2-(3-[2-phenylethenyl]-1H-1,2,4-triazol-5-yl)phenol | 65483-95-6

• 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-(3-[2-phenylethenyl]-1H-1,2,4-triazol-5-yl)phenol
• 英文别名: 2-(5-styryl-1H-[1,2,4]triazol-3-yl)-phenol；2-[5-(2-phenylethenyl)-1H-1,2,4-triazol-3-yl]phenol
• CAS: 65483-95-6
• 化学式: C₁₆H₁₃N₃O
• 分子量: 263.299
• InChiKey: SRMLEORVMLVKJQ-UHFFFAOYSA-N

物化性质

• 熔点：
  191-192 °C
• 沸点：
  520.1±60.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-[2-phenylethenyl]-1H-1,2,4-triazol-5-yl)phenol 以 丙酮 、 甘油 为溶剂， 生成 N-[3-(imidazol-1-yl)propyl]-2-[3-(2-hydroxyphenyl)-5-styryl-1,2,4-triazol-1-yl]acetamide
  参考文献：
  名称：

  新型三唑基取代的羧酸酯的合成及其氨解

  摘要：

  在肼基苯甲酸的作用下使4-氧代1，3-苯并恶嗪高氯酸盐再循环，得到先前未知的1,2,4-三唑基苯甲酸，将其酯化以获得相应的酯。3-（邻-羟基苯基）-1,2,4-三唑与氯乙酸乙酯的烷基化反应形成三唑基乙酸乙酯，其氨解反应可以合成新的双杂环酰亚胺。

  DOI：

  10.1134/s1070428019020155
• 作为产物：
  描述：

  2-styryl-1,3-benzoxazinonium perchlorate 在 一水合肼 作用下， 生成 2-(3-[2-phenylethenyl]-1H-1,2,4-triazol-5-yl)phenol
  参考文献：
  名称：

  Synthesis of 3-(2-hydroxyphenyl)-1,5-dialkyl-1H-1,2,4-triazoles and their Zn(II) complexes

  摘要：

  It has been demonstrated by C-13 NMR and quantum-chemical calculations that alkylation of 5-(2-hydroxyphenyl)-3-methyl(vinylphenyl)-1H-1,2,4-triazoles with dialkyl sulfates in aqueous DMSO in the presence of alkali occurs exclusively in the 2-position of the triazole ring to give 3-(2-hydroxyphenyl)-1,5-dialkyl(alkylvinylphenyl)-1H-1,2,4-triazoles. Emission spectra of these compounds show two weak bands (lambda(fl)(max) = 317-346 and 430-447 nm, phi = 0.002-0.007), whereas their zinc complexes emit in the violet range of the visible spectrum (lambda(fl)(max) = 373-377 nm, phi = 0.20-0.25).

  DOI：

  10.1134/s0012500817020045

文献信息

• Reactions of hydroxyphenyl-substituted 1,2,4-triazoles with electrophylic reagents
  作者：E. Yu. Shasheva、N. I. Vikrishchuk、L. D. Popov、A. D. Vikrishchuk、I. E. Mikhailov、K. A. Lysenko、M. E. Kletskii

  DOI：10.1134/s1070363209100259

  日期：2009.10

  Reactions of hydroxyphenyl substituted 1,2,4-triazoles with various electrophylic reagents were studied. Despite of the presence of several nucleophilic centers in the molecule, the reactions were shown to proceed regioselectively, with the formation of N-substituted 3-(2-hydroxyphenyl)-1,2,4-triazoles. As a result of the reactions of alkylation, tosylation, sulfoamination and aminomethylation by Mannich reaction earlier unknown potential biologically active N-derivatives of 1,2,4-triazole were obtained.
• Synthesis and properties of substituted [3-(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]acetonitriles
  作者：E. Yu. Shasheva、N. I. Vikrishchuk、L. D. Popov、V. I. Minkin、M. E. Kletskii、M. Yu. Antipin、A. D. Vikrishchuk、I. E. Mikhailov

  DOI：10.1134/s1070428010070201

  日期：2010.7

  Alkylation of 3-substituted 5-(2-hydroxyphenyl)-1H-1,2,4-triazoles with chloroacetonitrile gave hitherto unknown N-cyanomethyl derivatives whose structure was determined by X-ray analysis and (1)H and (13)C NMR spectroscopy. Condensation of substituted [3-(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]acetonitriles at the activated methylene group with acetone led to the formation of new 3-methyl-2-triazolylbut-2-enenitrile derivatives.