5-(4-methylphenyl)-3-[(E)-2-phenylethenyl]-1,2,4-oxadiazole | 1236970-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-methylphenyl)-3-[(E)-2-phenylethenyl]-1,2,4-oxadiazole
• 英文别名: 5-(4-Methylphenyl)-3-[(e)-2-phenylethenyl]-1,2,4-oxadiazole
• CAS: 1236970-33-4
• 化学式: C₁₇H₁₄N₂O
• 分子量: 262.311
• InChiKey: UXMCMXAFBINIMM-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-methylphenyl)-3-[(E)-2-phenylethenyl]-1,2,4-oxadiazole 、 氨基邻苯二甲胺 在 lead(IV) tetraacetate 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以66%的产率得到5-(4-methylphenyl)-3-[rel-(2R,3S)-3-phenyl-1-phthalimidoaziridin-2-yl]-1,2,4-oxadiazole
  参考文献：
  名称：

  Oxidative addition of N-aminophthalimide to styryl-1,2,4-oxadiazoles

  摘要：

  The oxidation of N-aminophthalimide with lead tetraacetate in the presence of 5-[(E)-2-arylethenyl]-3-(4-methylphenyl)-1,2,4-oxadiazoles and 5-(4-methylphenyl)-3-[E)-2-phenyl-ethenyl]-1,2,4-oxadiazole led to the formation of the corresponding (3-aryl-1-phthalimidoaziridin-2-yl)-(4-methylphenyl)-1,2,4-oxadiazoles. In the reaction with 3,5-distyryl-1,2,4-oxadiazole a mixture was obtained of two regioisomeric monoadducts and a diadduct in the ratio 80 : 15: 5; at the use of 3 equiv of the aziridinating reagents only diadduct was isolated as a mixture of two diastereoisomers in the similar to 3 : 2 ratio that were separated by recrystallization.

  DOI：

  10.1134/s1070428010050143
• 作为产物：
  描述：

  cinnamoylamidoxime 、 对甲基苯甲酰氯 在 N-甲基吗啉 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 10.17h， 以55%的产率得到5-(4-methylphenyl)-3-[(E)-2-phenylethenyl]-1,2,4-oxadiazole
  参考文献：
  名称：

  Oxidative addition of N-aminophthalimide to styryl-1,2,4-oxadiazoles

  摘要：

  The oxidation of N-aminophthalimide with lead tetraacetate in the presence of 5-[(E)-2-arylethenyl]-3-(4-methylphenyl)-1,2,4-oxadiazoles and 5-(4-methylphenyl)-3-[E)-2-phenyl-ethenyl]-1,2,4-oxadiazole led to the formation of the corresponding (3-aryl-1-phthalimidoaziridin-2-yl)-(4-methylphenyl)-1,2,4-oxadiazoles. In the reaction with 3,5-distyryl-1,2,4-oxadiazole a mixture was obtained of two regioisomeric monoadducts and a diadduct in the ratio 80 : 15: 5; at the use of 3 equiv of the aziridinating reagents only diadduct was isolated as a mixture of two diastereoisomers in the similar to 3 : 2 ratio that were separated by recrystallization.

  DOI：

  10.1134/s1070428010050143