2,2,2-trifluoro-1-phenylethyl 4-cyanobenzoate | 1359217-52-9

• 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: 2,2,2-trifluoro-1-phenylethyl 4-cyanobenzoate
• CAS: 1359217-52-9
• 化学式: C₁₆H₁₀F₃NO₂
• 分子量: 305.256
• InChiKey: JKLLYOWHGMVQFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2,2,2-三氟苯乙酮 、 4-氰基苯甲醛 在 [(Me3Si)2N]2Th[κ2-(N,C)-CH2Si(CH3)2N(SiMe3)] 作用下， 以 氘代苯 为溶剂， 反应 48.0h， 以92%的产率得到2,2,2-trifluoro-1-phenylethyl 4-cyanobenzoate
  参考文献：
  名称：

  Tishchenko反应中对称和不对称酯的苯并咪唑啉-2-亚氨基to系（IV）配合物的合成，表征和催化性能

  摘要：

  苯并咪唑啉-2-亚氨基to系-（IV）络合物的新家族[（Bim 7-Me Dipp / Me N）An（N（SiMe 3）2）3 ]（An = U（3），Th（4））和[（Bim 4-Me Dipp / Me N）An（N（SiMe 3）2）3 ]（An = U（5），Th（6））合成，并通过单晶X建立其固态结构射线衍射分析。研究了配合物3 – 6对醛的均相和交叉偶联（Tishchenko反应）的催化性能，并研究了complex配合物图4和图6显示出产生相应的对称和不对称酯的中等至高活性。这些th配合物还研究了醛与醇的偶联，称为串联质子转移酯化，以及醛与三氟甲基酮之间的分子间偶联反应，表明了选择性地获得不对称酯的互补方法。这些反应的合理机制是基于化学计量研究提出的。

  DOI：

  10.1016/j.jorganchem.2017.09.020

文献信息

• Selenide Ions as Catalysts for Homo- and Crossed-Tishchenko Reactions of Expanded Scope
  作者：Simon P. Curran、Stephen J. Connon

  DOI：10.1021/ol203439g

  日期：2012.2.17

  Selenide ions have been shown to catalyze the Tishchenko reaction for the first time. These catalysts are superior to previously reported thiolate analogues and promote the disproportionation of aldehydes with increased reaction rates and broader scope at lower catalyst loadings and temperatures. Significantly improved catalyst performance was also observed in the aryl selenide mediated crossed intermolecular Tishchenko reaction.
• Synthesis, Characterization, and Unique Catalytic Activities of a Fluorinated Nickel Enolate
  作者：Ryohei Doi、Kotaro Kikushima、Masato Ohashi、Sensuke Ogoshi

  DOI：10.1021/ja511730k

  日期：2015.3.11

  We have synthesized a new nickel enolate [(PhCOCF2)Ni(dcpe)][FB(C6F5)(3)] featuring fluorine atoms on the enolate moiety via B(C6F5)(3)-promoted C-F bond activation of alpha,alpha,alpha-trifluoroacetophenone. X-ray diffraction study of [(PhCOCF2)Ni(dcpe)][FB(C6F5)(3)] revealed that the complex had adopted an eta(3)-oxallyl coordination mode in the crystal lattice. The reaction of (BuNC)-Bu-t with [(PhCOCF2)Ni(dcpe)][FB(C6F5)(3)] resulted in the coordination of isocyanide to the nickel center to form a C-bound enolate complex. The reactions of [(PhCOCF2)Ni(dcpe)][FB(C6F5)(3)] with aldehydes gave insertion products quantitatively which were fully characterized by NMR spectroscopy. Furthermore, we established unique catalytic applications for [(PhCOCF2)Ni(dcpe)][FB(C6F5)(3)] toward a Tishchenko reaction, along with a highly selective crossed-esterification of alpha,alpha,alpha-trifluoroacetophenones with aldehydes.