4,5-bis(5-methyl-1,3,4-thiadiazol-2-ylthio)benzene-1,2-diol | 1169880-65-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4,5-bis(5-methyl-1,3,4-thiadiazol-2-ylthio)benzene-1,2-diol
• 英文别名: 4,5-Bis[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]benzene-1,2-diol；4,5-bis[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]benzene-1,2-diol
• CAS: 1169880-65-2
• 化学式: C₁₂H₁₀N₄O₂S₄
• 分子量: 370.501
• InChiKey: ZXNUEUFHSBAJGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  199
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  邻苯二酚 、 2-巯基-5-甲基-1,3,4-噻二唑 以 乙腈 为溶剂， 以31%的产率得到4-(5-methyl-1,3,4-thiadiazol-2-ylthio)benzene-1,2-diol
  参考文献：
  名称：

  Electrochemical synthesis of 1,3,4-thiadiazol-2-ylthio-substituted catechols in aqueous medium

  摘要：

  Anodic oxidation of catechols 1a-e in the presence of 5-methyl-2-mercapto-1,3,4-thiadiazole 2 has been studied in acetate buffer solution by cyclic voltammetry and controlled-potential electrolysis techniques. The effects of various electrolytic conditions (amount of passed charge, anodic materials, pH of the electrolytic Solution, applied potential, and concentration of substrates) oil the yield have also been investigated. The results showed that the position of the initial substituent of the starting catechol derivatives dominated the formation of monothiadiazol-2-ylthio-substituted or/and dithiadiazol-2-ylthio-substituted products. For 4-substituted catechols 1a-b, monothiadiazol-2-ylthio-substituted products (3a-b) were exclusively produced in high to excellent yields. However, in the cases of catechol itself(1c) and 3-substituted catechols (1d-e), both monothiadiazol-2-yl-substituted (3c-e and 5d-e) and dithiadiazol-2-ylthio-substituted products (4c-e) were isolated. in addition, the nature of the initial substituent of the starting 3-substituted catechols (1d and 1e) affected the relative ratio of the two monothiadiazol-2-ylthio-substituted isomers (3d-e vs 5d-e). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.101

文献信息

• Electrochemical synthesis of 1,3,4-thiadiazol-2-ylthio-substituted catechols in aqueous medium
  作者：Cheng-Chu Zeng、Fu-Jian Liu、Da-Wei Ping、Li-Ming Hu、Yuan-Li Cai、Ru-Gang Zhong

  DOI：10.1016/j.tet.2009.03.101

  日期：2009.6

  Anodic oxidation of catechols 1a-e in the presence of 5-methyl-2-mercapto-1,3,4-thiadiazole 2 has been studied in acetate buffer solution by cyclic voltammetry and controlled-potential electrolysis techniques. The effects of various electrolytic conditions (amount of passed charge, anodic materials, pH of the electrolytic Solution, applied potential, and concentration of substrates) oil the yield have also been investigated. The results showed that the position of the initial substituent of the starting catechol derivatives dominated the formation of monothiadiazol-2-ylthio-substituted or/and dithiadiazol-2-ylthio-substituted products. For 4-substituted catechols 1a-b, monothiadiazol-2-ylthio-substituted products (3a-b) were exclusively produced in high to excellent yields. However, in the cases of catechol itself(1c) and 3-substituted catechols (1d-e), both monothiadiazol-2-yl-substituted (3c-e and 5d-e) and dithiadiazol-2-ylthio-substituted products (4c-e) were isolated. in addition, the nature of the initial substituent of the starting 3-substituted catechols (1d and 1e) affected the relative ratio of the two monothiadiazol-2-ylthio-substituted isomers (3d-e vs 5d-e). (C) 2009 Elsevier Ltd. All rights reserved.