1253739-36-4

Basic information

• Product Name: (R)-3-phenyl-2-cyclohexen-1-yl acetate
• Synonyms: (R)-3-phenyl-2-cyclohexen-1-yl acetate
• CAS NO: 1253739-36-4
• Molecular Weight: 216.28
• Mol File: 1253739-36-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (R)-3-phenyl-2-cyclohexen-1-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-phenyl-2-cyclohexen-1-yl acetate(1253739-36-4)
• EPA Substance Registry System: (R)-3-phenyl-2-cyclohexen-1-yl acetate(1253739-36-4)

Safety Data

• Hazardous Substances Data: 1253739-36-4(Hazardous Substances Data)

Upstream product

• 100-59-4 phenylmagnesium chloride 
• 108-05-4 vinyl acetate 
• 60174-90-5 1-phenyl-2-cyclohex-2-en-1-ol 
• 108-86-1 bromobenzene 
• 876-27-7 4-chlorophenyl acetate 
• 17488-64-1 3-phenyl-cyclohex-2-enol 
• 108-22-5 Isopropenyl acetate 

Relevant articles and documents

Preparation of optically active cycloalkenes bearing all-carbon quaternary stereogenic centres: Via lipase-oxovanadium combo-catalysed dynamic kinetic resolution

In this study, a novel asymmetric synthesis of all-carbon quaternary stereogenic centres is developed by the connection of three prochiral or achiral components - conjugated enones, organometallic compounds and vinyl esters - at the C-1 position of the enones. This method involves three sequential steps: 1,2-nucleophilic addition of an organometallic compound to the enone, lipase-catalysed dynamic kinetic resolution (DKR) of the tert-allylic alcohol and the Ireland-Claisen rearrangement of the optically active allyl ester thus generated. This method features the effective use of acyl moieties installed by DKR for achieving high atom economy. The application of this method to the protective-group-free asymmetric total synthesis of (-)-crinane, a core structure of a class of natural alkaloids, has demonstrated that it can alter a known synthetic pathway of a racemate into an asymmetric synthesis of an optically pure molecule while reducing the total transformation steps and increasing the overall yield. With these advantages, this method is practical and attractive as a new environmentally benign protocol.

Enzyme- and ruthenium-catalyzed dynamic kinetic resolution of functionalized cyclic allylic alcohols

Enantioselective synthesis of functionalized cyclic allylic alcohols via dynamic kinetic resolution has been developed. Cyclopentadienylruthenium catalysts were used for the racemization, and lipase PS-IM or CALB was employed for the resolution. By optimization of the reaction conditions the formation of the enone byproduct was minimized, making it possible to prepare a range of optically active functionalized allylic alcohols in good yields and high ee's.

One-pot synthesis of optically active allyl esters via lipase-vanadium combo catalysis

The combination of vanadium-oxo compounds (3 or 4) with a lipase produced the regio- and enantioconvergent transformation of racemic allyl alcohols (1 or 2) into optically active allyl esters. In this system, the vanadium compounds catalyzed the continuous racemization of the alcohols along with the transposition of the hydroxyl group, while the lipase effected the chemo- and enantioselective esterification to achieve the dynamic kinetic resolution.