2-methyl-3-(4-methylphenylsulfonyl)-1H-indole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methyl-3-(4-methylphenylsulfonyl)-1H-indole
• 英文别名: 2-methyl-3-tosyl-1H-indole；2-methyl-3-(p-tolylsulfonyl)-1H-indole；2-methyl-3-(4-methylphenyl)sulfonyl-1H-indole
• 化学式: C₁₆H₁₅NO₂S
• 分子量: 285.367
• InChiKey: CRPZOZNEHYPSQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲基吲哚 、 对甲苯磺酰氯 在 indium(III) bromide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.5h， 以93%的产率得到2-methyl-3-(4-methylphenylsulfonyl)-1H-indole
  参考文献：
  名称：

  InBr 3催化的吲哚磺化：3-磺酰基吲哚的简便合成

  摘要：

  吲哚在环境温度下在催化量的三溴化铟存在下与磺酰氯平稳反应，以高收率和高区域选择性提供相应的3-芳基磺酰基吲哚衍生物。

  DOI：

  10.1016/s0040-4039(03)01507-7

文献信息

• The fast and efficient KI/H₂O₂ mediated 2-sulfonylation of indoles and <i>N</i>-methylpyrrole in water
  作者：Jun Zhang、Zhong Wang、Lingjuan Chen、Yan Liu、Ping Liu、Bin Dai

  DOI：10.1039/c8ra09367a

  日期：——

  The rapid and efficient KI/H2O2-mediated 2-sulfonylation of substituted indoles and N-methylpyrrole was established. The corresponding 2-sulfonylation products are synthesized from readily available sulfur sources, namely arylsulfonyl hydrazides, 4-methylbenzenesulfinic acid and sodium 4-methylbenzenesulfinate in good to excellent yields in only 5 min. Moreover, the aqueous solution of hydrogen peroxide

  建立了快速高效的KI/H 2 O 2介导的取代吲哚和N-甲基吡咯的2-磺酰化反应。相应的 2-磺酰化产物是由容易获得的硫源，即芳基磺酰肼、4-甲基苯亚磺酸和 4-甲基苯亚磺酸钠在 5 分钟内以良好至优异的产率合成的。此外，过氧化氢水溶液既用作氧化剂又用作溶剂。机理研究表明，2,3-二碘二氢吲哚是主要的磺酰化中间体。
• Catalyst-Controlled Selectivity in C−S Bond Formation: Highly Efficient Synthesis of C2- and C3-Sulfonylindoles
  作者：Yong Yang、Wanmei Li、Chengcai Xia、Beibei Ying、Chao Shen、Pengfei Zhang

  DOI：10.1002/cctc.201500917

  日期：2016.1

  Exploring a potential catalyst system for catalyst‐controlled selectivity in C−S bond formation is a fascinating challenge. Herein, we described two novel and highly efficient methods for the selective synthesis of C2‐ and C3‐sulfonylindoles showing good biological activities by employing iodide and copper catalysts, respectively. Mechanistic studies point to the crucial role of the electronic properties

  探索潜在的催化剂体系，以在CS键的形成中控制催化剂的选择性是一项引人入胜的挑战。在本文中，我们描述了两种新颖高效的方法，分别通过使用碘化物和铜催化剂选择性合成具有良好生物活性的C2和C3磺酰吲哚。机理研究指出了磺酰化中间体的电子性质的关键作用。
• Temperature Controlled Selective C–S or C–C Bond Formation: Photocatalytic Sulfonylation versus Arylation of Unactivated Heterocycles Utilizing Aryl Sulfonyl Chlorides
  作者：Santosh K. Pagire、Asik Hossain、Oliver Reiser

  DOI：10.1021/acs.orglett.7b03790

  日期：2018.2.2

  A visible-light-induced photocatalytic method for the arylsulfonylation of heterocycles has been developed. The synthetic utility of this reaction is reflected by the direct use of commercially available sulfonyl chlorides and heterocycles under room temperature conditions. Complementarily, the photocatalytic arylation of heterocycles by sulfonyl chlorides via extrusion of SO2 is feasible at elevated

  已经开发了可见光诱导的杂环芳基磺酰化的光催化方法。该反应的合成效用通过在室温条件下直接使用市售的磺酰氯和杂环来反映。补充地，在升高的温度条件下，通过磺酰氯通过挤出SO 2进行杂环的光催化芳基化是可行的，从而允许在芳基磺酰化或芳基磺酰化之间进行切换，并具有优异的化学选择性。
• Fe-pillared bentonite—an efficient catalyst for sulfonylation of arenes using aryl and alkyl sulfonyl chlorides
  作者：Devendrapratap U. Singh、Pankajkumar R. Singh、Shriniwas D. Samant

  DOI：10.1016/j.tetlet.2004.10.039

  日期：2004.11

  Fe-pillared bentonite (Fe-PILC) was shown to be an extremely efficient catalyst for the sulfonylation of activated as well as unactivated carbocyclic aromatic compounds and heterocyclic aromatic compounds. The catalyst was also found to be recyclable. (C) 2004 Elsevier Ltd. All rights reserved.
• ZnO-mediated regioselective C-arylsulfonylation of indoles: a facile solvent-free synthesis of 2- and 3-sulfonylindoles and preliminary evaluation of their activity against drug-resistant mutant HIV-1 reverse transcriptases (RTs)
  作者：Graziella Tocco、Michela Begala、Francesca Esposito、Pierluigi Caboni、Valeria Cannas、Enzo Tramontano

  DOI：10.1016/j.tetlet.2013.09.017

  日期：2013.11

  A ZnO-mediated one-pot solvent-free protocol for the regioselective C-arylsulfonylation of indoles is described and some novel derivatives were tested on wild type and non-nucleoside inhibitor resistant K103N and Y181C HIV-1 reverse transcriptases (RTs). (C) 2013 Elsevier Ltd. All rights reserved.