S-(o-tolyl) 4-methylbenzenesulfonothioate | 95493-62-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: S-(o-tolyl) 4-methylbenzenesulfonothioate
• 英文别名: 1-Methyl-2-(4-methylphenyl)sulfonylsulfanylbenzene
• CAS: 95493-62-2
• 化学式: C₁₄H₁₄O₂S₂
• 分子量: 278.396
• InChiKey: ZVDZQOUKOGVALX-UHFFFAOYSA-N

物化性质

• 熔点：
  100 °C
• 沸点：
  420.6±48.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-(o-tolyl) 4-methylbenzenesulfonothioate 在 四氯化碳 、 氯 作用下， 生成 2-(o-tolylthio)isoindoline-1,3-dione
  参考文献：
  名称：

  Klivenyi et al., Acta Chimica Academiae Scientiarum Hungaricae, 1955, vol. 6, p. 373,378

  摘要：

  DOI：
• 作为产物：
  描述：

  4-methylbenzenediazonium tetrafluoroborate 、 2-巯基甲苯 在 sodium metabisulfite 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 2.5h， 以72%的产率得到S-(o-tolyl) 4-methylbenzenesulfonothioate
  参考文献：
  名称：

  TFA promoted multi-component reaction of aryldiazonium with sodium metabisulphite and thiols: Construction of thiosulfonate under transition-metal free conditions

  摘要：

  A TFA promoted multi-component reaction of aryldiazonium with sodium metabisulphite and thiols to construct thiosulfonates under transition-metal free conditions is reported. The thiosulfonates were isolated in good yields with broad tolerance of functional group. Readily available inorganic Na2S2O5 was applied as the sulfur dioxide surrogate. This strategy features easily available substrates, mild reaction conditions and free transition-metal catalyst. (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2019.12.032

文献信息

• Electrochemical Oxidative Cross‐Coupling Reaction to Access Unsymmetrical Thiosulfonates and Selenosulfonates
  作者：Xiaofeng Zhang、Ting Cui、Yanghao Zhang、Weijin Gu、Ping Liu、Peipei Sun

  DOI：10.1002/adsc.201900047

  日期：2019.4.23

  The electrochemical oxidative cross‐dehydrogenative coupling of arylsulfinic acids with thiophenols was achieved via a radical process. A wide range of arylsulfinic acids and substituted thiophenols were found to be tolerated, providing unsymmetrical thiosulfonates in good to excellent yields. This electrochemical method can also be used for the reaction of arylsulfinic acids with disulfides or diselenides

  芳基亚磺酸与硫酚的电化学氧化交叉脱氢偶联是通过自由基过程实现的。发现宽范围的芳基亚磺酸和取代的苯硫酚是可以耐受的，从而以良好或优异的收率提供不对称的硫代磺酸盐。该电化学方法也可以用于芳基亚磺酸与二硫化物或二硒化物的反应以获得硫代磺酸盐或硒代磺酸盐。
• Copper-Catalyzed Synthesis of Thiosulfonates by Oxidative Coupling of Thiols with Sodium Sulfinates
  作者：Nobukazu Taniguchi

  DOI：10.1002/ejoc.201402847

  日期：2014.9

  sulfonylation of thiols was performed by using sodium sulfinates under an oxygen atmosphere. The procedure afforded thiosulfonates in good yields by using a CuI–Phen·H2O (Phen = 1,10-phenanthroline) catalyst and tolerated numerous combinations of arene- and alkanethiols with sodium sulfinates. Furthermore, it was found that the coupling of diaryl disulfides with sodium arylsulfinates proceeded in air and both

  硫醇的铜催化磺酰化是通过在氧气气氛下使用亚磺酸钠进行的。该程序通过使用 CuI-Phen·H2O（Phen = 1,10-菲咯啉）催化剂以良好的收率提供硫代磺酸盐，并且可以耐受芳烃和烷硫醇与亚磺酸钠的多种组合。此外，发现二芳基二硫化物与芳基亚磺酸钠的偶联在空气中进行，并且二硫化物上的两个硫化物基团都是可用的。
• Unsymmetrical disulfide and sulfenamide synthesis via reactions of thiosulfonates with thiols or amines
  作者：Nobukazu Taniguchi

  DOI：10.1016/j.tet.2017.02.047

  日期：2017.4

  The reactivity of thiosulfonates with nucleophilic reagents was investigated. When reactions of thiosulfonates with thiols were performed, unsymmetrical disulfides were obtained in excellent yields. This procedure could employ numerous aryl or alkyl thiols. On the other hand, reactions of thiosulfonates with amines proceeded in the presence of a copper catalyst. The procedure was performed efficiently

  研究了硫代磺酸盐与亲核试剂的反应性。当进行硫代磺酸盐与硫醇的反应时，以优异的产率获得了不对称的二硫化物。该程序可以使用多种芳基或烷基硫醇。另一方面，硫代磺酸盐与胺的反应在铜催化剂的存在下进行。该过程在空气中有效进行，得到相应的亚磺酰胺。
• Copper-Catalyzed TBHP-Mediated Radical Cross-Coupling Reaction of Sulfonylhydrazides with Thiols Leading to Thiosulfonates
  作者：Guo-Yu Zhang、Shuai-Shuai Lv、Adedamola Shoberu、Jian-Ping Zou

  DOI：10.1021/acs.joc.7b01121

  日期：2017.9.15

  A tert-butyl hydroperoxide (TBHP)-mediated coupling of sulfonylhydrazides with thiols catalyzed by CuBr2 to afford thiosulfonates via a radical process is described.

  描述了叔丁基氢过氧化物（TBHP）介导的磺酰肼与CuBr 2催化的硫醇通过自由基过程的偶联，得到硫代磺酸盐。
• H₂O₂-mediated metal-free protocol towards unsymmetrical thiosulfonates from sulfonyl hydrazides and disulfides in PEG-400
  作者：Zhihong Peng、Xiao Zheng、Yingjun Zhang、Delie An、Wanrong Dong

  DOI：10.1039/c8gc00381e

  日期：——

  A green and practical protocol between sulfonyl hydrazides and disulfides is herein reported for the synthesis of unsymmetrical thiosulfonates with the assistance of H2O2 in PEG-400, releasing N2 and H2O as the byproducts. The efficient and compatible process was considered to take place in the absence of metallic catalysts through a radical mechanism as determined by EPR analysis.

  磺酰基酰肼和二硫化物之间的绿色和实际协议在本文中报道的不对称硫代磺酸酯与H的援助合成2 Ó 2在PEG-400，释放Ñ 2和H 2 O作为副产物。有效和相容的过程被认为是在不存在金属催化剂的情况下通过EPR分析确定的自由基机理进行的。