2-(2-bromo-1N-methyl-1H-indol-3-yl)acetonitrile | 1215114-74-1

• 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-(2-bromo-1N-methyl-1H-indol-3-yl)acetonitrile
• 英文别名: 2-(2-bromo-N-methyl-1H-3-indolyl)acetonitrile；2-(2-bromo-1-methylindol-3-yl)acetonitrile
• CAS: 1215114-74-1
• 化学式: C₁₁H₉BrN₂
• 分子量: 249.11
• InChiKey: SNUOWTWFMSVERN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  28.72
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(2-bromo-1N-methyl-1H-indol-3-yl)acetonitrile 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of N-Functionalized/NH-Multisubstituted Indoles, Thienopyrroles, Pyrroloindoles, and Pyrazolopyrroles via Sequential One-Pot Base-Mediated and Copper-Catalyzed Inter- and Intramolecular Amination of 2-[2-Bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitriles

  摘要：

  A novel, efficient route to substituted 1-N-(het)aryl/NH-2-(het)aryl-3-cyanoindoles and related pyrrolo-fused heterocycles such as thienopyrroles, pyrroloindoles, and pyrazolopyrroles has been reported. The overall protocol involves sequential cycloamination of readily available 2-[2-bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitrile precursors with primary amines or amides via two key C-N bond-forming processes, one base-mediated intermolecular and the other Cu-catalyzed intramolecular arylamination leading to N(1)-C(2) and N(1)-C(7a) bond formation, respectively, in a two-step one-pot procedure.

  DOI：

  10.1021/jo501114a

文献信息

• One-Pot Synthesis of Functionalized Benzo[<i>b</i>]thiophenes and Their Hetero-Fused Analogues via Intramolecular Copper-Catalyzed S-Arylation of In Situ Generated Enethiolates
  作者：Anand Acharya、S. Vijay Kumar、B. Saraiah、H. Ila

  DOI：10.1021/acs.joc.5b00032

  日期：2015.3.6

  An efficient one-pot synthesis of highly functionalized multisubstituted benzo[b]thiophenes and their hetero-fused analogues, such as thieno[2,3-b]thiophenes, indolo[2,3-b]thiophenes, and pyrazolo[3,2-c]thiophenes, has been reported. The overall strategy involves sequential base-mediated condensation of 2-bromohet(aryl)acetonitrile precursors with (het)aryl/alkyl dithioesters or other thiocarbonyl

  高效一锅合成高官能度的多取代苯并[ b ]噻吩及其杂合类似物，如噻吩并[2,3- b ]噻吩，吲哚并[2,3- b ]噻吩和吡唑并[3,2] - ç ]噻吩，已有报道。总体策略涉及2-溴己基（芳基）乙腈前体与（杂）芳基/烷基二硫代酯或其他硫代羰基化合物如三硫代碳酸二甲酯，S-甲基黄原酸酯，N-咪唑基二硫代甲基酯，N-烷基二硫代氨基甲酸酯和苯基异硫氰酸酯，然后分子内铜催化的原位生成的烯硫醇酯的芳硫基化，以高收率提供了各种2-官能化的3-氰基苯并[ b ]-和/或杂稠噻吩。
• Synthesis of Novel Substituted Phenanthrenes and Polycyclic Heteroarenes by Pd-Catalyzed, Direct, Intramolecular Arylation/Heteroarylation
  作者：Ashok K. Yadav、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1002/ejoc.200901036

  日期：2010.1

  A novel route to substituted phenanthrenes and polycyclic heteroarenes by direct, Pd-catalyzed, intramolecular arylation/heteroarylation of 2-(2-bromoaryl/heteroaryl)-3-(aryl/heteroaryl)-3-(methylthio)acrylonitriles has been reported.

  已经报道了通过 2-(2-溴芳基/杂芳基)-3-(芳基/杂芳基)-3-(甲硫基)丙烯腈的直接、Pd 催化、分子内芳基化/杂芳基化制备取代菲和多环杂芳烃的新途径。
• A Novel Radical Cyclization Approach to Thieno-Fused Heterocycles
  作者：Prabal P. Singh、Ashok K. Yadav、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1002/ejoc.201100516

  日期：2011.7

  efficient synthesis of novel aryl/heteroaryl-substituted thieno-fused heterocycles, that is, thieno[2,3-b]thiophenes, thieno[2,3-b]indoles, and pyrazolo[3,2-c]thiophenes, involving radical-mediated cyclization of 2-(2-bromoheteroaryl)-3-methylthio-3-aryl/heteroaryl acrylonitriles has been reported.

  高效合成新型芳基/杂芳基取代的噻吩并稠合杂环，即噻吩并[2,3-b]噻吩、噻吩并[2,3-b]吲哚和吡唑并[3,2-c]噻吩，包括已经报道了 2-(2-溴杂芳基)-3-甲硫基-3-芳基/杂芳基丙烯腈的自由基介导的环化。