2,4-diphenyl-6-(trifluoromethyl)pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,4-diphenyl-6-(trifluoromethyl)pyridine
• 化学式: C₁₈H₁₂F₃N
• 分子量: 299.295
• InChiKey: XVDQMMUDDPHRAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-Buten-1-one, 4,4,4-trifluoro-3-hydroxy-1-phenyl-, (Z)- 以 乙醚 、 苯 为溶剂， 生成 2,4-diphenyl-6-(trifluoromethyl)pyridine
  参考文献：
  名称：

  Interaction of fluoroalkyl-containing ?-diketones with amines

  摘要：

  The composition of products of the interaction of asymmetric fluoroalkyl-containing beta-diketones with amines was studied. Mixtures of regioisomeric beta-aminovinylketones and products of cleavage and secondary condensation are formed, depending on the temperature, the solvent, the nature of the fluorinated and nonfluorinated substituents in the beta-diketone, and the basicity of the amine. The major product is a beta-aminovinylketone in which the NH2 group is removed from the fluoroalkyl substituent. No beta-aminovinylimines, products of condensation involving two electrophilic centers, were observed.

  DOI：

  10.1007/bf01430731

文献信息

• Regioselective Direct C–H Trifluoromethylation of Pyridine
  作者：Xiao Yang、Rui Sun、Shun Li、Xueli Zheng、Maolin Yuan、Bin Xu、Weidong Jiang、Hua Chen、Haiyan Fu、Ruixiang Li

  DOI：10.1021/acs.orglett.0c02413

  日期：2020.9.18

  A highly efficient and regioselective direct C–H trifluoromethylation of pyridine based on an N-methylpyridine quaternary ammonium activation strategy has been developed. A variety of trifluoromethylpyridines can be obtained in good yield and excellent regioselectivity by treating the pyridinium iodide salts with trifluoroacetic acid in the presence of silver carbonate in N,N-dimethylformamide. The

  基于N-甲基吡啶季铵活化策略，开发了一种高效且区域选择性的吡啶直接CH H三氟甲基化方法。通过在N，N-二甲基甲酰胺中在碳酸银存在下用三氟乙酸处理碘化吡啶鎓盐，可以以良好的产率和优异的区域选择性获得各种三氟甲基吡啶。该协议具有良好的功能组兼容性，易于获得的起始材料以及操作简便的特点。对照实验表明，该反应可能涉及亲核三氟甲基化机理。
• Efficient and convenient entry to β-hydroxy-β-trifluoromethyl-β-substituted ketones and 2,6-disubstituted 4-trifluoromethylpyridines based on the reaction of trifluoromethyl ketones with enamines or imines
  作者：Kazumasa Funabiki、Akie Isomura、Yoshihiro Yamaguchi、Wataru Hashimoto、Kei Matsunaga、Katsuyoshi Shibata、Masaki Matsui

  DOI：10.1039/b105636k

  日期：2001.10.11

  The reactions of trifluoromethyl ketones with enamines or imines are described. The reaction of trifluoroacetone with enamines or imines followed by hydrolysis gave the corresponding β-hydroxy-β-trifluoromethyl-β-methyl ketones in good yields. The reaction of trifluoromethylated β-diketones with enamines in the presence of ammonium acetate gave 4-trifluoromethylated pyridines exclusively in good yields, without any detectable amount of regioisomers.

  三氟甲基酮与烯胺或亚胺的反应进行了描述。三氟乙酰丙酮与烯胺或亚胺反应后经水解，以良好的产率得到了相应的β-羟基-β-三氟甲基-β-甲基酮。在醋酸铵存在下，三氟甲基化的β-二酮与烯胺反应，仅以良好的产率得到了4-三氟甲基化的吡啶，没有任何可检测到的位置异构体。
• Regioselective Synthesis of 2,4-Diaryl-6-trifluoromethylated Pyridines through Copper-Catalyzed Cyclization of CF₃-Ynones and Vinyl Azides
  作者：Jixin Wang、Da Ba、Mengqi Yang、Guolin Cheng、Lianhui Wang

  DOI：10.1021/acs.joc.1c00275

  日期：2021.5.7

  copper-catalyzed cyclization of readily available vinyl azides with CF3-ynones is steadily achieved under mild conditions to furnish the versatile 2,4-diaryl-6-trifluoromethylated pyridine products, which are of great interest in medicinal chemistry. The generation of the vinyl iminophosphorane intermediates from vinyl azides through the Staudinger–Meyer reaction ensures the subsequent 1,4-addition process with

  在温和的条件下稳定地实现了易于获得的乙烯基叠氮化物与CF 3-炔酮的新型铜催化环化，以提供通用的2,4-二芳基-6-三氟甲基化吡啶产物，这在药物化学中引起了人们的极大兴趣。通过Staudinger-Meyer反应从叠氮化乙烯中生成乙烯基亚氨基膦烷中间体，可确保随后的CF 3-炔酮在此转化过程中进行1,4-加成过程。
• Synthesis of 2‐Trifluoromethyl Pyridines through Multicomponent Kröhnke Reaction
  作者：Biqiong Hong、Yun Teng、Zheng Fang、Wei Wu、Zhiqiang Weng

  DOI：10.1002/ejoc.202400299

  日期：2024.6.24

  A multicomponent Kröhnke reaction of chalcones with 1-(3,3,3-trifluoro-2-oxopropyl)pyridin-1-ium bromide and ammonium acetate is described. This strategy allows efficiently construction of a series of 2-trifluoromethyl pyridines with broad functional groups.

  描述了查耳酮与 1-(3,3,3-三氟-2-氧代丙基)吡啶-1-溴化鎓和乙酸铵的多组分 Kröhnke 反应。该策略允许有效构建一系列具有广泛官能团的2-三氟甲基吡啶。
• CN112174877
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