4-(3,5-di-tert-butyl-4-hydroxyphenyl)-6-phenyl-pyrimidin-2(1H)-one | 1210889-74-9

• 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-(3,5-di-tert-butyl-4-hydroxyphenyl)-6-phenyl-pyrimidin-2(1H)-one
• 英文别名: 4-(3,5-Di-t-butyl-4-hydroxyphenyl)-6-phenyl-pyrimidin-2(1h)-one；4-(3,5-ditert-butyl-4-hydroxyphenyl)-6-phenyl-1H-pyrimidin-2-one
• CAS: 1210889-74-9
• 化学式: C₂₄H₂₈N₂O₂
• 分子量: 376.499
• InChiKey: HOBPLQJRKMDOIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙酮 、 尿素 、 3,5-二叔丁基-4-羟基苯甲醛 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 23.0h， 以32%的产率得到4-(3,5-di-tert-butyl-4-hydroxyphenyl)-6-phenyl-pyrimidin-2(1H)-one
  参考文献：
  名称：

  Synthesis of substituted 3,4-dihydropyrimidin-2(1H)-ones and pyrimidin-2(1H)-ones by the Biginelli reaction with 3,5-Di-tert-butyl-4-hydroxybenzaldehyde

  摘要：

  Three-component acid-catalyzed cyclocondensation of 3,5-di-tret-butyl-4-hydroxybenzaldehyde with urea and ethyl acetoacetate or alpha-nitroacetophenone (Biginelli reaction) under homogeneous conditions gave the corresponding 5-substituted 3,4-dihydropyrimidin-2(1H)-ones having in position 4 of the heteroring an aryl substituent with sterically shielded hydroxy group. The condensation catalyzed by inorganic salts (Fe3+, Co2+, Zn2+, Li+) was successful only with ethyl acetoacetate as initial methylene-active component. Under analogous conditions, acetophenone and 4-fluoroacetophenone gave rise to 4,6-diarylpyrimidin-2(1H)-ones which are capable of undergoing phenol-quinonemethide tautomerism.

  DOI：

  10.1134/s1070428009100200

文献信息

• Synthesis of substituted 3,4-dihydropyrimidin-2(1H)-ones and pyrimidin-2(1H)-ones by the Biginelli reaction with 3,5-Di-tert-butyl-4-hydroxybenzaldehyde
  作者：V. F. Sedova、V. P. Krivopalov、O. P. Shkurko

  DOI：10.1134/s1070428009100200

  日期：2009.10

  Three-component acid-catalyzed cyclocondensation of 3,5-di-tret-butyl-4-hydroxybenzaldehyde with urea and ethyl acetoacetate or alpha-nitroacetophenone (Biginelli reaction) under homogeneous conditions gave the corresponding 5-substituted 3,4-dihydropyrimidin-2(1H)-ones having in position 4 of the heteroring an aryl substituent with sterically shielded hydroxy group. The condensation catalyzed by inorganic salts (Fe3+, Co2+, Zn2+, Li+) was successful only with ethyl acetoacetate as initial methylene-active component. Under analogous conditions, acetophenone and 4-fluoroacetophenone gave rise to 4,6-diarylpyrimidin-2(1H)-ones which are capable of undergoing phenol-quinonemethide tautomerism.