5-ethoxycarbonyl-6-ethyl-4-(4-methoxyphenyl)-3,4-dihydropyrimidin-2(1H)-one

• 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: 5-ethoxycarbonyl-6-ethyl-4-(4-methoxyphenyl)-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: ethyl 6-ethyl-4-(4-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₆H₂₀N₂O₄
• 分子量: 304.346
• InChiKey: QFUYICCSVPZJCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-ethoxycarbonyl-6-ethyl-4-(4-methoxyphenyl)-3,4-dihydropyrimidin-2(1H)-one 在 硝酸 、 caesium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.08h， 生成
  参考文献：
  名称：

  Synthesis of dihydropyrimidine α,γ-diketobutanoic acid derivatives targeting HIV integrase

  摘要：

  The synthesis and antiviral evaluation of a series of dihydropyrimidinone and thiopyrimidine derivatives bearing aryl alpha, gamma-diketobutanoic acid moiety are described using the Biginelli multicomponent reaction as key step. The most active among 20 synthesized novel compounds were 4c, 4d and 5b, which possess nanomolar HIV-1 integrase (IN) stand transfer (ST) inhibition activities. In order to understand their mode of interactions within the IN active site, we docked all the compounds into the previously reported X-ray crystal structure of IN. We observed that compounds 4c, 4d and 5b occupied an area close to the two catalytic Mg2+ ions surrounded by their chelating triad (E221, D128 and D185), DC16, Y212 and the beta-diketo acid moiety of 4c, 4d and 5b chelating Mg2+. As those compounds lack anti-HIV activities in cell, their prodrugs were synthetized. The prodrug 4c' exhibited an anti-HIV activity of 0.19 mu M in primary human lymphocytes with some cytotoxicity. All together, these results indicate that the new analogs potentially interact within the catalytic site with highly conserved residues important for IN catalytic activity. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.015
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 尿素 、 丙酰乙酸乙酯 在 zinc(II) oxide 作用下， 以 水 为溶剂， 反应 0.42h， 以86%的产率得到5-ethoxycarbonyl-6-ethyl-4-(4-methoxyphenyl)-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  ZnO 纳米颗粒作为一种高效、多相、可重复使用且环保的催化剂，用于在水中一锅法、三组分合成 3,4-二氢嘧啶-2(1H)-(硫)酮衍生物

  摘要：

  摘要 报告了一种极其有效的异质方案，用于在作为绿色溶剂的水中存在 ZnO 纳米颗粒的情况下，一锅三组分合成一系列二氢嘧啶酮 (DHPM)。ZnO 纳米粒子表现出优异的催化活性，并且所提出的方法能够在短时间内以良好的产率（65-94%）提供所需的产物。反应过程结束后，ZnO 纳米颗粒可以回收再利用，而不会明显降低活性，这使得这种环保工艺具有成本效益。图形概要

  DOI：

  10.1080/00397911.2014.987350

文献信息

• ZnO Nanoparticles as an Efficient, Heterogeneous, Reusable, and Ecofriendly Catalyst for One-Pot, Three-Component Synthesis of 3,4-Dihydropyrimidin-2(1<i>H</i>)-(thio)one Derivatives in Water
  作者：Akbar Hassanpour、Rahim Hosseinzadeh Khanmiri、Jafar Abolhasani

  DOI：10.1080/00397911.2014.987350

  日期：2015.3.19

  Abstract An extremely efficient heterogeneous protocol is reported for the one-pot, three-component synthesis of a series of dihydropyrimidinones (DHPMs) in the presence of ZnO nanoparticles in water as a green solvent. The ZnO nanoparticles exhibited excellent catalytic activity and the proposed methodology is capable of providing the desired products in good yields (65–94%) within short reaction

