3-甲氧基-5-(4-氰基苯基)-1,2,4-恶二唑 | 163631-77-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-甲氧基-5-(4-氰基苯基)-1,2,4-恶二唑
• 英文名称: 3-Methoxy-5-(4-cyanophenyl)-1,2,4-oxadiazole
• 英文别名: 4-(3-Methoxy-1,2,4-oxadiazol-5-yl)benzonitrile
• CAS: 163631-77-4
• 化学式: C₁₀H₇N₃O₂
• 分子量: 201.184
• InChiKey: GSKGKEQWWYRILM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-甲氧基-5-(4-氰基苯基)-1,2,4-恶二唑 在 二苯基乙炔 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以38%的产率得到O-methyl-N-(4-cyanobenzoyl)isourea
  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：

  [[Amino(methoxy)methylidene]amino] 4-cyanobenzoate 以 melt 为溶剂， 以60%的产率得到3-甲氧基-5-(4-氰基苯基)-1,2,4-恶二唑
  参考文献：
  名称：

  Photoinduced Molecular Rearrangements. Some Investigations of the Photochemical Behavior of 3-(Acylamino)-1,2,5-Oxadiazoles (Furazans)

  摘要：

  Mechanistic investigations of the photochemical behavior of some 3-(acylamino)-1,2,5-oxadiazoles (furazans) are reported. Irradiations of 3-(aroylamino)-4-methyl- and 3-(acetylamino)-4-phenylfurazans at lambda = 254 nm in methanol, and in methanol containing pyrrolidine, are considered. Photochemical processes follow different routes depending on the actual chromophore in the photoreaction. In the irradiation of 3-(aroylamino)-4-methylfurazans, two photochemical pathways involving a different multiplicity of excited states are suggested: cleavage of the ring O(1)-N(5) bond via a singlet excited state (developing into nitrile oxides or carbodiimides, from which final products arise), or preliminary ring-closure involving the aroylamino group via a triplet excited state, respectively. In the irradiation of 3-(acetylamino)-4-phenylfurazan, photolytic intermediates arising from the cleavage of both the O(1)-N(2) and O(1)-N(5) bonds develop into the final products by reaction with the nucleophilic species present.

  DOI：

  10.1021/jo00118a028