51685-38-2

Basic information

• Product Name: 2-Pyrrolidinecarbonitrile, 5-oxo-1-(phenylmethyl)-
• CAS NO: 51685-38-2
• Molecular Formula: C12H12N2O
• Molecular Weight: 200.24
• Mol File: 51685-38-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-Pyrrolidinecarbonitrile, 5-oxo-1-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyrrolidinecarbonitrile, 5-oxo-1-(phenylmethyl)-(51685-38-2)
• EPA Substance Registry System: 2-Pyrrolidinecarbonitrile, 5-oxo-1-(phenylmethyl)-(51685-38-2)

Safety Data

• Hazardous Substances Data: 51685-38-2(Hazardous Substances Data)

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 133535-61-2 1-(phenylmethyl)-5-(phenylsulphonyl)-2-pyrrolidinone 
• 100-39-0 benzyl bromide 
• 29897-82-3 N-benzylpyrrolidine 
• 143-33-9 sodium cyanide 
• 151-50-8 potassium cyanide 
• 344872-39-5 1-Benzyl-5-(2,2,2-trifluoro-1-trifluoromethyl-ethoxy)-pyrrolidin-2-one 
• 88461-15-8 1-benzyl-5-oxopyrrolidin-2-yl acetate 
• 41194-02-9 1-benzyl-5-hydroxypyrrolidin-2-one 
• 2142-06-5 1-(phenylmethyl)-2,5-pyrrolidinedione 
• 82259-07-2 5-ethoxy-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.

Carbon-carbon bond forming reactions of ω-oxylactams in acid and neutral medium

1,3-Dicarbonyl compounds and hydroxybenzenes condense under the influence of acid with ω-hydroxylactams 1-7 in an intermolecular process, thereby affording ω-alkylated lactams 8-13.The reactive intermediate in the carbon-carbon bond forming step is a cyclic N-acyliminium ion.The intramolecular variant affords keto ester 19.Upon activation of the ω-hydroxylactam as a hexafluoroisopropoxy ester, condensations with cyanide in aprotic polar solvents under neutral conditions become possible.