4-phenyl[1,2,4]triazolo[4,3-a]quinoxaline-1(2H)-thione | 65407-82-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-phenyl[1,2,4]triazolo[4,3-a]quinoxaline-1(2H)-thione
• 英文别名: s-Triazolo<4.3-a>chinoxalin-1-thion；4-phenyl-2H-[1,2,4]triazolo[4,3-a]quinoxaline-1-thione；4-phenyl-2H-[1,2,4]triazolo[4,3-a]quinoxaline-1-thione
• CAS: 65407-82-1
• 化学式: C₁₅H₁₀N₄S
• 分子量: 278.337
• InChiKey: XLTROUURFDASTF-UHFFFAOYSA-N

物化性质

• 熔点：
  272-274 °C(Solv: acetic acid (64-19-7))
• 沸点：
  437.4±28.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-phenyl[1,2,4]triazolo[4,3-a]quinoxaline-1(2H)-thione 在 盐酸 、 一水合肼 、 三乙胺 、 sodium nitrite 作用下， 以 乙醇 、 水 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 58.0h， 生成 methyl 2-[2-(4-phenyl[1,2,4]triazolo[4,3-a]quinoxalin-1-ylsulfanyl)acetamido]propanoate
  参考文献：
  名称：

  Synthesis of methyl 2-[2-(4-phenyl[1,2,4]triazolo-[4,3-a]quinoxalin-1-ylsulfanyl)acetamido]alkanoates and their N-regioisomeric analogs

  摘要：

  Methyl 2-[2-(4-phenyl[1,2,4]triazolo[4,3-a]quinoxalin-1-ylsulfanyl)acetamido]alkanoates were formed by the reaction of 2-(4-phenyl-1,2-dihydro[1,2,4]triazolo[4,3-a]quinoxalin-1-ylsulfanyl)acetic acid with a variety of amino acid esters via DCC coupling method in the presence of N-hydroxybenzotriazole in good yields. These amino acid derivatives linked to triazoloquinoxaline moiety were also obtained by the reaction of 2-(4-phenyl[1,2,4]triazolo[4,3-a]quinoxalin-1-ylsulfanyl)acetohydrazide with amino acid ester derivatives via azide coupling method in poor yields due to the competing decomposition of the corresponding azide resulting in the starting 4-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline-1(2H)-thione. The N-regioisomeric methyl 2-[3-(4-phenyl-1-thioxo[1,2,4]triazolo[4,3-a]quinoxalin-2(1H)-yl)propanamido]alkanoates were efficiently produced from the 3-(4-phenyl-1-thioxo[1,2,4]triazolo[4,3-a]quinoxalin-2(1H)-yl)-propanohydrazide and amino acid esters via azide coupling method in good to moderate yields.

  DOI：

  10.1007/s10593-015-1662-0
• 作为产物：
  描述：

  在 盐酸 、 一水合肼 、 sodium nitrite 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 4-phenyl[1,2,4]triazolo[4,3-a]quinoxaline-1(2H)-thione
  参考文献：
  名称：

  Synthesis of methyl 2-[2-(4-phenyl[1,2,4]triazolo-[4,3-a]quinoxalin-1-ylsulfanyl)acetamido]alkanoates and their N-regioisomeric analogs

  摘要：

  Methyl 2-[2-(4-phenyl[1,2,4]triazolo[4,3-a]quinoxalin-1-ylsulfanyl)acetamido]alkanoates were formed by the reaction of 2-(4-phenyl-1,2-dihydro[1,2,4]triazolo[4,3-a]quinoxalin-1-ylsulfanyl)acetic acid with a variety of amino acid esters via DCC coupling method in the presence of N-hydroxybenzotriazole in good yields. These amino acid derivatives linked to triazoloquinoxaline moiety were also obtained by the reaction of 2-(4-phenyl[1,2,4]triazolo[4,3-a]quinoxalin-1-ylsulfanyl)acetohydrazide with amino acid ester derivatives via azide coupling method in poor yields due to the competing decomposition of the corresponding azide resulting in the starting 4-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline-1(2H)-thione. The N-regioisomeric methyl 2-[3-(4-phenyl-1-thioxo[1,2,4]triazolo[4,3-a]quinoxalin-2(1H)-yl)propanamido]alkanoates were efficiently produced from the 3-(4-phenyl-1-thioxo[1,2,4]triazolo[4,3-a]quinoxalin-2(1H)-yl)-propanohydrazide and amino acid esters via azide coupling method in good to moderate yields.

  DOI：

  10.1007/s10593-015-1662-0