6-methyl-2-(3-methyl-5-oxo-2,5-dihydropyrazol-1-yl)pyrimidin-4(1H)-one | 53068-50-1

• 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-(3-methyl-5-oxo-2,5-dihydropyrazol-1-yl)pyrimidin-4(1H)-one
• 英文别名: 6-methyl-2-(3-methyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)-4(3H)-pyrimidinone；4-methyl-2-(5-methyl-3-oxo-1H-pyrazol-2-yl)-1H-pyrimidin-6-one
• CAS: 53068-50-1
• 化学式: C₉H₁₀N₄O₂
• 分子量: 206.204
• InChiKey: ZWPLPUGPPROJDJ-UHFFFAOYSA-N

物化性质

• 熔点：
  203 °C(Solv: ethanol (64-17-5))
• 沸点：
  336.4±25.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  73.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-苯亚甲基巴比土酸 、 6-methyl-2-(3-methyl-5-oxo-2,5-dihydropyrazol-1-yl)pyrimidin-4(1H)-one 在 sodium ethanolate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.08h， 以20%的产率得到(2,4,6-trioxo-1,2,3,4,5,6-hexahydropyrimidin-5-yl)[2-(5-hydroxy-3-methylpyrazol-1-yl)-6-methyl-4-oxo-3,4-dihydropyrimidin-5-yl]phenylmethane
  参考文献：
  名称：

  6-Methyl-2-(3-methyl-5-oxo-2,5-dihydropyrazolyl)-pyrimidin-4(1H)-one as CH acid in Michael reaction

  摘要：

  Addition of 6-methyl-2-(3-methyl-5-oxo-2,5-dihydropyrazol-1-yl)pyrimidin-4(1H)-one, a compound with two CH-acidic centers, to 5-benzylidenepyrimidine-2,4,6(1H,3H,5H)-trione proceeds with the participation of the atom C-5 of pyrimidine ring. Under the realized reaction conditions the latter possesses a greater nucleophilicity as a result of the priority ionization. The obtained Michael adduct is unstable in the neutral aqueous medium and is decomposed into initial oxopyrazolylpyrimidinone, pyrimidine-2,4,6-(1H,3H,5H)-trione, and benzaldehyde.

  DOI：

  10.1134/s1070363209070214
• 作为产物：
  描述：

  2-肼基-6-甲基嘧啶-4-醇 、 乙酰乙酸乙酯 以 水 为溶剂， 反应 1.0h， 以43%的产率得到6-methyl-2-(3-methyl-5-oxo-2,5-dihydropyrazol-1-yl)pyrimidin-4(1H)-one
  参考文献：
  名称：

  6-Methyl-2-(3-methyl-5-oxo-2,5-dihydropyrazolyl)-pyrimidin-4(1H)-one as CH acid in Michael reaction

  摘要：

  Addition of 6-methyl-2-(3-methyl-5-oxo-2,5-dihydropyrazol-1-yl)pyrimidin-4(1H)-one, a compound with two CH-acidic centers, to 5-benzylidenepyrimidine-2,4,6(1H,3H,5H)-trione proceeds with the participation of the atom C-5 of pyrimidine ring. Under the realized reaction conditions the latter possesses a greater nucleophilicity as a result of the priority ionization. The obtained Michael adduct is unstable in the neutral aqueous medium and is decomposed into initial oxopyrazolylpyrimidinone, pyrimidine-2,4,6-(1H,3H,5H)-trione, and benzaldehyde.

  DOI：

  10.1134/s1070363209070214

文献信息

• Synthesis and tuberculocidic activity of some 4-arylaminomethylene-3-methyl-1-(pyrimidin-2-yl)pyrazol-5(4H)-ones
  作者：A. V. Erkin、V. I. Krutikov、A. A. Ivanov

  DOI：10.1134/s1070363212010252

  日期：2012.1

  4-Arylaminomethylene-3-methyl-1-(6-methyl-4-oxo-1,4-dihydropyrimidin-2-yl)pyrazol-5(4H)-ones were synthesized by a three-component reaction between the 6-methyl-2-(3-methyl-5-oxo-2,5-dihydropyrazol-1-yl)pyrimidin-4(1H)-one, triethoxymethane, and an aromatic amine. These compounds were found to exist as aminomethyleneketones regardless of the electronic effects of substituents in the aromatic fragments. The resulting compounds showed pronounced tuberculocidic activity.
• CRISTEA, IOAN;FARCASAN, VALER, REV. CHIM., 38,(1987) N 8, 674-679
  作者：CRISTEA, IOAN、FARCASAN, VALER

  DOI：——

  日期：——
• US3865825A
  申请人：——

  公开号：US3865825A

  公开（公告）日：1975-02-11
• 6-Methyl-2-(3-methyl-5-oxo-2,5-dihydropyrazolyl)-pyrimidin-4(1H)-one as CH acid in Michael reaction
  作者：A. V. Erkin、V. I. Krutikov

  DOI：10.1134/s1070363209070214

  日期：2009.7

  Addition of 6-methyl-2-(3-methyl-5-oxo-2,5-dihydropyrazol-1-yl)pyrimidin-4(1H)-one, a compound with two CH-acidic centers, to 5-benzylidenepyrimidine-2,4,6(1H,3H,5H)-trione proceeds with the participation of the atom C-5 of pyrimidine ring. Under the realized reaction conditions the latter possesses a greater nucleophilicity as a result of the priority ionization. The obtained Michael adduct is unstable in the neutral aqueous medium and is decomposed into initial oxopyrazolylpyrimidinone, pyrimidine-2,4,6-(1H,3H,5H)-trione, and benzaldehyde.