(9-methoxy-3-methyl-1,2,3,6-tetrahydroazepino[4,5-b]indol-4-yl)(phenyl)methanone

• 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: (9-methoxy-3-methyl-1,2,3,6-tetrahydroazepino[4,5-b]indol-4-yl)(phenyl)methanone
• 英文别名: (9-Methoxy-3-methyl-1,2,3,6-tetrahydroazepino-[4,5-b]indol-4-yl)(phenyl)methanone；(9-methoxy-3-methyl-2,6-dihydro-1H-azepino[4,5-b]indol-4-yl)-phenylmethanone
• 化学式: C₂₁H₂₀N₂O₂
• 分子量: 332.402
• InChiKey: MNQYAGQNHDJGOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,4-dihydro-6-methoxy-β-carboline 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 3.0h， 生成 (9-methoxy-3-methyl-1,2,3,6-tetrahydroazepino[4,5-b]indol-4-yl)(phenyl)methanone
  参考文献：
  名称：

  Pyridine—Azepine Structural Modification of 3,4-Dihydro-nor-isoharmine

  摘要：

  Structural modification of 3,4-dihydro-nor-isoharmine through expansion of the dihydropyridine ring to dihydroazepine was accomplished in two stages including pyridine-azepine recyclization of the quaternized substrate by the action of phenacyl halides and their heterocyclic analogs. The recyclization process can be accompanied by 1,2-migration of the acyl group to give mixtures of 4-acyl-9-methoxy-3-methyl-1,2-dihydroazepino[4,5-b]indoles and their 5-acyl-substituted isomers. Factor influencing the recyclization direction and product ratio were analyzed.

  DOI：

  10.1134/s1070428019010081

文献信息

• Pyridine—Azepine Structural Modification of 3,4-Dihydro-nor-isoharmine
  作者：A. A. Zubenko、A. S. Morkovnik、L. N. Divaeva、V. G. Kartsev、A. A. Anisimov、K. Yu. Suponitsky

  DOI：10.1134/s1070428019010081

  日期：2019.1

  Structural modification of 3,4-dihydro-nor-isoharmine through expansion of the dihydropyridine ring to dihydroazepine was accomplished in two stages including pyridine-azepine recyclization of the quaternized substrate by the action of phenacyl halides and their heterocyclic analogs. The recyclization process can be accompanied by 1,2-migration of the acyl group to give mixtures of 4-acyl-9-methoxy-3-methyl-1,2-dihydroazepino[4,5-b]indoles and their 5-acyl-substituted isomers. Factor influencing the recyclization direction and product ratio were analyzed.