4-(3,3-dimethoxypropyl)-6-(4-nitrophenyl)-2-pyrazol-1-yl-1,4-dihydropyrimidine-5-carboxylic acid ethyl ester | 911857-33-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-(3,3-dimethoxypropyl)-6-(4-nitrophenyl)-2-pyrazol-1-yl-1,4-dihydropyrimidine-5-carboxylic acid ethyl ester
• 英文别名: Ethyl 4-(3,3-dimethoxypropyl)-6-(4-nitrophenyl)-2-pyrazol-1-yl-1,4-dihydropyrimidine-5-carboxylate
• CAS: 911857-33-5
• 化学式: C₂₁H₂₅N₅O₆
• 分子量: 443.459
• InChiKey: KHTYGYORXWYOJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-(3,3-dimethoxypropyl)-6-(4-nitrophenyl)-2-pyrazol-1-yl-1,4-dihydropyrimidine-5-carboxylic acid ethyl ester 在 4-二甲氨基吡啶 、 氨 、 氯化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 24.0h， 生成 2-amino-6-(3,3-dimethoxypropyl)-4-(4-nitrophenyl)-6H-pyrimidine-1,5-dicarboxylic acid 1-tert-butyl ester 5-ethyl ester
  参考文献：
  名称：

  Concise Synthesis of Guanidine-Containing Heterocycles Using the Biginelli Reaction

  摘要：

  Two general methods for the synthesis of 2-imino-5-carboxy-3,4-dihydropyrimidines were developed using the three-component Biginelli reaction. The first method utilizes pyrazole carboxamidine, a beta-ketoester, and an aldehyde in an initial Biginelli reaction. After Boc protection, these products undergo aminolysis and acidic deprotection to generate 2-imino-5-carboxy-3,4-dihydropyrimidines in a four-step sequence. The second method utilizes a triazone-protected guanidine, a beta-ketoester, and an aldehyde in a Biginelli reaction. Acidic cleavage of the triazone yields 2-imino-5-carboxy-3,4-dihydropyrimidines in a two-step sequence. We also describe the further elaboration of several of these products using a tethered Biginelli reaction to give triazaacenaphthalene structures similar to those found in crambescidin and batzelladine alkaloids.

  DOI：

  10.1021/jo061199m
• 作为产物：
  描述：

  对硝基苯甲酰醋酸乙酯 、 4,4-二甲氧基丁醛 、 1H-吡唑-1-甲脒盐酸盐 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以73%的产率得到4-(3,3-dimethoxypropyl)-6-(4-nitrophenyl)-2-pyrazol-1-yl-1,4-dihydropyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Concise Synthesis of Guanidine-Containing Heterocycles Using the Biginelli Reaction

  摘要：

  Two general methods for the synthesis of 2-imino-5-carboxy-3,4-dihydropyrimidines were developed using the three-component Biginelli reaction. The first method utilizes pyrazole carboxamidine, a beta-ketoester, and an aldehyde in an initial Biginelli reaction. After Boc protection, these products undergo aminolysis and acidic deprotection to generate 2-imino-5-carboxy-3,4-dihydropyrimidines in a four-step sequence. The second method utilizes a triazone-protected guanidine, a beta-ketoester, and an aldehyde in a Biginelli reaction. Acidic cleavage of the triazone yields 2-imino-5-carboxy-3,4-dihydropyrimidines in a two-step sequence. We also describe the further elaboration of several of these products using a tethered Biginelli reaction to give triazaacenaphthalene structures similar to those found in crambescidin and batzelladine alkaloids.

  DOI：

  10.1021/jo061199m

文献信息

• Concise Synthesis of Guanidine-Containing Heterocycles Using the Biginelli Reaction
  作者：Bradley L. Nilsson、Larry E. Overman

  DOI：10.1021/jo061199m

  日期：2006.9.1

  Two general methods for the synthesis of 2-imino-5-carboxy-3,4-dihydropyrimidines were developed using the three-component Biginelli reaction. The first method utilizes pyrazole carboxamidine, a beta-ketoester, and an aldehyde in an initial Biginelli reaction. After Boc protection, these products undergo aminolysis and acidic deprotection to generate 2-imino-5-carboxy-3,4-dihydropyrimidines in a four-step sequence. The second method utilizes a triazone-protected guanidine, a beta-ketoester, and an aldehyde in a Biginelli reaction. Acidic cleavage of the triazone yields 2-imino-5-carboxy-3,4-dihydropyrimidines in a two-step sequence. We also describe the further elaboration of several of these products using a tethered Biginelli reaction to give triazaacenaphthalene structures similar to those found in crambescidin and batzelladine alkaloids.