133535-68-9

Basic information

• Product Name: 1-(phenylmethyl)-5-pent-4-enyl-2-pyrrolidinone
• Synonyms: 1-(phenylmethyl)-5-pent-4-enyl-2-pyrrolidinone
• CAS NO: 133535-68-9
• Molecular Weight: 243.349
• Mol File: 133535-68-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-(phenylmethyl)-5-pent-4-enyl-2-pyrrolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(phenylmethyl)-5-pent-4-enyl-2-pyrrolidinone(133535-68-9)
• EPA Substance Registry System: 1-(phenylmethyl)-5-pent-4-enyl-2-pyrrolidinone(133535-68-9)

Safety Data

• Hazardous Substances Data: 133535-68-9(Hazardous Substances Data)

Upstream product

• 82259-07-2 5-ethoxy-1-(phenylmethyl)-2-pyrrolidinone 
• 41194-02-9 1-benzyl-5-hydroxypyrrolidin-2-one 
• 2142-06-5 1-(phenylmethyl)-2,5-pyrrolidinedione 
• 34164-50-6 4-penten-1-ylmagnesium bromide 
• 133535-61-2 1-(phenylmethyl)-5-(phenylsulphonyl)-2-pyrrolidinone 

Relevant articles and documents

Carbocyclic Amino Ketones by Bredt's Rule-Arrested Kulinkovich-de Meijere Reaction

The TiII-mediated formation of cyclopropylamines from alkenes and amides, the Kulinkovich-de Meijere reaction, involves two carbon-carbon bond-forming steps. Strategic use of a tricyclic intermediate can arrest the process if the second step requires formation of a bridgehead double bond. Use of this Bredt's rule constraint results in the production of carbocyclic amino ketones, key alkaloid building blocks. Frustrated by Bredt's rule: An inability to consummate a Kulinkovich-de Meijere cyclopropanation that would involve a bridgehead double bond transforms the reaction into a transannular cyclization of an unsaturated lactam yielding an amino ketone product with potential for alkaloid synthesis.