(R(S))-N-[(R)-[5-chloro-2-(methylamino)phenyl](1-naphthyl)methyl]-2-methyl-2-propanesulfinamide | 1217898-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R(S))-N-[(R)-[5-chloro-2-(methylamino)phenyl](1-naphthyl)methyl]-2-methyl-2-propanesulfinamide
• 英文别名: (R)-N-[(R)-[5-chloro-2-(methylamino)phenyl]-naphthalen-1-ylmethyl]-2-methylpropane-2-sulfinamide
• CAS: 1217898-64-0
• 化学式: C₂₂H₂₅ClN₂OS
• 分子量: 400.972
• InChiKey: SLFNVLWJTSJHMM-JIPXPUAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  60.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R(S))-N-[(R)-[5-chloro-2-(methylamino)phenyl](1-naphthyl)methyl]-2-methyl-2-propanesulfinamide 在 盐酸 、 ammonium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 1.0h， 以99%的产率得到2-[(R)-amino(1-naphthyl)methyl]-4-chloro-N-methylaniline
  参考文献：
  名称：

  Asymmetric Synthesis of 1,3-Diamines by Diastereoselective Reduction of Enantiopure N-tert-Butanesulfinylketimines: Unusual Directing Effects of the ortho-Substituent

  摘要：

  Chiral, nonracemic 1,3-diamines were prepared in a highly diastereoselective reduction of diaryl N-tert-butanesulfinylketimines. Correlation between Facial selectivity of the reduction and E or Z geometry of the starting ketimines suggests involvement of a cyclic transition state for the reduction. The ortho-substituent controls the geometry of N-tert-butanesulfinylketimines in the solid state and provides additional stabilization of the cyclic transition state.

  DOI：

  10.1021/jo100173f
• 作为产物：
  描述：

  (R(S))-N-[(E)-[5-chloro-2-(methylamino)phenyl](1-naphthyl)methylidene]-2-methyl-2-propanesulfinamide 在 二异丁基氢化铝 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以94%的产率得到(R(S))-N-[(R)-[5-chloro-2-(methylamino)phenyl](1-naphthyl)methyl]-2-methyl-2-propanesulfinamide
  参考文献：
  名称：

  Asymmetric Synthesis of 1,3-Diamines by Diastereoselective Reduction of Enantiopure N-tert-Butanesulfinylketimines: Unusual Directing Effects of the ortho-Substituent

  摘要：

  Chiral, nonracemic 1,3-diamines were prepared in a highly diastereoselective reduction of diaryl N-tert-butanesulfinylketimines. Correlation between Facial selectivity of the reduction and E or Z geometry of the starting ketimines suggests involvement of a cyclic transition state for the reduction. The ortho-substituent controls the geometry of N-tert-butanesulfinylketimines in the solid state and provides additional stabilization of the cyclic transition state.

  DOI：

  10.1021/jo100173f

文献信息

• Asymmetric Synthesis of 1,3-Diamines by Diastereoselective Reduction of Enantiopure <i>N</i>-<i>tert</i>-Butanesulfinylketimines: Unusual Directing Effects of the <i>ortho</i>-Substituent
  作者：Marina Martjuga、Dmitry Shabashov、Sergey Belyakov、Edvards Liepinsh、Edgars Suna

  DOI：10.1021/jo100173f

  日期：2010.4.2

  Chiral, nonracemic 1,3-diamines were prepared in a highly diastereoselective reduction of diaryl N-tert-butanesulfinylketimines. Correlation between Facial selectivity of the reduction and E or Z geometry of the starting ketimines suggests involvement of a cyclic transition state for the reduction. The ortho-substituent controls the geometry of N-tert-butanesulfinylketimines in the solid state and provides additional stabilization of the cyclic transition state.