4,5-dihydro-1-methyl-1H-benzindole-2,3-dione | 111865-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,5-dihydro-1-methyl-1H-benzindole-2,3-dione
• 英文别名: 1-Methyl-4,5-dihydrobenzo[g]indole-2,3-dione
• CAS: 111865-20-4
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: LSXDXRVXHFNGNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-dihydro-1-methyl-1H-benzindole-2,3-dione 、 邻氨基苯甲酸 在 亚硝酸异戊酯 、 三氯乙酸 作用下， 生成 5-methyl-11,12-dihydrobenzophenanthridin-6(5H)-one
  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：

  草酰氯 、 N-methyl-3,4-dihydronaphthalen-1(2H )-imine 在 三乙胺 作用下， 以 乙二醇二甲醚 为溶剂， 以72%的产率得到4,5-dihydro-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

• Novel entry into the benzo(C)phenanthridine skeleton through the intermolecular benzyne cycloaddition (IBC) approach
  作者：Gloria Martin、Enrique Guitián、Luis Castedo、José M Saá

  DOI：10.1016/s0040-4039(00)96137-9

  日期：——

  A highly convergent synthesis of the skeleton of benzo(c)phenanthridine alkaloids based on the intermolecular benzyne cycloaddition (IBC) approach is described.

  描述了基于分子间苯并环加成（IBC）方法的苯并（c）菲啶生物碱骨架的高度收敛合成。
• MARTIN, G.;GUITIAN, E.;CASTEDO, L.;SAA, J. M., TETRAHEDRON LETT., 28,(1987) N 21, 2407-2408
  作者：MARTIN, G.、GUITIAN, E.、CASTEDO, L.、SAA, J. M.

  DOI：——

  日期：——