2-(2,2'-biindol-3-yl)-N-phenylsuccinimide | 144836-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-(2,2'-biindol-3-yl)-N-phenylsuccinimide
• 英文别名: 3-[2-(1H-indol-2-yl)-1H-indol-3-yl]-1-phenylpyrrolidine-2,5-dione
• CAS: 144836-02-2
• 化学式: C₂₆H₁₉N₃O₂
• 分子量: 405.456
• InChiKey: SAPWYAHARSYCST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  69
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2,2'-biindol-3-yl)-N-phenylsuccinimide 在 palladium on activated charcoal 作用下， 以 xylene 为溶剂， 以42%的产率得到6-phenylindolo<2,3-a>pyrrolo<3,4-c>carbazole-5,7(6H)-dione
  参考文献：
  名称：

  A Novel Synthesis of 2,2'-Bisindole and Its Application for the Synthesis of Indolo[2,3-a]carbazole Derivatives

  摘要：

  A novel oxidative coupling method of 2-lithio-1-methoxyindole was developed resulting in the formation of 2,2'-bis(l-methoxyindole) (6). Catalytic hydrogenation of 6 produced 2,2'-bisindole (9). Diels-Alder reaction of 9 with dienophiles afforded indolo-[2,3-a]carbazole derivatives.

  DOI：

  10.3987/com-92-6044
• 作为产物：
  描述：

  3-[1-methoxy-2-(1-methoxyindol-2-yl)indol-3-yl]-1-phenylpyrrolidine-2,5-dione 在 palladium on activated charcoal 作用下， 以 xylene 为溶剂， 以14%的产率得到2-(2,2'-biindol-3-yl)-N-phenylsuccinimide
  参考文献：
  名称：

  A Novel Synthesis of 2,2'-Bisindole and Its Application for the Synthesis of Indolo[2,3-a]carbazole Derivatives

  摘要：

  A novel oxidative coupling method of 2-lithio-1-methoxyindole was developed resulting in the formation of 2,2'-bis(l-methoxyindole) (6). Catalytic hydrogenation of 6 produced 2,2'-bisindole (9). Diels-Alder reaction of 9 with dienophiles afforded indolo-[2,3-a]carbazole derivatives.

  DOI：

  10.3987/com-92-6044

文献信息

• On the [42]Cycloaddition Approach to Indolo[2,3-a]carbazoles
  作者：John F. Barry、Timothy W. Wallace、Nigel D.A. Walshe

  DOI：10.1016/0040-4020(95)00735-q

  日期：1995.11

  2,2'-Biindolyl 9 reacts with electron-deficient dienophiles at 100-110 degrees C to give low to moderate yields of Michael addition and formal [4 + 2] cycloaddition products, with the former predominant; the products derived from 9 and 2-(phenylsulphinyl)maleimides 14 and 15 undergo in situ elimination of benzenesulphenic acid, leading to 2,2'-biindolyl-substituted maleimides which can be efficiently photocyclised into indolo[2,3-a]carbazoles.
• On the [4 + 2] cycloaddition approach to indolo[2,3-a]carbazoles
  作者：John F. Barry、Timothy W. Wallace、Nigel D.A. Walshe

  DOI：10.1016/s0040-4039(00)73988-8

  日期：1993.8

  2,2'-Biindolyl 4 reacts with electron-deficient dienophiles at 100-110-degrees-C to give low to moderate yields of Michael addition and formal [4 + 2] cycloaddition products, with the former predominant; the products derived from 4 and 2-(phenylsulphinyl)maleimides 7 and 8 undergo in situ elimination of benzenesulphenic acid, leading to 2,2'-biindolyl-substituted maleimides which can be efficiently photocyclised into indolo[2,3-a]carbazoles.
• A Novel Synthesis of 2,2'-Bisindole and Its Application for the Synthesis of Indolo[2,3-a]carbazole Derivatives
  作者：Masanori Somei、Atsushi Kodama

  DOI：10.3987/com-92-6044

  日期：——

  A novel oxidative coupling method of 2-lithio-1-methoxyindole was developed resulting in the formation of 2,2'-bis(l-methoxyindole) (6). Catalytic hydrogenation of 6 produced 2,2'-bisindole (9). Diels-Alder reaction of 9 with dienophiles afforded indolo-[2,3-a]carbazole derivatives.