N-[(Z)-3,3,3-trifluoropropenyl]-N-phenyl-p-toluenesulfonamide

• 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: N-[(Z)-3,3,3-trifluoropropenyl]-N-phenyl-p-toluenesulfonamide
• 英文别名: 4-methyl-N-phenyl-N-[(Z)-3,3,3-trifluoroprop-1-enyl]benzenesulfonamide
• 化学式: C₁₆H₁₄F₃NO₂S
• 分子量: 341.354
• InChiKey: CHLAVOUCZLRVLJ-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[(Z)-3,3,3-trifluoropropenyl]-N-phenyl-p-toluenesulfonamide 在 三氟化硼乙醚 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 1.0h， 以96%的产率得到N-[(E)-3,3,3-trifluoropropenyl]-N-phenyl-p-toluenesulfonamide
  参考文献：
  名称：

  Stereoselective synthesis of (Z)-trifluoromethyl enamines and their Lewis acid-mediated conversion into (E)-isomers

  摘要：

  (Z)-beta-Trifluoromethyl enamines were prepared in high yield stereoselectively by reaction of 2-bromo-3,3,3-trifluoropropene with N-alkyl toluenesulfonamides and potassium t-butoxide in one pot via Michael addition and elimination processes. The (Z)-beta-trifluoromethyl enamines could be converted to the corresponding thermodynamically stable (E)-isomers promoted by Lewis acid catalysts at room temperature or thermal isomerization. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01157-7
• 作为产物：
  描述：

  2-溴-3,3,3-三氟丙烯 、 对甲苯硫酰苯胺 在 potassium tert-butylate 作用下， 以 二甲基亚砜 、 叔丁醇 为溶剂， 反应 5.0h， 以80%的产率得到N-[(Z)-3,3,3-trifluoropropenyl]-N-phenyl-p-toluenesulfonamide
  参考文献：
  名称：

  Stereoselective synthesis of (Z)-trifluoromethyl enamines and their Lewis acid-mediated conversion into (E)-isomers

  摘要：

  (Z)-beta-Trifluoromethyl enamines were prepared in high yield stereoselectively by reaction of 2-bromo-3,3,3-trifluoropropene with N-alkyl toluenesulfonamides and potassium t-butoxide in one pot via Michael addition and elimination processes. The (Z)-beta-trifluoromethyl enamines could be converted to the corresponding thermodynamically stable (E)-isomers promoted by Lewis acid catalysts at room temperature or thermal isomerization. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01157-7

文献信息

• Stereoselective synthesis of (Z)-trifluoromethyl enamines and their Lewis acid-mediated conversion into (E)-isomers
  作者：Biao Jiang、Fangjiang Zhang、Wennan Xiong

  DOI：10.1016/s0040-4020(01)01157-7

  日期：2002.1

  (Z)-beta-Trifluoromethyl enamines were prepared in high yield stereoselectively by reaction of 2-bromo-3,3,3-trifluoropropene with N-alkyl toluenesulfonamides and potassium t-butoxide in one pot via Michael addition and elimination processes. The (Z)-beta-trifluoromethyl enamines could be converted to the corresponding thermodynamically stable (E)-isomers promoted by Lewis acid catalysts at room temperature or thermal isomerization. (C) 2002 Elsevier Science Ltd. All rights reserved.