2-(4-nitrophenyl)-1-tosyl-1H-indole

• 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-(4-nitrophenyl)-1-tosyl-1H-indole
• 英文别名: N-Ts-2-(4-nitrophenyl)indole；1-(4-Methylphenyl)sulfonyl-2-(4-nitrophenyl)indole；1-(4-methylphenyl)sulfonyl-2-(4-nitrophenyl)indole
• 化学式: C₂₁H₁₆N₂O₄S
• 分子量: 392.435
• InChiKey: LASKWOAGXRFAQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  93.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-硝基苯乙烯 在 吡啶 、 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 、 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

文献信息

• Silver(I)-Mediated CH Amination of 2-Alkenylanilines: Unique Solvent-Dependent Migratory Aptitude
  作者：So Won Youn、Tae Yun Ko、Min Jung Jang、Su San Jang

  DOI：10.1002/adsc.201400759

  日期：2015.1.12

  A highly effective silver(I)‐mediated CH amination of 2‐alkenylanilines has been developed to afford a diverse range of substituted indoles. High functional group tolerance, broad substrate scope, simple/fast/high‐yielding reaction, and recovery/reuse of the inexpensive silver oxidant are noteworthy. Furthermore, an uncommon migratory process of β‐monosubstituted 2‐alkenylanilines with solvent‐dependence

  已开发出一种高效的银（I）介导的2-烯基苯胺的CH胺化反应，以提供各种取代的吲哚。值得注意的是，高官能团耐受性，广泛的底物范围，简单/快速/高产率的反应以及廉价的银氧化剂的回收/再利用。此外，还证明了具有溶剂依赖性的β-单取代2-烯基苯胺的不常见迁移过程。
• “Quick and click” assembly of functionalised indole rings via metal-promoted cyclative tandem reactions
  作者：Francesca Capitta、Lidia De Luca、Andrea Porcheddu

  DOI：10.1039/c4ra12000k

  日期：——

  An efficient and convenient synthesis of a variety of decorated indoles using a three-component tandem metal-catalysed process is described.

  描述了一种高效且方便的合成多种修饰吲哚的方法，该方法使用了三组分串联金属催化过程。
• Unusual 1,2-aryl migration in Pd(<scp>ii</scp>)-catalyzed aza-Wacker-type cyclization of 2-alkenylanilines
  作者：So Won Youn、So Ra Lee

  DOI：10.1039/c5ob00361j

  日期：——

  Hegedus aza-Wacker indole synthesis, we were intrigued with the fate of the aminopalladation intermediate if syn β-hydrogen is made inaccessible or unavailable. In contrast to our previously reported β-carbon elimination, cyclization of a variety of 2-alkenylaniline substrates under electrophilic palladium conditions unexpectedly afforded C3-substituted indoles. This unusual 1,2-migratory process was

  受Hegedus aza-Wacker吲哚合成的启发，如果无法获得或无法获得顺式β-氢，我们会对氨基palpalation中间体的命运深感兴趣。与我们先前报道的β-碳消除相反，在亲电钯条件下，各种2-链烯基苯胺底物的环化出乎意料地提供了C3取代的吲哚。发现这种异常的1,2-迁移过程可在各种底物上以可预测的迁徙能力进行操作。提出了机械建议以合理化所观察到的底物依赖性，并且该意外发现可以为其他相关工艺提供机会。
• The cooperative FeCl₃/DDQ system for the regioselective synthesis of 3-arylindoles from β-monosubstituted 2-alkenylanilines
  作者：Su San Jang、So Won Youn

  DOI：10.1039/c6ob00074f

  日期：——

  A highly regioselective synthesis of 3-arylindoles by using the cooperative FeCl3/DDQ system has been developed. This new protocol represents an attractive route for the synthesis of 3-arylindoles from readily accessible non-indole precursors, β-aryl-substituted 2-styrylanilines, using an inexpensive catalyst and oxidant. Noteworthy is the unique synergetic and synergistic effect of FeCl3 and DDQ on

  已经开发了通过使用FeCl 3 / DDQ协同系统的高区域选择性合成3-芳基吲哚的方法。该新方案代表了使用廉价的催化剂和氧化剂由易于获得的非吲哚前体（β-芳基取代的2-苯乙烯基苯胺）合成3-芳基吲哚的诱人途径。值得注意的是FeCl 3和DDQ对1,2-芳基迁移过程的独特协同作用。
• Tandem Phospha‐Michael Addition/ <i>N</i> ‐Acylation/ Intramolecular Wittig Reaction of aza‐ <i>o</i> ‐Quinone Methides: Approaches to 2,3‐Disubstituted Indoles
  作者：Ting‐Bi Hua、Fei Chao、Long Wang、Chen‐Yang Yan、Cong Xiao、Qing‐Qing Yang、Wen‐Jing Xiao

  DOI：10.1002/adsc.202000343

  日期：2020.7.16

  A tandem phospha‐Michael addition/N‐acylation/intramolecular Wittig reaction of in situ formed aza‐o‐QMs is disclosed. This approach features high functional group tolerance and provides a convenient and practical access to biologically significant indole derivatives (37 examples, up to 91% yield) under mild reaction conditions.

  一种串联磷迈克尔加成/ Ñ酰化分子内形成的原位Wittig反应氮杂/ ö -QMs中公开。该方法具有高度的官能团耐受性，在温和的反应条件下，可方便实用地获得生物学上重要的吲哚衍生物（37个实例，产率高达91％）。