N-[(1S,2S)-2-chlorocyclopentyl]-4-methylbenzenesulfonamide

• 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: N-[(1S,2S)-2-chlorocyclopentyl]-4-methylbenzenesulfonamide
• 化学式: C₁₂H₁₆ClNO₂S
• 分子量: 273.784
• InChiKey: YFHNKAAHIKQLST-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-tosyl-6-azabicyclo[3.1.0]hexane 在 三甲基氯硅烷 、 三甲基硅醇 、 C₄₉H₄₀N₅O₃⁽¹⁺⁾*Cl^(1-) 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 N-((1R,2R)-2-Chloro-cyclopentyl)-4-methyl-benzenesulfonamide 、 N-[(1S,2S)-2-chlorocyclopentyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Catalytic Asymmetric Ring Openings of Meso and Terminal Aziridines with Halides Mediated by Chiral 1,2,3-Triazolium Silicates

  摘要：

  Catalytic asymmetric chloride and bromide ring openings of meso aziridines with trimethylsilyl halides have been developed using modular chiral 1,2,3-triazolium chlorides as catalysts. Control experiments suggest the reaction pathway involving hypervalent silicate ions as reactive intermediates. The application of this system to the efficient kinetic resolution of terminal aziridines is also reported.

  DOI：

  10.1021/ja3028668

文献信息

• Catalytic Asymmetric Ring Openings of Meso and Terminal Aziridines with Halides Mediated by Chiral 1,2,3-Triazolium Silicates
  作者：Kohsuke Ohmatsu、Yuta Hamajima、Takashi Ooi

  DOI：10.1021/ja3028668

  日期：2012.5.30

  Catalytic asymmetric chloride and bromide ring openings of meso aziridines with trimethylsilyl halides have been developed using modular chiral 1,2,3-triazolium chlorides as catalysts. Control experiments suggest the reaction pathway involving hypervalent silicate ions as reactive intermediates. The application of this system to the efficient kinetic resolution of terminal aziridines is also reported.