2-((4-chlorophenyl)thio)cyclohexa-2,5-diene-1,4-dione | 18232-05-8

• 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-((4-chlorophenyl)thio)cyclohexa-2,5-diene-1,4-dione
• 英文别名: 2-(4-Chlorophenyl)sulfanylcyclohexa-2,5-diene-1,4-dione；2-(4-chlorophenyl)sulfanylcyclohexa-2,5-diene-1,4-dione
• CAS: 18232-05-8
• 化学式: C₁₂H₇ClO₂S
• 分子量: 250.705
• InChiKey: QSNQCLATJIJOES-UHFFFAOYSA-N

物化性质

• 沸点：
  382.2±42.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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-((4-chlorophenyl)thio)cyclohexa-2,5-diene-1,4-dione 、 乙酸酐 在 高氯酸 作用下， 生成 2-(p-Chlor-phenylthio)-1.4.5-triacetoxy-benzol
  参考文献：
  名称：

  Ukai,S.; Hirose,K., Chemical and pharmaceutical bulletin, 1968, vol. 16, # 2, p. 202 - 210

  摘要：

  DOI：
• 作为产物：
  描述：

  对-氯苯基甲基亚砜 在 三氯化铁 作用下， 以 乙醇 为溶剂， 生成 2-((4-chlorophenyl)thio)cyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Ukai,S.; Hirose,K., Chemical and pharmaceutical bulletin, 1968, vol. 16, # 2, p. 195 - 201

  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。
• Copper‐Catalyzed Reaction Cascade of Thiophenol Hydroxylation and S‐Arylation through Disulfide‐Directed C−H Activation
  作者：Dawei Wang、Xin Yu、Wei Yao、Wenkang Hu、Chenyang Ge、Xiaodong Shi

  DOI：10.1002/chem.201600597

  日期：2016.4.11

  Copper‐catalyzed thiophenol C−H activation is described. Through an initial attempt to conduct C‐arylation with arylboronic acid, a rather surprising sequential C−H activation and S‐arylation was discovered. Mechanistic investigation revealed the disulfide intermediate as the key component in directing C−H oxidation. The overall reaction proceeded under mild conditions with molecular oxygen as the

  描述了铜催化的硫酚CH活化。通过初步尝试与芳基硼酸进行C-芳基化，发现了令人惊讶的连续CH活化和S-芳基化。机理研究表明，二硫化物中间体是指导CH氧化的关键组分。整个反应在温和条件下以分子氧作为氧化剂进行。二硫化物作为指导基团的发现为在温和条件下催化C H官能化提供了潜在的新方向。