ethyl 4-(4-(methoxycarbonyl)phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 301320-10-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 4-(4-(methoxycarbonyl)phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: 5-ethoxycarbonyl-4-[(4-methoxycarbonyl)phenyl]-6-methyl-3,4-dihydropyrimidin-2(1H)-one；5-ethoxycarbonyl-4-[4-(methoxycarbonyl)phenyl]-6-methyl-3,4-dihydropyrimidin-2(1H)-one；Ethyl 4-[4-(methoxycarbonyl)phenyl]-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 4-(4-methoxycarbonylphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 301320-10-5
• 化学式: C₁₆H₁₈N₂O₅
• 分子量: 318.329
• InChiKey: ILZNSWYLTUXJSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-(4-(methoxycarbonyl)phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 17.0h， 生成 5-ethoxycarbonyl-6-methyl-4-[4-(2-(3-nitrobenzylidene)hydrazinecarbonyl)phenyl]-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  含有腙部分的 3,4-二氢嘧啶-2(1H)-one 衍生物的合成和抗菌活性

  摘要：

  摘要 合成了标题化合物，并通过IR、1H NMR、13C NMR和HRMS数据进行了表征。评价了它们对细菌菌株大肠杆菌和真菌菌株黑曲霉的抗微生物活性。

  DOI：

  10.1515/hc-2017-0227
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 尿素 、 对甲酰基苯甲酸甲酯 在 copper doped mesoporous silica MCM-41 supported dual acidic ionic liquid-HSO₄ 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以99%的产率得到ethyl 4-(4-(methoxycarbonyl)phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  铜掺杂介孔二氧化硅负载的双酸性离子液体可作为Biginelli反应的高效协同重用催化剂

  摘要：

  制备了一系列掺杂有铜物质的MCM-41负载型官能化离子液体，对其进行了表征和评估，作为Biginelli反应的催化剂。这些负载型离子液体大多数在反应中表现良好，尤其是多官能铜配位的MCM-41负载型多相催化剂（0.5）IL-TiCl 5 @ [受电子邮件保护]（15）和（0.5）IL-HSO 4 @ [受电子邮件保护] ]（15）。催化试验表明，（0.5）IL-HSO 4@ [受电子邮件保护]（15）是Biginelli反应中最好的和强大的催化剂，用于制备3,4-二氢嘧啶酮，产率高至优异。通过过滤可以很容易地将催化剂从反应混合物中分离出来，并在六个连续的循环中重复使用，而不会明显降低催化活性。

  DOI：

  10.1016/j.molliq.2018.04.121

文献信息

• Brønsted Acidic Ionic Liquid–Catalyzed One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones and Thiones Under Solvent-Free Conditions
  作者：Abdol R. Hajipour、Leila Khazdooz、Amin Zarei

  DOI：10.1080/00397911.2010.501471

  日期：2011.8

  Abstract An efficient and convenient procedure for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and thiones by condensation of ethylacetoacetate, aldehydes, and urea or thiourea in the presence of methylimidazolium hydrogensulfate is described. Aromatic and aliphatic aldehydes reacted easily to afford the corresponding 3,4-dihydropyrimidin-2(1H)-ones and thiones under solvent-free conditions. The use

  摘要 描述了在甲基咪唑鎓硫酸氢盐存在下，通过乙酰乙酸乙酯、醛和尿素或硫脲的缩合反应合成 3,4-二氢嘧啶-2(1H)-酮和硫酮的一种高效便捷的方法。芳香醛和脂肪醛在无溶剂条件下很容易反应得到相应的 3,4-二氢嘧啶-2(1H)-酮和硫酮。使用无毒且廉价的材料、简单干净的后处理、较短的反应时间和良好的收率是该方法的优点。
• A microwave-assisted, copper-catalyzed three-component synthesis of dihydropyrimidinones under mild conditions
  作者：Kalyan Kumar Pasunooti、Hua Chai、Chantel Nixon Jensen、Bala Kishan Gorityala、Siming Wang、Xue-Wei Liu

