S-(4-methoxyphenyl) 4-methylbenzenesulfonothioate | 80472-59-9

• 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-(4-methoxyphenyl) 4-methylbenzenesulfonothioate
• 英文别名: S-(4-methoxyphenyl) (4-methylbenzene)thiosulfonate；S-(4-methoxyphenyl) 4-toluenethiosulfonate；S-(4-Methoxyphenyl) 4-methylbenzene-1-sulfonothioate；1-(4-methoxyphenyl)sulfanylsulfonyl-4-methylbenzene
• CAS: 80472-59-9
• 化学式: C₁₄H₁₄O₃S₂
• 分子量: 294.395
• InChiKey: JACNIVPNONPQPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  S-(4-methoxyphenyl) 4-methylbenzenesulfonothioate 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.18h， 生成 1-(4-methoxyphenyl)-3-phenyltrisulfane
  参考文献：
  名称：

  Unsymmetrical Organotrisulfide Formation via Low-Temperature Disulfanyl Anion Transfer to an Organothiosulfonate

  摘要：

  New methodology is presented for the formation of unsymmetrical organotrisulfides in a high yield and purity, relatively free of polysulfide byproducts. The highlight of the method is the low-temperature (-78 degrees C) deprotection of a disulfanyl acetate with sodium methoxide in THF to form a disulfanyl anion, which reacts rapidly in situ with an organothiosulfonate (S-aryl or S-alkyl) within 30 seconds followed by quenching. The discovery of these new reaction conditions together with the relative greenness of the chemistry overall makes for an efficient protocol, from which a range of organotrisulfides covering aliphatic, aromatic, as well as cysteine and sugar groups can be accessed in a high yield and purity.

  DOI：

  10.1021/acs.joc.8b03262
• 作为产物：
  描述：

  4-甲基苯硫代磺酸 S-(4-甲基苯基)酯 在 potassium phosphate 、 [Rh(OH)(cod)]2 、 碘 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 S-(4-methoxyphenyl) 4-methylbenzenesulfonothioate
  参考文献：
  名称：

  铑催化的从芳烃基芳烃和S-芳基硫代磺酸盐无味合成二芳基硫醚

  摘要：

  各种二芳基硫醚，包括含杂芳基和氮的硫化物，已经通过有机硼与S-芳基硫代磺酸盐的铑催化的无味脱硼烷基芳基硫醇化反应而得到了有效制备。原料的易得性和硫化物的进一步转化已使各种有机硫化合物易于获得。

  DOI：

  10.1039/c7cc05868c

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。
• Organocatalytic Transformation of Aldehydes to Thioesters with Visible Light
  作者：Yueteng Zhang、Peng Ji、Wenbo Hu、Yongyi Wei、He Huang、Wei Wang

  DOI：10.1002/chem.201900932

  日期：2019.6.21

  A metal‐ and oxidant‐free catalytic method for accessing structurally diverse thioesters from readily accessible, widespread aldehydes, is described. A strategy of a simple organic 9,10‐phenanthrenequinone‐promoted hydrogen atom transfer (HAT) with visible light was successfully implemented to selectively generate acyl radicals without inducing crossover reactivity of thioester products. The preparative

  描述了一种无金属和无氧化剂的催化方法，该方法可从易于获得的广泛醛中获得结构多样的硫酯。成功实施了一种具有可见光的简单有机9,10-菲醌促进的氢原子转移（HAT）策略，可选择性地产生酰基自由基，而不会引起硫酯产物的交叉反应性。广泛的底物范围和广泛的官能团耐受性证明了该方法的制备能力，并且使复杂结构的后期修饰成为可能，这是现有协议难以实现的。
• Synthesis of<i>S</i>-Aryl Arenethiosulfonates from<i>N</i>,<i>N</i>-Di(arenesulfonyl)hydrazines: Reduction of Sulfonyl Chlorides with an Organic Reagent
  作者：Satoshi Iwata、Masato Senoo、Takeshi Hata、Hirokazu Urabe

  DOI：10.1002/hc.21088

  日期：2013.7

  N,N-Di(arenesulfonyl)-N′,N′-dimethyl-hydrazines, readily prepared from arenesulfonyl chlorides and N,N-dimethylhydrazine, were heated at 120°C in chlorobenzene to give S-aryl arenethiosulfonates, ArSSO2Ar, in good yields.

  N,N-二（芳烃磺酰基）-N',N'-二甲基肼，很容易由芳烃磺酰氯和 N,N-二甲基肼制备，在 120°C 下在氯苯中加热，得到 S-芳基芳烃硫代磺酸盐 ArSSO2Ar，质量良好产量。
• PTAB mediated open air synthesis of sulfonamides, thiosulfonates and symmetrical disulfanes
  作者：Debayan Sarkar、Manoj Kumar Ghosh、Nilendri Rout

  DOI：10.1016/j.tetlet.2018.05.017

  日期：2018.6

  A facile methodology has been described which has successfully simplified the generation of sulfonamides, thiosulfonates and symmetric disulfanes. This “trio” of reactions occur in an open air metal free atmosphere and has also been scaled up to grams making it suitable for commercialization. The reactions also have been successfully carried out with asymmetric variants, thus contributing to the chiral

  已经描述了一种简便的方法，该方法已成功简化了磺酰胺，硫代磺酸盐和对称二硫烷的生成。这种“三重”反应发生在无金属的露天气氛中，并且也已按比例放大至克，使其适合商业化。该反应还已经成功地用不对称变体进行，因此有助于手性库。用户友好的“三重奏”能够轻松生成这些多用途的硫类似物，并且所采用的反应条件反映了经济状况。
• Nickel-Catalyzed Difunctionalization of Alkynyl Bromides with Thiosulfonates and N-Arylthio Succinimides: A Convenient Synthesis of 1,2-Thiosulfonylethenes and 1,1-Dithioethenes
  作者：Raju Jannapu Reddy、Arram Haritha Kumari、Jangam Jagadesh Kumar、Gamidi Rama Krishna

  DOI：10.1055/a-1482-2486

  日期：2021.8

  cesium carbonate is described. An operationally simple and highly regioselective atom transfer radical addition (ATRA) of alkynyl bromides provides a wide range of (E)-1,2-thiosulfonylethenes (α-aryl-β-thioarylvinyl sulfones) in moderate to high yields. The extensive substrate scope of both alkynyl bromides and thiosulfonates is explored with a broad range of functional groups. Indole-derived 1,1-bromoalkenes

  描述了在碳酸铯存在下用硫代磺酸盐有效地催化1-溴炔烃的镍催化邻位硫磺酰化。炔基溴化物的操作简单且高度区域选择性的原子转移自由基加成（ATRA），可提供中等至高收率的多种（E）-1,2-硫代磺酰基（α-芳基-β-硫代芳基乙烯基砜）。炔基溴化物和硫代磺酸盐的底物范围广泛，具有广泛的官能团。在此1,2-硫磺酰化过程中，还成功地探索了吲哚衍生的1,1-溴代烯烃。而且，炔基溴化物与N-芳硫基琥珀酰亚胺的镍催化的双-二硫代化以高收率提供了1，1-二硫代烯烃。本协议在克级上是可靠的，并在大规模合成中实现了苯乙炔的顺序一锅法溴化和硫磺酰化。在对照实验之后，提出了合理的机制来合理化实验结果和邻近的硫磺酰化反应。