4-(4-fluorophenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carbothioamide | 1574646-48-2

• 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: 4-(4-fluorophenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carbothioamide
• 英文别名: 4-(4-fluorophenyl)-6-methyl-2-oxo-N-phenyl-3,4-dihydro-1H-pyrimidine-5-carbothioamide
• CAS: 1574646-48-2
• 化学式: C₁₈H₁₆FN₃OS
• 分子量: 341.409
• InChiKey: PCJUJUNANWFKSA-UHFFFAOYSA-N

物化性质

• 熔点：
  162-165 °C(Solvent: Ethanol)
• 密度：
  1.317±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  85.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-fluorophenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carbothioamide 在 溶剂黄146 、 sodium nitrite 作用下， 反应 8.0h， 以41%的产率得到4-(4-fluorophenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide
  参考文献：
  名称：

  2-Acylthioacetamides in the Biginelli Reaction

  摘要：

  We have demonstrated for the first time a Biginelli reaction of 2-acylthioacetamides with aromatic aldehydes and ureas or thioureas, leading to N-Ar-1-4-Ar-2-6-R-1-1-R-2-2-oxo(thioxo)-1,2,3,4-tetrahydro-pyrimidine-5-carbothioamides. The regioselectivity of this process matched the concept of hard/soft Lewis acids and bases. It was established that nitrous acid or other oxidants converted the synthesized compounds into N-Ar-1-4-Ar-2-6-R-1-1-R-2-2-oxo(thioxo)-1,2,3,4-tetrahydropyrimidine-5-carboxamides, and not the expected 4-Ar-2-6-R-1-1-R-2-5-(1,3-benzothiazol-2-yl)-1,2,3,4-tetrahydropyrimidin-2-ones(thiones).

  DOI：

  10.1007/s10593-014-1429-z
• 作为产物：
  描述：

  对氟苯甲醛 、 尿素 、 丁硫代酰胺,3-羰基-N-苯基- 在 硼酸 、 溶剂黄146 作用下， 以64%的产率得到4-(4-fluorophenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carbothioamide
  参考文献：
  名称：

  2-Acylthioacetamides in the Biginelli Reaction

  摘要：

  We have demonstrated for the first time a Biginelli reaction of 2-acylthioacetamides with aromatic aldehydes and ureas or thioureas, leading to N-Ar-1-4-Ar-2-6-R-1-1-R-2-2-oxo(thioxo)-1,2,3,4-tetrahydro-pyrimidine-5-carbothioamides. The regioselectivity of this process matched the concept of hard/soft Lewis acids and bases. It was established that nitrous acid or other oxidants converted the synthesized compounds into N-Ar-1-4-Ar-2-6-R-1-1-R-2-2-oxo(thioxo)-1,2,3,4-tetrahydropyrimidine-5-carboxamides, and not the expected 4-Ar-2-6-R-1-1-R-2-5-(1,3-benzothiazol-2-yl)-1,2,3,4-tetrahydropyrimidin-2-ones(thiones).

  DOI：

  10.1007/s10593-014-1429-z

文献信息

• 2-Acylthioacetamides in the Biginelli Reaction
  作者：M. N. Kurmach、A. B. Ryabitskiy、V. N. Britsun

  DOI：10.1007/s10593-014-1429-z

  日期：2014.3

  We have demonstrated for the first time a Biginelli reaction of 2-acylthioacetamides with aromatic aldehydes and ureas or thioureas, leading to N-Ar-1-4-Ar-2-6-R-1-1-R-2-2-oxo(thioxo)-1,2,3,4-tetrahydro-pyrimidine-5-carbothioamides. The regioselectivity of this process matched the concept of hard/soft Lewis acids and bases. It was established that nitrous acid or other oxidants converted the synthesized compounds into N-Ar-1-4-Ar-2-6-R-1-1-R-2-2-oxo(thioxo)-1,2,3,4-tetrahydropyrimidine-5-carboxamides, and not the expected 4-Ar-2-6-R-1-1-R-2-5-(1,3-benzothiazol-2-yl)-1,2,3,4-tetrahydropyrimidin-2-ones(thiones).