5,5'-dimercapto-2,2'-bis(1,3,4-thiadiazole) | 27608-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5,5'-dimercapto-2,2'-bis(1,3,4-thiadiazole)
• 英文别名: 2,2''-bi(1,3,4-thiadiazole)-5,5''(4H,4''H)-dithione；5-(2-sulfanylidene-3H-1,3,4-thiadiazol-5-yl)-3H-1,3,4-thiadiazole-2-thione
• CAS: 27608-31-7
• 化学式: C₄H₂N₄S₄
• 分子量: 234.351
• InChiKey: DAHNZAVSTBXUBS-UHFFFAOYSA-N

物化性质

• 沸点：
  349.6±25.0 °C(Predicted)
• 密度：
  2.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  164
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,5'-dimercapto-2,2'-bis(1,3,4-thiadiazole) 、 硝基氯苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以25%的产率得到Bis<5-<2-(2'-nitrophenylthio)-1,3,4-thiadiazolyl>>
  参考文献：
  名称：

  一些双[5-（2-巯基-1,3,4-噻二唑基）]甲基和芳基衍生物的质谱

  摘要：

  描述了五个选定的标题化合物的一般片段化模式。最重要的质谱特征来自芳基取代基与相邻杂环的相互作用。突出的“邻位效应”强烈影响在S-芳基部分带有邻硝基的化合物的分解。

  DOI：

  10.1002/jhet.5570210436
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 作用下， 生成 5,5'-dimercapto-2,2'-bis(1,3,4-thiadiazole)
  参考文献：
  名称：

  Kato; Ohta, Nippon Kagaku Zasshi, 1957, vol. 78, p. 1588,1590

  摘要：

  DOI：

文献信息

• New potent inhibitors of tyrosinase: Novel clues to binding of 1,3,4-thiadiazole-2(3H)-thiones, 1,3,4-oxadiazole-2(3H)-thiones, 4-amino-1,2,4-triazole-5(4H)-thiones, and substituted hydrazides to the dicopper active site
  作者：Usman Ghani、Nisar Ullah

  DOI：10.1016/j.bmc.2010.04.021

  日期：2010.6.1

  hydrazides were tailored and synthesized as new potent inhibitors of tyrosinase. The rationale for inhibitor design was based on the active site structural evidence from the crystal structures of bacterial tyrosinase and potato catechol oxidase enzymes. Kinetic and active site binding studies suggested mono-dentate binding of thiadiazole, oxadiazole, and triazole rings to the active site dicopper center

  一系列1,3,4-噻二唑-2（3 H）-硫酮，1,3,4-恶二唑-2（3 H）-硫酮，4-氨基-1,2,4-三唑-5（4）H）-硫酮和取代的酰肼被定制并合成为酪氨酸酶的新型有效抑制剂。设计抑制剂的基本原理是基于细菌酪氨酸酶和马铃薯儿茶酚氧化酶的晶体结构的活性位点结构证据。动力学和活性位点结合研究表明，噻二唑，恶二唑和三唑环与酪氨酸酶活性位点双铜中心的单齿结合包括疏水性，有助于有效抑制。动力学图显示了所有25种化合物的混合抑制类型。发现在对酪氨酸酶的高结合亲和力中，三唑环的C3取代和噻二唑/恶二唑环的C5取代起主要作用。
• Sulfur Bridged Multidentate Ligands Based on (Bi)pyridyl-(Bi)-1,3,4-Thiadiazolyl Conjugates
  作者：Antonino Mamo、Andrea Pappalardo、M. Clasadonte

  DOI：10.3390/80300310

  日期：——

  The synthesis of a series of mixed (bi)pyridyl/(bi)1,3,4-thiadiazolyl ligands, derived from the condensation of 2-mercapto-5-methylthio-1,3,4-thiadiazole or 5-mercapto-5'-methylthio-2,2'-bi-1,3,4-thiadiazole with 2,6-bis(chloromethyl)pyridine or 6,6’-bis(chloromethyl)-2,2’-bipyridine (compounds L1–L4), and of 2,5-dimercapto-1,3,4-thiadiazole or 5,5'-dimercapto-2,2'-di-1,3,4-thiadiazole with picolyl

  一系列混合（双）吡啶基/（双）1,3,4-噻二唑基配体的合成，衍生自 2-mercapto-5-methylthio-1,3,4-thiadiazole 或 5-mercapto-5 '-甲硫基-2,2'-双-1,3,4-噻二唑与 2,6-双（氯甲基）吡啶或 6,6'-双（氯甲基）-2,2'-联吡啶（化合物 L1–L4 ), 和 2,5-dimercapto-1,3,4-thiadiazole 或 5,5'-dimercapto-2,2'-di-1,3,4-thiadiazole 与盐酸吡啶甲酰氯或 6-chloromethyl-6'描述了在三乙胺存在下的-甲基-2,2'-联吡啶（化合物 L5-L8）。所有新化合物均已通过 FAB (+) 光谱法和 NMR 光谱法进行表征。13C-NMR 光谱对于牢固建立标题配体的硫醇结构至关重要。
• Efficacy of Organophosphorus Derivatives against Fungal Pathogens of Sugarcane
  作者：A. K. Jaiswal、G. P. Rao、O. P. Pandey、S. K. Sengupta

  DOI：10.1021/jf970544t

  日期：1998.4.1

  Several novel oraganophosphorus derivatives have been prepared by the reactions of O,O-diethyl chlorophosphate/thiophosphate with three important series of heterocyclic compounds, viz., bis(mercaptotriazoles), bis(mercaptooxadiazoles), and bis(mercaptothiadiazoles). The derivatives have been characterized on the basis of analyses and spectral (IR, (1)H NMR, and (31)P NMR) data. The fungicidal activity of these derivatives against Colletotrichum falcatum, Fusarium oxysporum, and Curvularia pallescens have been evaluated. The screening results have been correlated with the structural features of the tested compounds. The greater potency has been observed with dithiophosphates compared to phosphates, with organophosphorus derivatives containing bis(mercaptotriazole) rings compared to other heterocyclic rings, and with long spacers between the rings.
• Kato; Ohta, Nippon Kagaku Zasshi, 1957, vol. 78, p. 1588,1590
  作者：Kato、Ohta

  DOI：——

  日期：——
• The mass spectra of some bis[5-(2-mercapto-1,3,4-thiadiazolyl)]methyl and aryl derivatives
  作者：Sebastiano Pappalardo、Francesco Bottino、Michele Di Grazia

  DOI：10.1002/jhet.5570210436

  日期：1984.7

  The general fragmentation patterns of five selected title compounds are described. The most significant mass spectral features arise from the interaction of aryl substituents with the adjacent heterocyclic ring. The decomposition of the compounds bearing an ortho nitro group in the S-aryl moieties is strongly affected by a prominent “ortho effect”.

  描述了五个选定的标题化合物的一般片段化模式。最重要的质谱特征来自芳基取代基与相邻杂环的相互作用。突出的“邻位效应”强烈影响在S-芳基部分带有邻硝基的化合物的分解。