4-(3-三氟甲基苯基)苯甲酸甲酯 | 127783-72-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(3-三氟甲基苯基)苯甲酸甲酯
• 英文名称: methyl 4-(3-trifluoromethylphenyl)benzoate
• 英文别名: Methyl 3'-(trifluoromethyl)[1,1'-biphenyl]-4-carboxylate；methyl 4-[3-(trifluoromethyl)phenyl]benzoate
• CAS: 127783-72-6
• 化学式: C₁₅H₁₁F₃O₂
• 分子量: 280.246
• InChiKey: QEJLGUUJIJBMOO-UHFFFAOYSA-N

物化性质

• 熔点：
  73 °C
• 沸点：
  346.8±42.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  3
• 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：

  、 3-(三氟甲基)苯硼酸 在 1,4-双(二苯基膦丁烷)二氯化钯 、 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以71%的产率得到4-(3-三氟甲基苯基)苯甲酸甲酯
  参考文献：
  名称：

  通过碳-氮键活化，钯催化酰胺的 Suzuki-Miyaura 交叉偶联。

  摘要：

  钯催化的铃木-宫浦交叉偶联或芳基卤化物广泛应用于合成化学中许多重要分子的合成，包括药物、聚合物和功能材料。在此，我们公开了第一个钯催化的酰胺脱羰 Suzuki-Miyaura 交叉偶联，通过选择性活化酰胺的 NC(O) 键来合成联芳基化合物。这种新方法依赖于催化循环的精确序列工程，其中脱羰作用发生在金属转移步骤之前。该反应与多种硼酸和酰胺相容，以高产率提供有价值的联芳基化合物（> 60 个实例）。DFT 研究支持涉及氧化加成、脱羰和金属转移的机制，并提供了对高 NC(O) 键激活选择性的见解。最重要的是，该反应确立了钯催化在酰胺键的联芳铃木-宫浦交叉偶联中的应用，并且应该能够设计出多种交叉偶联方法，其中钯可与传统的由芳基卤化物合成联芳基和拟卤化物。

  DOI：

  10.1039/c9sc03169c

文献信息

• Metal-free oxidative decarbonylative coupling of aromatic aldehydes with arenes: direct access to biaryls
  作者：Ren-Jin Tang、Qing He、Luo Yang

  DOI：10.1039/c4cc10155c

  日期：——

  A metal-free oxidative decarbonylative coupling of aromatic aldehydes with electron-rich or electron-deficient arenes to produce biaryl compounds was developed. This novel coupling was proposed to proceed via a non-chain radical homolytic aromatic substitution (HAS) type mechanism, based on the substrate scope, ortho-regioselectivity, radical trapping experiments and DFT calculation studies. With the

  开发了芳香醛与富电子或缺电子的芳烃的无金属氧化脱羰基偶联剂，以生产联芳基化合物。基于底物范围，邻位区域选择性，自由基捕获实验和DFT计算研究，提出了通过非链自由基均相芳香族取代（HAS）类型的机理进行这种新型偶联。随着芳香醛和芳烃的现成可用，无金属条件应使这种偶联对于联芳基合成具有吸引力。
• Process for the preparation of unsymmetric biaryl compounds
  申请人：Bayer Aktiengesellschaft

  公开号：US04990647A1

  公开（公告）日：1991-02-05

  Unsymmetric biaryl compounds are prepared by coupling two different halogenoaromatics by reaction with a metal and carrying out the reaction in the presence of catalytic amounts of a nickel compound, a promoter and a phosphorus-containing ligand.

  非对称双芳基化合物是通过将两种不同的卤代芳香化合物与金属反应并在催化量的镍化合物、促进剂和含磷配体的存在下进行反应而制备的。
• Mechanism insight and scope of PEPPSI-catalyzed cross-coupling reaction between triarylbismuth and arylbromide
  作者：Bénédicte Cassirame、Sylvie Condon、Christophe Pichon

  DOI：10.1016/j.molcata.2016.07.016

  日期：2016.12

  In this paper we report the first cross-coupling reaction of Ar3Bi with Ar'X mediated by Pd-NHC complexes by keeping the ability of Ar3Bi to transfer the three aryl moieties. Investigations were carried out in order to minimize the quantity of the side product Ar-Ar coming from the conversion of Ar3Bi. The results showed that PEPPSI IPr was a good catalyst precursor. Efforts were focussed on the rule of each additive such as PPh3 and the base. It was notably found that the presence of PPh3 (ratio PEPPSI IPriPPh(3): 1/1) was essential to keep the process efficient. Therefore NHC-Pd-PPh3 has been assumed as being the catalytic species. Under the optimized reaction conditions the concomitant formation of the undesired biaryl side product was restricted to its inherent formation consecutive to the reduction of the catalyst precursor to Pd(0). In a last study, the scope and the limitation of the new catalytic methodology were examined and a large range of unsymmetrical biaryl compounds Ar-Ar' bearing various substituents from strongly electron-donating to electron-withdrawing ones have been prepared and fully characterized. (C) 2016 Elsevier B.V. All rights reserved.
• Efficient Cobalt-Catalyzed Formation of Unsymmetrical Biaryl Compounds and Its Application in the Synthesis of a Sartan Intermediate
  作者：Muriel Amatore、Corinne Gosmini

  DOI：10.1002/anie.200704402

  日期：2008.2.28
• HIMMLER, J.;BRADEN, R.
  作者：HIMMLER, J.、BRADEN, R.

  DOI：——

  日期：——