4,5-dihydro-7-isopropoxy-8-methoxy-1-methyl-1H-benzindole-2,3-dione | 143237-37-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,5-dihydro-7-isopropoxy-8-methoxy-1-methyl-1H-benzindole-2,3-dione
• 英文别名: 8-Methoxy-1-methyl-7-propan-2-yloxy-4,5-dihydrobenzo[g]indole-2,3-dione
• CAS: 143237-37-0
• 化学式: C₁₇H₁₉NO₄
• 分子量: 301.342
• InChiKey: IRSBFLBDCJZIAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5-dihydro-7-isopropoxy-8-methoxy-1-methyl-1H-benzindole-2,3-dione 、 2-氨基-4,5-二甲氧基苯甲酸 在 亚硝酸异戊酯 、 三氯乙酸 作用下， 生成 dihydrooxyfagaronine
  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：

  6-isopropoxy-7-methoxy-1-tetralone 在 四氯化钛 、 三乙胺 作用下， 以 乙二醇二甲醚 、 氯仿 为溶剂， 反应 27.25h， 生成 4,5-dihydro-7-isopropoxy-8-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

文献信息

• Intermolecular benzyne cycloaddition (IBC), a versatile approach to benzophenanthridine antitumor alkaloids. Formal synthesis of nitidine and chelerythrine
  作者：Gloria Martin、Enrique Guitian、Luis Castedo、Jose M. Saa

  DOI：10.1021/jo00048a024

  日期：1992.10

  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.