697287-01-7

Basic information

• Product Name: (E)-N-benzyl-N-(3-phenyl-2-propenyl)glycine methyl ester
• Synonyms: (E)-N-benzyl-N-(3-phenyl-2-propenyl)glycine methyl ester
• CAS NO: 697287-01-7
• Molecular Weight: 295.381
• Mol File: 697287-01-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E)-N-benzyl-N-(3-phenyl-2-propenyl)glycine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-N-benzyl-N-(3-phenyl-2-propenyl)glycine methyl ester(697287-01-7)
• EPA Substance Registry System: (E)-N-benzyl-N-(3-phenyl-2-propenyl)glycine methyl ester(697287-01-7)

Safety Data

• Hazardous Substances Data: 697287-01-7(Hazardous Substances Data)

Upstream product

• 697286-98-9 (E)-N-benzyl-2,4-dinitro-N-(3-phenyl-2-propenyl)benzenesulfonamide 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 57620-22-1 N-benzyl-2,4-dinitro-benzenesulfonamide 
• 40032-55-1 N-cinnamylbenzylamine 
• 96-32-2 bromoacetic acid methyl ester 

Downstream Products

• 552321-84-3 1-[((E)-N-benzyl-N-(3-phenyl-2-propenyl)amino)acetyl]pyrrolidine 

Relevant articles and documents

Lewis Acid Mediated [2,3]-Sigmatropic Rearrangement of Allylic α-Amino Amides

Boron trifluoride and BBr3 mediated [2,3]-sigmatropic rearrangements of allylic α-amino amides have been developed affording secondary amines in good yields. (E)-Crotyl and (E)-cinnamyl α-amino amides 2b and 2c exhibit excellent syn-diastereoselectivity upon rearrangement with either Lewis acid. The allylic amine 2a forms upon treatment with BF 3 or BBr3 a five-membered heterocylic complex in which a single halide anion has been displaced by the carbonyl oxygen atom. The structures of the Lewis acid-amine complexes were elucidated using NMR spectroscopy. A plausible reaction mechanism, based on DFT calculations, is presented. Thus, BF3- or BBr3-complexed allylic amines 2 are shown to preferentially proceed, after deprotonation, via an endo transition state.