ethyl 1-(2-ethoxy-2-oxoethyl)-2-mercapto-6-(p-methoxyphenyl)-4-methyl-1,6-dihydropyrimidine-5-carboxylate | 1449431-70-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 1-(2-ethoxy-2-oxoethyl)-2-mercapto-6-(p-methoxyphenyl)-4-methyl-1,6-dihydropyrimidine-5-carboxylate
• 英文别名: Ethyl 3-(2-ethoxy-2-oxoethyl)-4-(4-methoxyphenyl)-6-methyl-2-sulfanylidene-1,4-dihydropyrimidine-5-carboxylate
• CAS: 1449431-70-2
• 化学式: C₁₉H₂₄N₂O₅S
• 分子量: 392.476
• InChiKey: MDJVPHIGUJDDIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 1-(2-ethoxy-2-oxoethyl)-2-mercapto-6-(p-methoxyphenyl)-4-methyl-1,6-dihydropyrimidine-5-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以70%的产率得到6-(p-methoxyphenyl)-8-methyl-3-oxo-1,3,4,6-tetrahydro-2H-pyrimido[2,1-c][1,2,4]triazine-7-carbohydrazide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Some New Pyrimidine Derivatives

  摘要：

  Reaction of 2-mercaptopyrimidine 1 with ethyl chloroacetate afforded isomeric pyrimidines 2 and 3. Interaction of 3 with bifunctional nitrogen nucleophiles yielded pyrimidotriazine 5 and 7. Hydrazinolysis of 2 by hydrazine hydrate afforded hydrazinopyrimidine 8. Treatment of 8 with acetophenone gave 9. Cyclization of 9 with Vilsmeier reagent afforded the pyrazole carbaldehyde 10. Interaction of 8 with benzylidenemalononitrile and/or ethyl ethoxymethylenecyanoacetate afforded the pyrazoles 11 and 12. The reaction of 8 with p-chlorobenzaldehyde yielded 13, which was cyclized with thioglycolic acid to give thiazolidinone 14. The biological activity of selected compounds was investigated.

  DOI：

  10.3987/com-13-12663
• 作为产物：
  描述：

  氯乙酸乙酯 、 2-巯基-4-(4-甲氧基苯基)-6-甲基-1,4-二氢嘧啶-5-羧酸乙酯 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以75%的产率得到ethyl 2-[(2-ethoxy-2-oxoethyl)sulfanyl]-6-(4-methoxyphenyl)-4-methyl-1,6-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Some New Pyrimidine Derivatives

  摘要：

  Reaction of 2-mercaptopyrimidine 1 with ethyl chloroacetate afforded isomeric pyrimidines 2 and 3. Interaction of 3 with bifunctional nitrogen nucleophiles yielded pyrimidotriazine 5 and 7. Hydrazinolysis of 2 by hydrazine hydrate afforded hydrazinopyrimidine 8. Treatment of 8 with acetophenone gave 9. Cyclization of 9 with Vilsmeier reagent afforded the pyrazole carbaldehyde 10. Interaction of 8 with benzylidenemalononitrile and/or ethyl ethoxymethylenecyanoacetate afforded the pyrazoles 11 and 12. The reaction of 8 with p-chlorobenzaldehyde yielded 13, which was cyclized with thioglycolic acid to give thiazolidinone 14. The biological activity of selected compounds was investigated.

  DOI：

  10.3987/com-13-12663