2-n-butyl-1H-indole-3-carbonitrile | 1397290-24-2

• 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-n-butyl-1H-indole-3-carbonitrile
• 英文别名: 2-butyl-1H-indole-3-carbonitrile
• CAS: 1397290-24-2
• 化学式: C₁₃H₁₄N₂
• 分子量: 198.268
• InChiKey: OHIHCNZNKGRJBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  39.58
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  异氰酸叔丁酯 、 2-butyl-1H-indole 在 palladium diacetate 、 copper(II) trifluoroacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以51%的产率得到2-n-butyl-1H-indole-3-carbonitrile
  参考文献：
  名称：

  Palladium-Catalyzed C(sp²)–H Cyanation Using Tertiary Amine Derived Isocyanide as a Cyano Source

  摘要：

  An unprecedented palladium-catalyzed cyanation of aromatic C-H bonds by using tertiary amine derived isocyanide as a novel cyano source was developed. Cu(TFA)(2) was used as a requisite stoichiometric oxidant. Mechanistic studies suggest that a tertiary carbon cation-based intermediate Is involved following the C-N bond breakage.

  DOI：

  10.1021/ol302372p

文献信息

• Copper-catalyzed tandem intramolecular cyclization/coupling reaction: solvent effect on reaction pathway
  作者：Mitsuaki Yamashita、Toshiaki Noro、Akira Iida

  DOI：10.1016/j.tetlet.2013.10.012

  日期：2013.12

  In this study, we developed direct methods for the synthesis of 3-substituted indoles from o-allcynylan-ilines by utilizing a copper-catalyzed tandem intramolecular cyclization/coupling reaction under mild and simple reaction conditions. Our investigation revealed that choice of the aprotic polar solvents and additives such as camphorsulfonic acid is critical in this reaction. (C) 2013 Elsevier Ltd. All rights reserved.