3-methoxy-5-(4-chlorophenyl)-1,2,4-oxadiazole | 21084-91-3

• 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-5-(4-chlorophenyl)-1,2,4-oxadiazole
• 英文别名: 3-Methoxy-5-(4-chlor-phenyl)-1,2,4-oxadiazol；5-(4-chloro-phenyl)-3-methoxy-[1,2,4]oxadiazole；5-(4-Chlorophenyl)-3-methoxy-1,2,4-oxadiazole
• CAS: 21084-91-3
• 化学式: C₉H₇ClN₂O₂
• 分子量: 210.62
• InChiKey: ZVQIHXBXRQNDLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  48.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methoxy-5-(4-chlorophenyl)-1,2,4-oxadiazole 在 二苯基乙炔 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以40%的产率得到2-methoxy-7-chloroquinazolin-4-one
  参考文献：
  名称：

  Photoinduced Single Electron Transfer on 5-Aryl-1,2,4-oxadiazoles:  Some Mechanistic Investigations in the Synthesis of Quinazolin-4-ones

  摘要：

  The photochemistry of some 5-aryl-3-methoxy- (or 5-aryl-3-phenyl-) 1,2,4-oxadiazoles irradiated in the presence of different sensitizers [such as diphenylacetylene (DAC), 9,10-diphenylanthracene (DAN), or triphenylene (TPH)] or ground-state donors such as triethylamine (TEA) has been investigated. Intermediates arising from breaking of the ring O-N bond develop both into quinazolin-4-ones (by a heterocyclization reaction involving the aryl at the C-5 of the oxadiazole nucleus) and into open-chain products (corresponding to a reduction at the ring O-N bond), in different ratios depending on their structures and photoreaction conditions. A reasonable explanation considers sensitization by photoinduced electron transfer either from the sensitizer in its excited state to the oxadiazole in its ground state or from the electron donor reagent (TEA) to the excited oxadiazole; in both cases an oxadiazole radical anion is formed as a key species from which breaking of the ring O-N bond takes place. Reduction potentials of representative oxadiazoles confirm this hypothesis. Possible applications in the synthesis of variously substituted quinazolin-4-ones are recognized.

  DOI：

  10.1021/jo990298f
• 作为产物：
  描述：

  N-(4-Chlorbenzoyl)-carbamidsaeureazid 以 甲醇 、 水 、 苯 为溶剂， 生成 3-methoxy-5-(4-chlorophenyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Neidlein,R.; Kruell,H., Justus Liebigs Annalen der Chemie, 1968, vol. 716, p. 156 - 159

  摘要：

  DOI：