(E)-dimethyl 2-(trifluoromethyl)-2-(3-(4-(trifluoromethyl)phenyl)allyl)malonate | 1440140-71-5

• 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: (E)-dimethyl 2-(trifluoromethyl)-2-(3-(4-(trifluoromethyl)phenyl)allyl)malonate
• 英文别名: dimethyl 2-(trifluoromethyl)-2-[(E)-3-[4-(trifluoromethyl)phenyl]prop-2-enyl]propanedioate
• CAS: 1440140-71-5
• 化学式: C₁₆H₁₄F₆O₄
• 分子量: 384.275
• InChiKey: AOPYVCHQPVTJJI-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-三氟甲基丙二酸二甲酯 、 (E)-methyl (3-(4-(trifluoromethyl)phenyl)allyl) carbonate 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以85%的产率得到(E)-dimethyl 2-(trifluoromethyl)-2-(3-(4-(trifluoromethyl)phenyl)allyl)malonate
  参考文献：
  名称：

  Pd-Catalyzed Allylic Alkylation of CF3-Containing Esters with Three Electron-Withdrawing Groups

  摘要：

  Tsuji-Trost reaction (Pd-catalyzed allylic alkylation) of CF3-containing esters with three electron-withdrawing groups is reported. The reactions with methyl bis(trifluoromethyl) acetate and dimethyl ( trifluoromethyl) malonate were carried out with low-loading catalysts of Pd(0) and XPhos at ambient temperature in THF, giving the products in high yields. This method efficiently overcomes the beta-defluorination, which is hard to control in the chemical transformation of alpha-trifluoromethyl carbanions, and provides versatile fluorinated compounds with quaternary carbon centers, which are highly demanded in drug discovery.

  DOI：

  10.1055/s-0032-1318313