5-(1-Hydroxy-ethylidene)-pyrimidine-2,4,6-trione

• 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: 5-(1-Hydroxy-ethylidene)-pyrimidine-2,4,6-trione
• 英文别名: 5-(1-hydroxyethylidene)-1,3-diazinane-2,4,6-trione
• 化学式: C₆H₆N₂O₄
• 分子量: 170.125
• InChiKey: FZYQXHPLCISFQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(1-Hydroxy-ethylidene)-pyrimidine-2,4,6-trione 以 氘代二甲亚砜 为溶剂， 生成 5-acetyl-6-hydroxypyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  摘要：

  Tautomerism of 5-formyl- and 5-acetyl derivatives of pyrimidine-2,4,6-trione, 2-thioxopyrimidine-4,6-dione, and 4,6-dihidroxy-2-methylthiopyrimidine was studied by NMR, UV, and IR spectroscopy, as well as by quantum chemistry. An equilibrium mixture of exo- and endo-enols in the neutral state and the presence of the same tautomers in monoanions were found. The energies of intramolecular hydrogen bonds in the gas phase and their changes in going to solutions in water, DMSO, and chloroform were calculated. The energies of intra-and intermolecular hydrogen bonds are close to each other. This fact suggests existence in solutions of two forms: tautomers with intramolecular H bond and H-bonded complexes with the solvents studied, whose formation involves cleavage of the intramolecular H bond. Characteristics of intermolecular hydrogen bonds are determined by the relative proton-donor and proton-acceptor powers of polyhydroxypyrimidines and solvents and are almost independent of the polarity of the medium.

  DOI：

  10.1023/a:1020450811301
• 作为产物：
  描述：

  5-acetyl-6-hydroxypyrimidine-2,4(1H,3H)-dione 以 氘代二甲亚砜 为溶剂， 生成 5-(1-Hydroxy-ethylidene)-pyrimidine-2,4,6-trione
  参考文献：
  名称：

  摘要：

  Tautomerism of 5-formyl- and 5-acetyl derivatives of pyrimidine-2,4,6-trione, 2-thioxopyrimidine-4,6-dione, and 4,6-dihidroxy-2-methylthiopyrimidine was studied by NMR, UV, and IR spectroscopy, as well as by quantum chemistry. An equilibrium mixture of exo- and endo-enols in the neutral state and the presence of the same tautomers in monoanions were found. The energies of intramolecular hydrogen bonds in the gas phase and their changes in going to solutions in water, DMSO, and chloroform were calculated. The energies of intra-and intermolecular hydrogen bonds are close to each other. This fact suggests existence in solutions of two forms: tautomers with intramolecular H bond and H-bonded complexes with the solvents studied, whose formation involves cleavage of the intramolecular H bond. Characteristics of intermolecular hydrogen bonds are determined by the relative proton-donor and proton-acceptor powers of polyhydroxypyrimidines and solvents and are almost independent of the polarity of the medium.

  DOI：

  10.1023/a:1020450811301