(E)-2,6-Di-tert-butyl-4-methylphenyl 4,4,4-trifluoro-2-butenoate | 169823-29-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (E)-2,6-Di-tert-butyl-4-methylphenyl 4,4,4-trifluoro-2-butenoate
• 英文别名: (2,6-ditert-butyl-4-methylphenyl) (E)-4,4,4-trifluorobut-2-enoate
• CAS: 169823-29-4
• 化学式: C₁₉H₂₅F₃O₂
• 分子量: 342.402
• InChiKey: GPWLVHDTQGCBNQ-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-甲基吡咯烷酮 、 (E)-2,6-Di-tert-butyl-4-methylphenyl 4,4,4-trifluoro-2-butenoate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以80%的产率得到2,6-Di-tert-butyl-4-methylphenyl 3-(N-methyl-2'-pyrrolidinon-3'-yl)-3-(trifluoromethyl)propionate
  参考文献：
  名称：

  Stereoselective Synthesis of Trifluoromethylated Compounds with Controlled Adjacent Tertiary Carbons by Michael Addition to (E)-3-(Trifluoromethyl)acrylates

  摘要：

  Michael addition reaction of various lithium enolates to ethyl (E)-3-(trifluoromethyl)acrylate (E)-1 was found to be one of the most effective routes to construct materials not only with a CF3 group but also with readily distinguishable multiple functionalities by the routine chemical transformations. Particularly, employment of lithium enolates from chiral acyloxazolidinones as Michael donors resulted in the formation of 1,4-adducts, usually with a high degree of diastereoselectivity as well as with a high degree of diastereofacial selectivities only in a single step. Further, it was suggested by both the experimental results and the ab initio calculations that interaction between fluorine-(s) and lithium strongly stabilized the present Michael intermediates, allowing for the smooth reactions even with ketone enolates under kinetically controlled conditions.

  DOI：

  10.1021/jo00119a013
• 作为产物：
  描述：

  (E)-4,4,4-trifluorobut-2-enoyl chloride 、 2,6-二叔丁基-4-甲基苯酚 在 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 以67%的产率得到(E)-2,6-Di-tert-butyl-4-methylphenyl 4,4,4-trifluoro-2-butenoate
  参考文献：
  名称：

  Stereoselective Synthesis of Trifluoromethylated Compounds with Controlled Adjacent Tertiary Carbons by Michael Addition to (E)-3-(Trifluoromethyl)acrylates

  摘要：

  Michael addition reaction of various lithium enolates to ethyl (E)-3-(trifluoromethyl)acrylate (E)-1 was found to be one of the most effective routes to construct materials not only with a CF3 group but also with readily distinguishable multiple functionalities by the routine chemical transformations. Particularly, employment of lithium enolates from chiral acyloxazolidinones as Michael donors resulted in the formation of 1,4-adducts, usually with a high degree of diastereoselectivity as well as with a high degree of diastereofacial selectivities only in a single step. Further, it was suggested by both the experimental results and the ab initio calculations that interaction between fluorine-(s) and lithium strongly stabilized the present Michael intermediates, allowing for the smooth reactions even with ketone enolates under kinetically controlled conditions.

  DOI：

  10.1021/jo00119a013