2,5-二(苯硫基)-1,4-苯醌 | 17058-53-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 2,5-二(苯硫基)-1,4-苯醌
• 英文名称: 2,5-bis(phenylthio)-1,4-benzoquinone
• 英文别名: 2,5-di-(thiophenyl)benzoquinone；2,5-bis-phenylsulfanyl-[1,4]benzoquinone；2,5-Bis-phenylmercapto-[1,4]benzochinon；2,5-Bis(phenylthio)-p-benzoquinone；2,5-bis(phenylsulfanyl)cyclohexa-2,5-diene-1,4-dione
• CAS: 17058-53-6
• 化学式: C₁₈H₁₂O₂S₂
• 分子量: 324.424
• InChiKey: CQBMMTIVMOJHSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 potassium permanganate 作用下， 生成 2,5-二(苯硫基)-1,4-苯醌
  参考文献：
  名称：

  Posner, Justus Liebigs Annalen der Chemie, 1904, vol. 336, p. 88,117

  摘要：

  DOI：

文献信息

• On the inapplicability of the Lehnert reagent for 1,2-dicyanomethylation of 2,5- and 2,6-diphenylthiobenzoquinones: synthesis and structure of isomeric 2-amino-5-hydroxy-4,6- and 2-amino-5-hydroxy-4,7-diphenylthiobenzo[b]furan-3-carbonitriles
  作者：James Y. Becker、Joel Bernstein、Shmuel Bittner、Eli Harlev、Jagarlapudi A. R. P. Sarma

  DOI：10.1039/p29890001157

  日期：——

  has been shown not to activate the carbonyl groups of dithiophenyl-substituted benzoquinone isomers in nucleophilic attack by dicyanomalonate. Instead, 1,4-addition to the quinone ring results in the title benzofuran derivatives. The reaction mechanism is shown to be unlike those where carbon atoms are attached to the quinone ring or when the sulphur atom is part of an aromatic system. The crystal

  Lehnert试剂（TiCl 4-吡啶）在双氰基丙二酸酯的亲核攻击中不会激活二硫代苯基取代的苯醌异构体的羰基。取而代之的是，在醌环上加成1,4，得到标题为苯并呋喃的衍生物。已表明该反应机理与其中碳原子连接至醌环或当硫原子为芳族体系的一部分时的反应机理不同。2-氨基-5-羟基-4,6-二苯硫基-苯并[ b ]呋喃-3-腈的晶体数据为：三斜晶系，P 1，a = 10.092（6），b = 10.828（7），c = 9.976（6）A，α= 73.35（5），β= 100.13（4），γ= 116.13（4）°，V = 936.2（9）埃3，Z＝ 2。提出并讨论了所提出的反应机理和标题化合物的晶体结构。
• Process for production of vinyl chloride polymer
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP0172427A2

  公开（公告）日：1986-02-26

  This process is a process for production of a vinyl chloride polymer by suspension polymerization or emulsion polymerization of vinyl chloride monomer or a mixture of vinyl chloride monomer with a vinyl monomer copolymerizable with said vinyl chloride monomer in an aqueous medium, characterized in that the polymerization is carried out in a polymerizer, the inner wall surface and portions of the auxiliary equipment thereof which may come into contact with the monomer during polymerization being previously coated with a scaling preventive comprising at least one selected from dyes, pigments and aromatic or heterocyclic compounds having at least 5 conjugated π bonds, while controlling the chloride ion concentration in the reaction mixture to not higher than 100 ppm. According to said process, scaling onto the inner wall surface of a polymerizer, etc. during polymerization can be prevented effectively and surely.

  该工艺是通过氯乙烯单体或氯乙烯单体与可与所述氯乙烯单体共聚的乙烯基单体混合物在水介质中进行悬浮聚合或乳液聚合来生产氯乙烯聚合物的工艺，其特征在于聚合是在聚合器中进行的、内壁表面及其辅助设备中可能在聚合过程中与单体接触的部分事先涂上一层防垢剂，该防垢剂至少包括一种选自染料、颜料和至少有 5 个共轭 π 键的芳香族或杂环化合物的防垢剂，同时控制反应混合物中的氯离子浓度不高于 100 ppm。根据上述工艺，可有效、可靠地防止聚合过程中聚合器等内壁表面结垢。
• 228. Quinones. Part II. The addition of mercapto-acids to benzoquinones and 1 : 4-naphthaquinone
  作者：A. Blackhall、R. H. Thomson

  DOI：10.1039/jr9530001138

  日期：——
• Dimroth; Kraft; Aichinger, Justus Liebigs Annalen der Chemie, 1940, vol. 545, p. 124,133
  作者：Dimroth、Kraft、Aichinger

  DOI：——

  日期：——
• 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.