82202-14-0

Basic information

• Product Name: 5,5-dimethyl-3-(phenyldimethylsilyl)-cyclohex-2-enone
• Synonyms: 5,5-dimethyl-3-(phenyldimethylsilyl)-cyclohex-2-enone
• CAS NO: 82202-14-0
• Molecular Weight: 258.436
• Mol File: 82202-14-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5,5-dimethyl-3-(phenyldimethylsilyl)-cyclohex-2-enone(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-dimethyl-3-(phenyldimethylsilyl)-cyclohex-2-enone(82202-14-0)
• EPA Substance Registry System: 5,5-dimethyl-3-(phenyldimethylsilyl)-cyclohex-2-enone(82202-14-0)

Safety Data

• Hazardous Substances Data: 82202-14-0(Hazardous Substances Data)

Upstream product

• 17530-69-7 3-chloro-5,5-dimethylcyclohex-2-en-1-one 
• 3839-31-4 dimethyl(phenyl)silyl lithium 
• 31039-88-0 3-(dimethylamino)-5,5-dimethyl-2-cyclohexen-1-one 
• 3839-31-4 dimethyl(phenyl)silyllithium 

Relevant articles and documents

Reactions of phenyldimethylsilyllithium with β-N,N- dimethylaminoenones: A convenient synthesis of β-dimethyl(phenyl) silylacrylic acid and its derivatives

Phenyldimethylsilyllithium reacted with 5,5-dimethyl-3-(N,N,-dimethylamino) cyclohex-2-enone (7), 3-(E)-N,N-dimethylaminopropenal (11), and 4-N,N-dimethylaminobut-3-en-2-one (13) to give the corresponding β-silyl-α,β-unsaturated carbonyl compounds 8, 12, and 14, in which the dimethylamino group has been displaced by the phenyldimethylsilyl group. Phenyldimethylsilyllithium reacted with ethyl β-N,N- dimethylaminopropenoate (15) by conjugate addition, but, in contrast to the ketones 7 and 13 and the aldehyde 11, the intermediate enolate 16 was C-protonated in the aqueous work-up to give ethyl 3-N,N-dimethylamino-3- dimethyl(phenyl)silylpropanoate (17). When the enolate 16 was instead given a mysteriously brief treatment with methyl iodide before work-up, the product was ethyl 3-(E)-dimethy(phenyl)silylpropenoate (18). Phenyllithium and methyllithium also added conjugatively to ethyl β-N,N-dimethylaminoacrylate (15) but, in contrast to the silyl case, the intermediate enolate 22 reacted unexceptionally with methyl iodide to give the products 25 and 26 of stereoselective C-methylation. This synthesis of the ester 18 was used to synthesize the Oppolzer sultam derivative 30.

THE SYNTHESIS OF αβ-UNSATURATED KETONES FROM β-SILYLENONES AND β-SILYLYNONES

Conjugate addition, followed by alkylation, bromination and desilyl-bromination make the β-silylketone (4) an a3d2-synthon (5) and the β-silylynone (6) a 2a3d2-synthon (7).