1-allyl-1H-indole-2-carbonitrile | 1448448-63-2

• 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: 1-allyl-1H-indole-2-carbonitrile
• 英文别名: 1-Prop-2-enylindole-2-carbonitrile
• CAS: 1448448-63-2
• 化学式: C₁₂H₁₀N₂
• 分子量: 182.225
• InChiKey: PONOFKJHUJPQEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-allyl-1H-indole-2-carbonitrile 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 以60%的产率得到1-(prop-1-enyl)-1H-indole-2-carbonitrile
  参考文献：
  名称：

  Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (±)-debromoarborescidine B

  摘要：

  Double bond migration in N-allylindoles has been investigated as a method to access N-vinyl derivatives of this heterocycle. The optimal reaction conditions employed t-BuOK or NaH in DMSO as the solvent at room temperature to afford the products in yields ranging from 51 to 99%. Although in some cases a high degree of stereoselectivity was observed, preferential formation of either the Z- or E-isomer was not predictable. The developed methodology was employed in the synthesis of (+/-)-debromoarborescidine B. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.069
• 作为产物：
  描述：

  1-烯丙基-1H-吲哚 、 三甲基氰硅烷 在 三(4-溴苯基)胺 、 tetrabutylammonium tetrafluoroborate 、 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 2.5h， 以62%的产率得到1-allyl-1H-indole-2-carbonitrile
  参考文献：
  名称：

  Site-Selective Electrochemical C–H Cyanation of Indoles

  摘要：

  DOI：

  10.1021/acs.orglett.1c02063

文献信息

• Acylated indole derivatives, processes for their preparation and pharmaceutical compositions and drugs comprising them
  申请人：TEIJIN LIMITED

  公开号：EP0022634B1

  公开（公告）日：1983-04-06
• Site-Selective Electrochemical C–H Cyanation of Indoles
  作者：Laiqiang Li、Zhong-Wei Hou、Pinhua Li、Lei Wang

  DOI：10.1021/acs.orglett.1c02063

  日期：2021.8.6
• Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (±)-debromoarborescidine B
  作者：Gordana Tasic、Milena Simic、Stanimir Popovic、Suren Husinec、Veselin Maslak、Vladimir Savic

  DOI：10.1016/j.tetlet.2013.06.069

  日期：2013.8

  Double bond migration in N-allylindoles has been investigated as a method to access N-vinyl derivatives of this heterocycle. The optimal reaction conditions employed t-BuOK or NaH in DMSO as the solvent at room temperature to afford the products in yields ranging from 51 to 99%. Although in some cases a high degree of stereoselectivity was observed, preferential formation of either the Z- or E-isomer was not predictable. The developed methodology was employed in the synthesis of (+/-)-debromoarborescidine B. (C) 2013 Elsevier Ltd. All rights reserved.