4,4-bis(ethylsulfanyl)-3-trifluoromethyl-2,2-dimethylbut-3-enoic acid | 804564-07-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4,4-bis(ethylsulfanyl)-3-trifluoromethyl-2,2-dimethylbut-3-enoic acid
• 英文别名: 4,4-Bis(ethylsulfanyl)-2,2-dimethyl-3-(trifluoromethyl)but-3-enoic acid；4,4-bis(ethylsulfanyl)-2,2-dimethyl-3-(trifluoromethyl)but-3-enoic acid
• CAS: 804564-07-6
• 化学式: C₁₁H₁₇F₃O₂S₂
• 分子量: 302.382
• InChiKey: KNKKWDVYQDGGGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  perfluoroketene dithioacetal 、 异丁酸 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以53%的产率得到4,4-bis(ethylsulfanyl)-3-trifluoromethyl-2,2-dimethylbut-3-enoic acid
  参考文献：
  名称：

  Reaction of lithium enediolates with perfluoroketene dithioacetals. Synthesis of α-trifluoromethyl γ-dicarboxylic acid derivatives

  摘要：

  The reaction of perfluoroketene dithioacetals with dianions of carboxylic acids proceeds through the substitution of the vinylic fluoride. The preparative value of this reaction depends strongly on the reaction and work-up conditions, the optimisation of which led to use LDA as a base and multiple extraction techniques. The overall process may be considered as a formal synthesis of alpha-trifluoromethyl gamma-dicarboxylic acid derivatives. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.081

文献信息

• Reaction of lithium enediolates with perfluoroketene dithioacetals. Synthesis of α-trifluoromethyl γ-dicarboxylic acid derivatives
  作者：Enrique Sotoca、Jean-Philippe Bouillon、Salvador Gil、Margarita Parra、Charles Portella

  DOI：10.1016/j.tetlet.2004.09.081

  日期：2004.11

  The reaction of perfluoroketene dithioacetals with dianions of carboxylic acids proceeds through the substitution of the vinylic fluoride. The preparative value of this reaction depends strongly on the reaction and work-up conditions, the optimisation of which led to use LDA as a base and multiple extraction techniques. The overall process may be considered as a formal synthesis of alpha-trifluoromethyl gamma-dicarboxylic acid derivatives. (C) 2004 Elsevier Ltd. All rights reserved.
• A new strategy for the synthesis of highly functionalised fluorinated compounds by reaction of lithium dianions of carboxylic acids with perfluoroketene dithioacetals
  作者：Enrique Sotoca、Jean-Philippe Bouillon、Salvador Gil、Margarita Parra、Charles Portella

  DOI：10.1016/j.tet.2005.02.082

  日期：2005.5

  The reaction of perfluoroketene dithioacetal with lithium dienediolates of carboxylic acids proceeds at the W position probably through an addition to the pi system followed by elimination of the vinylic fluoride. The preparative value of this reaction depends strongly on the reaction and work-up conditions. The overall process lead to highly functionalised synthons containing a trifluoromethyl group. (c) 2005 Elsevier Ltd. All rights reserved.