(E)-2-(4-nitrostyryl)aniline

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-2-(4-nitrostyryl)aniline
• 英文别名: 2-[(E)-2-(4-nitrophenyl)ethenyl]aniline
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: PRWKRSVNKQLMBN-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(4-nitrostyryl)aniline 在 吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 三氯乙烷 为溶剂， 反应 26.0h， 生成 2-(4-nitrophenyl)-1-tosyl-1H-indole
  参考文献：
  名称：

  Metal-Free C–H Amination for Indole Synthesis

  摘要：

  An effective metal-free C-H amination of N-Ts-2-alkenylanilines by using DDQ as an oxidant has been developed to afford a diverse range of substituted indoles. This protocol is operationally simple and robust, obviates the need of expensive transition-metal catalysts, and offers a broad substrate scope. A mechanism involving a radical cation generated by SET and a migratorial process via a phenonium ion intermediate is proposed.

  DOI：

  10.1021/ol5015398
• 作为产物：
  描述：

  4-硝基苯乙烯 、 2-溴苯胺 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以49%的产率得到(E)-2-(4-nitrostyryl)aniline
  参考文献：
  名称：

  Bi(OTf) 3 -mediated intramolecular hydroamination of 2-aminostilbenes for the synthesis of 2-arylindolines

  摘要：

  An efficient Bi(OTf)(3)-mediated intramolecular hydroamination of 2-aminostilbenes for the synthesis of various 2-arylindolines has been developed. Various advantages using Bi(OTf)(3) as a catalyst, such as the operationally easy, simple, and safe procedure, good to excellent chemical yields, and the use of relatively low catalyst loading are noteworthy. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.06.063

文献信息

• Synthesis of 3-Selenylindoles through Organoselenium-Promoted Selenocyclization of 2-Vinylaniline
  作者：Zhiwei Zhao、Yetong Zhang、Yinlin Shao、Wenzhang Xiong、Renhao Li、Jiuxi Chen

  DOI：10.1021/acs.joc.0c01918

  日期：2020.12.4

  synthetic route could be readily scaled up to gram quantity without difficulty. Mechanistic studies have revealed that in situ formed selenium electrophile species may be the key intermediate for the selenocyclization process.

  已经开发了一种新颖的无金属一锅方案，该方案通过简单的2-乙烯基苯胺通过分子内环化/硒化反应合成潜在的生物活性分子3-硒基吲哚，具有中等至良好的收率，因此代表了它是通往多种取代模式的便捷途径围绕吲哚核。反应在宽的底物范围和优异的官能团耐受性下顺利进行。而且，本合成路线可以容易地按比例放大至克量而没有困难。机理研究表明，原位形成的硒亲电物种可能是硒环化过程的关键中间体。
• Bi(OTf) 3 -mediated intramolecular hydroamination of 2-aminostilbenes for the synthesis of 2-arylindolines
  作者：So Won Youn、Su San Jang、So Ra Lee

  DOI：10.1016/j.tet.2016.06.063

  日期：2016.8

  An efficient Bi(OTf)(3)-mediated intramolecular hydroamination of 2-aminostilbenes for the synthesis of various 2-arylindolines has been developed. Various advantages using Bi(OTf)(3) as a catalyst, such as the operationally easy, simple, and safe procedure, good to excellent chemical yields, and the use of relatively low catalyst loading are noteworthy. (C) 2016 Elsevier Ltd. All rights reserved.
• Metal-Free C–H Amination for Indole Synthesis
  作者：Young Ho Jang、So Won Youn

  DOI：10.1021/ol5015398

  日期：2014.7.18

  An effective metal-free C-H amination of N-Ts-2-alkenylanilines by using DDQ as an oxidant has been developed to afford a diverse range of substituted indoles. This protocol is operationally simple and robust, obviates the need of expensive transition-metal catalysts, and offers a broad substrate scope. A mechanism involving a radical cation generated by SET and a migratorial process via a phenonium ion intermediate is proposed.
• Discovery of styrylaniline derivatives as novel alpha-synuclein aggregates ligands
  作者：Jiang Bian、Yi-Qi Liu、Jie He、Xin Lin、Chen-Yang Qiu、Wen-Bo Yu、Yan Shen、Ze-Yun Zhu、De-Yong Ye、Jian Wang、Yong Chu

  DOI：10.1016/j.ejmech.2021.113887

  日期：2021.12