5-chloro-2-methyl-1-tosyl-1H-indole | 700836-90-4

• 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: 5-chloro-2-methyl-1-tosyl-1H-indole
• 英文别名: 1-(4'-methylbenzenesulfonyl)-5-chloro-2-methyl-1H-indole；5-Chloro-2-methyl-1-(4-methylphenyl)sulfonylindole；5-chloro-2-methyl-1-(4-methylphenyl)sulfonylindole
• CAS: 700836-90-4
• 化学式: C₁₆H₁₄ClNO₂S
• 分子量: 319.812
• InChiKey: DRWYUDKASJYTBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 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：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(2,5-dichlorophenyl)-3-methyl-1-tosylaziridine 在 三氟化硼乙醚 、 苯硫酚 、 铜 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 以70%的产率得到5-chloro-2-methyl-1-tosyl-1H-indole
  参考文献：
  名称：

  A Synthetic Route to 2-Alkyl Indoles via Thiophenol-Mediated Ring-Opening of N-Tosylaziridines Followed by Copper Powder-Mediated C–N Cyclization/Aromatization

  摘要：

  A simple strategy for the syntheses of 2-alkyl indoles via regioselective ring-opening of 2-(2-haloaryl)-3-alkyl-N-tosylaziridines with thiophenol, followed by copper powder-mediated intramolecular C-N cyclization and subsequent aromatization by the elimination of thiophenol, with good yields is described. Utilizing this protocol, 2-carboxyindole has been synthesized easily.

  DOI：

  10.1021/acs.joc.5b02251

文献信息

• Supported palladium nanoparticles-catalyzed decarboxylative coupling approaches to aryl alkynes, indoles and pyrrolines synthesis
  作者：C. Bal Reddy、Richa Bharti、Sandeep Kumar、Pralay Das

  DOI：10.1039/c6ra12046f

  日期：——

  The polystyrene supported palladium (Pd@PS) nanoparticles (NPs) catalyzed decarboxylative coupling (DC) of arylhalides and alkynyl carboxylic acids was developed for the synthesis of diaryl alkynes. Indole and 3-pyrroline heterocycles were also synthesized from 2-iodo anilines/amino benzocycloheptene bromide and alkynyl carboxylic acids, following a domino decarboxylative coupling-cyclization (DCC)

  聚苯乙烯负载的钯（Pd @ PS）纳米粒子（NPs）催化芳基卤化物和炔基羧酸的脱羧偶联（DC）用于合成二芳基炔烃。在相同的催化条件下，按照多米诺脱羧偶联-环化（DCC）方法，还从2-碘苯胺/氨基苯并环庚烯溴化物​​和炔基羧酸合成了吲哚和3-吡咯啉杂环。Pd @ PS的结合锚固和催化性能使该方法有利于产物的形成。
• N-ARYLSULFONYL-3-AMINOALKOXYINDOLES
  申请人：Suven Life Sciences Limited

  公开号：EP1567492B1

  公开（公告）日：2013-05-22
• A Synthetic Route to 2-Alkyl Indoles via Thiophenol-Mediated Ring-Opening of <i>N</i>-Tosylaziridines Followed by Copper Powder-Mediated C–N Cyclization/Aromatization
  作者：Masthanvali Sayyad、Yerramsetti Nanaji、Manas K. Ghorai

  DOI：10.1021/acs.joc.5b02251

  日期：2015.12.18

  A simple strategy for the syntheses of 2-alkyl indoles via regioselective ring-opening of 2-(2-haloaryl)-3-alkyl-N-tosylaziridines with thiophenol, followed by copper powder-mediated intramolecular C-N cyclization and subsequent aromatization by the elimination of thiophenol, with good yields is described. Utilizing this protocol, 2-carboxyindole has been synthesized easily.