2,6-bis(3-methoxyphenyl)-4-(1-hydroxystyr-2-yl)pyrimidine | 143889-58-1

• 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: 2,6-bis(3-methoxyphenyl)-4-(1-hydroxystyr-2-yl)pyrimidine
• 英文别名: (Z)-2-[2,6-bis(3-methoxyphenyl)pyrimidin-4-yl]-1-phenylethenol
• CAS: 143889-58-1
• 化学式: C₂₆H₂₂N₂O₃
• 分子量: 410.472
• InChiKey: CDJRXCZUSKIMPK-UQQQWYQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  64.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-甲氧基苯腈 、 (Z)-3-(isopropylamino)-1-phenylbut-2-en-1-one 生成 2,6-bis(3-methoxyphenyl)-4-(1-hydroxystyr-2-yl)pyrimidine
  参考文献：
  名称：

  Reaction of dianions of acyclic .beta.-enamino ketones with electrophiles. 3. Nitriles: synthesis of pyridine and pyrimidine derivatives

  摘要：

  A new method for the construction of pyridine and pyrimidine derivatives is described, based on the electrophilic attack of nitriles to dianions of beta-(monoalkylamino)-alpha,beta-unsaturated ketones and the subsequent cyclization of the addition product. The reaction proceeds in good to high yields with both alpha'- and gamma-dianions which are regioselectively generated. The reaction of gamma-dianions with nitriles is strongly influenced by temperature. The gamma-addition products cyclize to 4-aminopyridines when the reaction is run below -50-degrees-C. From reactions performed over 0-degrees-C pyrimidines arising from addition of 2 mol of nitriles are isolated. Owing to the polar conditions employed, a side metalation reaction is observed with aliphatic nitriles. On the other hand, the alpha'-addition products can be isolated in neutral conditions but they cyclize to 4-pyridinones in strong acidic media.

  DOI：

  10.1021/jo00048a043