1,2-bis(5-mercapto-4H-1,2,4-triazol-3-yl)ethane-1,2-diol | 7271-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,2-bis(5-mercapto-4H-1,2,4-triazol-3-yl)ethane-1,2-diol
• CAS: 7271-27-4
• 化学式: C₆H₈N₆O₂S₂
• 分子量: 260.301
• InChiKey: HBNWFZDCGANZHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.73
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  123.6
• 氢给体数：
  6.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  氯磷酸二乙酯 、 1,2-bis(5-mercapto-4H-1,2,4-triazol-3-yl)ethane-1,2-diol 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 60.0h， 以48%的产率得到1,2-bis(3-diethoxyphosphorylsulfanyl-1H-1,2,4-triazol-5-yl)ethane-1,2-diol
  参考文献：
  名称：

  Efficacy of Organophosphorus Derivatives against Fungal Pathogens of Sugarcane

  摘要：

  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.

  DOI：

  10.1021/jf970544t
• 作为产物：
  描述：

  硫氰酸铵 、 tartaric acid dihydrazide 在 sodium hydroxide 作用下， 生成 1,2-bis(5-mercapto-4H-1,2,4-triazol-3-yl)ethane-1,2-diol
  参考文献：
  名称：

  Efficacy of Organophosphorus Derivatives against Fungal Pathogens of Sugarcane

  摘要：

  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.

  DOI：

  10.1021/jf970544t

文献信息

• Synthesis and Characterization of Mono- and Bicycle Heterocyclic Derivatives Containing 1, 2,4-Triazole, 1,3,4-Thiadiazine and 1,3-Thiazole Rings
  作者：Navabeh Nami、Mehdi Forozani、Vida Khosravimoghadam、Rahmatallah Taherinasab

  DOI：10.1155/2012/867637

  日期：——

  Reaction of tartaric acid with thiocarbohydrazide(2)and thiosemicarbazide(6)afforded 1,2-bis(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)-ethane-1,2-diol(3)and 1,2-bis(5-mercapto-4H-1,2,4-triazol-3-yl)-ethane-1,2-diol(7). Reaction of compounds3and7with DMAD (dimethylacety lendi carboxylate) and DEAD (diethylacetylendicarboxylate) gave 1,2-bis(7-[(z)-methoxycarbonylmethylen]-5,6-dihydro-5H-6-one-[1,2,4] riazolo[3,4-b] [1,3,4] thiadiazin-3-yl)-ethan-1,2-diol(4), 1,2-bis(7-[(z)-ethoxycarbonylmethylen] -5,6-dihydro -5H-6-one-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-ethan-1,2- diol(5)and 1,2-bis(6-[(z)-methoxycarbonylmethylen]-5-oxo-[1,3]thiazolo[2,3-c] [1,2,4]triazol-3-yl)-ethan-1,2-diol(8)in good yields.

  酒石酸与硫代卡巴肼（2）和硫代半卡巴肼（6）反应，得到1,2-双（4-氨基-5-巯基-4H-1,2,4-三唑-3-基）-乙烷-1,2-二醇（3）和1,2-双（5-巯基-4H-1,2,4-三唑-3-基）-乙烷-1,2-二醇（7）。化合物3和7与DMAD（二甲基乙烯基羧酸酯）和DEAD（二乙基乙烯基二羧酸酯）反应，得到1,2-双（7-[(Z)-甲氧羰基甲基亚乙烯基]-5,6-二氢-5H-6-酮-[1,2,4]三唑并[3,4-b][1,3,4]噻二嗪-3-基）-乙烷-1,2-二醇（4）、1,2-双（7-[(Z)-乙氧羰基甲基亚乙烯基]-5,6-二氢-5H-6-酮-[1,2,4]三唑并[3,4-b][1,3,4]噻二嗪-3-基）-乙烷-1,2-二醇（5）和1,2-双（6-[(Z)-甲氧羰基甲基亚乙烯基]-5-氧代-[1,3]噻唑并[2,3-c][1,2,4]三唑-3-基）-乙烷-1,2-二醇（8），收率良好。