2,3,5,6-tetra(phenylthio)-1,4-benzoquinone

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,3,5,6-tetra(phenylthio)-1,4-benzoquinone
• 英文别名: 2,3,5,6-tetra-(thiophenyl)benzoquinone；tetrakis-phenylsulfanyl-[1,4]benzoquinone；Tetrakis-phenylmercapto-[1,4]benzochinon；2,3,5,6-Tetrakis(phenylsulfanyl)cyclohexa-2,5-diene-1,4-dione
• 化学式: C₃₀H₂₀O₂S₄
• 分子量: 540.752
• InChiKey: CKBKZOGXBHNFFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2,5-二(苯硫基)-1,4-苯醌 在 溶剂黄146 作用下， 生成 2,3,5,6-tetra(phenylthio)-1,4-benzoquinone
  参考文献：
  名称：

  苯硫基取代醌的构象多态性和消失的核磁共振谱

  摘要：

  苯硫酚与苯醌的逐步加成得到苯并苯醌 (1b)、2,5-和 2,6-二-(噻吩) 苯醌 (2,3)、2,3,6-三(噻吩) 苯醌 (4) 和 2 ,3,5,6-四(噻吩)苯醌。(5). 化合物 1-4 可以结晶，并且 13 C NMR 光谱很容易解释。化合物5不易结晶，核磁共振显示的谱线数是碳原子数的两倍多。在 NMR 管中缓慢蒸发产生三种不同的晶体。两个晶体 (5a 和 5c) 的 X 射线分析表明化合物是构象多晶型物。由四氯苯醌和苯硫酚直接合成 5 仅产生构象异构体 5a，13 C NMR 光谱仅显示预期的 6 条线是苯醌上的四个等效苯基取代基。使 5a 经受多种溶剂，试剂和温度没有重新生成原始的 13 C NMR 谱。讨论了晶体结构、构象和多晶型物。

  DOI：

  10.1007/bf01796060

文献信息

• Synthesis of Novel S,O-Substituted 1,4-Benzoquinones
  作者：F. Serpil Goksel、Nilufer Bayrak、Cemil Ibis

  DOI：10.1080/10426507.2013.798787

  日期：2014.1

  Abstract This study presents the synthesis and characterization of novel derivatives of S,O-substituted 1,4-benzoquinones obtained from the reactions of 2,6-diethoxy-3,5-dichloro-1,4-benzoquinone; 2,5-diethoxy-3,6-dichloro-1,4-benzoquinone; and p-chloranil with some aliphatic and aromatic thiols. The structures of these novel compounds were characterized by microanalysis, FT-IR, 1H NMR, 13C NMR, MS

  摘要 本研究介绍了由 2,6-二乙氧基-3,5-二氯-1,4-苯醌反应获得的 S,O-取代 1,4-苯醌的新型衍生物的合成和表征；2,5-二乙氧基-3,6-二氯-1,4-苯醌；和对氯苯醌与一些脂肪族和芳香族硫醇。这些新化合物的结构通过微量分析、FT-IR、1H NMR、13C NMR、MS 和 UV-vis 光谱表征。图形概要
• 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.