6-phenylindolo<2,3-a>pyrrolo<3,4-c>carbazole-5,7(6H)-dione | 144823-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-phenylindolo<2,3-a>pyrrolo<3,4-c>carbazole-5,7(6H)-dione
• 英文别名: 13-Phenyl-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4,6,8,10,15,17,19,21-nonaene-12,14-dione
• CAS: 144823-21-2
• 化学式: C₂₆H₁₅N₃O₂
• 分子量: 401.424
• InChiKey: JJHLKWZWTQDETQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  31
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  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

文献信息

• 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.
• 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.
• FURTHER INDOLE DERIVATIVES WITH ANTIVIRAL ACTIVITY
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0630242B1

  公开（公告）日：1999-01-20
• 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.