2-Oxo-3-phenyl-5,7-dimethylisoxazolo<2,3-a>pyrimidine | 166319-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-Oxo-3-phenyl-5,7-dimethylisoxazolo<2,3-a>pyrimidine
• 英文别名: 5,7-Dimethyl-3-phenyl-[1,2]oxazolo[2,3-a]pyrimidin-2-one
• CAS: 166319-05-7
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: GKVPSOIFCZRQEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Oxo-3-phenyl-5,7-dimethylisoxazolo<2,3-a>pyrimidine 在 水 作用下， 反应 48.0h， 以56%的产率得到(4,6-二甲基-嘧啶-2-基)-苯基-甲醇
  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：

  3-Amino-4-phenylisoxazol-5-one 、 乙酰丙酮 在 盐酸 作用下， 以 乙醇 为溶剂， 以85%的产率得到2-Oxo-3-phenyl-5,7-dimethylisoxazolo<2,3-a>pyrimidine
  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

文献信息

• Oxidative Ring Opening of 2-Oxoisoxazolo[2,3-<i>a</i>]pyrimidines. Formation of Pyrimidin-2-yl Phenyl Ketones
  作者：Gury Zvilichovsky、Vadim Gurvich

  DOI：10.1021/jo952200c

  日期：1996.1.1
• 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.