3-methoxy-1-methyl-5-phenyl-1,2,4-triazole | 50369-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methoxy-1-methyl-5-phenyl-1,2,4-triazole
• 英文别名: 5-Methoxy-2-methyl-3-phenyl-1,2,4-triazol；2-Methyl-5-methoxy-3-phenyl-1,2,4-triazol；3-methoxy-1-methyl-5-phenyl-1H-[1,2,4]triazole
• CAS: 50369-38-5
• 化学式: C₁₀H₁₁N₃O
• 分子量: 189.217
• InChiKey: JGXPXBYYLXBKTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-Methoxy-5-phenyl-1,2,4-oxadiazole 在 甲胺 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.0h， 以18%的产率得到3-methoxy-1-methyl-5-phenyl-1,2,4-triazole
  参考文献：
  名称：

  Photoinduced Molecular Rearrangements. The Photochemistry of Some 1,2,4-Oxadiazoles in the Presence of Nitrogen Nucleophiles. Formation of 1,2,4-Triazoles, Indazoles, and Benzimidazoles

  摘要：

  The photochemistry of some 3,5-disubstituted 1,2,4-oxadiazoles in the presence of nitrogen nucleophiles [external, such as added amines or hydrazines, or internal, such as an o-aminophenyl moiety at C(3) of the oxadiazole ring] has been investigated. In the irradiation of 5-amino-(or 5-N-substituted amino) 3-phenyl-1,2,4-oxadiazoles in the presence of aliphatic primary amines (or ammonia), photolytic species arising from heterolytic cleavage of the ring O-N bond capture the nucleophilic reagent to give open-chain intermediates, which develop into 1,2,4-triazolin-5-ones. Similarly, irradiations of 3,5-diphenyl-, 3-methoxy-5-phenyl-, and 5-methyl-3-phenyl-1,2,4-oxadiazoles gave 1,2,4-triazoles. In the same context, irradiations of representative substrates in the presence of hydrazines have been also investigated. In the irradiation of 3-(o-aminophenyl)-5-methyl-, 3-[o-(methylamino)phenyl]-5-methyl-, and 3-(o-aminophenyl)-5-phenyl-1,2,4-oxadiazoles, concomitant formation of indazoles and benzimidazoles, presumably arising from a common photolytic species, has been observed. Some mechanistic aspects have been considered, and possible applications in synthesis have been pointed out.

  DOI：

  10.1021/jo960765i