6-(3,3-dimethoxypropyl)-4-(4-nitrophenyl)-2-pyrazol-1-yl-6H-pyrimidine-1,5-dicarboxylic acid 1-tert-butyl ester 5-ethyl ester | 911857-38-0

• 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: 6-(3,3-dimethoxypropyl)-4-(4-nitrophenyl)-2-pyrazol-1-yl-6H-pyrimidine-1,5-dicarboxylic acid 1-tert-butyl ester 5-ethyl ester
• 英文别名: 3-O-tert-butyl 5-O-ethyl 4-(3,3-dimethoxypropyl)-6-(4-nitrophenyl)-2-pyrazol-1-yl-4H-pyrimidine-3,5-dicarboxylate
• CAS: 911857-38-0
• 化学式: C₂₆H₃₃N₅O₈
• 分子量: 543.577
• InChiKey: DYIGKCHNALQVDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6-(3,3-dimethoxypropyl)-4-(4-nitrophenyl)-2-pyrazol-1-yl-6H-pyrimidine-1,5-dicarboxylic acid 1-tert-butyl ester 5-ethyl ester 在 氨 、 乙酸吗啉 、 氯化铵 、 sodium sulfate 作用下， 以 四氢呋喃 、 二氯甲烷 、 2,2,2-三氟乙醇 为溶剂， 反应 85.0h， 生成 5-O-benzyl 11-O-ethyl (1R,4R)-6-methyl-10-(4-nitrophenyl)-7,9-diaza-12-azoniatricyclo[6.3.1.04,12]dodeca-5,8(12),10-triene-5,11-dicarboxylate;2,2,2-trifluoroacetate
  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：

  4,4-二甲氧基丁醛 在 4-二甲氨基吡啶 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 60.0h， 生成 6-(3,3-dimethoxypropyl)-4-(4-nitrophenyl)-2-pyrazol-1-yl-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

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.