4,4-bis-(5-bromo-1H-indol-3-yl)butan-1-ol

• 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: 4,4-bis-(5-bromo-1H-indol-3-yl)butan-1-ol
• 英文别名: 4,4-bis(5-bromo-1H-indol-3-yl)butan-1-ol
• 化学式: C₂₀H₁₈Br₂N₂O
• 分子量: 462.184
• InChiKey: OLCJDDULGHJCSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.8
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,3-二氢呋喃 、 5-溴吲哚 在 indium(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 以77%的产率得到4,4-bis-(5-bromo-1H-indol-3-yl)butan-1-ol
  参考文献：
  名称：

  Unprecedented InCl3-catalyzed formation of cis-fused perhydrofuro[2,3-b]oxepines

  摘要：

  2-Methylindole and its N-substituted derivatives react smoothly with 2,3-dihydrofuran (DHF) in the presence of a catalytic amount of InCl3 under mild conditions to afford the corresponding 2-methyl-3-perhydrofuro[2,3-b]oxepin-4-yl-1H-indole derivatives in fairly good yields with high diastereoselectivity, while 3,4-dihydro-2H-pyran (DHP) affords exclusively 5,5-di(1H-3-indolyl)-1-pentanol derivatives in high yields under similar reaction conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00036-4

文献信息

• One-Pot Synthesis of Symmetric and Unsymmetric 1,1-Bis-indolylmethanes via Tandem Iron-Catalyzed C−H Bond Oxidation and C−O Bond Cleavage
  作者：Xingwei Guo、Shiguang Pan、Jinhua Liu、Zhiping Li

  DOI：10.1021/jo902093p

  日期：2009.11.20

  The reactions of indoles with ethers give a variety of symmetric and unsymmetric 1,1-bis-indolylmethane derivatives via iron-catalyzed C−H bond oxidation and C−O bond cleavage.

  吲哚与醚的反应通过铁催化的CH键氧化和CO键断裂，产生了各种对称和不对称的1,1-双吲哚甲烷衍生物。
• Unprecedented InCl3-catalyzed formation of cis-fused perhydrofuro[2,3-b]oxepines
  作者：J.S. Yadav、B.V.S. Reddy、G. Satheesh、A. Prabhakar、A.C. Kunwar

  DOI：10.1016/s0040-4039(03)00036-4

  日期：2003.3

  2-Methylindole and its N-substituted derivatives react smoothly with 2,3-dihydrofuran (DHF) in the presence of a catalytic amount of InCl3 under mild conditions to afford the corresponding 2-methyl-3-perhydrofuro[2,3-b]oxepin-4-yl-1H-indole derivatives in fairly good yields with high diastereoselectivity, while 3,4-dihydro-2H-pyran (DHP) affords exclusively 5,5-di(1H-3-indolyl)-1-pentanol derivatives in high yields under similar reaction conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.