(4-methoxyphenyl)(2,3,5,6-tetrafluorophenyl)sulfane

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (4-methoxyphenyl)(2,3,5,6-tetrafluorophenyl)sulfane
• 英文别名: 1--2,3,5,6-tetrafluor-benzol；1,2,4,5-Tetrafluoro-3-(4-methoxyphenyl)sulfanylbenzene；1,2,4,5-tetrafluoro-3-(4-methoxyphenyl)sulfanylbenzene
• 化学式: C₁₃H₈F₄OS
• 分子量: 288.266
• InChiKey: ZERWFRXVMFDDCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-甲氧基苯硫酚 、 五氟苯 在 potassium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 以91%的产率得到(4-methoxyphenyl)(2,3,5,6-tetrafluorophenyl)sulfane
  参考文献：
  名称：

  区域选择性的CS键形成完成的区域选择性CF取代聚氟芳烃取代硫酚。

  摘要：

  五氟苯，2,3,4,5-四氟苯甲酸甲酯和1,2,4,5-四氟苯与取代的苯酚的亲核芳族取代反应显示出良好的区域选择性，而五氟苯的收率很高。计算结果表明，多氟苯之间的特异性差异源自其电子性能。

  DOI：

  10.2174/157017812800167493

文献信息

• Synthesis of polyfluorinated aromatic ethers and thioethers by synergistic cleavage of C-B bond and C-F bond of B(C6F5)3
  作者：Cui-Cui Ma、Xing-Xing Zhu、Li Liu、Jian-Jun Dai、Jun Xu、Hua-Jian Xu

  DOI：10.1016/j.tetlet.2021.153387

  日期：2021.10

  A concise and efficient method for the synthesis of polyfluorinated aromatic ethers and thioethers by synergistic cleavage of C-B bond and C-F bond of B(C6F5)3 is reported. The reaction could proceed smoothly with excellent functional-group compatibility. In addition, the transformation represents the first general application of B(C6F5)3 as reaction partners in cross-coupling reaction.

  报道了一种通过协同裂解 B(C 6 F 5 ) 3的 CB 键和 CF 键合成多氟芳族醚和硫醚的简洁有效的方法。反应可以顺利进行，具有良好的官能团相容性。此外，该转变代表了 B(C 6 F 5 ) 3作为交叉偶联反应中的反应伙伴的首次普遍应用。
• Regioselective C–S bond formation accomplished by copper-catalyzed regioselective C–F substitution of perfluoroarenes with aryl thioacetates or benzyl thioacetate
  作者：Qizhong Zhou、Bin Zhang、Tieqi Du、Haining Gu、Huajiang Jiang、Rener Chen

  DOI：10.1016/j.tet.2012.03.091

  日期：2012.6

  Practical and straightforward method for regioselective C-S bond formation accomplished by copper-catalyzed regioselective C-F substitution of electron-deficient perfluoroarenes with aryl thioacetates or benzyl thioacetate has been developed. Because of its high reaction efficiency, good chemoselectivity and regioselectivity, and excellent functional-group compatibility, this protocol provides a useful and operationally simple access to polyfluoroaryl thioethers used for drugs and material chemistry. (C) 2012 Elsevier Ltd. All rights reserved.
• Regioselective C-S Bond Formation Accomplished by Regioselective C-F Substitution of Polyfluoroarenes with Substituted Thiophenols
  作者：Qizhong Zhou、Bin Zhang、Haining Gu、Aiguo Zhong、Tieqi Du、Qiong Zhou、Yuyuan Ye、Zhengneng Jin、Huajiang Jiang、Rener Chen

  DOI：10.2174/157017812800167493

  日期：2012.3.1

  The nucleophilic aromatic substitution reaction of pentafluorobenzene, methyl 2,3,4,5-tetrafluorobenzoic acid ester and 1,2,4,5-tetrafluorobenzene with substituted thiophenols showed good regioselectivity while pentafluorobenzene gave high yields. The computational results suggest that the specificity difference between polyfluorobenzenes originates from their electronic properties.

  五氟苯，2,3,4,5-四氟苯甲酸甲酯和1,2,4,5-四氟苯与取代的苯酚的亲核芳族取代反应显示出良好的区域选择性，而五氟苯的收率很高。计算结果表明，多氟苯之间的特异性差异源自其电子性能。