5-((2-hydroxybenzylidene)amino)-4-phenyl-1,2,3-oxadiazole 3-oxide | 1113056-48-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-((2-hydroxybenzylidene)amino)-4-phenyl-1,2,3-oxadiazole 3-oxide
• CAS: 1113056-48-6
• 化学式: C₁₅H₁₁N₃O₃
• 分子量: 281.271
• InChiKey: CXNNFHPJJKMXBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.56
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3-oxo-4phenyl-5-amino-1,2,3-oxadiazole 、 水杨醛 以 甲苯 为溶剂， 反应 24.0h， 以42.5%的产率得到5-((2-hydroxybenzylidene)amino)-4-phenyl-1,2,3-oxadiazole 3-oxide
  参考文献：
  名称：

  A New Synthetic Route to 3-Oxo-4-amino-1,2,3-oxadiazole from the Diazeniumdiolation of Benzyl Cyanide: Stable Sydnone Iminium N-Oxides

  摘要：

  Treating benzylcyanide with nitric oxide in basic methanol returns 3-oxo-4-phenyl-5-amino-1,2,3-oxadiazole (a 5-iminium-sydnone N-oxide), 5, in addition to the known 2-(hydroxyimino)-2-phenylacetonitrile, 6, and the bisdiazeniumdiolate imidate salt, 7. Conditions for the separation and purification of the new 1,2,3-oxadiazole 5 are described along with its theory, structure, spectroscopy, and reactivity which demonstrate the predominance of the amino tautomer over the N-hydroxide tautomer. New derivatives of 5 include a Schiff base, from the condensation with salicylaldehyde, 8, and a dimethylamino analogue of 5, from its reaction with methyliodide and NaH. As with other related 3-oxo-1,2,3-oxadiazoles 5 has pronounced acid/base stability. Theoretical calculations demonstrate that the only other prior sydnone N-oxides prepared were misformulated as the N-hydroxide imines and are better described as 3-oxo-5-amino-derivatives of 1,2,3-oxadiazoles.

  DOI：

  10.1021/jo802343k