N-[(E)-1-[2-(methylamino)phenyl]ethylidene]-2-methyl-(R(S))-2-propanesulfinamide | 1287718-15-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[(E)-1-[2-(methylamino)phenyl]ethylidene]-2-methyl-(R(S))-2-propanesulfinamide
• 英文别名: (NE,R)-2-methyl-N-[1-[2-(methylamino)phenyl]ethylidene]propane-2-sulfinamide
• CAS: 1287718-15-3
• 化学式: C₁₃H₂₀N₂OS
• 分子量: 252.381
• InChiKey: JNLSNZVJIPBWPY-IUYQLWOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  60.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(E)-1-[2-(methylamino)phenyl]ethylidene]-2-methyl-(R(S))-2-propanesulfinamide 在 盐酸 、 二异丁基氢化铝 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (1R)-N-methyl-1-[2-(methylamino)phenyl]-1-ethanamine
  参考文献：
  名称：

  Asymmetric Synthesis of 1,3-Diamines. II: Diastereoselective Reduction of Atropisomeric N-tert-Butanesulfinylketimines

  摘要：

  Chiral, nonracemic o-aminobenzylamines were prepared in a highly diastereoselective reduction of atropisomeric N-tert-butanesulfinylketimines. The ortho-substituent ensures the distinct reactivity of atropisomers 4d-f. The free energy of activation for atropisomerization of sulfinylimines 4d-f in THF-d(8) was determined by NMR methods to range from 70.8 to 97.9 kJ/mol.

  DOI：

  10.1021/jo1025767
• 作为产物：
  描述：

  邻氨基苯乙酮 在 titanium(IV) tetraethanolate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 60.17h， 生成 N-[(E)-1-[2-(methylamino)phenyl]ethylidene]-2-methyl-(R(S))-2-propanesulfinamide
  参考文献：
  名称：

  Asymmetric Synthesis of 1,3-Diamines. II: Diastereoselective Reduction of Atropisomeric N-tert-Butanesulfinylketimines

  摘要：

  Chiral, nonracemic o-aminobenzylamines were prepared in a highly diastereoselective reduction of atropisomeric N-tert-butanesulfinylketimines. The ortho-substituent ensures the distinct reactivity of atropisomers 4d-f. The free energy of activation for atropisomerization of sulfinylimines 4d-f in THF-d(8) was determined by NMR methods to range from 70.8 to 97.9 kJ/mol.

  DOI：

  10.1021/jo1025767

文献信息

• Asymmetric Synthesis of 1,3-Diamines. II: Diastereoselective Reduction of Atropisomeric <i>N</i>-<i>tert</i>-Butanesulfinylketimines
  作者：Marina Martjuga、Sergey Belyakov、Edvards Liepinsh、Edgars Suna

  DOI：10.1021/jo1025767

  日期：2011.4.15

  Chiral, nonracemic o-aminobenzylamines were prepared in a highly diastereoselective reduction of atropisomeric N-tert-butanesulfinylketimines. The ortho-substituent ensures the distinct reactivity of atropisomers 4d-f. The free energy of activation for atropisomerization of sulfinylimines 4d-f in THF-d(8) was determined by NMR methods to range from 70.8 to 97.9 kJ/mol.