2,3,4,6-tetrafluoro-5-phenylpyridine | 29636-84-8

• 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: 2,3,4,6-tetrafluoro-5-phenylpyridine
• 英文别名: 3-C6H5-C5F4N
• CAS: 29636-84-8
• 化学式: C₁₁H₅F₄N
• 分子量: 227.161
• InChiKey: YXFLUJOSDNFFHB-UHFFFAOYSA-N

物化性质

• 沸点：
  252.5±35.0 °C(predicted)
• 密度：
  1.378±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3,4,6-四氟吡啶 、 苯 在 2,2'-硫代二丙烷 、 palladium diacetate 、 溶剂黄146 、 silver carbonate 作用下， 反应 20.0h， 以79%的产率得到2,3,4,6-tetrafluoro-5-phenylpyridine
  参考文献：
  名称：

  Palladium-Catalyzed Cross-Coupling of Polyfluoroarenes with Simple Arenes

  摘要：

  The most efficient method to construct biaryls is the direct dehydrogenative cross-coupling of two different aromatic rings. Such an ideal cross arylation starting from distinct polyfluoroarenes and simple arenes was presented. The selectivity of the cross-coupling was controlled by both of the electronic property of fluoroarenes and steric hindrance of simple arenes. Diisopropyl sulfide was essential to promote the efficacy.

  DOI：

  10.1021/ol102688e

文献信息

• Pd-catalyzed direct arylation of electron-deficient polyfluoroarenes with aryliodine(III) diacetates
  作者：Zhengjiang Fu、Qiheng Xiong、Wenbiao Zhang、Zhaojie Li、Hu Cai

  DOI：10.1016/j.tetlet.2014.11.033

  日期：2015.1

  polyfluoroarenes with readily available aryliodine(III) diacetates was developed with moderate to good yields. The process exhibited good functional tolerance with respect to methyl, methoxy, bromo, chloro, trifluoromethyl, cyano, and aldehyde groups. Mechanistic studies revealed this coupling involved in situ generation of aryl iodide from heating-promoted decomposition of aryliodine(III) diacetate, followed by

  现已开发出Pd催化的缺电子多氟芳烃与易于获得的芳基碘（III）二乙酸酯的直接芳基化反应，产率中等至良好。该方法对于甲基，甲氧基，溴，氯，三氟甲基，氰基和醛基表现出良好的功能耐受性。机理研究表明，这种偶联涉及加热促进的二乙酸芳基碘（III）的分解，原位生成芳基碘化物，然后与多氟芳烃底物偶联，得到所需的产物。
• Homolytic reactions of perfluoroaromatic compounds. Part III. Reactions of benzoyl peroxide with hexafluorobenzene, chloro-, bromo-, and nitro-pentafluorobenzene, and pentafluoropyridine
  作者：P. H. Oldham、Gareth H. Williams、Barbara A. Wilson

  DOI：10.1039/j29700001346

  日期：——

  The reaction of benzoyl peroxide with hexafluorobenzene has been shown to give 2,3,4,5,6-pentafluorobiphenyl and a residue whose relative yields depend mainly on the conditions used for the distillation of the biaryl from the reaction mixtures. This supports the suggestion made previously that the biaryl is formed partly by defluorination of σ-complexes during reaction, and partly by thermal breakdown

  已经显示过氧化苯甲酰与六氟苯的反应产生2,3,4,5,6-五氟联苯和其相对产率主要取决于用于从反应混合物中蒸馏联芳基的条件的残余物。这支持了先前提出的建议，即联芳基部分是通过在反应过程中σ配合物的脱氟，部分是通过在蒸馏过程中σ配合物的二聚体的热分解而形成的。氯，溴和硝基五氟苯与五氟吡啶的类似苯基化反应可得到异构体产物的混合物。已测量并讨论了这些异构体与氯和溴五氟苯和五氟吡啶形成的比例。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.5, 4, page 115 - 148
  作者：

  DOI：——

  日期：——