2,3,5,6-tetrakis(cyclohexylsulfanyl)-p-benziquinone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5,6-tetrakis(cyclohexylsulfanyl)-p-benziquinone
• 英文别名: 2,3:5,6-tetra(cyclohexylthio)-1,4-benzoquinone；2,3,5,6-Tetrakis(cyclohexylsulfanyl)cyclohexa-2,5-diene-1,4-dione
• 化学式: C₃₀H₄₄O₂S₄
• 分子量: 564.942
• InChiKey: JCGVNTAFHLHWCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3,5,6-tetrakis(cyclohexylsulfanyl)benzene-1,4-diol 在 对苯醌 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以80%的产率得到2,3,5,6-tetrakis(cyclohexylsulfanyl)-p-benziquinone
  参考文献：
  名称：

  对苯醌与硫亲核试剂的反应

  摘要：

  讨论了对称对苯醌与亲核试剂反应的取向。对苯醌与烷基硫醇的一锅反应生成了2-、2,6-和2,5-连接加成产物。通过顺序加成/原位氧化法获得了新颖的2,6-和2,5-双(烷基硫基)-、2,3,5-三(烷基硫基)-和2,3,5,6-四(烷基硫基)-对苯醌及其相应的氢醌，收率良好，进一步用于测试作为橡胶和石油产品的聚合抑制剂。通过X射线晶体学确定了五种2,5-和2,6-二取代异构体的结构。

  DOI：

  10.1055/s-2008-1032186

文献信息

• Micelles catalyzed chemo- and regio-selective one pot and one step synthesis of 2,3,5,6-tetrakis(alkyl and arylsulfanyl)-1,4-benzoquinones and 2,5-diaminosubstituted-1,4-benzoquinones “In-Water” and their biological evaluation as antibacterial and antifungal agents
  作者：Vishnu K. Tandon、Sandeep Kumar、Nripendra N. Mishra、Praveen K. Shukla

  DOI：10.1016/j.ejmech.2012.07.022

  日期：2012.10

  Chemo- and regio-selective one pot and one step synthesis of novel 2,3,5,6-tetrakis (substituted thio) cyclohexa-2,5-diene-1,4-diones (4d-14), 2,5-dichloro-3,6-diaminocyclohexa-2,5-diene-1,4-diones and 2,5-diaminocyclohexa-2,5-diene-1,4-diones (16) by economical green methodology approach using LD (Laundry detergent) as a catalyst "In-Water" by nucleophilic addition and substitution reactions of 1,4-benzoquinone and chloranil with sulfur and nitrogen nucleophiles in high yields has been demonstrated. The antifungal profile of 4 and 16 indicates that compounds 4d and 16f had better antifungal activity compared to clinically prevalent antifungal drugs Fluconazole, 5-Fluorocytosine and Clotrimazole against Sporothrix schenckii and Trichophyton mentagraphytes. 16f had also been found to possess better antibacterial activity compared to Ampicillin in vitro against Escherichia coli, Staphylococcus aureus and Klebsiella pneumoniae. Compound 16f did not exhibit any toxicity towards mammalian cells L929. (C) 2012 Elsevier Masson SAS. All rights reserved.
• New Bis(thio)-, Tris(thio)-, and Tetrakis(thio)-substituted Quinones from the Reactions of p-Chloranil with Some Thiols and Dithiols
  作者：F. Serpil Göksel、Cemil İbiş、Nilüfer Akgün Bayrak

  DOI：10.1080/104265090902723

  日期：2005.8.1

  p-Chloranil (1), when reacted with different thiol compounds, namely 1-buthylthiol, cyclohexylthiol, and 2,2-oxydiethanethiol in ethanol in the presence of Na2CO3, yielded the corresponding S-substituted quinone derivatives.
• Reactions of <i>p</i>-Benzoquinone with Sulfur Nucleophiles
  作者：Alan Katritzky、Dmytro Fedoseyenko、Prabhu Mohapatra、Peter Steel

  DOI：10.1055/s-2008-1032186

  日期：2008.3

  The orientations of the reactions of p-benzoquinone with nucleophiles are discussed. The one-pot reaction of p-benzoquinone with alkanethiols gave the 2-, 2,6-, and 2,5-conjugate addition products. Novel 2,6- and 2,5-bis(alkylsulfanyl)-, 2,3,5-tris(alkylsulfanyl)-, and 2,3,5,6-tetrakis(alkylsulfanyl)-p-benzoquinones, and their corresponding hydroquinones, were obtained in good yields through a sequential addition/in situ oxidation protocol for further testing as polymerization inhibitors in rubber and petroleum products. The structures of five 2,5- and 2,6-disubstituted isomers were established by X-ray crystallography.

  讨论了对称对苯醌与亲核试剂反应的取向。对苯醌与烷基硫醇的一锅反应生成了2-、2,6-和2,5-连接加成产物。通过顺序加成/原位氧化法获得了新颖的2,6-和2,5-双(烷基硫基)-、2,3,5-三(烷基硫基)-和2,3,5,6-四(烷基硫基)-对苯醌及其相应的氢醌，收率良好，进一步用于测试作为橡胶和石油产品的聚合抑制剂。通过X射线晶体学确定了五种2,5-和2,6-二取代异构体的结构。