methyl 4-methyl-2,2-bis(trifluoromethyl)pent-4-enoate | 1440140-59-9

• 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: methyl 4-methyl-2,2-bis(trifluoromethyl)pent-4-enoate
• 英文别名: Methyl 4-methyl-2,2-bis(trifluoromethyl)pent-4-enoate
• CAS: 1440140-59-9
• 化学式: C₉H₁₀F₆O₂
• 分子量: 264.168
• InChiKey: CVZXVEKGEOPVRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-(三氟甲基)-3,3,3-三幅丙酸甲酯 、 methyl 2-methylprop-2-enyl 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45%的产率得到methyl 4-methyl-2,2-bis(trifluoromethyl)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.