5-(4-chloro-2-nitrophenyl)-2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indole | 173034-14-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-(4-chloro-2-nitrophenyl)-2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indole
• CAS: 173034-14-5
• 化学式: C₁₉H₁₈ClN₃O₂
• 分子量: 355.824
• InChiKey: PCMWYZVXSYXMQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-chloro-2-nitrophenyl)-2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indole 在 铁粉 作用下， 以 乙醇 、 水 为溶剂， 以80%的产率得到5-chloro-2-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5-yl)aniline
  参考文献：
  名称：

  Pictet-Spengler reaction in trifluoroacetic acid. Large scale synthesis of pyridoindolobenzodiazepine as an atypical antipsychotic agent

  摘要：

  Traditional syntheses of benzodiazepines involve a Bischler-Napieralski reaction which is a three step process and gives low overall yields. An attractive alternative is to construct the diazepine ring under Pictet-Spengler conditions. This paper reports the synthesis of a novel pyridoindolo-benzodiazepine as a potent atypical antipsychotic agent. The key step in the synthesis is the ring formation of the diazepine ring in neat trifluoroacetic acid.

  DOI：

  10.1016/0040-4039(95)01812-v
• 作为产物：
  描述：

  对甲基苯肼 在 caesium carbonate 、 三氟乙酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-(4-chloro-2-nitrophenyl)-2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indole
  参考文献：
  名称：

  Pictet-Spengler reaction in trifluoroacetic acid. Large scale synthesis of pyridoindolobenzodiazepine as an atypical antipsychotic agent

  摘要：

  Traditional syntheses of benzodiazepines involve a Bischler-Napieralski reaction which is a three step process and gives low overall yields. An attractive alternative is to construct the diazepine ring under Pictet-Spengler conditions. This paper reports the synthesis of a novel pyridoindolo-benzodiazepine as a potent atypical antipsychotic agent. The key step in the synthesis is the ring formation of the diazepine ring in neat trifluoroacetic acid.

  DOI：

  10.1016/0040-4039(95)01812-v

文献信息

• Pictet-Spengler reaction in trifluoroacetic acid. Large scale synthesis of pyridoindolobenzodiazepine as an atypical antipsychotic agent
  作者：Lin-hua Zhang、W. Meier、E. Wats、T.D. Costello、P. Ma、C.L. Ensinger、J.M. Rodgers、I.C. Jacobson、P. Rajagopalan

  DOI：10.1016/0040-4039(95)01812-v

  日期：1995.11

  Traditional syntheses of benzodiazepines involve a Bischler-Napieralski reaction which is a three step process and gives low overall yields. An attractive alternative is to construct the diazepine ring under Pictet-Spengler conditions. This paper reports the synthesis of a novel pyridoindolo-benzodiazepine as a potent atypical antipsychotic agent. The key step in the synthesis is the ring formation of the diazepine ring in neat trifluoroacetic acid.