S-m-tolyl 4-methylbenzenesulfonothioate | 95493-61-1

• 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-m-tolyl 4-methylbenzenesulfonothioate
• 英文别名: S-(m-tolyl) 4-methylbenzenesulfonothioate；4-tolylsulfonothioic 3-tolyl ester；p-Toluolthiosulfonsaeure-S-(3-methyl-phenylester)
• CAS: 95493-61-1
• 化学式: C₁₄H₁₄O₂S₂
• 分子量: 278.396
• InChiKey: HVKQYSTYEJPACZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  S-m-tolyl 4-methylbenzenesulfonothioate 、 二苯基N,N'-二异丙基亚磷酰胺 以 aq. phosphate buffer 、 二甲基亚砜 为溶剂， 反应 0.08h， 以88%的产率得到O-benzyl S-(m-tolyl) diisopropylphosphoramidothioate
  参考文献：
  名称：

  Sulfonyl-Promoted Michaelis–Arbuzov-Type Reaction: An Approach to S/Se–P Bonds

  摘要：

  DOI：

  10.1021/acs.joc.1c01681
• 作为产物：
  描述：

  3-甲基苯硫酚 、 4-methylbenzenediazonium tetrafluoroborate 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-m-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 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。
• Metal-Free Radical Annulation of Oxygen-Containing 1,7-Enynes: Configuration-Selective Synthesis of (<i>E</i>)-3-((Arylsulfonyl)methyl)-4-Substituted Arylidenechromene Derivatives
  作者：Kaimin Mao、Mouwang Bian、Lei Dai、Jinghang Zhang、Qiuyu Yu、Chang Wang、Liangce Rong

  DOI：10.1021/acs.orglett.0c03946

  日期：2021.1.1

  A novel strategy for the synthesis of (E)-3-((arylsulfonyl)methyl)-4-substituted benzylidenechromene derivatives via a metal-free radical annulation reaction of oxygen-containing 1,7-enynes with thiosulfonates has been developed. The reaction shows broad substrate scope, wide functional group tolerance, and moderate to excellent yields. Moreover, thiosulfonates were well driven to achieve the bifunctionalization

  通过含氧的1,7-烯炔与硫代磺酸盐的金属自由基环合反应，开发了一种新的策略来合成（E）-3-（（芳基磺酰基）甲基）-4-取代的亚苄基亚甲基衍生物。该反应显示出宽的底物范围，宽的官能团耐受性和中等至优异的产率。此外，硫代磺酸盐被很好地驱动以实现衍生自脂族炔烃的oxo-1,7-烯炔的双官能化反应。另外，产物的（E）-构型由1，7-烯炔的结构高度控制。
• 一种硒代磷化物和硫代磷化物的制备方法
  申请人：烟台大学

  公开号：CN114805430A

  公开（公告）日：2022-07-29

  本发明公开了一种硒代磷化物和硫代磷化物的制备方法。所述方法将硒代磺酸酯或硫代磺酸酯与磷试剂在室温条件下自发的发生反应，并在很短的时间内完成反应，以高反应效率得到硒代磷化物和硫代磷化物。正因为反应中不需要加入金属、强碱、强氧化剂等容易破坏底物结构的试剂，所以本发明中底物以及官能团的兼容性非常好。本发明仅利用反应物本身的高反应活性自发进行反应，避免了外加试剂（金属、强氧化剂、强碱）对底物官能团的破坏，因此本发明具有很高的底物和官能团兼容性，这同时也使得本发明的反应效率和产率都普遍很高。