636580-94-4

Basic information

• Product Name: (S,E)-N⁽³⁾-(3'-phenyl-prop-1'-enyl)-4-phenyl-5,5-dimethyloxazolidin-2-one
• Synonyms: (S,E)-N⁽³⁾-(3'-phenyl-prop-1'-enyl)-4-phenyl-5,5-dimethyloxazolidin-2-one
• CAS NO: 636580-94-4
• Molecular Weight: 307.392
• Mol File: 636580-94-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (S,E)-N⁽³⁾-(3'-phenyl-prop-1'-enyl)-4-phenyl-5,5-dimethyloxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S,E)-N⁽³⁾-(3'-phenyl-prop-1'-enyl)-4-phenyl-5,5-dimethyloxazolidin-2-one(636580-94-4)
• EPA Substance Registry System: (S,E)-N⁽³⁾-(3'-phenyl-prop-1'-enyl)-4-phenyl-5,5-dimethyloxazolidin-2-one(636580-94-4)

Safety Data

• Hazardous Substances Data: 636580-94-4(Hazardous Substances Data)

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 168297-84-5 (4S)-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one 

Downstream Products

• 636580-97-7 (4S,1'R,2'S)-N⁽³⁾-(1'-m-chlorobenzoyl-2'-hydroxy-3'-phenyl-prop-1'-yl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 636580-93-3 (4S,1'R,2'S)-N⁽³⁾-[1'-(m-chlorobenzoyl)-2'-hydroxy-2'-phenyl-ethan-1'-yl]-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 636580-99-9 (4S,1'R,2'S)-N⁽³⁾-(1'-m-chlorobenzoyl-2'-hydroxy-3',3'-dimethyl-but-1'-yl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 636580-98-8 (4S,1'R,2'S)-N-⁽³⁾-(1'-m-chlorobenzoyl-2'-hydroxy-3'-methyl-but-1'-yl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 636580-92-2 (4S,2'R,3'S)-N⁽³⁾-(3'-phenyloxiran-2'-yl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 636580-91-1 (4S,1'E)-3-(2'-phenylethenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one 
• 636580-96-6 (S,E)-N⁽³⁾-(3',3'-dimethyl-but-1'-enyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 636580-95-5 (S,E)-N⁽³⁾-(3'-methyl-but-1'-enyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 168297-84-5 (4S)-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one 
• 17131-14-5 (S)-(-)-3-phenyl-1,2-propanediol 

Relevant articles and documents

Oxidative functionalisation of superquat enamides: Asymmetric synthesis of homochiral 1,2 diols

Homochiral (E)-enamides derived from (S)-4-phenyl-5,5-dimethyl-oxazolidin-2-one undergo highly diastereoselective epoxidation upon treatment with dimethyldioxirane (DMDO). Treatment with m-chloroperbenzoic acid (MCPBA) produces syn-(4S, 1′R,2′)-1′ -acyloxy-2′-hydroxy derivatives with high diastereoselectivity, consistent with a mechanism involving initial epoxidation and subsequent in situ SN1 type epoxide opening and trapping with m-chlorobenzoic acid. Reductive cleavage of the isolated 1′-acyloxy-2′-hydroxy derivatives generates 1,2-diols in high yields and in high ee.