1-benzyl-1H-pyrrole-3,4-dicarbonitrile | 927203-48-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-benzyl-1H-pyrrole-3,4-dicarbonitrile
• 英文别名: N-benzyl-3,4-dicyanopyrrole；1-Benzylpyrrole-3,4-dicarbonitrile
• CAS: 927203-48-3
• 化学式: C₁₃H₉N₃
• 分子量: 207.235
• InChiKey: BOOVABKSJGZUBU-UHFFFAOYSA-N

物化性质

• 沸点：
  419.3±35.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52.51
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-benzyl-1H-pyrrole-3,4-dicarbonitrile 在 二异丁基氢化铝 、 二乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成
  参考文献：
  名称：

  Transnitrosation of Thiols from Aliphatic N-Nitrosamines:  S-Nitrosation and Indirect Generation of Nitric Oxide

  摘要：

  S-Nitrosothiols and heme nitrosyl species are nitric oxide (NO)-derived metabolites that provide an endogenous reservoir of NO and also play roles in protein S-nitrosation, that is, transnitrosation of thiols (or thiolates) in proteins, thereby regulating protein functions and signal transduction pathways. Intriguingly, endogenous N-nitrosamines are present in similar abundance to S-nitrosothiols, and though they are thought to play similar physiological roles to S-nitrosothiols, their transnitrosation reactivities and their contribution to biological events are little understood. Herein we report aliphatic N-nitroso derivatives of 7-azabicyclo[2.2.1]heptanes, which do not act as NO donors themselves, but can transnitrosate thiols. On the basis of the calculated activation energies of transnitrosation and the aorta smooth-muscle relaxation activities of these N-nitrosamines, we present a possible scenario of Stransnitrosation from aliphatic N-nitrosamines, leading to indirect generation of NO.

  DOI：

  10.1021/ja0658259
• 作为产物：
  描述：

  对甲基苯磺酰甲基异腈 、 溴甲苯 、 反丁烯二腈 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 四氢呋喃 为溶剂， 反应 12.0h， 以79%的产率得到1-benzyl-1H-pyrrole-3,4-dicarbonitrile
  参考文献：
  名称：

  Transnitrosation of Thiols from Aliphatic N-Nitrosamines:  S-Nitrosation and Indirect Generation of Nitric Oxide

  摘要：

  S-Nitrosothiols and heme nitrosyl species are nitric oxide (NO)-derived metabolites that provide an endogenous reservoir of NO and also play roles in protein S-nitrosation, that is, transnitrosation of thiols (or thiolates) in proteins, thereby regulating protein functions and signal transduction pathways. Intriguingly, endogenous N-nitrosamines are present in similar abundance to S-nitrosothiols, and though they are thought to play similar physiological roles to S-nitrosothiols, their transnitrosation reactivities and their contribution to biological events are little understood. Herein we report aliphatic N-nitroso derivatives of 7-azabicyclo[2.2.1]heptanes, which do not act as NO donors themselves, but can transnitrosate thiols. On the basis of the calculated activation energies of transnitrosation and the aorta smooth-muscle relaxation activities of these N-nitrosamines, we present a possible scenario of Stransnitrosation from aliphatic N-nitrosamines, leading to indirect generation of NO.

  DOI：

  10.1021/ja0658259