3-cyano-1-p-nitrophenyl-2-piperidino-1H-pyrido[3,2-b]indole | 436811-94-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-cyano-1-p-nitrophenyl-2-piperidino-1H-pyrido[3,2-b]indole
• 英文别名: 1-(4-Nitrophenyl)-2-piperidin-1-ylpyrido[3,2-b]indole-3-carbonitrile
• CAS: 436811-94-8
• 化学式: C₂₃H₁₉N₅O₂
• 分子量: 397.436
• InChiKey: UNLKOJDETLBRLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  90.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-cyano-1-p-nitrophenyl-2-piperidino-1H-pyrido[3,2-b]indole 在 potassium carbonate 作用下， 以 苯 为溶剂， 反应 38.0h， 生成 4-acetonyl-3-cyano-5-methyl-1-p-nitrophenyl-2-piperidino-1H-pyrido[3,2-b]indole
  参考文献：
  名称：

  摘要：

  The possibility of transformation of 3-cyano-1-p-nitrophenyl-delta-carbolin-2-one into 2-amino-3-cyano-1-p-nitrophenyl-1H-pyrido[3,2-b]indole derivatives and 2-imino-3-cyanol-p-nitrophenyl-5H-pyrido[3,2-b]indole derivatives (delta-carbolines) is demonstrated. Methylation of 1-p-nitrophenyl-2-piperidino-1H-delta-carboline followed by treatment with acetone in an alkaline medium yields 4-acetonyl-5-methyl-1,4-dihydro-5H-pyrido[3,2-b]indole derivative. The rearrangement of 2-arylimino-3-cyano-1-p-nitrophenyl-5H-pyrido[3,2-b]indoles into 2-(aryl)nitrophenylamino-3-cyano-5H-pyrido[3.2-b]indoles was accomplished on heating above the melting point or on treatment with potassium tert-butoxide. The structures of the resulting compounds were proved by H-1 and C-13 NMR spectroscopy and X-ray diffraction analysis.

  DOI：

  10.1023/a:1012749426699
• 作为产物：
  描述：

  哌啶 、 1-(4-nitrophenyl)-2-oxo-2,5-dihydro-1H-pyrido[3,2-b]indole-3-carbonitrile 在 三乙胺盐酸盐 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以29%的产率得到3-cyano-1-p-nitrophenyl-2-piperidino-1H-pyrido[3,2-b]indole
  参考文献：
  名称：

  摘要：

  The possibility of transformation of 3-cyano-1-p-nitrophenyl-delta-carbolin-2-one into 2-amino-3-cyano-1-p-nitrophenyl-1H-pyrido[3,2-b]indole derivatives and 2-imino-3-cyanol-p-nitrophenyl-5H-pyrido[3,2-b]indole derivatives (delta-carbolines) is demonstrated. Methylation of 1-p-nitrophenyl-2-piperidino-1H-delta-carboline followed by treatment with acetone in an alkaline medium yields 4-acetonyl-5-methyl-1,4-dihydro-5H-pyrido[3,2-b]indole derivative. The rearrangement of 2-arylimino-3-cyano-1-p-nitrophenyl-5H-pyrido[3,2-b]indoles into 2-(aryl)nitrophenylamino-3-cyano-5H-pyrido[3.2-b]indoles was accomplished on heating above the melting point or on treatment with potassium tert-butoxide. The structures of the resulting compounds were proved by H-1 and C-13 NMR spectroscopy and X-ray diffraction analysis.

  DOI：

  10.1023/a:1012749426699