trans-1-Benzoylamino-2-chlor-cyclohexan | 1180536-79-1

• 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: trans-1-Benzoylamino-2-chlor-cyclohexan
• 英文别名: (1R,2R)-N-(2-chlorocyclohexyl)benzamide；N-[(1R,2R)-2-chlorocyclohexyl]benzamide
• CAS: 1180536-79-1
• 化学式: C₁₃H₁₆ClNO
• 分子量: 237.729
• InChiKey: ULDPPCLUGPGBJJ-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-tert-butyl-N-[(1R,2R)-2-chlorocyclohexyl]benzenesulfonamide 在 氢溴酸 、 N,N-二异丙基乙胺 、 苯酚 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 trans-1-Benzoylamino-2-chlor-cyclohexan
  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

• Bifunctional Asymmetric Catalysis with Hydrogen Chloride: Enantioselective Ring Opening of Aziridines Catalyzed by a Phosphinothiourea
  作者：Eric Jacobsen、Tsuyoshi Mita

  DOI：10.1055/s-0029-1217344

  日期：——

  Ring-opening of aziridines with hydrogen chloride to form β-chloroamine derivatives is catalyzed by a chiral phosphinothiourea derivative in high yields and with high enantioselectivities. On the basis of (31)P NMR studies, activation of HCl appears to proceed via quantitative protonation of the catalyst to afford a phosphonium chloride complex.

  氮丙啶与氯化氢开环形成 β-氯胺衍生物是由手性膦硫脲衍生物以高产率和高对映选择性催化的。在 (31)P NMR 研究的基础上，HCl 的活化似乎是通过催化剂的定量质子化进行的，以提供氯化鏻络合物。
• 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.