82259-07-2

Basic information

• Product Name: (+-)-5-Ethoxy-1-(phenylmethyl)-2-pyrrolidinone
• Synonyms: 1-benzyl-5-ethoxy-pyrrolidin-2-one;2-Pyrrolidinone, 5-ethoxy-1-(phenylmethyl)-, (+-)-
• CAS NO: 82259-07-2
• Molecular Formula: C₁₃H₁₇NO₂
• Molecular Weight: 219.283
• Mol File: 82259-07-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 377.2°Cat760mmHg
• Flash Point: 181.9°C
• Density: 1.11g/cm³
• CAS DataBase Reference: (+-)-5-Ethoxy-1-(phenylmethyl)-2-pyrrolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (+-)-5-Ethoxy-1-(phenylmethyl)-2-pyrrolidinone(82259-07-2)
• EPA Substance Registry System: (+-)-5-Ethoxy-1-(phenylmethyl)-2-pyrrolidinone(82259-07-2)

Safety Data

• Hazardous Substances Data: 82259-07-2(Hazardous Substances Data)

Upstream product

• 96-48-0 4-butanolide 
• 64-17-5 ethanol 
• 100-46-9 benzylamine 
• 39662-63-0 5-ethoxy-pyrrolidin-2-one 
• 100-39-0 benzyl bromide 
• 2142-06-5 1-(phenylmethyl)-2,5-pyrrolidinedione 

Downstream Products

• 88996-03-6 1-benzyl-5-ethoxy-3-(3-hexenyl)-2-pyrrolidinone 
• 88996-04-7 1-Benzyl-5-ethoxy-3-(5-trimethylsilanyl-pent-3-ynyl)-pyrrolidin-2-one 
• 121823-51-6 1-benzyl-5-ethoxy-3-<4-(trimethylsilyl)-2-butynyl>-2-pyrrolidinone 
• 133535-61-2 1-(phenylmethyl)-5-(phenylsulphonyl)-2-pyrrolidinone 
• 82259-11-8 1-(phenylmethyl)-5-prop-2-enyl-2-pyrrolidinone 
• 133535-70-3 1-(phenylmethyl)-5-<2-(ethyl)-1,3-dioxane>-2-pyrrolidinone 
• 133535-69-0 5-cyclohexyl-1-(phenylmethyl)-2-pyrrolidinone 
• 134415-17-1 5-phenyl-1-(phenylmethyl)-2-pyrrolidinone 
• 127419-78-7 1,5-bis(phenylmethyl)-2-pyrrolidinone 
• 133535-68-9 1-(phenylmethyl)-5-pent-4-enyl-2-pyrrolidinone 
• 51685-38-2 5-cyano-1-(phenylmethyl)-2-pyrrolidinone 
• 133535-66-7 5-ethyl-1-(phenylmethyl)-2-pyrrolidinone 
• 91640-09-4 5-methyl-1-(phenylmethyl)-2-pyrrolidinone 

Relevant articles and documents

Microbial decyanation of 1-benzylpyrrolidine-2,5-dicarbonitrile. Mechanistic investigations

Various bacterial and fungal strains were screened for their ability to catalyse the regioselective hydrolysis of 1-benzylpyrrolidine-2,5-dicarbonitrile (1). Among the examined strains, Rhodococcus opacus sp-lma whole cells transformed both isomers of 1 into 1-benzyl-5-cyano-2-pyrrolidinone (2) and N-benzylacetamide (3). These reactions are difficult to achieve chemically and the synthesis of compound 2 did not compete with microbiological catalysis in terms of efficiency and respect for the guidelines of green chemistry. To distinguish between an oxidative or hydrolytic based-mechanism, the origin of the oxygen atom in 2 was investigated by using 18O2 and 18OH2 coupled with GC-MS analysis. These experiments confirmed that the oxygen atom in 2 came from water and not from molecular oxygen. The reaction is probably initiated by the dehydrogenation of 1 to generate the iminium ion, which could be trapped by a water molecule to form the cyanohydrin. The cyanohydrin intermediate would spontaneously break down to the γ-lactam product 2. Conversion of 1 to 2 by induced rat liver microsomes suggests the involvement of a Cyt P-450-type enzyme. A mechanism that accounts for the formation of 3 is also proposed.

Acyliminium Ion Cyclisations to Pyrrolo- and Pyrido-phenanthridine and Benzopyrroloisoquinoline Ring Systems

Pyrrolo- and pyrido-phenanthridines and benzopyrroloisoquinolines are obtained by acid-catalysed cyclodehydration of appropriate hydroxy lactams and keto amides derived from N-substituted succinimide and glutarimide derivatives.

Amnesia-reversal activity of a series of 5-alkoxy-1-arylcarbonyl-2-pyrrolidinones and 5-alkoxy-1-arylmethyl-2-pyrrolidinones

A series of 5-alkoxy-1-arylcarbonyl-2-pyrrolidinones (1-27) were prepared by condensation of arylcarbonyl chlorides with 5-alkoxy-2-pyrrolidinones in the presence of butyl lithium in tetrahydrofuran.Alkylation of these intermediates with substituted benzy