6-methoxy-N-methyl-3,4-dihydro-2H-naphthalen-1-imine | 111865-19-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6-methoxy-N-methyl-3,4-dihydro-2H-naphthalen-1-imine
• CAS: 111865-19-1
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: KGHQXSGHIGCLJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  草酰氯 、 6-methoxy-N-methyl-3,4-dihydro-2H-naphthalen-1-imine 在 三乙胺 作用下， 以 乙二醇二甲醚 为溶剂， 以57%的产率得到4,5-dihydro-7-methoxy-1-methyl-1H-benzindole-2,3-dione
  参考文献：
  名称：

  Intermolecular benzyne cycloaddition (IBC), a versatile approach to benzophenanthridine antitumor alkaloids. Formal synthesis of nitidine and chelerythrine

  摘要：

  A new approach to the synthesis of benzophenanthridine alkaloids is described which is based on cycloaddition of arynes to pyrrolinediones, the pyrrolinediones behaving as aza diene equivalents. The synthesis of 2,3,8,9-substituted benzophenanthridines and the regioselective synthesis of a 2,3,7,8-substituted benzophenanthridine were performed. The formal synthesis of chelerythrine and the antitumor alkaloid nitidine is described.

  DOI：

  10.1021/jo00048a024
• 作为产物：
  描述：

  甲胺 、 6-甲氧基-1-萘满酮 在 四氯化钛 作用下， 以 氯仿 为溶剂， 以92%的产率得到6-methoxy-N-methyl-3,4-dihydro-2H-naphthalen-1-imine
  参考文献：
  名称：

  Intermolecular benzyne cycloaddition (IBC), a versatile approach to benzophenanthridine antitumor alkaloids. Formal synthesis of nitidine and chelerythrine

  摘要：

  A new approach to the synthesis of benzophenanthridine alkaloids is described which is based on cycloaddition of arynes to pyrrolinediones, the pyrrolinediones behaving as aza diene equivalents. The synthesis of 2,3,8,9-substituted benzophenanthridines and the regioselective synthesis of a 2,3,7,8-substituted benzophenanthridine were performed. The formal synthesis of chelerythrine and the antitumor alkaloid nitidine is described.

  DOI：

  10.1021/jo00048a024