1-benzylpyrrolidine-2,5-dicarbonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzylpyrrolidine-2,5-dicarbonitrile
• 化学式: C₁₃H₁₃N₃
• 分子量: 211.266
• InChiKey: ATVRTPLXCZGBEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzylpyrrolidine-2,5-dicarbonitrile 在 rat liver microsomes 作用下， 反应 2.0h， 以7%的产率得到1-benzyl-5-cyano-2-pyrrolidinone
  参考文献：
  名称：

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

  摘要：

  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 O-18(2) and (OH2)-O-18 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 gamma-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. (c) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.11.006

文献信息

• Microbial decyanation of 1-benzylpyrrolidine-2,5-dicarbonitrile. Mechanistic investigations
  作者：Lucimar Pinheiro、Didier Buisson、Sylvie Cortial、Marcel Delaforge、Jamal Ouazzani

  DOI：10.1016/j.molcatb.2010.11.006

  日期：2011.2

  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 O-18(2) and (OH2)-O-18 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 gamma-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. (c) 2010 Elsevier B.V. All rights reserved.