  DOI：10.1016/j.tetlet.2010.10.150

  日期：2011.1

  The synthesis of dihydropyrimidinones via a clean multi-component Biginelli reaction under microwave irradiation is reported. The copper-catalyzed process proved to be simple, efficient, economical, and environmentally friendly. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis, Crystal Structure, and Spectroscopic Properties of 5-Ethoxycarbonyl-4-[(4-methoxy-carbonyl)phenyl] -6-methyl-3,4-dihydropyrimidin2(1H)-ones
  作者：H.-N. Peng、D.-G. Zheng、X.-H. Zeng、J.-R. Hu、H.-D. Ye

  DOI：10.1080/15421406.2014.963211

  日期：2015.3.4

  The title compound, 5-ethoxycarbonyl-4-[(4-methoxycarbonyl)phenyl]-6-methyl-3,4-dihydropyrimidin-2(1H)-ones (1), was synthesized from the one-pot, three-component condensation reactions and characterized by FTIR, H-1 NMR, HRMS, and single crystal X-ray diffraction. The compound (1) crystallizes in a triclinic system, space group P-1 with a = 6.1874(12), b = 7.5715(15), c = 17.369(4)angstrom, alpha = 80.24(3), beta = 81.15(3), gamma = 76.93(3)degrees, and Z = 2. The molecules are linked by hydrogen bonds N-H center dot center dot center dot O and C-H center dot center dot center dot O to generate a 2D network. In addition, UV-visible and fluorescence spectral measurements prove that it shows positive solvatochromic effect as the solvent polarity was increased.
• Copper-doped mesoporous silica supported dual acidic ionic liquid as an efficient and cooperative reusability catalyst for Biginelli reaction
  作者：Nan Yao、Ming Lu、Xiao Bing Liu、Jin Tan、Yu Lin Hu

  DOI：10.1016/j.molliq.2018.04.121

  日期：2018.7

  A series of MCM-41 supported functionalized ionic liquids doped with copper species were prepared, characterized and evaluated as catalysts in the Biginelli reaction. Most of these supported ionic liquids perform well in the reaction, especially the multifunctional copper coordinated MCM-41 supported heterogeneous catalysts (0.5)IL-TiCl5@[email protected](15) and (0.5)IL-HSO4@[email protected](15)

  制备了一系列掺杂有铜物质的MCM-41负载型官能化离子液体，对其进行了表征和评估，作为Biginelli反应的催化剂。这些负载型离子液体大多数在反应中表现良好，尤其是多官能铜配位的MCM-41负载型多相催化剂（0.5）IL-TiCl 5 @ [受电子邮件保护]（15）和（0.5）IL-HSO 4 @ [受电子邮件保护] ]（15）。催化试验表明，（0.5）IL-HSO 4@ [受电子邮件保护]（15）是Biginelli反应中最好的和强大的催化剂，用于制备3,4-二氢嘧啶酮，产率高至优异。通过过滤可以很容易地将催化剂从反应混合物中分离出来，并在六个连续的循环中重复使用，而不会明显降低催化活性。
• Synthesis and antimicrobial activity of 3,4-dihydropyrimidin-2(1<i>H</i>)-one derivatives containing a hydrazone moiety
  作者：Hua-Nan Peng、Li-Min Ye、Ming Zhang、Yan-Chun Yang、Jie Zheng

  DOI：10.1515/hc-2017-0227

  日期：2018.4.25

  Abstract The title compounds were synthesized and characterized by IR, 1H NMR, 13C NMR and HRMS data. Their antimicrobial activities against bacterial strains Escherichia coli and fungal strains Aspergillus niger were evaluated.

  摘要 合成了标题化合物，并通过IR、1H NMR、13C NMR和HRMS数据进行了表征。评价了它们对细菌菌株大肠杆菌和真菌菌株黑曲霉的抗微生物活性。