3-(5-bromo-2-chloro-1H-indol-3-yl)-4-(1H-indol-3-yl)pyrrole-2,5-dione | 551001-10-6

• 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: 3-(5-bromo-2-chloro-1H-indol-3-yl)-4-(1H-indol-3-yl)pyrrole-2,5-dione
• CAS: 551001-10-6
• 化学式: C₂₀H₁₁BrClN₃O₂
• 分子量: 440.683
• InChiKey: YZOIWHKODGHCQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(5-bromo-2-chloro-1H-indol-3-yl)-4-(1H-indol-3-yl)pyrrole-2,5-dione 在 偶氮二甲酸二异丙酯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 1.5h， 生成 3-bromo-13-[4-(tert-butyldimethylsilanyloxy)-cyclopent-2-enyl]-arcyriaflavin A
  参考文献：
  名称：

  Regiospecific Synthesis of Mono-N-substituted Indolopyrrolocarbazoles

  摘要：

  Two complementary and efficient strategies have been developed for the regiospecific synthesis of unsymmetrical indolopyrrolocarbazoles (IPCs) mono-N-substituted with a pentacycle. A halogen in position 2 of the intermediate bisindolylmaleimides 3a-e allows a selective Mitsunobu coupling by exploiting the increased acidity of the 2-chloro-substituted indole nitrogen. It also promotes an easier cyclization of bisindolylmaleimides 4a-e and 7b-e to IPCs. Alkylation of the 2-unsubstituted indole-3-carboxamides 2a,b and further processing to the corresponding IPCs gives access to the opposite regioisomers.

  DOI：

  10.1021/ol051550a
• 作为产物：
  描述：

  5-溴氧化吲哚 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 69.25h， 生成 3-(5-bromo-2-chloro-1H-indol-3-yl)-4-(1H-indol-3-yl)pyrrole-2,5-dione
  参考文献：
  名称：

  Regiospecific Synthesis of Mono-N-substituted Indolopyrrolocarbazoles

  摘要：

  Two complementary and efficient strategies have been developed for the regiospecific synthesis of unsymmetrical indolopyrrolocarbazoles (IPCs) mono-N-substituted with a pentacycle. A halogen in position 2 of the intermediate bisindolylmaleimides 3a-e allows a selective Mitsunobu coupling by exploiting the increased acidity of the 2-chloro-substituted indole nitrogen. It also promotes an easier cyclization of bisindolylmaleimides 4a-e and 7b-e to IPCs. Alkylation of the 2-unsubstituted indole-3-carboxamides 2a,b and further processing to the corresponding IPCs gives access to the opposite regioisomers.

  DOI：

  10.1021/ol051550a

文献信息

• US7262215B2
  申请人：——

  公开号：US7262215B2

  公开（公告）日：2007-08-28
• Regiospecific Synthesis of Mono-N-substituted Indolopyrrolocarbazoles
  作者：Wolfgang Fröhner、Barbara Monse、Tobias M. Braxmeier、Laura Casiraghi、Heidi Sahagún、Pierfausto Seneci

  DOI：10.1021/ol051550a

  日期：2005.10.1

  Two complementary and efficient strategies have been developed for the regiospecific synthesis of unsymmetrical indolopyrrolocarbazoles (IPCs) mono-N-substituted with a pentacycle. A halogen in position 2 of the intermediate bisindolylmaleimides 3a-e allows a selective Mitsunobu coupling by exploiting the increased acidity of the 2-chloro-substituted indole nitrogen. It also promotes an easier cyclization of bisindolylmaleimides 4a-e and 7b-e to IPCs. Alkylation of the 2-unsubstituted indole-3-carboxamides 2a,b and further processing to the corresponding IPCs gives access to the opposite regioisomers.