3,3'-(propane-1,1-diyl)bis(1-methyl-1H-indole)

• 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: 3,3'-(propane-1,1-diyl)bis(1-methyl-1H-indole)
• 英文别名: 1,1-bis(1-methyl-1H-indol-3-yl)propane；1-Methyl-3-[1-(1-methylindol-3-yl)propyl]indole
• 化学式: C₂₁H₂₂N₂
• 分子量: 302.419
• InChiKey: VWCRTCBJPZZSHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  9.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  吲哚 在 三乙基硅烷 、 三(五氟苯基)硼烷 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 3,3'-(propane-1,1-diyl)bis(1-methyl-1H-indole)
  参考文献：
  名称：

  在温和条件下使用羧酸和氢硅烷直接将吲哚与3,3'-双吲哚甲烷桥联

  摘要：

  首次开发了一种简单的路易斯酸促进的3,3'-二吲哚基甲烷（BIM）合成方法，该方法是在存在氢硅烷的情况下，通过羧酸在C3位的吲哚还原烷基化来合成3,3'-二吲哚基甲烷（BIM）。代替醛，更容易获得，稳定和易于处理的羧酸已被用作替代烷基化剂。作为有效的有机催化剂，B（C 6 F 5）3使在室温下和在纯净条件下，各种取代的吲哚衍生物与羧酸进行还原性烷基化反应，收率可达98％。这种无金属的策略为将吲哚直接用羧酸直接官能化为BIM提供了另一种方法，该方案允许将羧酸选择性还原为醛，并形成C-C键。

  DOI：

  10.1002/asia.201800766

文献信息

• Reactivity of indole-3-alkoxides in the absence of acids: Rapid synthesis of homo-bisindolylmethanes
  作者：Bhavani Shankar Chinta、Beeraiah Baire

  DOI：10.1016/j.tet.2016.10.067

  日期：2016.12

  properties of the alkoxides offered the direct and selective construction of bisindolylmethanes and indole-3-carbinols. This process shows very broad scope and represents the reagent (external) free, greener synthesis of structurally divergent bisindolylmethanes.

  据报道，原位生成的吲哚-3-醇盐（MgX或Li）具有空前的行为。调节醇盐的电子性质可以直接和选择性地构建双吲哚甲烷和吲哚-3-甲醇。该方法显示出非常广泛的范围，并且代表了无试剂（外部），绿色发散的结构不同的双吲哚甲烷的合成。
• One-pot total synthesis of streptindole, arsindoline B and their congeners through tandem decarboxylative deaminative dual-coupling reaction of amino acids with indoles
  作者：Jiachen Xiang、Jungang Wang、Miao Wang、Xianggao Meng、Anxin Wu

  DOI：10.1039/c5ob00025d

  日期：——

  This paper described a decarboxylative deaminative dual-coupling reaction of amino acids with indoles to afford BIM scaffolds and its further application to the one-pot total synthesis of natural products.

  本文描述了氨基酸与吲哚的脱羧脱氨双偶联反应，形成BIM骨架，并进一步应用于天然产物的一锅式全合成。
• Aminocatalytic preparation of bisindolylalkanes
  作者：Timothy J. K. Gibbs、Nicholas C. O. Tomkinson

  DOI：10.1039/b513394g

  日期：——

  An aminocatalytic method for the formation of bisindolylalkanes is described; the reaction proceeds effectively at ambient temperature in the presence of moisture and air for both aldehyde and ketone substrates and has been applied to the one-step preparation of a series of naturally-occurring bis- and tris-indolylalkanes.

  描述了一种用于形成双吲哚基烷烃的氨基催化方法；对于醛和酮底物，该反应在湿气和空气存在下在环境温度下有效进行，并已应用于一系列天然存在的双和三吲哚基烷烃的一步制备。
• One-Pot Synthesis of <i>N</i>-(α-Peroxy)Indole/Carbazole via Chemoselective Three-Component Condensation Reaction in Open Atmosphere
  作者：Xinbo Wang、Yupeng Pan、Kuo-Wei Huang、Zhiping Lai

  DOI：10.1021/acs.orglett.5b02881

  日期：2015.11.20

  A facile one-pot synthesis of N-(alpha-peroxy)indole and N-(alpha-peroxy)carbazole has been developed using metal-free, organo-acid-catalyzed three-component condensation reactions of indole/carbazole, aldehyde, and peroxide. Based on the reaction discovered, a new synthetic proposal for Fumitremorgin A and Verruculogen is introduced. Such a protocol could be easily handled and scaled up in an open atmosphere with a wide substrate scope, enabling the construction of a new molecule library.
• Iron(II) Chloride–1,1′-Binaphthyl-2,2′-diamine (FeCl2–BINAM) Complex Catalyzed Domino Synthesis of Bisindolylmethanes from Indoles and Primary Alcohols
  作者：Govindasamy Sekar、Sindhura Badigenchala、Dhandapani Ganapathy、Ankita Das、Rahul Singh

  DOI：10.1055/s-0033-1340052

  日期：——

  Biologically important bisindolylmethanes are synthesized in a domino fashion by using an iron(II) chloride-(+/-)-1,1-binaphthyl-2,2-diamine [FeCl2-(+/-)-BINAM] complex as the catalyst. This method proceeds via oxidation of a primary alcohol into the corresponding aldehyde followed by nucleophilic addition of an indole in the presence of the catalyst. A reaction intermediate is synthesized separately and converted into the bisindolylmethane product under the same reaction conditions as support for the proposed mechanism.