1,4-bis(4-chlorophenylthio)-2,3,5,6-tetrafluorobenzene | 122127-55-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,4-bis(4-chlorophenylthio)-2,3,5,6-tetrafluorobenzene
• 英文别名: (perfluoro-1,4-phenylene)bis((4-chlorophenyl)sulfane)；benzoyl fluoride；1,4-bis[(4-chlorophenyl)sulfanyl]-2,3,5,6-tetrafluorobenzene
• CAS: 122127-55-3
• 化学式: C₁₈H₈Cl₂F₄S₂
• 分子量: 435.293
• InChiKey: QHUWTDOIHAIDNG-UHFFFAOYSA-N

物化性质

• 熔点：
  168-170 °C
• 沸点：
  428.8±45.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.85
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-((4-chlorophenyl)disulfanyl)pyridine 、 五氟苯 在 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以43%的产率得到1,4-bis(4-chlorophenylthio)-2,3,5,6-tetrafluorobenzene
  参考文献：
  名称：

  通过C–H，C–F键激活和C–S键形成，将五氟苯与二硫键硫醇化†

  摘要：

  据报道，五氟苯与二硫化物之间通过CH，CF键活化和CS键形成而发生无金属的硫醇化反应。在温和的条件下，由五氟苯和二硫化物可以中等至良好的产率制备双硫代四氟苯衍生物。给出了反应的可能机理。

  DOI：

  10.1039/c7ob02836a

文献信息

• The organocatalytic synthesis of perfluorophenylsulfides <i>via</i> the thiolation of trimethyl(perfluorophenyl)silanes and thiosulfonates
  作者：Jinyun Luo、Muze Lin、Leifang Wu、Zhihua Cai、Lin He、Guangfen Du

  DOI：10.1039/d1ob01350e

  日期：——

  The organic superbase t-Bu-P4-catalyzed direct thiolation of trimethyl(perfluorophenyl)silanes and thiosulfonates was developed. Yields of perfluorophenylsulfides of up to 97% under catalysis of 5 mol% t-Bu-P4 were achieved. This method was shown to provide an efficient way to construct the perfluorophenyl–sulfur bond under mild metal-free reaction conditions.

  开发了有机超碱t -Bu-P 4催化的三甲基（全氟苯基）硅烷和硫代磺酸盐的直接硫醇化反应。在 5 mol% t -Bu-P 4的催化下，全氟苯硫醚的产率高达 97% 。该方法被证明提供了一种在温和的无金属反应条件下构建全氟苯基-硫键的有效方法。
• Expedient synthesis of tetrafluorophenoxthiines and derivatives by copper(I)-catalyzed cross-coupling reaction
  作者：Chuanming Yu、Gaobo Hu、Cuiling Zhang、Ran Wu、Haiwei Ye、Guanghui Yang、Xiangjun Shi

  DOI：10.1016/j.jfluchem.2013.05.023

  日期：2013.9

  synthesized from pentafluorobenzene and aryl thiols or diaryl disulfides in the presence of copper catalyst and ligand by using O2 as the oxidant, t-BuOLi as the base at 100 °C. The ligand (E)-3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one (L) played an indispensable role in the reaction. This work contains a notable mode of CF bond activation, which is in the ortho position to the CH bond of pentafluorobenzene

  在这项研究中，在100℃下，以O 2为氧化剂，t- BuOLi为碱，在铜催化剂和配体存在下，由五氟苯和芳基硫醇或二芳基二硫化物成功合成了四氟苯氧噻吨。配体（E）-3-（二甲基氨基）-1-（2-羟基苯基）丙-2-烯-1-酮（L）在反应中起不可或缺的作用。这项工作包含一个显着的C F键激活模式，该模式位于五氟苯C H键的邻位。
• The thiolate anion as a nucleophile Part XIV. further reactions of tin(II) arenethiolates
  作者：J.Joseph Jesudason、Michael E. Peach

  DOI：10.1016/s0022-1139(00)81036-2

  日期：1988.12

  The reactions of tin(II) benzenethiolate in DMF with hexafluorobenzene, chloropentafluorobenzene and bromopentafluorobenzene have been compared. Replacement of fluorine and chlorine by the phenylthio group and protodebromination were observed. DMF was a better solvent than either ethylene glycol/pyridine mixture (1:2) or diglyme for the reaction. New products have been isolated and characterized from

  比较了DMF中苯硫醇锡（II）与六氟苯，氯五氟苯和溴五氟苯的反应。观察到苯硫基取代了氟和氯，并进行了原脱溴作用。对于反应，DMF比乙二醇/吡啶混合物（1：2）或二甘醇二甲醚是更好的溶剂。从对氯苯硫醇锡（II）与六氟苯，十氟联苯，八氟甲苯和五氟苄基溴的反应中分离并鉴定了新产品。
• Copper-Catalyzed Direct Thiolation of Pentafluorobenzene with Diaryl Disulfides or Aryl Thiols by C-H and C-F Bond Activation
  作者：Chuanming Yu、Cuiling Zhang、Xiangjun Shi

  DOI：10.1002/ejoc.201101676

  日期：2012.4

  A Cu-catalyzed cross-coupling reaction of diaryl disulfides or aryl thiols with pentafluorobenzene using CuBr as the catalyst, tBuOLi or tBuOK as the base in DMSO at 60 °C under an O2 atmosphere was investigated. The corresponding bisarylthiolation products were obtained in moderate to good yields by C–H bond and C–F bond activation. When 1,10-phenanthroline·H2O and DDQ were added to the above system

  使用 CuBr 作为催化剂，tBuOLi 或 tBuOK 作为碱在 DMSO 中，在 60 °C 和 O2 气氛下，Cu 催化二芳基二硫化物或芳基硫醇与五氟苯的交叉偶联反应。通过 C-H 键和 C-F 键活化，以中等至良好的产率获得了相应的双芳基硫醇化产物。当1,10-菲咯啉·H2O和DDQ加入到上述体系中时，可以以中等产率分离出有/没有双芳基硫代产物的单芳基硫代产物。给出了这些转换的合理机制。因此，它代表了一种通过 C-H 键和 C-F 键活化合成多氟二芳基硫化物和多氟三芳基二硫化物的方法。
• Rhodium-catalyzed interconversion between acid fluorides and thioesters controlled using heteroatom acceptors
  作者：Mieko Arisawa、Toru Yamada、Masahiko Yamaguchi

  DOI：10.1016/j.tetlet.2010.09.009

  日期：2010.11

  A rhodium complex catalyzed the equilibrium acyl transfer reaction between acid fluorides and thioesters. In the presence of fluoride or thiolate acceptors, the reaction could be shifted to either product. RhH(PPh3)(4)-dppe catalyzed the reaction of acid fluorides and diorgano disulfides in the presence of triphenylphosphine giving thioesters, which was accompanied by triphenylphosphine difluoride. The same complex catalyzed the reaction of aryl thioesters and hexafluorobenzene giving acid fluorides, which was accompanied by 1,4-di(arylthio)-2,3,5,6-tetrafluorobenzenes. (C) 2010 Published by Elsevier Ltd.