64839-19-6

Basic information

• Product Name: 4(S)-2,6,6-trimethyl-4-acetoxy-cyclohex-2-en-1-one
• Synonyms: 4(S)-2,6,6-trimethyl-4-acetoxy-cyclohex-2-en-1-one
• CAS NO: 64839-19-6
• Molecular Weight: 196.246
• Mol File: 64839-19-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4(S)-2,6,6-trimethyl-4-acetoxy-cyclohex-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4(S)-2,6,6-trimethyl-4-acetoxy-cyclohex-2-en-1-one(64839-19-6)
• EPA Substance Registry System: 4(S)-2,6,6-trimethyl-4-acetoxy-cyclohex-2-en-1-one(64839-19-6)

Safety Data

• Hazardous Substances Data: 64839-19-6(Hazardous Substances Data)

Upstream product

• 141037-63-0 (+/-)-trans-2,6,6-trimethyl-2-cyclohexen-1,4-diol 
• 1125-21-9 2,6,6-trimethyl-2-cyclohexene-1,4-dione 
• 20548-02-1 (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one 
• 64839-18-5 (1R,5R)-3,3,5-trimethyl-4-oxocyclohexyl acetate 
• 124743-97-1 4-acetoxy-2,6,6-trimethylcyclohexa-2,4-dienone 
• 199921-92-1 (2R,4S)-4-acetoxy-2-bromo-2,6,6-trimethylcyclohexanone 
• 169219-60-7 Acetic acid (1S,4R)-4-hydroxy-3,5,5-trimethyl-cyclohex-2-enyl ester 
• 20107-09-9 (2S,4S)-4-acetoxy-2-bromo-2,6,6-trimethylcyclohexanone 

Downstream Products

• 64809-51-4 4(S)-2,6,6-trimethyl-4-[(trimethylsilyl)oxy]-cyclohex-2-en-1-one 
• 64809-50-3 (4S)-4-hydroxy-2,6,6-trimethyl-cyclohex-2-en-one 

Relevant articles and documents

New amidophosphine-phosphinites (tLANOPs) as chiral ligands for asymmetric hydrogenation reactions

The new amidophosphine-phosphinite (AMPP) ligands 4a-g (called tLANOP ligands) derived from the chiral hydroxy amide (R)- or (S)-2-hydroxy-3,3,N- trimethylbutyramide have been prepared in 48-83% yield. The crystal structures of the square planar complexes

Lipase-catalyzed asymmetric synthesis of (R)- and (S)-4-tert-butyldimethylsilyloxy-2,6,6-trimethyl-2-cyclohexenone and their dihydro derivatives

Racemic 4-hydroxy-2,6,6-trimethyl-2-cyclohexenone, trans- and cis-2,6,6-trimethyl-2-cyclohexene-1,4-diols were prepared by reduction of 4-oxoisophorone with sodium borohydride-cerium chloride. Lipase (PS-30)-catalyzed kinetic resolution of (±)-cis-2,6,6-trimethyl-2-cyclohexene-1,4-diol with vinyl acetate led to (1R, 4S)-4-acetoxy-2,6,6-trimethyl-2-cyclohexen-1-ol (81%ee) and (1S,4R)-1-acetoxy-2,6,6-trimethyl-2-cyclohexene-4-ol (92%ee). Hydrolysis of the former monoacetate and recrystallization of the resulting material afforded enantiomerically pure (1R, 4S)-2,6,6-trimethyl-2-cyclohexene-1,4-diol. On the other hand, recrystallization of (1S,4R) monoacetate itself provided an optically pure sample, which was then hydrolyzed to give (1S, 4R)-2,6,6-trimethylcyclohexene-1,4-diol. Transformation of both diols into (S)- and (R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethyl-2-cyclohexenone was conducted in two steps including silylation and oxidation. Catalytic hydrogenation of these (S)- and (R)-silyloxy enones over Raney nickel afforded the corresponding dihydro derivatives.

Synthesis of optically active natural carotenoids and structurally related compounds. II. Synthesis of (3S,3'S)-astaxanthin

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