2-(p-tolylthio)cyclohexa-2,5-diene-1,4-dione | 5831-37-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(p-tolylthio)cyclohexa-2,5-diene-1,4-dione
• 英文别名: 2-(p-Tolylthio)-p-benzochinon；2-(4-Methylphenyl)sulfanylcyclohexa-2,5-diene-1,4-dione
• CAS: 5831-37-8
• 化学式: C₁₃H₁₀O₂S
• 分子量: 230.287
• InChiKey: PAVXCXTZRWSPDO-UHFFFAOYSA-N

物化性质

• 沸点：
  367.6±42.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 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：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(p-tolylthio)cyclohexa-2,5-diene-1,4-dione 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 endo-<4aS*,5R*,8S*,8aR*,(S)S*>-5,8-methano-2-(p-tolylsulfinyl)-4a,5,8,8a-tetrahydro-1,4-naphthoquinone
  参考文献：
  名称：

  Influence of the Sulfinyl Group on the Chemoselectivity and π-Facial Selectivity of Diels−Alder Reactions of (S)-2-(p-Tolylsulfinyl)-1,4-benzoquinone

  摘要：

  Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-benzoquinone (1a) with cyclic (cyclopentadiene and cyclohexadiene) and acyclic dienes (1-[(trimethylsilyl)oxy]-1,3-butadiene and trans-piperylene) under different thermal and Lewis acid conditions are reported. Chemoselectivity (reactions on C-2-C-3 versus C-5-C-6 double bonds) is mainly related to the cyclic (on C-5-C-6) or acyclic (on C-2-C-3) structure of the diene. The high pi-facial selectivity observed could be controlled by choosing adequate experimental conditions.

  DOI：

  10.1021/jo951438y
• 作为产物：
  描述：

  2-氯-1,4-苯醌 在 periodate form of Amberlyst A₂₆ 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-(p-tolylthio)cyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Harrison, Charles R.; Hodge, Philip, Journal of the Chemical Society. Perkin transactions I, 1982, p. 509 - 511

  摘要：

  DOI：

文献信息

• Copper and triphenylphosphine-promoted sulfenylation of quinones with arylsulfonyl chlorides
  作者：Xiaoli Yu、Qiujin Wu、Huida Wan、Zhaojun Xu、Xingle Xu、Dawei Wang

  DOI：10.1039/c6ra11301j

  日期：——

  The efficient copper and triphenylphosphine-promoted sulfenylation of quinones with arylsulfonyl chlorides has been developed under mild conditions with moderate to good yields. Significantly, this provides an alternative method to synthesise arylthioquinone derivatives. This is the first time that arylthioquinones with arylsulfonyl chlorides as starting material have been prepared, which avoids the

  已经在温和的条件下以中等到良好的产率开发了用芳基磺酰氯对铜进行有效的铜和三苯膦促进的亚砜基化。重要的是，这提供了另一种合成芳基硫醌衍生物的方法。这是首次制备以芳基磺酰氯为原料的芳基硫醌，避免了使用难闻的硫醇和硫酚。
• Oxidative radical coupling of hydroquinones and thiols using chromic acid: one-pot synthesis of quinonyl alkyl/aryl thioethers
  作者：T. P. Adarsh Krishna、Sakthivel Pandaram、Suresh Chinnasamy、Andivelu Ilangovan

  DOI：10.1039/d0ra01519a

  日期：——

  An efficient, simple and practical protocol for one-pot sequential oxidative radical C–H/S–H cross-coupling of thiols with hydroquinones (HQs) and oxidation leading to the formation of quinonyl alkyl/aryl thioethers using H2CrO4 was developed. This cross-coupling of thiyl and aryl radicals offers mono thioethers in good to moderate yield and works well with a wide variety of thiols. Similarly, this

