6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde oxime

• 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: 6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde oxime
• 英文别名: 5-(hydroxyiminomethyl)-6-methyl-1H-pyrimidine-2,4-dione
• 化学式: C₆H₇N₃O₃
• 分子量: 169.14
• InChiKey: QASVBXKZOASRMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  90.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde oxime 在 硫酸 、 双氧水 、 potassium bromide 作用下， 反应 5.0h， 以85%的产率得到5-溴-6-甲基尿嘧啶
  参考文献：
  名称：

  6－甲基尿嘧啶－5－甲醛肟的化学性质

  摘要：

  在两相体系中对6-甲基尿嘧啶-5甲醛肟进行氧化氯化，得到7V-羟基-6-甲基尿嘧啶-5-羧酰亚胺基氯，其溴化反应可得到ipso取代产物5-溴6-甲基尿嘧啶和5， 5-二溴-6-羟基-6-甲基-5,6-二氢尿嘧啶。取决于温度，标题化合物与乙酸酐的反应导致形成6-甲基尿嘧啶-5-腈或O-乙酰基衍生物。7V-羟基-6-甲基尿嘧啶-5-羧酰亚胺基氯与乙酸在100°C或碘化钾在沸腾的丙酮中反应生成尿嘧啶-5-异羟肟酸，将其高产率转化为相应的甲酯和氢氧酰胺。通过N反应获得季铵盐-羟基-6-甲基尿嘧啶-5-羧酰亚胺基氯与吡啶和1-甲基-1 H-咪唑。

  DOI：

  10.1134/s1070428019090045
• 作为产物：
  描述：

  6-甲基-2,4-二氧代-1,2,3,4-四氢-嘧啶-5-甲醛 在 盐酸羟胺 、 sodium acetate 作用下， 以 水 为溶剂， 反应 5.0h， 以95%的产率得到6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde oxime
  参考文献：
  名称：

  Synthesis of New N-Hydroxy-6-methyluracil-5-carboximidoyl Chloride Derivatives

  摘要：

  N-Hydroxy-6-methyluracil-5-carboximidoyl chloride was synthesized for the first time, and its halogenation and reactions with amines (imidazole, aniline) were studied. The reaction of the title compound with sodium azide gave the corresponding N-hydroxycarboximidoyl azide. The Z isomer of the latter was stable, and it did not undergo isomerization to the E isomer, which prevented transformation to 1-hydroxytetrazole. 6-Methyluracil-5-carbaldehyde oxime was readily acylated at the oxime oxygen atom.

  DOI：

  10.1134/s1070428019030084

文献信息

• Synthesis of New N-Hydroxy-6-methyluracil-5-carboximidoyl Chloride Derivatives
  作者：I. B. Chernikova、I. Z. Sagadatova、M. S. Yunusov、R. F. Talipov

  DOI：10.1134/s1070428019030084

  日期：2019.3

  N-Hydroxy-6-methyluracil-5-carboximidoyl chloride was synthesized for the first time, and its halogenation and reactions with amines (imidazole, aniline) were studied. The reaction of the title compound with sodium azide gave the corresponding N-hydroxycarboximidoyl azide. The Z isomer of the latter was stable, and it did not undergo isomerization to the E isomer, which prevented transformation to 1-hydroxytetrazole. 6-Methyluracil-5-carbaldehyde oxime was readily acylated at the oxime oxygen atom.
• Chemical Properties of 6-Methyluracil-5-carbaldehyde Oxime
  作者：I. B. Chernikova、S. L. Khursan、L. V. Spirikhin、M. S. Yunusov

  DOI：10.1134/s1070428019090045

  日期：2019.9

  yl chloride, and its bromination afforded ipso-substitution products, 5-bromo-6-methyluracil and 5,5-dibromo-6-hydroxy-6-methyl-5,6-dihydrouracil. The reaction of the title compound with acetic anhydride led to the formation of 6-methyluracil-5-carbonitrile or O-acetyl derivative, depending on the temperature. 7V-Hydroxy-6-methyluracyl-5-carboximidoyl chloride reacted with acetic acid at 100°C or with

  在两相体系中对6-甲基尿嘧啶-5甲醛肟进行氧化氯化，得到7V-羟基-6-甲基尿嘧啶-5-羧酰亚胺基氯，其溴化反应可得到ipso取代产物5-溴6-甲基尿嘧啶和5， 5-二溴-6-羟基-6-甲基-5,6-二氢尿嘧啶。取决于温度，标题化合物与乙酸酐的反应导致形成6-甲基尿嘧啶-5-腈或O-乙酰基衍生物。7V-羟基-6-甲基尿嘧啶-5-羧酰亚胺基氯与乙酸在100°C或碘化钾在沸腾的丙酮中反应生成尿嘧啶-5-异羟肟酸，将其高产率转化为相应的甲酯和氢氧酰胺。通过N反应获得季铵盐-羟基-6-甲基尿嘧啶-5-羧酰亚胺基氯与吡啶和1-甲基-1 H-咪唑。