(R,S)-N-benzyl-N-(1-phenylethyl)-p-fluorobenzenesulfinamide | 1307296-50-9

• 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: (R,S)-N-benzyl-N-(1-phenylethyl)-p-fluorobenzenesulfinamide
• 英文别名: (S)-N-benzyl-4-fluoro-N-[(1R)-1-phenylethyl]benzenesulfinamide
• CAS: 1307296-50-9
• 化学式: C₂₁H₂₀FNOS
• 分子量: 353.46
• InChiKey: LNYLHKJNRXERHE-NSYGIPOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  39.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R,S)-N-benzyl-N-(1-phenylethyl)-p-fluorobenzenesulfinamide 在 三氟化硼乙醚 、 lithium hexamethyldisilazane 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 160.0h， 生成 (S)-4-fluorobenzenesulfinamide
  参考文献：
  名称：

  Practical and highly stereoselective method for the preparation of several chiral arylsulfinamides and arylsulfinates based on the spontaneous crystallization of diastereomerically pure N-benzyl-N-(1-phenylethyl)-arylsulfinamides

  摘要：

  A novel and simple process for the preparation of enantiomerically pure (S(s))-benzenesulfinamide (S(s))-3a, (S(s))-p-toluenesulfinamide (S(s))-3b, (S(s))-p-chloro-benzenesulfinamide (S(s))-3c and (S(s))-p-fluorobenzenesulfinamide (S(s))-3d has been developed. The treatment of arylsulfinyl chlorides with (R)-N-benzyl-1-phenylethanamine in the presence of excess triethylamine gave diastereomeric mixtures of N-benzyl-N-(1-phenylethyl)-arylsulfinamides 1, which underwent spontaneous crystallization to furnish diastereomerically pure (R,S(s))-N-benzyl-N-(1-phenylethyl)-arylsulfinamides (R,S(s))-1a-1d in 28%, 29%, 27% and 31% yields, respectively. The diastereomerically pure compounds (R,S(s))-1 were then converted into four enantiopure (R(s))-methyl arylsulfinates (R(s))-2, and finally into four enantiopure (S(s))-arylsulfinamides (S(s))-3 in good yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.01.028
• 作为产物：
  描述：

  (R,S)-N-benzyl-N-(1-phenylethyl)-p-chlorobenzenesulfinamide 在 三氟化硼乙醚 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 157.25h， 生成 (R,R)-N-benzyl-N-(1-phenylethyl)-p-fluorobenzenesulfinamide 、 (R,S)-N-benzyl-N-(1-phenylethyl)-p-fluorobenzenesulfinamide
  参考文献：
  名称：

  Practical and highly stereoselective method for the preparation of several chiral arylsulfinamides and arylsulfinates based on the spontaneous crystallization of diastereomerically pure N-benzyl-N-(1-phenylethyl)-arylsulfinamides

  摘要：

  A novel and simple process for the preparation of enantiomerically pure (S(s))-benzenesulfinamide (S(s))-3a, (S(s))-p-toluenesulfinamide (S(s))-3b, (S(s))-p-chloro-benzenesulfinamide (S(s))-3c and (S(s))-p-fluorobenzenesulfinamide (S(s))-3d has been developed. The treatment of arylsulfinyl chlorides with (R)-N-benzyl-1-phenylethanamine in the presence of excess triethylamine gave diastereomeric mixtures of N-benzyl-N-(1-phenylethyl)-arylsulfinamides 1, which underwent spontaneous crystallization to furnish diastereomerically pure (R,S(s))-N-benzyl-N-(1-phenylethyl)-arylsulfinamides (R,S(s))-1a-1d in 28%, 29%, 27% and 31% yields, respectively. The diastereomerically pure compounds (R,S(s))-1 were then converted into four enantiopure (R(s))-methyl arylsulfinates (R(s))-2, and finally into four enantiopure (S(s))-arylsulfinamides (S(s))-3 in good yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.01.028

文献信息

• Practical and highly stereoselective method for the preparation of several chiral arylsulfinamides and arylsulfinates based on the spontaneous crystallization of diastereomerically pure N-benzyl-N-(1-phenylethyl)-arylsulfinamides
  作者：Rui-Heng Zhu、Xiao-Xin Shi

  DOI：10.1016/j.tetasy.2011.01.028

  日期：2011.2

  A novel and simple process for the preparation of enantiomerically pure (S(s))-benzenesulfinamide (S(s))-3a, (S(s))-p-toluenesulfinamide (S(s))-3b, (S(s))-p-chloro-benzenesulfinamide (S(s))-3c and (S(s))-p-fluorobenzenesulfinamide (S(s))-3d has been developed. The treatment of arylsulfinyl chlorides with (R)-N-benzyl-1-phenylethanamine in the presence of excess triethylamine gave diastereomeric mixtures of N-benzyl-N-(1-phenylethyl)-arylsulfinamides 1, which underwent spontaneous crystallization to furnish diastereomerically pure (R,S(s))-N-benzyl-N-(1-phenylethyl)-arylsulfinamides (R,S(s))-1a-1d in 28%, 29%, 27% and 31% yields, respectively. The diastereomerically pure compounds (R,S(s))-1 were then converted into four enantiopure (R(s))-methyl arylsulfinates (R(s))-2, and finally into four enantiopure (S(s))-arylsulfinamides (S(s))-3 in good yields. (C) 2011 Elsevier Ltd. All rights reserved.