  开发了一种高效、简单且实用的方案，用于硫醇与氢醌 (HQ) 的一锅顺序氧化自由基 C–H/S–H 交叉偶联和氧化，从而使用 H 2 CrO 4形成醌基烷基/芳基硫醚。硫基和芳基的这种交叉偶联以良好至中等的产率提供单硫醚，并且与多种硫醇配合良好。同样，该方法适用于 2-氨基苯硫酚和 HQ 的偶联形成吩噻嗪-3-酮5a–c 。首次使用铬试剂观察到通过硫醚合成形成 C-S 键。对化合物5a–c药代动力学特性的理论研究表明，由于具有药物样特性，化合物5b与阿尔茨海默病 (AD) 相关的 AChE 靶位点强烈结合。
• The convenient synthesis and reaction of 2-(arylthio)phenols under ligand-free conditions: arylthioquinone preparation through cascade C–H functionalization and oxidation from arylthiols and aryl iodides
  作者：Dawei Wang、Xiaoli Yu、Likui Wang、Wei Yao、Zhaojun Xu、Huida Wan

  DOI：10.1016/j.tetlet.2016.10.028

  日期：2016.11

  A convenient and simple method for copper-catalyzed synthesis of 2-(arylthio)phenols through C–H functionalization of arylthiols and aryl iodides was developed under ligand-free conditions without nitrogen protection. In addition, arylthioquinone derivatives were very easily prepared for one more step of oxidation with moderate to good yields. This provide an alternative and efficient way to 2-(arylthio)phenols

  在没有氮保护的无配体条件下，开发了一种方便，简单的铜催化芳基硫醇和芳基碘化物通过CH官能化合成2-（芳硫基）酚的方法。另外，非常容易地制备芳基硫醌衍生物以进行另一步氧化，产率中等至良好。这提供了一种平稳有效的2-（芳硫基）苯酚和芳硫基苯醌衍生物的替代方法，而无需使用配体和氮保护剂或昂贵的芳基硼酸。
• Chemoselective method for the synthesis of 4-allyl-4-hydroxycyclohexa-2,5-dienone derivatives from 1,4-quinones by an indium-mediated allylation protocol
  作者：Dipanjan Pan、Sajal K Mal、Gandhi K Kar、Jayanta K Ray

  DOI：10.1016/s0040-4020(02)00133-3

  日期：2002.4

  Allyl indium halide on reaction with 1,4-quinones produced 4-allyl-4-hydroxycyclohexa-2,5-dienone derivatives. Unsymmetrical quinones show high chemoselectivity in addition of allyl indium halide reagent to the carbonyl group.

  烯丙基卤化铟与1，4-醌反应生成4-烯丙基-4-羟基环己-2,5-二烯酮衍生物。除烯丙基卤化铟试剂加到羰基上外，不对称醌还显示出高化学选择性。
• Oxidation reactions using sodium metaperiodate supported on silica gel
  作者：Dharmendra N. Gupta、Philip Hodge、J. Eric Davies

  DOI：10.1039/p19810002970

  日期：——

  were stirred with sodium metaperiodiate supported on silica gel. The supported reagent was prepared by evaporating to dryness an aqueous solution of sodium metaperiodate in the presence of silica gel, followed by heating at 120 °C in vacuo. The reagent appears to consist mainly of a monomolecular layer of sodium metaperiodate bound to the silica gel by the surface hydroxy-groups, together with a minor

  将2，5-二叔丁基氢醌，二苄基硫醚，反式环己烷-1,2-二醇或diol苯的二氯甲烷溶液与偏高碘酸钠粉末在20°C下搅拌数小时，则没有反应发生。然而，当将二氯甲烷中的溶液以及在某些情况下为苯或醚的溶液与负载在硅胶上的偏高碘酸钠一起搅拌时，通常会在数小时内以高收率氧化这些底物和几种紧密相关的底物。通过在硅胶存在下将偏高碘酸钠水溶液蒸发至干，然后在120℃真空加热，来制备负载的试剂。。该试剂似乎主要由通过表面羟基与硅胶结合的偏高碘酸钠单分子层以及少量结晶无水偏高碘酸钠组成。