2-Hydrazino-1,4-dimethyl-pyrimidon-(6) | 3493-94-5

• 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-Hydrazino-1,4-dimethyl-pyrimidon-(6)
• 英文别名: 2-Hydrazinyl-3,6-dimethylpyrimidin-4(3H)-one；2-hydrazinyl-3,6-dimethylpyrimidin-4-one
• CAS: 3493-94-5
• 化学式: C₆H₁₀N₄O
• mdl: MFCD09881132
• 分子量: 154.172
• InChiKey: WZNVBQVBMGZPTQ-UHFFFAOYSA-N

物化性质

• 熔点：
  206-207 °C (decomp)(Solv: ethanol (64-17-5); ethyl acetate (141-78-6))
• 沸点：
  270.7±23.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Hydrazino-1,4-dimethyl-pyrimidon-(6) 在 盐酸 作用下， 以 水 为溶剂， 反应 3.25h， 生成 2-[4-(4-chlorophenyl)-1,3-thiazol-2-ylhydrazino]-3,6-dimethyl-3,4-dihydropyrimidin-4-one hydrochloride
  参考文献：
  名称：

  Synthesis and molecular structure of 1-(pyrimidin-2-yl)-2-(4-aryl-1,3-thiazol-2-yl)hydrazines

  摘要：

  Reactions of some 2-hydrazinopyrimidine hydrochlorides with potassium thiocyanate gave 1-(pyrimidin-2-yl)thiosemicarbazides which underwent Hantzsch condensation with aryl chloromethyl ketones to produce 1-(pyrimidin-2-yl)-2-(4-aryl-1,3-thiazol-2-yl)hydrazine hydrochlorides. The protonation was accompanied by mutually dependent tautomeric rearrangements of heterocyclic fragments.

  DOI：

  10.1134/s1070363211080196
• 作为产物：
  描述：

  6-甲基-4-羟基-2-甲硫基嘧啶 在 一水合肼 作用下， 反应 2.0h， 生成 2-Hydrazino-1,4-dimethyl-pyrimidon-(6)
  参考文献：
  名称：

  Claesen; Vanderhaeghe, Bulletin des Societes Chimiques Belges, 1959, vol. 68, p. 30,55

  摘要：

  DOI：

文献信息

• Sirakawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 1395,1400
  作者：Sirakawa

  DOI：——

  日期：——
• 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.
• Anomalous cyclization of ethyl acetoacetate (3,6-dimethyl-4-oxo-3,4-dihydropyrimidin-2-yl)hydrazone
  作者：A. V. Erkin、V. I. Krutikov

  DOI：10.1134/s1070363207010173

  日期：2007.1

  Structural modification of some (pyrimidin-2-yl)hydrazones derived from ethyl acetoacetate via methylation at the N-3 atom promotes anomalous cyclization to give [1,2,4]triazolo[1,5-a]pyrimidine derivatives. The mechanism of this transformation includes specific cleavage of the aliphatic fragment in the substrate with subsequent rearrangement of carbene-like intermediate.
• Claesen; Vanderhaeghe, Bulletin des Societes Chimiques Belges, 1959, vol. 68, p. 30,55
  作者：Claesen、Vanderhaeghe

  DOI：——

  日期：——
• Synthesis and molecular structure of 1-(pyrimidin-2-yl)-2-(4-aryl-1,3-thiazol-2-yl)hydrazines
  作者：A. V. Erkin、V. I. Krutikov

  DOI：10.1134/s1070363211080196

  日期：2011.8

  Reactions of some 2-hydrazinopyrimidine hydrochlorides with potassium thiocyanate gave 1-(pyrimidin-2-yl)thiosemicarbazides which underwent Hantzsch condensation with aryl chloromethyl ketones to produce 1-(pyrimidin-2-yl)-2-(4-aryl-1,3-thiazol-2-yl)hydrazine hydrochlorides. The protonation was accompanied by mutually dependent tautomeric rearrangements of heterocyclic fragments.