(S)-N-(1-(4-chlorophenyl)-2,2,2-trifluoroethylidene)-2-methylpropane-2-sulfinamide | 884595-99-7

• 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-(1-(4-chlorophenyl)-2,2,2-trifluoroethylidene)-2-methylpropane-2-sulfinamide
• CAS: 884595-99-7
• 化学式: C₁₂H₁₃ClF₃NOS
• 分子量: 311.756
• InChiKey: FQAWSAZOWFLXBD-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.43
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (S)-N-(1-(4-chlorophenyl)-2,2,2-trifluoroethylidene)-2-methylpropane-2-sulfinamide 、 苯乙炔 在 正丁基锂 、 titanium(IV) isopropylate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以80%的产率得到(S)-N-((R)-2-(4-chlorophenyl)-1,1,1-trifluoro-4-phenylbut-3-yn-2-yl)-2-methylprop-2-ylsulfinamide
  参考文献：
  名称：

  Highly diastereoselective synthesis of α-trifluoromethylated α-propargylamines by acetylide addition to chiral CF3-substituted N-tert-butanesulfinyl ketimines

  摘要：

  A convenient and practical method for the preparation of enantiomerically pure alpha-trifluoromethylated alpha-propargylamines is described. A range of enantiopure alpha-trifluoromethylated alpha-propargyl sulfinamides were obtained by the addition of lithium acetylides generated in situ with n-BuLi and terminal alkynes to diverse chiral CF3-substituted (S)-N-tert-butanesulfinyl ketimines in moderate to excellent yields (56-97%) and with uniformly excellent diastereoselectivities (>99:1) by using Ti((OPr)-Pr-i)(4) as the catalyst and THF as the polar solvent. Enantiomerically pure alpha-trifluoromethylated alpha,alpha-dibranched propargyl amines were then readily obtained in excellent yields (87-97%) by acidic cleavage of the tert-butanesulfinyl group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.028
• 作为产物：
  描述：

  4'-氯-2,2,2-三氟苯乙酮 、 S-叔丁基亚磺酰胺 在 titanium(IV) isopropylate 作用下， 以 正己烷 为溶剂， 生成 (S)-N-(1-(4-chlorophenyl)-2,2,2-trifluoroethylidene)-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  Highly diastereoselective synthesis of α-trifluoromethylated α-propargylamines by acetylide addition to chiral CF3-substituted N-tert-butanesulfinyl ketimines

  摘要：

  A convenient and practical method for the preparation of enantiomerically pure alpha-trifluoromethylated alpha-propargylamines is described. A range of enantiopure alpha-trifluoromethylated alpha-propargyl sulfinamides were obtained by the addition of lithium acetylides generated in situ with n-BuLi and terminal alkynes to diverse chiral CF3-substituted (S)-N-tert-butanesulfinyl ketimines in moderate to excellent yields (56-97%) and with uniformly excellent diastereoselectivities (>99:1) by using Ti((OPr)-Pr-i)(4) as the catalyst and THF as the polar solvent. Enantiomerically pure alpha-trifluoromethylated alpha,alpha-dibranched propargyl amines were then readily obtained in excellent yields (87-97%) by acidic cleavage of the tert-butanesulfinyl group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.028