(4-nitrophenyl)(4-(trifluoromethyl)phenyl)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-nitrophenyl)(4-(trifluoromethyl)phenyl)sulfane
• 英文别名: 4-[4-(trifluoromethyl)phenylthio]nitrobenzene；1-(4-Nitrophenyl)sulfanyl-4-(trifluoromethyl)benzene；1-(4-nitrophenyl)sulfanyl-4-(trifluoromethyl)benzene
• 化学式: C₁₃H₈F₃NO₂S
• 分子量: 299.273
• InChiKey: GIADFHSRYZVJQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4-nitrophenyl)(4-(trifluoromethyl)phenyl)sulfane 在 tin(ll) chloride 作用下， 生成 4-((4-(trifluoromethyl)phenyl)thio)aniline
  参考文献：
  名称：

  发现和作为SARS的前列环素受体拮抗剂的SAR的发展[校正]。

  摘要：

  基于筛选结果（1a，b），开发了一系列选择性，高亲和力的前列环素受体拮抗剂。优化的铅化合物25d [（4,5-二氢-1H-咪唑-2-基）-[4-（4-异丙氧基苄基）苯基]胺]在大鼠中具有镇痛作用。

  DOI：

  10.1016/j.bmcl.2003.10.070
• 作为产物：
  描述：

  4-三氟甲基苯硼酸 、 4-硝基苯硫醇 在 copper diacetate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以91%的产率得到(4-nitrophenyl)(4-(trifluoromethyl)phenyl)sulfane
  参考文献：
  名称：

  Copper Mediated Formation of Carbon-Heteroatom Bonds Using Organoboron Reagents and Ultrasound

  摘要：

  This report summarizes research efforts focused on copper acetate mediated reactions to form new carbon-heteroatom bonds using organoboron reagents under ultrasound irradiation. The method involves the application of ultrasound irradiation to the Chan-Evans-Lam reaction to achieve O-arylation of phenols, N-arylation of anilines and indoles, and S-arylation of thiols. Ultrasound irradiation was found to decrease reaction times from 72 hours to 4 hours while improving the product yields an average of 20%(1) Representative C-O, C-N, and C-S coupling reactions were successfully scaled-up from the milligram to gram levels while maintaining good product yields offering potential applications in industrial processes.

  DOI：

  10.3987/com-14-s(k)18

文献信息

• Microwave-assisted Ullmann-Buchwald C-S bond formation using a copper(I) catalyst and trans-cyclohexane-1,2-diol as ligand
  作者：Mark C. Bagley、Vincenzo Fusillo、Edward G. B. Hills、Alex T. Mulholland、Joseph Newcombe、Leanne J. Pentecost、Emily L. Radley、Bethan R. Stephens、Christopher C. Turrell

  DOI：10.3998/ark.5550190.0013.720

  日期：——

  aryl halide (1 equiv.) in 2propanol at 120 °C for three hours in the presence of K2CO3 (2 equiv.) as base using copper(I) iodide as catalyst (5 mol%) and trans-cyclohexane-1,2-diol (2 equiv.) as ligand provides a rapid and convenient method for C−S bond formation. The process is most efficient using thiophenol and aryl iodide precursors, both of which may contain electron-donating and electronwithdrawing

  在 K2CO3（2 当量）作为碱存在下，使用碘化铜（I）作为碱，在 120 °C 下，将苯硫酚或烷基硫醇（1 当量）和芳基卤化物（1 当量）在 2 丙醇中微波照射三小时催化剂（5 mol%）和反式-环己烷-1,2-二醇（2当量）作为配体为C-S键的形成提供了一种快速方便的方法。该方法使用苯硫酚和芳基碘前体最有效，这两种前体都可能含有给电子和吸电子基团，从而以良好至极好的收率得到相应的二芳基硫醚。
• Copper-Promoted Sandmeyer Trifluoromethylation Reaction
  作者：Jian-Jun Dai、Chi Fang、Bin Xiao、Jun Yi、Jun Xu、Zhao-Jing Liu、Xi Lu、Lei Liu、Yao Fu

  DOI：10.1021/ja404217t

  日期：2013.6.12

  A copper-promoted trifluoromethylation reaction of aromatic amines is described. This transformation proceeds smoothly under mild conditions and exhibits good tolerance of many synthetically relevant functional groups. It provides an alternative approach for the synthesis of trifluoromethylated arenes and heteroarenes. It also constitutes a new example of the Sandmeyer reaction.

  描述了芳香胺的铜促进的三氟甲基化反应。这种转化在温和条件下顺利进行，并且对许多合成相关的官能团表现出良好的耐受性。它为合成三氟甲基化芳烃和杂芳烃提供了一种替代方法。它也构成了桑德迈尔反应的一个新例子。
• C-S coupling with nitro group as leaving group via simple inorganic salt catalysis
  作者：Maojie Xuan、Chunlei Lu、Bo-Lin Lin

  DOI：10.1016/j.cclet.2019.07.012

  日期：2020.1

  An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (SNAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step addition elimination mechanism. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
• Reaction under Ball-Milling: Solvent-, Ligand-, and Metal-Free Synthesis of Unsymmetrical Diaryl Chalcogenides
  作者：Nirmalya Mukherjee、Tanmay Chatterjee、Brindaban C. Ranu

  DOI：10.1021/jo402071b

  日期：2013.11.1

  A convenient, efficient, and general procedure for the synthesis of diaryl chalcogenides including sulfides, selenides and tellurides has been developed by the reaction of diazonium tetrafluoroborates and diaryl dichalcogenides on the surface of alumina under ball-milling without any solvent or metal. A wide range of functionalized diaryl chalcogenides are obtained in high purity by this procedure.
• Copper Mediated Formation of Carbon-Heteroatom Bonds Using Organoboron Reagents and Ultrasound
  作者：George W. Kabalka、Bryan J. Musolino

  DOI：10.3987/com-14-s(k)18

  日期：——

  This report summarizes research efforts focused on copper acetate mediated reactions to form new carbon-heteroatom bonds using organoboron reagents under ultrasound irradiation. The method involves the application of ultrasound irradiation to the Chan-Evans-Lam reaction to achieve O-arylation of phenols, N-arylation of anilines and indoles, and S-arylation of thiols. Ultrasound irradiation was found to decrease reaction times from 72 hours to 4 hours while improving the product yields an average of 20%(1) Representative C-O, C-N, and C-S coupling reactions were successfully scaled-up from the milligram to gram levels while maintaining good product yields offering potential applications in industrial processes.