2-(2,2'-biindol-3-yl)-N-phenylmaleimide | 153615-79-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 2-(2,2'-biindol-3-yl)-N-phenylmaleimide
• CAS: 153615-79-3
• 化学式: C₂₆H₁₇N₃O₂
• 分子量: 403.44
• InChiKey: RQLFZGYPTSARQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.96
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(2,2'-biindol-3-yl)-N-phenylmaleimide 以 乙醇 为溶剂， 反应 5.0h， 以80%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：

  On the [42]Cycloaddition Approach to Indolo[2,3-a]carbazoles

  摘要：

  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.

  DOI：

  10.1016/0040-4020(95)00735-q
• 作为产物：
  描述：

  1-phenyl-3-(phenylthio)pyrrolidine-2,5-dione 在 N-氯代丁二酰亚胺 、 间氯过氧苯甲酸 作用下， 以 四氯化碳 、 二氯甲烷 、 乙腈 为溶剂， 反应 17.17h， 生成 2-(2,2'-biindol-3-yl)-N-phenylmaleimide
  参考文献：
  名称：

  On the [42]Cycloaddition Approach to Indolo[2,3-a]carbazoles

  摘要：

  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.

  DOI：

  10.1016/0040-4020(95)00735-q

文献信息

• 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.
• 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.