

The β-hydroxysulfoxide moiety, after oxidation to sulfone, acts as a masked carbonyl group in a cyclic system, opening an easy access to differently substituted enantiomerically pure cyclic ketones by means of aluminium-mediated conjugate additions, stereoselective reductions and elimination by retrocondensation in basic medium.

Hydrolase-catalyzed preparation of (R)- and (S)-4-hydroxy-2,6,6- trimethyl-2-cyclohexen-1-ones (phorenols), the key synthetic intermediates for abscisic acid

Preparation of both the enantiomers of 4-hydroxy-2,6,6-trimethyl-2- cyclohexen-1-one (phorenol), which are versatile synthetic intermediates for abscisic acid and carotenoids, was achieved by hydrolase-catalyzed hydrolysis of the corresponding chloroaceta

Enzymatic Preparation of Chiral 4-Hydroxy-2,2-dimethyl-1-cyclohexanone as a Chiral Building Block

(S)-4-Hydroxy-2,2-dimethyl-1-cyclohexanone (1a) was prepared by two enzymatic methods. 1,4-Cyclohexanediol was converted to monoacetal (11) via (+/-)-1a.Enzymatic reduction of 11 by baker's yeast gave (S)-1 of almost 100 percent e.e.Direct hydroxylation of 2,2-dimethyl-1-cyclohexanone (14) by P-450 camphor monooxygenase of the cloned genes of Pseudomonas putida PpG1 gave (S)-1a of almost 100 percent e.e., too.According to Mitsunobu's method, SN-2 inversion of (S)-1 gave (R)-1.