2-(tert-butyl)-1H-indole-3-carbonitrile

• 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: 2-(tert-butyl)-1H-indole-3-carbonitrile
• 英文别名: 2-tert-butyl-1H-indole-3-carbonitrile
• 化学式: C₁₃H₁₄N₂
• mdl: MFCD09722956
• 分子量: 198.268
• InChiKey: GZMLREZSXZOPPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-氰基吲哚 、 S-tert-butyl O-ethyl carbonodithioate 在 过氧化双月桂酰 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以63%的产率得到2-(tert-butyl)-1H-indole-3-carbonitrile
  参考文献：
  名称：

  Xanthate-Mediated Incorporation of Quaternary Centers into Heteroarenes

  摘要：

  The xanthate-mediated addition of tertiary alkyl radicals to heteroarenes enabled the easy functionalization of heteroaromatic rings as well as more decorated structures, such as marketed drugs or agrochemicals. This work provides a synthetic tool for efficiently exploring the chemical space by allowing late-stage diversification with a high tolerance toward functional groups.

  DOI：

  10.1021/acs.orglett.8b01299

文献信息

• Efficient solid-phase synthesis of 2,3-substituted indoles
  作者：Dean A Wacker、Padmaja Kasireddy

  DOI：10.1016/s0040-4039(02)01025-0

  日期：2002.7

  The development of the solid-phase version of the modified Madelung indole synthesis is reported. The chemistry was initiated with the reductive amination of Bal resin using an ortho substituted aniline. The resin bound aniline was acylated with a variety of acid chlorides followed by cyclization with base to provide the desired indole after TFA-promoted cleavage from the resin. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Xanthate-Mediated Incorporation of Quaternary Centers into Heteroarenes
  作者：Vincent L. Revil-Baudard、Jean-Pierre Vors、Samir Z. Zard

  DOI：10.1021/acs.orglett.8b01299

  日期：2018.6.15

  The xanthate-mediated addition of tertiary alkyl radicals to heteroarenes enabled the easy functionalization of heteroaromatic rings as well as more decorated structures, such as marketed drugs or agrochemicals. This work provides a synthetic tool for efficiently exploring the chemical space by allowing late-stage diversification with a high tolerance toward functional groups.