2-(5-phenyl-1H-1,2,4-triazol-3-ylsulfanyl)ethanol | 838898-35-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(5-phenyl-1H-1,2,4-triazol-3-ylsulfanyl)ethanol
• 英文别名: 2-[(5-phenyl-1H-1,2,4-triazol-3-yl)sulfanyl]ethanol
• CAS: 838898-35-4
• 化学式: C₁₀H₁₁N₃OS
• 分子量: 221.283
• InChiKey: YSHMMLWNYHCGRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯乙醇 、 3-苯基-1,2,4-三唑-5-硫醇水合物 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以23%的产率得到2-(5-phenyl-1H-1,2,4-triazol-3-ylsulfanyl)ethanol
  参考文献：
  名称：

  Tautomerism of aza cycles: II. Synthesis and structure of 5-substituted 3-(2-hydroxyethylsulfanyl)-1H-1,2,4-triazoles and their salts. Preference of the 1H,4H-1,2,4-triazolium tautomers

  摘要：

  New complexing agents, potentially tautomeric 3-(2-hydroxyethylsulfanyl)-1H-1,2,4-triazole, its 5-methyl- and 5-phenyl-substituted analogs, and some their salts, were synthesized, and their structure was discussed on the basis of the H-1 and C-13 NMR, IR, and mass spectra, X-ray diffraction data, and published data. In keeping with the rule formulated previously for N-unsubstituted 1,2,4-triazoles having dissimilar substituents, the synthesized compounds were found to exist as 3-(2-hydroxyethylsulfanyl)-5-R-1H-1,2,4-triazole tautomers (3-R-A-5-R-D-1H-1,2,4-triazoly). They are protonated at the nitrogen atom in position 4 of the triazole ring. The H-1 and C-13 NMR spectra of these compounds in trifluoroacetic acid suggest the presence of two forms due to equilibrium between the neutral and protonated species. Analysis of the crystallographic data for the triazolium. salts and published data showed preference of the 1H,4H-1,2,4-triazolium tautomer.

  DOI：

  10.1134/s1070363208030225

文献信息

• Certain triazole-based compounds, compositions, and uses thereof
  申请人：Hodge Nicholas Carl

  公开号：US20050288347A1

  公开（公告）日：2005-12-29

  Thiotriazole-based chemical entities exhibiting ATP-utilizing enzyme inhibitory activity, methods of using such chemical entities, and compositions comprising such chemical entities, are described.

  描述了具有 ATP 利用酶抑制活性的硫代三唑类化学实体、使用此类化学实体的方法以及包含此类化学实体的组合物。
• Tautomerism of aza cycles: II. Synthesis and structure of 5-substituted 3-(2-hydroxyethylsulfanyl)-1H-1,2,4-triazoles and their salts. Preference of the 1H,4H-1,2,4-triazolium tautomers
  作者：B. I. Buzykin、E. V. Mironova、V. N. Nabiullin、N. M. Azancheev、L. V. Avvakumova、I. Kh. Rizvanov、A. T. Gubaidullin、I. A. Litvinov、V. V. Syakaev

  DOI：10.1134/s1070363208030225

  日期：2008.3

  New complexing agents, potentially tautomeric 3-(2-hydroxyethylsulfanyl)-1H-1,2,4-triazole, its 5-methyl- and 5-phenyl-substituted analogs, and some their salts, were synthesized, and their structure was discussed on the basis of the H-1 and C-13 NMR, IR, and mass spectra, X-ray diffraction data, and published data. In keeping with the rule formulated previously for N-unsubstituted 1,2,4-triazoles having dissimilar substituents, the synthesized compounds were found to exist as 3-(2-hydroxyethylsulfanyl)-5-R-1H-1,2,4-triazole tautomers (3-R-A-5-R-D-1H-1,2,4-triazoly). They are protonated at the nitrogen atom in position 4 of the triazole ring. The H-1 and C-13 NMR spectra of these compounds in trifluoroacetic acid suggest the presence of two forms due to equilibrium between the neutral and protonated species. Analysis of the crystallographic data for the triazolium. salts and published data showed preference of the 1H,4H-1,2,4-triazolium tautomer.