(+)-(S)-N-propanoyl-N-benzyl-p-toluenesulfinamide | 169330-85-2

• 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: (+)-(S)-N-propanoyl-N-benzyl-p-toluenesulfinamide
• 英文别名: N-benzyl-N-[(S)-(4-methylphenyl)sulfinyl]propanamide
• CAS: 169330-85-2
• 化学式: C₁₇H₁₉NO₂S
• 分子量: 301.409
• InChiKey: OEGKVTSQNLJLAT-NRFANRHFSA-N

物化性质

• 沸点：
  466.6±48.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  56.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-(S)-N-benzyl-p-toluenesulfinamide 、 (+)-(S)-N-propanoyl-N-benzyl-p-toluenesulfinamide 在 正丁基锂 作用下， 生成 N-benzyl-bis-p-toluenesulfinamide
  参考文献：
  名称：

  Synthesis and reactivity of enantiomerically pure N-acylN-alkyl p-toluenesulfinamides

  摘要：

  The syntheses of different enantiomerically N-acyl N-alkyl p-toluenesulfinamides 5, by N-sulfinylation of primary amines with (S)-menthyl-p-tolylsulfinate followed by N-acylation of the resulting sulfinamides are reported. Their reactions with some C-nucleophiles take place at the sulfur atom exclusively with complete retention of the enantiomeric purity, revealing their ability as sulfinylating agents. In this sense, their comparison with other reagents popularly used, revealed that 5 have some important advantages.

  DOI：

  10.1016/0957-4166(95)00139-g
• 作为产物：
  描述：

  (-)-menthyl p-toluenesulfinate 在 正丁基锂 作用下， 反应 1.63h， 生成 (+)-(S)-N-propanoyl-N-benzyl-p-toluenesulfinamide
  参考文献：
  名称：

  Synthesis and reactivity of enantiomerically pure N-acylN-alkyl p-toluenesulfinamides

  摘要：

  The syntheses of different enantiomerically N-acyl N-alkyl p-toluenesulfinamides 5, by N-sulfinylation of primary amines with (S)-menthyl-p-tolylsulfinate followed by N-acylation of the resulting sulfinamides are reported. Their reactions with some C-nucleophiles take place at the sulfur atom exclusively with complete retention of the enantiomeric purity, revealing their ability as sulfinylating agents. In this sense, their comparison with other reagents popularly used, revealed that 5 have some important advantages.

  DOI：

  10.1016/0957-4166(95)00139-g

文献信息

• Synthesis and reactivity of enantiomerically pure N-acylN-alkyl p-toluenesulfinamides
  作者：JoséL. García-Ruano、Raquel Alonso、María M. Zarzuelo、Pedro Noheda

  DOI：10.1016/0957-4166(95)00139-g

  日期：1995.5

  The syntheses of different enantiomerically N-acyl N-alkyl p-toluenesulfinamides 5, by N-sulfinylation of primary amines with (S)-menthyl-p-tolylsulfinate followed by N-acylation of the resulting sulfinamides are reported. Their reactions with some C-nucleophiles take place at the sulfur atom exclusively with complete retention of the enantiomeric purity, revealing their ability as sulfinylating agents. In this sense, their comparison with other reagents popularly used, revealed that 5 have some important advantages.