2-oxo-1-phenyl-1,2,3,4,5,6-hexahydro[1,4]diazepino[6,5-b]indole | 474642-28-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-oxo-1-phenyl-1,2,3,4,5,6-hexahydro[1,4]diazepino[6,5-b]indole
• 英文别名: 1-phenyl-3,4,5,6-tetrahydro[1,4]diazepino[6,5-b]indol-2(1H)-one；1-phenyl-3,4,5,6-tetrahydro-[1,4]diazepino[6,5-b]indol-2-one
• CAS: 474642-28-9
• 化学式: C₁₇H₁₅N₃O
• 分子量: 277.326
• InChiKey: PYOYPRBFNVHLDP-UHFFFAOYSA-N

物化性质

• 沸点：
  596.4±50.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  48.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-oxo-1-phenyl-1,2,3,4,5,6-hexahydro[1,4]diazepino[6,5-b]indole 在 palladium on activated charcoal 作用下， 以 甲醇 为溶剂， 反应 64.0h， 以25%的产率得到2-oxo-1-phenyl-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole
  参考文献：
  名称：

  摘要：

  A number of 1-aryl-2-oxo-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole 4-oxides were synthesized based on 3-[N-aryl-N-(chloroacetyl)amino]-2-formylindoles. The nature of the substituent in the 1-aryl fragment has a pronounced influence on the course of reactions throughout the whole sequence of transformations during the synthesis of diazepinoindoles. The reduction of 4-oxides by formamidinosulfinic acid, hydrogen in the presence of Pd/C, and sodium bisulfite was studied. The structures of the reaction products were confirmed using IR and H-1 NMR spectroscopy and mass spectrometry.

  DOI：

  10.1023/a:1024887429776
• 作为产物：
  描述：

  2-formyl-3-(N'-chloroacetyl-N'-phenyl)aminoindole 在 sodium hydroxide 、 盐酸羟胺 、 potassium acetate 、 甲脒 作用下， 以 乙醇 、 水 为溶剂， 反应 61.25h， 生成 2-oxo-1-phenyl-1,2,3,4,5,6-hexahydro[1,4]diazepino[6,5-b]indole
  参考文献：
  名称：

  摘要：

  1-Aryl-2-oxo-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole N-oxides were synthesized based on 3-(N'-aryl-N'-chloroacetyl)amino-2-formylindoles. Deoxidation of 2-oxo-1-phenyl-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole N-oxide afforded 1,2,3,6-tetrallydro- and 1,2,3,4,5,6-hexahydro[1,4]diazepino[6,5-b]indole derivatives. A new approach to the synthesis of pyrido[3,2-b]indole and pyrimido[5,4-b]indole derivatives was developed.

  DOI：

  10.1023/a:1015520621450