1,1,3-tris(5-bromo-3-indolyl)propane | 1207533-42-3

• 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: 1,1,3-tris(5-bromo-3-indolyl)propane
• 英文别名: 3-[1,3-bis(5-bromo-1H-indol-3-yl)propyl]-5-bromo-1H-indole
• CAS: 1207533-42-3
• 化学式: C₂₇H₂₀Br₃N₃
• 分子量: 626.188
• InChiKey: QDVNWPBCYOCYKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  47.4
• 氢给体数：
  3
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  5-溴吲哚 、 丙烯醛 在 aluminum (III) chloride 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以96%的产率得到1,1,3-tris(5-bromo-3-indolyl)propane
  参考文献：
  名称：

  AlCl3 as a powerful catalyst for the one-pot preparation of 1,1,3-triheteroaryl compounds

  摘要：

  A general and efficient procedure for the synthesis of 1,1,3-triheteroaryl compounds in good to excellent yield at room temperature is developed. The reaction proceeds via mixed Michael and Friedel-Crafts reactions of alpha,beta-enals or alpha,beta-enones and indoles, 2-methylfuran or 2-methylthiophene in the presence of a catalytic amount of AlCl3. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.10.127

文献信息

• A Facile Synthesis of Tris(indolyl)propanes by Concerted 1,2- and 1,4-Friedel-Crafts Attack of Indoles to α,β-Unsaturated Aldimines
  作者：Manping Zhao、Xiuli Zhang、Chengxiang He、Pinaki S. Bhadury、Zhihua Sun

  DOI：10.1071/ch14156

  日期：——

  The Friedel-Crafts reaction of indoles with a wide range of α,β-unsaturated aldimines catalysed by binaphthyl phosphoric acid is demonstrated. The resulting tris(indolyl)propanes are presumably generated by a concerted 1,2- and 1,4-nucleophilic attack to the conjugated imines. According to the preliminary bioassay results, the compound 4e exhibits moderate activity against pancreatic cancer cells.

  在二萘基磷酸的催化下，吲哚与多种 α、β-不饱和醛亚胺发生了 Friedel-Crafts 反应。由此产生的三(吲哚基)丙烷可能是通过对共轭亚胺进行 1,2- 和 1,4- 亲核攻击而生成的。根据初步的生物测定结果，化合物 4e 对胰腺癌细胞具有中等程度的活性。
• AlCl3 as a powerful catalyst for the one-pot preparation of 1,1,3-triheteroaryl compounds
  作者：Morteza Shiri、Mohammad Ali Zolfigol、Roya Ayazi-Nasrabadi

  DOI：10.1016/j.tetlet.2009.10.127

  日期：2010.1

  A general and efficient procedure for the synthesis of 1,1,3-triheteroaryl compounds in good to excellent yield at room temperature is developed. The reaction proceeds via mixed Michael and Friedel-Crafts reactions of alpha,beta-enals or alpha,beta-enones and indoles, 2-methylfuran or 2-methylthiophene in the presence of a catalytic amount of AlCl3. (C) 2009 Elsevier Ltd. All rights reserved.