N-[5-Chloro-2-(2,8-dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-phenyl]-hydroxylamine | 173034-15-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-[5-Chloro-2-(2,8-dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-phenyl]-hydroxylamine
• CAS: 173034-15-6
• 化学式: C₁₉H₂₀ClN₃O
• 分子量: 341.84
• InChiKey: FUUJOWPVPNCVCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  40.43
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 甲烷磺酸 、 N-[5-Chloro-2-(2,8-dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-phenyl]-hydroxylamine 在 盐酸 作用下， 以6%的产率得到pyridoindolobenzodiazepine*methanesulfonic acid
  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：

  N-甲基-4-哌啶酮 在 sulfide carbon 、 铂 氢气 、 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 N-[5-Chloro-2-(2,8-dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-phenyl]-hydroxylamine
  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