1-benzyl-5-methyl-1H-indole-3-carbonitrile | 1334159-63-5

• 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-benzyl-5-methyl-1H-indole-3-carbonitrile
• 英文别名: 1-Benzyl-5-methyl-1H-indole-3-carbonitrile；1-benzyl-5-methylindole-3-carbonitrile
• CAS: 1334159-63-5
• 化学式: C₁₇H₁₄N₂
• 分子量: 246.312
• InChiKey: UITXDGRVLOIIDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  461.3±33.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 1-benzyl-5-methyl-1H-indole 在 copper(l) iodide 、 氧气 、 三氟乙酸 作用下， 130.0 ℃ 、101.33 kPa 条件下， 反应 96.0h， 以60%的产率得到1-benzyl-5-methyl-1H-indole-3-carbonitrile
  参考文献：
  名称：

  Copper-mediated selective aerobic oxidative C3-cyanation of indoles with DMF

  摘要：

  Under an oxygen atmosphere, the copper-mediated direct C3-cyanation of indole C-H bonds, using cheap and safe DMF as a CN source, took place selectively to produce the corresponding C3-cyanoindoles in good yields. A possible mechanism for this selective cyanation was proposed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.09.044

文献信息

• Lewis Acid Catalyzed Direct Cyanation of Indoles and Pyrroles with <i>N</i>-Cyano-<i>N</i>-phenyl-<i>p</i>-toluenesulfonamide (NCTS)
  作者：Yang Yang、Yan Zhang、Jianbo Wang

  DOI：10.1021/ol202335p

  日期：2011.10.21

  BF3·OEt2-catalyzed direct cyanation of indoles and pyrroles using a less toxic, bench-stable, and easily handled electrophilic cyanating agent N-cyano-N-phenyl-para-toluenesulfonamide (NCTS) affords 3-cyanoindoles and 2-cyanopyrroles in good yields with excellent regioselectivity. The substrate scope is broad with respect to indoles and pyrroles.

  BF 3 ·OEt 2使用毒性较小，稳定且易于处理的亲电子氰化剂，将吲哚和吡咯直接氰化N-氰基-N-苯基-对甲苯磺酰胺（NCTS）可提供3-氰基吲哚和2-氰基吡咯产量高，区域选择性好。关于吲哚和吡咯，底物范围很广。
• Synthesis of 3-Cyanoindole Derivatives Mediated by Copper(I) Iodide Using Benzyl Cyanide
  作者：On Ying Yuen、Pui Ying Choy、Wing Kin Chow、Wing Tak Wong、Fuk Yee Kwong

  DOI：10.1021/jo3028278

  日期：2013.4.5

  Copper-mediated direct and regioselective C3-cyanation of indoles using benzyl cyanide as the cyanide anion source is presented. A wide range of indoles undergo cyanation smoothly by employing a reaction system of copper(I) iodide under open-to-air vessels.

  提出了使用苄基氰化物作为氰化物阴离子源的铜介导的吲哚的直接和区域选择性C3-氰化反应。通过在露天容器下使用碘化亚铜（I）的反应系统，各种吲哚都能顺利进行氰化。
• Copper-mediated selective aerobic oxidative C3-cyanation of indoles with DMF
  作者：Jing Xiao、Qiang Li、Tieqiao Chen、Li-Biao Han

  DOI：10.1016/j.tetlet.2015.09.044

  日期：2015.10

  Under an oxygen atmosphere, the copper-mediated direct C3-cyanation of indole C-H bonds, using cheap and safe DMF as a CN source, took place selectively to produce the corresponding C3-cyanoindoles in good yields. A possible mechanism for this selective cyanation was proposed. (C) 2015 Elsevier Ltd. All rights reserved.