(4,6-二甲基-嘧啶-2-基)-苯基-甲醇 | 32416-43-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: (4,6-二甲基-嘧啶-2-基)-苯基-甲醇
• 英文名称: 2-(α-Hydroxybenzyl)-4,6-dimethylpyrimidin
• 英文别名: (4,6-dimethyl-pyrimidin-2-yl)-phenyl-methanol；(4,6-Dimethylpyrimidin-2-yl)(phenyl)methanol；(4,6-dimethylpyrimidin-2-yl)-phenylmethanol
• CAS: 32416-43-6
• 化学式: C₁₃H₁₄N₂O
• 分子量: 214.267
• InChiKey: IJQGOSDEQRRWNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  46
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-Amino-4-phenylisoxazol-5-one 在 盐酸 、 水 作用下， 以 乙醇 为溶剂， 反应 49.02h， 生成 (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

文献信息

• Molecular rearrangements. Synthesis, stability, and rearrangements of 2-imino-2H-isoxazolo[2,3-a]pyrimidines and 2-aminoisoxazolo[2,3-a]pyrimidinium salts
  作者：Gury Zvilichovsky、Mordechai David

  DOI：10.1021/jo00152a032

  日期：1983.2
• 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
• ZVILICHOVSKY, G.;DAVID, M., J. ORG. CHEM., 1983, 48, N 4, 575-579
  作者：ZVILICHOVSKY, G.、DAVID, M.

  DOI：——

  日期：——
• 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.