4-nitrophenyl 4-trifluoromethylbenzoate | 37156-44-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 4-nitrophenyl 4-trifluoromethylbenzoate
• 英文别名: 4-Trifluoromethylbenzoic acid, 4-nitrophenyl ester；(4-nitrophenyl) 4-(trifluoromethyl)benzoate
• CAS: 37156-44-8
• 化学式: C₁₄H₈F₃NO₄
• 分子量: 311.217
• InChiKey: PEYJNSMYALTQJK-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86 °C(Solv: hexane (110-54-3); chloroform (67-66-3))
• 沸点：
  410.9±45.0 °C(Predicted)
• 密度：
  1.426±0.06 g/cm3(Predicted)
• 保留指数：
  2014

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl 4-trifluoromethylbenzoate 、 对氯苯酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以72%的产率得到(4-氯苯基)4-(三氟甲基)苯甲酸酯
  参考文献：
  名称：

  Kinetics of the reaction of 4-nitrophenyl benzoates with 4-chlorophenol in the presence of potassium carbonate in dimethylformamide

  摘要：

  The effect of the substituent in the benzoyl group on the relative rate and activation parameters of transesterification of substituted 4-nitrophenyl benzoates with 4-chlorophenol in dimethylformamide in the presence of potassium carbonate was studied by the competing reaction technique. The whole series of benzoates showed the enthalpy-entropy compensation effect. 4-Nitrophenyl benzoates having electron-acceptor substituents give rise to isokinetic relationship with an isokinetic temperature beta of 382 K. The mechanism of the transesterification process is discussed.

  DOI：

  10.1134/s1070428006060091
• 作为产物：
  描述：

  4-三氟甲基苯甲酸 、 对硝基苯基氯甲酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-nitrophenyl 4-trifluoromethylbenzoate
  参考文献：
  名称：

  Pd-Catalyzed Decarbonylative Olefination of Aryl Esters: Towards a Waste-Free Heck Reaction

  摘要：

  DOI：

  10.1002/1521-3773(20020402)41:7<1237::aid-anie1237>3.0.co;2-f

文献信息

• Carbene-Catalyzed Alkylation of Carboxylic Esters via Direct Photoexcitation of Acyl Azolium Intermediates
  作者：Shi-Chao Ren、Wen-Xin Lv、Xing Yang、Jia-Lei Yan、Jun Xu、Fang-Xin Wang、Lin Hao、Huifang Chai、Zhichao Jin、Yonggui Robin Chi

  DOI：10.1021/acscatal.1c00165

  日期：2021.3.5

  A carbene-catalyzed reductive coupling reaction of carboxylic esters and substituted Hantzsch esters is disclosed. Key steps of this reaction include one-electron reduction of a carbene catalyst-bound acyl azolium intermediate to generate the corresponding radical intermediate for subsequent alkylation reactions. The reaction is promoted by irradiation with visible light without the involvement of

  公开了羧酸酯和取代的汉茨tz酯的卡宾催化的还原偶联反应。该反应的关键步骤包括单电子还原卡宾催化剂所结合的酰基偶氮中间体，以产生相应的自由基中间体用于随后的烷基化反应。在不涉及过渡金属光催化剂的情况下，通过可见光照射可促进反应。机理研究表明，原位形成的酰基偶氮鎓中间体的直接光激发可能是这种光诱导的单电子还原过程的原因。光激发将酰基偶氮中间体转化为单电子氧化剂，从而使Hantzsch酯进行单电子氧化以生成自由基中间体。我们的反应适用于各种芳基羧酸酯和Hantzsch酯底物。可以使用我们的方法，通过非常温和的条件（可以耐受各种官能团）将复杂的结构（包括药物中存在的结构）并入酮分子中。
• Dell'Erba, Carlo; Sancassan, Fernando; Leandri, Giuseppe, Gazzetta Chimica Italiana, 1989, vol. 119, # 12, p. 643 - 648
  作者：Dell'Erba, Carlo、Sancassan, Fernando、Leandri, Giuseppe、Novi, Marino、Petrillo, Giovanni、et al.

  DOI：——

  日期：——
• Activation parameters of the reactions of 4-nitrophenyl benzoates and S-phenyl benzothioate with 4-chlorophenol in dimethylformamide in the presence of potassium carbonate
  作者：I. A. Os’kina、V. M. Vlasov

  DOI：10.1134/s1070428009040095

  日期：2009.4

  The kinetics of transesterification of 4-nitrophenyl benzoates and S-phenyl benzothioate with 4-chlorophenol in dimethylformamide in the presence of potassium carbonate were studied. Variation of the substrate reactivity and activation parameters of the process is discussed with respect to the substituent in the benzoic acid fragment.
• Kinetics of the reaction of substituted 4-nitrophenyl benzoates with benzenethiol in the presence of potassium carbonate in dimethylformamide
  作者：I. A. Os’kina、V. M. Vlasov

  DOI：10.1134/s1070428008040167

  日期：2008.4

  The effect of the substituent nature on the rate and activation parameters of transesterification of a series of 4-nitrophenyl benzoates with benzenethiol in dimethylformamide in the presence of potassium carbonate was studied by the competing reaction method. In all cases, change of the Gibbs energy of activation is determined mainly by variation of the enthalpy of activation. 4-Nitrophenyl benzoates having electron-withdrawing substituents in the benzoyl fragment were found to fit an isokinetic relation with an isokinetic temperature beta of 318 K. Enthalpy-entropy compensation effect was observed in the reactions with all the examined 4-nitrophenyl benzoates. The relation between the reactivity and polarizability of nucleophilic center in S- and O-nucleophiles is discussed.