(E)-methyl 2,2-bis(trifluoromethyl)-5-(4-(trifluoromethyl)phenyl)pent-4-enoate | 1440140-52-2

• 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)-methyl 2,2-bis(trifluoromethyl)-5-(4-(trifluoromethyl)phenyl)pent-4-enoate
• 英文别名: methyl (E)-2,2-bis(trifluoromethyl)-5-[4-(trifluoromethyl)phenyl]pent-4-enoate
• CAS: 1440140-52-2
• 化学式: C₁₅H₁₁F₉O₂
• 分子量: 394.237
• InChiKey: XPWKUIPQXKEBCI-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-(三氟甲基)-3,3,3-三幅丙酸甲酯 、 (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90%的产率得到(E)-methyl 2,2-bis(trifluoromethyl)-5-(4-(trifluoromethyl)phenyl)pent-4-enoate
  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

文献信息

• Pd-Catalyzed Allylic Alkylation of CF3-Containing Esters with Three Electron-Withdrawing Groups
  作者：Yong Guo、Lun Li、Donghui Huang、Qing-Yun Chen

  DOI：10.1055/s-0032-1318313

  日期：——

  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.