(R(S))-N-[(E)-[5-chloro-2-(methylamino)phenyl](2-naphthyl)methylidene]-2-methyl-2-propanesulfinamide | 1217898-54-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R(S))-N-[(E)-[5-chloro-2-(methylamino)phenyl](2-naphthyl)methylidene]-2-methyl-2-propanesulfinamide
• 英文别名: (NE,R)-N-[[5-chloro-2-(methylamino)phenyl]-naphthalen-2-ylmethylidene]-2-methylpropane-2-sulfinamide
• CAS: 1217898-54-8
• 化学式: C₂₂H₂₃ClN₂OS
• 分子量: 398.956
• InChiKey: BJLVDFLXIRWYPF-JQOMMLKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  60.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (5-chloro-2-(methylamino)phenyl)(2-naphthyl)methanone 、 (R)-(+)-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以78%的产率得到(R(S))-N-[(E)-[5-chloro-2-(methylamino)phenyl](2-naphthyl)methylidene]-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.