1-苄氧基-2,2-二(3'-吲哚基)乙烷 | 200347-50-8

• 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
• 中文名称: 1-苄氧基-2,2-二(3'-吲哚基)乙烷
• 英文名称: 1-benzyloxy-2,2-di(3'-indolyl)ethane
• 英文别名: 3-[1-(1H-indol-3-yl)-2-phenylmethoxyethyl]-1H-indole
• CAS: 200347-50-8
• 化学式: C₂₅H₂₂N₂O
• 分子量: 366.462
• InChiKey: XBEOKSQGAYSRBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-苄氧基-2,2-二(3'-吲哚基)乙烷 在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 18.0h， 生成 2,2-di(1H-indol-3-yl)ethan-1-ol
  参考文献：
  名称：

  The reaction of nitrones with indoles. Synthesis of asymmetrical diindolylalcanes

  摘要：

  The reaction of nitrones with indoles in the presence of HCl gives indolyl N-hydroxylamines. In the presence of Me3SiCl symmetrical diindolylalcanes are obtained. A synthesis of asymmetrical diindolylalcanes and the syntheses of three natural symmetrical diindolylalcanes are reported. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10302-1
• 作为产物：
  描述：

  吲哚 、 N-benzyl-2-benzyloxyethylideneamine N-oxide 在 三甲基氯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以91%的产率得到1-苄氧基-2,2-二(3'-吲哚基)乙烷
  参考文献：
  名称：

  The reaction of nitrones with indoles. Synthesis of asymmetrical diindolylalcanes

  摘要：

  The reaction of nitrones with indoles in the presence of HCl gives indolyl N-hydroxylamines. In the presence of Me3SiCl symmetrical diindolylalcanes are obtained. A synthesis of asymmetrical diindolylalcanes and the syntheses of three natural symmetrical diindolylalcanes are reported. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10302-1

文献信息

• Expedient Access to Indolyl-Substituted Tri- and Diarylmethanes and (±)-Colletotryptin E by Silica Sulfuric Acid Catalyzed Transindolylation
  作者：Jaray Jaratjaroonphong、Jirapat Yimyaem、Chayamon Chantana、Suthimon Boonmee

  DOI：10.1055/s-0040-1719915

  日期：2022.9

  nonsymmetrical bis(indolyl)methanes (BIMs) through transindolylation of readily available symmetrical 3,3′-BIMs with various indoles catalyzed by silica-supported sulfuric acid has been established. This approach not only provides a useful strategy for the synthesis of structurally diverse BIMs, but also provides examples of nucleophilic substitution of BIMs with aromatic and nonaromatic π-systems

  已经建立了通过容易获得的对称 3,3'-BIM 与由二氧化硅负载的硫酸催化的各种吲哚的转吲哚反应来获得一系列非对称双（吲哚基）甲烷（BIM）的便捷途径。这种方法不仅为合成结构多样的 BIMs 提供了一种有用的策略，而且还提供了用芳香族和非芳香族 π-体系对 BIMs 进行亲核取代的例子，从而形成了一个吲哚基取代的三芳基甲烷和二芳基甲烷库。此外，该方法成功应用于首次三步全合成2,3'-BIM生物碱(±)-colletotryptin E，总收率为46%。该过程的特点包括无金属工艺、廉价且环保的催化剂、温和的反应条件、广泛的官能团耐受性、良好的收率、
• The Reactions of Nitrones with Indoles
  作者：Hélène Chalaye-Mauger、Jean-Noël Denis、Marie-Thérèse Averbuch-Pouchot、Yannick Vallée

  DOI：10.1016/s0040-4020(99)01051-0

  日期：2000.1

  The reaction of nitrones with various indole derivatives has been studied. When the reaction was promoted by ClSiMe3, the isolated products were 3,3'-diindolylalkanes. With HCl as the activating reagent, 3-indolylhydroxylamines were isolated. The diastereoselectivity of this condensation with a nitrone derived from cysteine was investigated. A method for the introduction of an alkylhydroxylamino group onto position 2 of indole, the synthesis of three natural 3,3'-diindolylalkanes and of non-symmetric diindolylalkanes are also reported. (C) 2000 Elsevier Science Ltd. All rights reserved.