1-cyclohexyl-2-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: 1-cyclohexyl-2-methyl-1H-indole
• 英文别名: 1-Cyclohexyl-2-methylindole
• 化学式: C₁₅H₁₉N
• 分子量: 213.323
• InChiKey: NSVNOSODIIDWKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-Cyclohexyl-2-methyl-2,3-dihydroindole 在 tetrakis(acetonitrile)copper(I)tetrafluoroborate 、 叔丁基过氧化碳酸-2-乙基己酯 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以87%的产率得到1-cyclohexyl-2-methyl-1H-indole
  参考文献：
  名称：

  A Mild Cu(I)-Catalyzed Oxidative Aromatization of Indolines to Indoles

  摘要：

  A novel method for the oxidation of indolines to indoles is described. The method uses a Cu(I) catalyst and an organic percarbonate as the stoichiometric oxidant. The procedure was successfully applied at 0.5 kg scale in the production of a key intermediate in the synthesis of Elbasvir, which is a novel therapy for the treatment of hepatitis C virus infection.

  DOI：

  10.1021/acs.joc.6b01854

文献信息

• Utilizing Mor-DalPhos/Palladium-Catalyzed Monoarylation in the Multicomponent One-Pot Synthesis of Indoles
  作者：Nicolas L. Rotta-Loria、Andrey Borzenko、Pamela G. Alsabeh、Christopher B. Lavery、Mark Stradiotto

  DOI：10.1002/adsc.201400903

  日期：2015.1.12

  in the one‐pot, multicomponent assembly of substituted indoles from ortho‐chlorohaloarenes, alkyl ketones (including acetone), and primary amines is reported. The described protocols offer improved substrate scope in all three reaction components, under more mild conditions and without the need for an additional drying agent. Also reported are the first examples of such multicomponent reactions where

  据报道，Mor-DalPhos /钯催化剂体系在邻氯卤代芳烃，烷基酮（包括丙酮）和伯胺的一锅多组分取代吲哚的组装中得到了应用。所描述的方案在更温和的条件下并且不需要其他干燥剂的情况下，可在所有三种反应组分中提供改进的底物范围。还报道了这种多组分反应的第一个例子，其中所有反应物在反应开始时就被合并，而不需要惰性气氛反应条件。
• Formal aromaticity transfer for palladium-catalyzed coupling between phenols and pyrrolidines/indolines
  作者：Zihang Qiu、Jiang-Sheng Li、Chao-Jun Li

  DOI：10.1039/c7sc02578e

  日期：——

  aromaticity transfer coupling reaction between phenols and pyrrolidines or indolines to generate the corresponding N-cyclohexyl pyrroles or indoles. In this transformation, the aromaticity of phenols is formally passed on to the pyrrolidine or indoline units. Substituted phenols thus can serve as latent cyclohexyl equivalents for the fast construction of various N-cyclohexyl pyrroles and indoles.

  我们在本文中描述了酚和吡咯烷或二氢吲哚之间的钯催化的形式芳族转移偶联反应，以产生相应的N-环己基吡咯或吲哚。在该转化中，苯酚的芳香性正式传递给吡咯烷或二氢吲哚单元。因此，取代的苯酚可以用作潜在的环己基当量，用于快速构建各种N-环己基吡咯和吲哚。
• A Mild Cu(I)-Catalyzed Oxidative Aromatization of Indolines to Indoles
  作者：Feng Peng、Mark McLaughlin、Yizhou Liu、Ian Mangion、David M. Tschaen、Yingju Xu

  DOI：10.1021/acs.joc.6b01854

  日期：2016.10.21

  A novel method for the oxidation of indolines to indoles is described. The method uses a Cu(I) catalyst and an organic percarbonate as the stoichiometric oxidant. The procedure was successfully applied at 0.5 kg scale in the production of a key intermediate in the synthesis of Elbasvir, which is a novel therapy for the treatment of hepatitis C virus infection.