(E)-dimethyl 2-(3-(4-methoxyphenyl)allyl)-2-(trifluoromethyl)malonate | 1440140-65-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-dimethyl 2-(3-(4-methoxyphenyl)allyl)-2-(trifluoromethyl)malonate
• 英文别名: dimethyl 2-[(E)-3-(4-methoxyphenyl)prop-2-enyl]-2-(trifluoromethyl)propanedioate
• CAS: 1440140-65-7
• 化学式: C₁₆H₁₇F₃O₅
• 分子量: 346.303
• InChiKey: BINUOJFYTRUCOZ-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-三氟甲基丙二酸二甲酯 、 (E)-p-methoxycinnamyl methyl 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97%的产率得到(E)-dimethyl 2-(3-(4-methoxyphenyl)allyl)-2-(trifluoromethyl)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

文献信息

• Allylic C–H alkylation with a CF3-containing nucleophile
  作者：Lun Li、Qing-Yun Chen、Yong Guo

  DOI：10.1039/c3cc43120g

  日期：——

  Allylic C-H alkylation of allylarenes with dimethyl 2-trifluoromethylmalonate was successfully developed. The reactions were carried out at room temperature in the presence of a catalytic amount of Pd(OAc)2/Ph3P and a stoichiometric amount of 2,6-dimethylbenzoquinone. The reactions avoided defluorination successfully, providing a new method to construct a CF3-containing all-carbon quaternary center

  用2-三氟甲基丙二酸二甲酯成功开发了烯丙基芳烃的烯丙基CH烷基化反应。反应在室温下在催化量的Pd（OAc）2 / Ph3P和化学计量的2,6-二甲基苯醌的存在下进行。该反应成功地避免了脱氟，为构建含CF3的全碳四元中心提供了一种新方法。