methyl 2-hydroxy-6-phenylpyrimidine-4-carboxylate | 1181234-85-4

• 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: methyl 2-hydroxy-6-phenylpyrimidine-4-carboxylate
• 英文别名: methyl 2-oxo-4-phenyl-1H-pyrimidine-6-carboxylate
• CAS: 1181234-85-4
• 化学式: C₁₂H₁₀N₂O₃
• 分子量: 230.223
• InChiKey: CFPLMTDPWYMZLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-hydroxy-6-phenylpyrimidine-4-carboxylate 、 烯丙醇 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以87%的产率得到methyl 2-(allyloxy)-6-phenylpyrimidine-4-carboxylate
  参考文献：
  名称：

  SYNTHESIS AND AChE INHIBITING ACTIVITY OF 2, 4 SUBSTITUTED 6-PHENYL PYRIMIDINES

  摘要：

  Novel substituted pyrimidines were synthesized from methyl 2,4-dioxo-4-phenyl-butanoate (I-A) and urea, followed by Mitsunobu coupling of I-A with benzyl or allyl alcohol to give the corresponding 2-hydroxypyrimidine ethers in good yields. Saponification of I-A, followed by reaction with benzyl or allyl amines in the presence of TBTU yielded 2-hydroxy-6-phenyl-pyrimidine 4-carboxamides. AChE and BuChE assays revealed 2-hydroxy-6-phenyl-pyrimidine-4-carboxyallyamide as the most active compound, IC50=90 mu M, with no inhibition of BuChE.

  DOI：

  10.4067/s0717-97072012000300020
• 作为产物：
  描述：

  苯乙酮 在 硫酸 、 sodium hydride 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 4.0h， 生成 methyl 2-hydroxy-6-phenylpyrimidine-4-carboxylate
  参考文献：
  名称：

  SYNTHESIS AND AChE INHIBITING ACTIVITY OF 2, 4 SUBSTITUTED 6-PHENYL PYRIMIDINES

  摘要：

  Novel substituted pyrimidines were synthesized from methyl 2,4-dioxo-4-phenyl-butanoate (I-A) and urea, followed by Mitsunobu coupling of I-A with benzyl or allyl alcohol to give the corresponding 2-hydroxypyrimidine ethers in good yields. Saponification of I-A, followed by reaction with benzyl or allyl amines in the presence of TBTU yielded 2-hydroxy-6-phenyl-pyrimidine 4-carboxamides. AChE and BuChE assays revealed 2-hydroxy-6-phenyl-pyrimidine-4-carboxyallyamide as the most active compound, IC50=90 mu M, with no inhibition of BuChE.

  DOI：

  10.4067/s0717-97072012000300020