  摘要 报告了一种极其有效的异质方案，用于在作为绿色溶剂的水中存在 ZnO 纳米颗粒的情况下，一锅三组分合成一系列二氢嘧啶酮 (DHPM)。ZnO 纳米粒子表现出优异的催化活性，并且所提出的方法能够在短时间内以良好的产率（65-94%）提供所需的产物。反应过程结束后，ZnO 纳米颗粒可以回收再利用，而不会明显降低活性，这使得这种环保工艺具有成本效益。图形概要
• Cu-Mn Bimetallic Complex Immobilized on Magnetic NPs as an Efficient Catalyst for Domino One-Pot Preparation of Benzimidazole and Biginelli Reactions from Alcohols
  作者：Mohammad Ali Nasseri、Zinat Rezazadeh、Milad Kazemnejadi、Ali Allahresani

  DOI：10.1007/s10562-020-03371-0

  日期：2021.4

  An efficient magnetically recyclable bimetallic catalyst by anchoring copper and manganese complexes on the Fe3O4 NPs was prepared and named as Fe3O4@Cu-Mn. It was founded as a powerful catalyst for the domino one-pot oxidative benzimidazole and Biginelli reactions from benzyl alcohols as a green protocol in the presence of air, under solvent-free and mild conditions. Fe3O4@Cu-Mn NPs were well characterized

  通过将铜和锰配合物锚定在 Fe3O4 NPs 上制备了一种高效的磁性可回收双金属催化剂，并将其命名为 Fe3O4@Cu-Mn。它被认为是一种强大的催化剂，用于多米诺单锅氧化苯并咪唑和苯甲醇的 Biginelli 反应，作为一种绿色方案，在空气存在下，在无溶剂和温和条件下。Fe3O4@Cu-Mn NPs 通过 FT-IR、XRD、FE-SEM、TEM、VSM、TGA、EDX、DLS 和 ICP 分析得到了很好的表征。研究了多米诺一锅苯并咪唑和Biginelli反应的时间、温度、催化剂用量和溶剂等参数的最佳范围，以寻找最佳反应条件。该催化剂与多种苯甲醇相容，为所有衍生物提供了具有良好到高产率的有利产品。纳米催化剂的热过滤和汞中毒测试揭示了催化剂的稳定性、低金属浸出和多相性质。为了证明催化体系的协同和协同作用，制备了催化剂的各种同系物，然后分别应用于模型反应。最后，催化剂可以简单地从反应混合物中
• Synthesis of 3,4-Dihydropyrimidinones via Phase Transfer Catalysis
  作者：Younes Moussaoui、Ridha Ben Salem

  DOI：10.1002/jhet.830

  日期：2013.7

  4‐Dihydropyrimidinone and derivatives were synthesized by the one‐pot, three‐component Biginelli condensation of an aldehyde, β‐dicarbonyl compound and urea. Synthesis was carried out in aqueous sodium hydroxide using Aliquat‐336 as a phase transfer agent. Compared to the classical Biginelli reaction conditions, this new method cousistently has the advantage of excellent yields and short reaction time

  通过一锅，三组分醛，β-二羰基化合物和尿素的Biginelli缩合反应合成了3,4-二氢嘧啶酮及其衍生物。使用Aliquat-336作为相转移剂，在氢氧化钠水溶液中进行合成。与经典的Biginelli反应条件相比，该新方法始终具有高收率和短反应时间的优点。
• Indium(III) Chloride-Catalyzed One-Pot Synthesis of Dihydropyrimidinones by a Three-Component Coupling of 1,3-Dicarbonyl Compounds, Aldehydes, and Urea: An Improved Procedure for the Biginelli Reaction
  作者：Brindaban C. Ranu、Alakananda Hajra、Umasish Jana

  DOI：10.1021/jo000711f

  日期：2000.9.1
• Unprecedented Catalytic Three Component One-Pot Condensation Reaction:  An Efficient Synthesis of 5-Alkoxycarbonyl- 4-aryl-3,4-dihydropyrimidin-2(1H)-ones
  作者：Essa H. Hu、Daniel R. Sidler、Ulf-H. Dolling

  DOI：10.1021/jo970846u

  日期：1998.5.1