2,2,2-trifluoroethyl [1,1’-biphenyl]-4-carboxylate

• 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-trifluoroethyl [1,1’-biphenyl]-4-carboxylate
• 英文别名: 2,2,2-trifluoroethyl biphenyl-4-carboxylate；Biphenyl-4-carboxylic acid, 2,2,2-trifluoroethyl ester；2,2,2-trifluoroethyl 4-phenylbenzoate
• 化学式: C₁₅H₁₁F₃O₂
• 分子量: 280.246
• InChiKey: AOLROFVAQZENPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,2,2-三氟乙醇 、 4-苯基苯甲酸 在 N-(methylpolystyrene)-4-(methylamino)pyridine 、 TEA 、 (2-chloro-1-pyridinio)-(Wang resin) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到2,2,2-trifluoroethyl [1,1’-biphenyl]-4-carboxylate
  参考文献：
  名称：

  聚合物支持的Mukaiyama试剂：一种用于合成酯和酰胺的有用偶联剂。

  摘要：

  由Wang树脂一步合成了聚合物负载的N-烷基-2-氯吡啶鎓三氟甲磺酸盐。该试剂被证明是从羧酸和醇或胺（伯和仲）合成​​酯或酰胺的非常有效的偶联剂。[反应：看文字]

  DOI：

  10.1021/ol0480372

文献信息

• Polymer-Supported Mukaiyama Reagent:  A Useful Coupling Reagent for the Synthesis of Esters and Amides
  作者：Stefano Crosignani、Jerome Gonzalez、Dominique Swinnen

  DOI：10.1021/ol0480372

  日期：2004.11.1

  Polymer-supported N-alkyl-2-chloro pyridinium triflate was synthesized in one step from Wang resin. This reagent proved to be a very effective coupling reagent for the synthesis of esters or amides from carboxylic acids and alcohols or amines (primary and secondary). [reaction: see text]

  由Wang树脂一步合成了聚合物负载的N-烷基-2-氯吡啶鎓三氟甲磺酸盐。该试剂被证明是从羧酸和醇或胺（伯和仲）合成​​酯或酰胺的非常有效的偶联剂。[反应：看文字]
• 10.1055/s-0043-1774910
  作者：Vankar, Jigarkumar K.、Jadav, Jaydeepbhai P.、Gururaja, Guddeangadi N.

  DOI：10.1055/s-0043-1774910

  日期：——

  AbstractA mild and efficient reaction for synthesizing esters from thioamide precursors has been established. This method is accomplished in one pot under mild conditions. The process involves the alkylation and activation of inert thioamides, which leads to the cleavage of stable C–N and C–S bonds, eventually resulting in valuable esters with a broad range of substrates. The transformation can be easily carried out at room temperature using thioamide substrates, reactants, and activating agents. This protocol has been demonstrated by synthesizing important esters with applications.
• Direct Esterification of Carboxylic Acids with Perfluorinated Alcohols Mediated by XtalFluor-E
  作者：Mathilde Vandamme、Léa Bouchard、Audrey Gilbert、Massaba Keita、Jean-François Paquin

  DOI：10.1021/acs.orglett.6b03365

  日期：2016.12.16

  The direct esterification of carboxylic acids with perfluorinated alcohols mediated by XtalFluor-E is reported. The corresponding polyfluorinated esters are obtained in moderate to excellent yields with a broad range of carboxylic acids, including aromatic, heteroaromatic, aliphatic, and nonracemic chiral substrates, using only a slight excess (2 equiv) of the perfluorinated alcohol. Control experiments

  据报道，由XtalFluor-E介导的羧酸与全氟化醇直接酯化。仅使用稍微过量的（2当量）全氟化醇，就可以以中等到极高的收率，用宽范围的羧酸（包括芳族，杂芳族，脂族和非外消旋手性底物）获得相应的多氟化酯。对照实验表明，该反应不通过的酰基氟化物的形成继续进行，但最有可能通过一个（二乙基氨基）二氟- λ 4硫烷基羧酸盐中间体。