4-(5-methyl-2-thiophenyl)benzoic acid methyl ester | 1404372-08-2

• 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: 4-(5-methyl-2-thiophenyl)benzoic acid methyl ester
• 英文别名: methyl 4-(5-methylthiophene-2-yl)benzoate；methyl 4-(5-methylthiophen-2-yl)benzoate
• CAS: 1404372-08-2
• 化学式: C₁₃H₁₂O₂S
• 分子量: 232.303
• InChiKey: PCLJJDMZOJRNSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-甲基噻吩 、 对氯苯甲酸甲酯 在 C₃₆H₅₀Cl₂N₃OPPd 、 potassium carbonate 、 三甲基丙酮酸 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 以60%的产率得到4-(5-methyl-2-thiophenyl)benzoic acid methyl ester
  参考文献：
  名称：

  Efficient Pd-Catalyzed Direct Arylations of Heterocycles with Unreactive and Hindered Aryl Chlorides

  摘要：

  A highly electron-rich Pd complex can efficiently catalyze the direct arylation of heteroaromatics with unreactive and sterically congested aryl chlorides.

  DOI：

  10.1021/ol302635e

文献信息

• Direct C–H Arylation of Thiophenes at Low Catalyst Loading of a Phosphine-Free Bis(alkoxo)palladium Complex
  作者：Yabo Li、Jingran Wang、Mengmeng Huang、Zhiwei Wang、Yusheng Wu、Yangjie Wu

  DOI：10.1021/jo402745b

  日期：2014.4.4

  An efficient phosphine-free direct C–H arylation of thiophenes at the α-position has been developed at low catalyst loading of bis(alkoxo)palladium complex (Cat.I, 0.1–0.2 mol %). The developed synthetic method can be applied to the synthesis of α-aryl/heteroaryl thiophenes from aryl or heteroaryl bromides in good to excellent yields and is compatible with the substrates bearing electron-donating or

  在双（烷氧基）钯配合物（Cat.I，0.1-0.2 mol％）的低催化剂负载下，已开发出一种有效的无磷的噻吩在α位上无膦直接CH芳基化的化合物。所开发的合成方法可用于从芳基或杂芳基溴化物以良好至优异的产率合成α-芳基/杂芳基噻吩，并且与带有给电子或吸电子基团的底物相容。噻吩2位和5位的反应性是相同的，并且在最佳条件下不依赖于空间位阻。该条件还可以以高转化率应用于其他杂环部分，例如苯并噻吩，苯并呋喃和吡咯。
• Non‐Directed C−H Arylation of Anisole Derivatives via Pd/S,O‐Ligand Catalysis
  作者：Ke‐Zuan Deng、Verena Sukowski、M. Ángeles Fernández‐Ibáñez

  DOI：10.1002/anie.202400689

  日期：2024.5.6

  An efficient directing group free C−H arylation of anisoles via Pd/S,O-ligand catalytic system is reported. This method can be applied to a wide variety of anisole derivatives and aryl iodides and is also applicable for late-stage arylation of bioactive molecules.

  据报道，苯甲醚通过 Pd/S,O-配体催化系统进行有效的无导向基团 C−H 芳基化。该方法可应用于多种苯甲醚衍生物和芳基碘化物，也适用于生物活性分子的后期芳基化。
• Visible light induced cross-coupling synthesis of asymmetrical heterobiaryls using Pd/CeO2 nanocomposite photocatalyst
  作者：Yanqin Ge、Pinhui Diao、Chen Xu、Nannan Zhang、Cheng Guo

  DOI：10.1016/j.cclet.2018.01.002

  日期：2018.6

  A simple, mild and green approach has been developed for the synthesis of asymmetrical heterobiaryls under the irradiation of visible light without any oxidants and promoting reagents through using Pd/CeO2 nanocomposite photocatalyst. This method can tolerate considerable functional groups such as electron donating groups and electron-withdrawing groups through C-C cross-coupling. Moreover, we obtain the products with moderate yields in an efficient way. Finally, a plausible mechanism is proposed. (C) 2018 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.