2,3-diphenyl-1-tosyl-1H-indole | 135190-00-0

• 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: 2,3-diphenyl-1-tosyl-1H-indole
• 英文别名: N-Ts-2,3-diphenylindole；1-((4-Methylphenyl)sulfonyl)-2,3-diphenyl-1H-indole；1-(4-methylphenyl)sulfonyl-2,3-diphenylindole
• CAS: 135190-00-0
• 化学式: C₂₇H₂₁NO₂S
• 分子量: 423.535
• InChiKey: REJLZBHFAFIOFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(2,2-diphenylvinyl)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 2,3-diphenyl-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。
• Palladium-Catalyzed Sequential Vinylic C–H Arylation/Amination of 2-Vinylanilines with Aryl boronic Acids: Access to 2-Arylindoles
  作者：Ruixia Yu、Dejun Li、Fanlong Zeng

  DOI：10.1021/acs.joc.7b02728

  日期：2018.1.5

  A palladium-catalyzed selective and successive vinylic C–H arylation/amination of 2-vinylanilines with arylboronic acids to generate indoles has been developed. This procedure represents a straightforward and practical approach to valuable multifunctionalized indoles.

  已开发出钯催化的2-乙烯基苯胺与芳基硼酸的选择性和连续乙烯基C–H芳基化/胺化反应，生成吲哚。该程序代表了一种有价值的多功能吲哚的直接而实用的方法。
• “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。
• Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles
  作者：Chun-Yang Zhao、Kun Li、Yu Pang、Jia-Qing Li、Cui Liang、Gui-Fa Su、Dong-Liang Mo

  DOI：10.1002/adsc.201701551

  日期：2018.5.16

  A variety of 3‐substituted and 2,3‐disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2‐alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3‐acetoxy indoline was the key intermediate in the indole formation. The indole

  通过在很短的反应时间内即可获得的碘（III）试剂促进的2-烯基苯胺的分子内胺化反应，可以高收率高效合成各种3-取代和2,3-二取代的吲哚。机理研究表明，反应路径通过一个氮离子，3-乙酰氧基吲哚是吲哚形成的关键中间体。吲哚产物很容易以克为单位制备，并且在m CPBA存在下，使用催化的3,5-二甲基苯基碘也可以顺利进行胺化反应。此外，吲哚并[3,2-a]咔唑支架的制备要比市售邻碘碘苯胺分6步高收率。
• 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。