5-Amino-4-phenylisoxazol-3-one | 878-88-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-Amino-4-phenylisoxazol-3-one
• 英文别名: 5-amino-4-phenyl-isoxazol-3-one；4-Phenyl-5-amino-isoxazolin-3-on；5-Amino-4-phenyl-isoxazolon-(3)；4-Phenyl-5-amino-3-isoxazolon；5-Amino-4-phenylisoxazol-3(2H)-one；5-amino-4-phenyl-1,2-oxazol-3-one
• CAS: 878-88-6
• 化学式: C₉H₈N₂O₂
• 分子量: 176.175
• InChiKey: JKAAEJFCZAZVTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Amino-4-phenylisoxazol-3-one 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 生成 2-苯基丙二酰胺
  参考文献：
  名称：

  Synthesis and Rearrangement of 2-Oxo-3-phenylisoxazolo[2,3-a]pyrimidines

  摘要：

  2-Oxo-3-phenylisoxazolo[2,3-alpha]pyrimidine derivatives were synthesized by the reaction of 3-amino-4-phenyl-5-isoxazolone with malonaldehyde tetraacetal, 3-oxobutyraldehyde diacetal, 2,4-pentanedione, and 1-phenyl-1,3-butanedione. The regioselectivity of this reaction was determined by X-ray single crystal structural analysis. Upon heating either in water or in ethanol this bicyclic system underwent a ring opening, followed by decarboxylation to yield phenylpyrimidylmethanol and phenylpyrimidyl methyl ethers. The structures of these 2-oxoisoxazolo[2,3-alpha]pyrimidines and the mechanism of their rearrangement is discussed.

  DOI：

  10.1021/jo00121a049
• 作为产物：
  描述：

  苯基氰基乙酸乙酯 在 羟胺 、 sodium ethanolate 作用下， 生成 5-Amino-4-phenylisoxazol-3-one
  参考文献：
  名称：

  Isoxazoles—I

  摘要：

  DOI：

  10.1016/s0040-4020(01)88837-2

文献信息

• Isoxazoles—II
  作者：W. Barbieri、L. Bernardi、S. Coda、V. Colò、G. Diqual、G. Palamidessi

  DOI：10.1016/s0040-4020(01)88838-4

  日期：1967.1
• Isoxazoles—I
  作者：W. Barbieri、L. Bernardi、S. Coda、V. Colò、G. Palamidessi

  DOI：10.1016/s0040-4020(01)88837-2

  日期：1967.1
• Synthesis and Rearrangement of 2-Oxo-3-phenylisoxazolo[2,3-a]pyrimidines
  作者：Gury Zvilichovsky、Vadim Gurvich、Shlomo Segev

  DOI：10.1021/jo00121a049

  日期：1995.8

  2-Oxo-3-phenylisoxazolo[2,3-alpha]pyrimidine derivatives were synthesized by the reaction of 3-amino-4-phenyl-5-isoxazolone with malonaldehyde tetraacetal, 3-oxobutyraldehyde diacetal, 2,4-pentanedione, and 1-phenyl-1,3-butanedione. The regioselectivity of this reaction was determined by X-ray single crystal structural analysis. Upon heating either in water or in ethanol this bicyclic system underwent a ring opening, followed by decarboxylation to yield phenylpyrimidylmethanol and phenylpyrimidyl methyl ethers. The structures of these 2-oxoisoxazolo[2,3-alpha]pyrimidines and the mechanism of their rearrangement is discussed.