3-[(5-chloro-2-nitrophenyl)-(1H-indol-3-yl)methyl]-1H-indole | 910792-63-1

• 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-chloro-2-nitrophenyl)-(1H-indol-3-yl)methyl]-1H-indole
• CAS: 910792-63-1
• 化学式: C₂₃H₁₆ClN₃O₂
• 分子量: 401.852
• InChiKey: HBDCAVFCVNLRCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[(5-chloro-2-nitrophenyl)-(1H-indol-3-yl)methyl]-1H-indole 在 tin(ll) chloride 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以91%的产率得到2-chloro-11-(1H-indol-3-yl)-6H-indolo[2,3-b]quinoline
  参考文献：
  名称：

  Unprecedented SnCl2·2H2O-mediated intramolecular cyclization of nitroarenes via C–N bond formation: a new entry to the synthesis of cryptotackieine and related skeletons

  摘要：

  A mild, efficient, and one-pot protocol for the intramolecular cyclization of 2-substituted nitroarenes via C-N bond formation using SnCl2 center dot 2H(2)O is described. The versatility of the method has been demonstrated by synthesizing two sets of polycyclic structures based oil privileged structures of indole and pyrrole, and of the alkaloid cryptotackieine associated with antimalarial activity. Our new approach provides a powerful entry into polycyclic structures related to an alkaloid. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.154
• 作为产物：
  描述：

  吲哚 、 5-氯-2-硝基苯甲醛 在 碘 作用下， 以 乙腈 为溶剂， 反应 0.33h， 生成 3-[(5-chloro-2-nitrophenyl)-(1H-indol-3-yl)methyl]-1H-indole
  参考文献：
  名称：

  Unprecedented SnCl2·2H2O-mediated intramolecular cyclization of nitroarenes via C–N bond formation: a new entry to the synthesis of cryptotackieine and related skeletons

  摘要：

  A mild, efficient, and one-pot protocol for the intramolecular cyclization of 2-substituted nitroarenes via C-N bond formation using SnCl2 center dot 2H(2)O is described. The versatility of the method has been demonstrated by synthesizing two sets of polycyclic structures based oil privileged structures of indole and pyrrole, and of the alkaloid cryptotackieine associated with antimalarial activity. Our new approach provides a powerful entry into polycyclic structures related to an alkaloid. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.154

文献信息

• Unprecedented SnCl2·2H2O-mediated intramolecular cyclization of nitroarenes via C–N bond formation: a new entry to the synthesis of cryptotackieine and related skeletons
  作者：Sunil Sharma、Bijoy Kundu

  DOI：10.1016/j.tetlet.2008.09.154

  日期：2008.12

  A mild, efficient, and one-pot protocol for the intramolecular cyclization of 2-substituted nitroarenes via C-N bond formation using SnCl2 center dot 2H(2)O is described. The versatility of the method has been demonstrated by synthesizing two sets of polycyclic structures based oil privileged structures of indole and pyrrole, and of the alkaloid cryptotackieine associated with antimalarial activity. Our new approach provides a powerful entry into polycyclic structures related to an alkaloid. (c) 2008 Elsevier Ltd. All rights reserved.