3-(phenylthio)-1-tosylindoline | 1429656-41-6

• 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: 3-(phenylthio)-1-tosylindoline
• 英文别名: 1-(4-Methylphenyl)sulfonyl-3-phenylsulfanyl-2,3-dihydroindole；1-(4-methylphenyl)sulfonyl-3-phenylsulfanyl-2,3-dihydroindole
• CAS: 1429656-41-6
• 化学式: C₂₁H₁₉NO₂S₂
• 分子量: 381.519
• InChiKey: ZVMHRFWGLYNSHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(2-(2-bromophenyl)-2-(phenylthio)ethyl)-4-methylbenzenesulfonamide 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以90%的产率得到3-(phenylthio)-1-tosylindoline
  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

• Synthetic Route to Chiral Indolines via Ring-Opening/C–N Cyclization of Activated 2-Haloarylaziridines
  作者：Manas K. Ghorai、Y. Nanaji

  DOI：10.1021/jo400287a

  日期：2013.4.19

  A practical approach for the synthesis of 3-substituted indolines via regio- and stereoselective S(N)2-type ring opening of 2-(2-halophenyl)-N-tosylaziridines with heteroatomic nucleophiles (O, N, and S) followed by palladium catalyzed intramolecular C-N cyclization is reported in excellent yields (up to >99%) and enantiomeric excess (ee 99%)
• 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.