107536-93-6

Basic information

• Product Name: (+/-)-4-acetoxy-2,6,6-trimethyl-2-cyclohexenone
• Synonyms: (+/-)-4-acetoxy-2,6,6-trimethyl-2-cyclohexenone
• CAS NO: 107536-93-6
• Molecular Weight: 196.246
• Mol File: 107536-93-6.mol

Chemical Properties

• CAS DataBase Reference: (+/-)-4-acetoxy-2,6,6-trimethyl-2-cyclohexenone(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-4-acetoxy-2,6,6-trimethyl-2-cyclohexenone(107536-93-6)
• EPA Substance Registry System: (+/-)-4-acetoxy-2,6,6-trimethyl-2-cyclohexenone(107536-93-6)

Safety Data

• Hazardous Substances Data: 107536-93-6(Hazardous Substances Data)

Upstream product

• 1125-21-9 2,6,6-trimethyl-2-cyclohexene-1,4-dione 
• 20548-02-1 trans (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone 
• 124743-97-1 4-acetoxy-2,6,6-trimethylcyclohexa-2,4-dienone 
• 91413-25-1 (1-Isopropylidene-2-methyl-pent-4-enyloxy)-methyl-diphenyl-silane 
• 19620-37-2 (+/-)-4-hydroxy-2,6,6-trimethyl-2-cyclohexenone 
• 108-24-7 acetic anhydride 
• 3375-31-3 palladium diacetate 

Downstream Products

• 13487-30-4 2,6,6-trimethylcyclohexa-2,4-dienone 

Relevant articles and documents

A New Access to 2,6,6-Trimethylcyclohexa-2,4-dienone from 4-Oxoisophorone

2,6,6-Trimethylcyclohexa-2,4-dienone (1), a versatile starting material for the preparation of some carotenoids and several natural products, was efficiently (73 percent yield) prepared from oxoisophorone 3.After conversion of 3 to the alcohol 4 or the acetate 5, H2O was eliminated (4 -> 1) under acidic distillative conditions, whereas AcOH could be eliminated (5 -> 1) under Pd(O) catalysis.

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.

THE PALLADIUM (II) ACETATE PROMOTED 6-ENDO-TRIG CYCLIZATION OF 1,1-DIALKYL-2-SILYLOXY-1,5-DIENES.

A route to cyclohexenones via the treatment of selected γ,δ-unsaturated enol silyl ethers with palladium (II) acetate is presented.