3-((4-nitrophenyl)thio)-2-phenyl-1H-indole | 1213786-18-5

• 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: 3-((4-nitrophenyl)thio)-2-phenyl-1H-indole
• 英文别名: 3-(4-nitrophenyl)sulfanyl-2-phenyl-1H-indole
• CAS: 1213786-18-5
• 化学式: C₂₀H₁₄N₂O₂S
• 分子量: 346.409
• InChiKey: PWSIDGVKSWXYLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-苯胺基-1-苯基乙酮 在 三氟甲磺酸 、 碘 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 36.0h， 生成 3-((4-nitrophenyl)thio)-2-phenyl-1H-indole
  参考文献：
  名称：

  Aniline-initiated and BrØnsted acid-catalyzed one-pot reaction toward 2-aryl-3-sulfenylindoles by using α-aminocarbonyl compounds and primary amines with RSSR

  摘要：

  DOI：

  10.1016/j.catcom.2020.106217

文献信息

• Palladium-Catalyzed Annulation of 2-(1-Alkynyl)benzenamines with Disulfides: Synthesis of 3-Sulfenylindoles
  作者：Yan-Jin Guo、Ri-Yuan Tang、Jin-Heng Li、Ping Zhong、Xing-Guo Zhang

  DOI：10.1002/adsc.200900055

  日期：2009.11

  3-Sulfenylindoles can be efficiently prepared in moderate to good yields from 2-(1-alkynyl)benzenamines and disulfides using the palladium/air catalytic systems. The study also provides a useful route to the synthesis of fipronil analogues.

  使用钯/空气催化系统，可以由2-（1-炔基）苯胺和二硫化物有效地以中等到良好的产率制备3-亚磺酰基吲哚。该研究还提供了合成氟虫腈类似物的有用途径。
• Metal-Free Synthesis of 3-Sulfenylindoles via an Iodine-Mediated Electrophilic Cyclisation of 2-Alkynylanilines with Disulfides
  作者：Li-Ming Tao、Wen-Qi Liu、Yun Zhou、Ai-Tao Li

  DOI：10.3184/174751912x13467835639963

  日期：2012.11

  An efficient and metal-free method was developed to synthesise 3-sulfenylindoles via the iodine-mediated electrophilic cyclisation of 2-alkynylanilines with disulfides. In the presence of I₂, various 3-sulfenylindoles were obtained in moderate to high yields.

  通过碘介导的 2-炔基苯胺与二硫化物的亲电环化反应，开发了一种合成 3-亚磺酰基吲哚的高效无金属方法。在 I2 的存在下，以中等到较高的产率获得了各种 3-亚磺酰基吲哚。
• Microwave assisted metal-/oxidant-free cascade electrophilic sulfenylation/5-endo-dig cyclization of 2-alkynylanilines to generate diversified 3-sulfenylindoles
  作者：Shivani Sharma、Ramdas S. Pathare、Sukanya、Antim K. Maurya、Bhagyashree Goswami、Vijai K. Agnihotri、Devesh M. Sawant、Ram T. Pardasani

  DOI：10.1016/j.tetlet.2017.08.046

  日期：2017.10

  A metal-/oxidant-free sustainable protocol for the synthesis of 3-sulfenylindoles based on electrophilic cyclization of 2-alkynylanilines has been developed under microwave irradiation. Herein, catalytic amount of iodine and stoichiometric amount of sulfonyl hydrazides were employed as catalyst and electrophiles respectively to induce the 5-endo-dig cyclization of 2-alkynylanilines. This strategy allows a wide substrate scope, demonstrates good functional group tolerance, utilizes easily available reagents and overcome multistep synthesis. (C) 2017 Elsevier Ltd. All rights reserved.
• Aniline-initiated and BrØnsted acid-catalyzed one-pot reaction toward 2-aryl-3-sulfenylindoles by using α-aminocarbonyl compounds and primary amines with RSSR
  作者：Yuxuan Liu、De Chen、Chaozhihui Cheng、Wenjian Guan、Yongyue Luo、Jiajia Zhang、Wei Deng、Jiannan Xiang

  DOI：10.1016/j.catcom.2020.106217

  日期：2021.1