1,2,3,4-tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-1-(2-propenyl)-5-pyrimidinecarboxylic acid 1-methylethyl ester | 123505-60-2

• 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: 1,2,3,4-tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-1-(2-propenyl)-5-pyrimidinecarboxylic acid 1-methylethyl ester
• 英文别名: Propan-2-yl 4-methyl-6-(3-nitrophenyl)-2-oxo-3-prop-2-enyl-1,6-dihydropyrimidine-5-carboxylate
• CAS: 123505-60-2
• 化学式: C₁₈H₂₁N₃O₅
• 分子量: 359.382
• InChiKey: NFHHEGCOPKBSLY-UHFFFAOYSA-N

物化性质

• 沸点：
  541.3±50.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  戊酸酐 、 1,2,3,4-tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-1-(2-propenyl)-5-pyrimidinecarboxylic acid 1-methylethyl ester 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 propan-2-yl 6-methyl-4-(3-nitrophenyl)-2-oxo-3-pentanoyl-1-prop-2-enyl-4H-pyrimidine-5-carboxylate
  参考文献：
  名称：

  High-Throughput Synthesis of N3-Acylated Dihydropyrimidines Combining Microwave-Assisted Synthesis and Scavenging Techniques

  摘要：

  The solution-phase synthesis of N3-acylated dihydropyrimidines was achieved utilizing microwave flash heating both in the synthesis (acylation) and purification (scavenging) steps. Quenching times for excess anhydrides using polystyrene or silica-supported diamine sequestration reagents were reduced from several hours to minutes utilizing microwave irradiation. The use of water as sequestration agent, coupled with an efficient solid-phase extraction workup technique allowed the rapid generation of a 20-member library of N3-acylated dihydropyrimidines.

  DOI：

  10.1021/ol034085v
• 作为产物：
  描述：

  1,4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-1-(2-propenyl)-5-pyrimidinecarboxylic acid 1-methylethyl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以61 mg的产率得到1,2,3,4-tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-1-(2-propenyl)-5-pyrimidinecarboxylic acid 1-methylethyl ester
  参考文献：
  名称：

  Substituted 1,4-dihydropyrimidines. 3. Synthesis of selectively functionalized 2-hetero-1,4-dihydropyrimidines

  摘要：

  DOI：

  10.1021/jo00286a020

文献信息

• High-Throughput Synthesis of <i>N</i>3-Acylated Dihydropyrimidines Combining Microwave-Assisted Synthesis and Scavenging Techniques
  作者：Doris Dallinger、Nikolay Yu. Gorobets、C. Oliver Kappe

  DOI：10.1021/ol034085v

  日期：2003.4.1

  The solution-phase synthesis of N3-acylated dihydropyrimidines was achieved utilizing microwave flash heating both in the synthesis (acylation) and purification (scavenging) steps. Quenching times for excess anhydrides using polystyrene or silica-supported diamine sequestration reagents were reduced from several hours to minutes utilizing microwave irradiation. The use of water as sequestration agent, coupled with an efficient solid-phase extraction workup technique allowed the rapid generation of a 20-member library of N3-acylated dihydropyrimidines.
• Substituted 1,4-dihydropyrimidines. 3. Synthesis of selectively functionalized 2-hetero-1,4-dihydropyrimidines
  作者：Karnail S. Atwal、George C. Rovnyak、Brian C. O'Reilly、Joseph Schwartz

  DOI：10.1021/jo00286a020

  日期：1989.12