methyl 4-(4'-(dimethylamino)phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

• 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: methyl 4-(4'-(dimethylamino)phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: 4-(4-N,N-dimethylaminophenyl)-5-methoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one；5-methoxycarbonyl-4-(4-dimethylaminophenyl)-6-methyl-3,4-dihydropyrimidin-2-(1H)-one；5-methoxycarbonyl-4-(4-dimethylaminophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one；Methyl 4-[4-(dimethylamino)phenyl]-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；methyl 4-[4-(dimethylamino)phenyl]-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₅H₁₉N₃O₃
• 分子量: 289.334
• InChiKey: JKXZZCNQWHPQPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 methyl 4-(4'-(dimethylamino)phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 吡啶 作用下， 以 苯 为溶剂， 生成
  参考文献：
  名称：

  QSAR analysis of 2-oxo-1,2,3,4-tetrahydropyrimidine analogues of antibacterials

  摘要：

  对两组2-氧代-1,2,3,4-四氢嘧啶类似物进行QSAR分析，以研究它们的理化参数与抗菌活性之间的关系。生成了具有预测性和统计显著性的模型。基于这些模型，合成了新化合物，进行了结构表征，并评估了它们的抗菌潜力。新合成化合物的潜力高于训练集中的化合物，与QSAR预测结果密切一致。

  DOI：

  10.1135/cccc2009054
• 作为产物：
  描述：

  乙酰乙酸甲酯 、 对二甲氨基苯甲醛 、 尿素 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以88%的产率得到methyl 4-(4'-(dimethylamino)phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  A Remarkable Rate Acceleration of the One-Pot Three-Component Cyclo­condensation Reaction at Room Temperature: An Expedient Synthesis of ­Mitotic Kinesin Eg5 Inhibitor Monastrol

  摘要：

  本文描述了一种通用且实用的合成3,4-二氢嘧啶-2(1H)-酮的方法，通过在室温下使用三甲基硅基三氟醋酸酯（1 mol%）介导的环状缩合反应将醛、β-酮酯和脲一次性缩合反应，反应时间为15分钟。与经典的Biginelli反应条件相比，产率显著提高。已经成功合成了有丝分裂动力蛋白Eg5抑制剂monastrol，分离产率高达95%。

  DOI：

  10.1055/s-2004-815416

文献信息

• The development of an ecofriendly procedure for alkaline metal (II) sulfate promoted synthesis of<i>N</i>,<i>N</i>′-dimethyl substituted (unsubstituted)-4-aryl-3,4-dihydropyrimidones (thiones) and corresponding bis-analogues in aqueous medium: Evaluation by green chemistry metrics
  作者：Chhanda Mukhopadhyay、Arup Datta

  DOI：10.1002/jhet.283

  日期：——

  Different alkaline metal (II) sulfates were used as catalysts for the N,N′-dimethyl substituted as well as unsubstituted 4-aryl-3,4-dihydropyrimidones (thiones) and their corresponding bis-analogues in aqueous medium. Among the various salts, MgSO4·7H2O (Epsom salt) proved to be the best catalyst giving the desired products in good to excellent yields. This catalyst enables the construction of a series

  在水性介质中，将不同的碱金属（II）硫酸盐用作N，N'-二甲基取代的和未取代的4-芳基-3,4-二氢嘧啶酮（硫酮）及其相应的双类似物的催化剂。在各种盐中，MgSO 4 ·7H 2 O（泻盐）被证明是最好的催化剂，以良好至极佳的收率提供了所需的产物。该催化剂能够构建一系列化合物库，特别是对于N，N'-二甲基取代的DHPM，其合成在文献中非常罕见。通过绿色化学的应用评估了在多种底物上的反应指标和非常好的相关性。J.杂环化​​学.2010。
• A practical and green approach towards synthesis of dihydropyrimidinones: Using heteropoly acids as efficient catalysts
  作者：Ezzat Rafiee、Hadi Jafari

  DOI：10.1016/j.bmcl.2006.01.087

  日期：2006.5

  A simple and green chemistry procedure for the synthesis of dihydropyrimidinones using heteropoly acid mediated cyclocondensation reaction is described. This method provides an efficient and much improved modification of the original Biginelli reaction reported in 1893, in terms of high yields, and short reaction times. It has the ability to allow a wide variety of substitutions in all three components

  描述了一种使用杂多酸介导的环缩合反应合成二氢嘧啶酮的简单而绿色的化学方法。就高收率和较短的反应时间而言，该方法提供了对1893年报道的原始Biginelli反应的有效且大大改进的修饰。它具有允许在所有三个组件中进行多种替换的能力。
• Three Component Reaction: An Efficient Synthesis of 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones and Thiones Using Heterogeneous Catalyst
  作者：Vinod Tribhuvannathji Kamble、Dnyanoba Baburao Muley、Sandeep Tukaram Atkore、Sharad Digambarrao Dakore

  DOI：10.1002/cjoc.201090084

  日期：2010.1

  supported on silica gel (HBF4‐SiO2) catalyzes efficiently the three component condensation of an aldehyde, a 1,3‐dicarbonyl compound and urea or thiourea to afford the corresponding 3,4‐dihydropyrimidin‐ 2(1H)‐ones and thiones in high yields. The ambient conditions, fast reaction rates, and excellent product yields are the important characteristics of this reaction.

  负载在硅胶上的氟硼酸（HBF 4 -SiO 2）有效催化醛，1,3-二羰基化合物与尿素或硫脲的三组分缩合，从而提供相应的3,4-二氢嘧啶-2（1 H）-和高产的硫酮。环境条件，快速的反应速率和优异的产物收率是该反应的重要特征。
• A Remarkable Rate Acceleration of the One-Pot Three-Component Cyclo­condensation Reaction at Room Temperature: An Expedient Synthesis of ­Mitotic Kinesin Eg5 Inhibitor Monastrol
  作者：D. Subhas Bose、Racherla Kishore Kumar、Liyakat Fatima

  DOI：10.1055/s-2004-815416

  日期：——

  A general and practical route for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones by a one-pot condensation of ­aldehydes, β-ketoesters, and urea is described using trimethylsilyltriflate (1 mol%)-mediated cyclocondensation reaction at room temperature within 15 minutes. Yields are significantly higher than utilizing classical Biginelli reaction conditions. Synthesis of mitotic Kinesin Eg5 inhibitor monastrol has been achieved in 95% isolated yield.

  本文描述了一种通用且实用的合成3,4-二氢嘧啶-2(1H)-酮的方法，通过在室温下使用三甲基硅基三氟醋酸酯（1 mol%）介导的环状缩合反应将醛、β-酮酯和脲一次性缩合反应，反应时间为15分钟。与经典的Biginelli反应条件相比，产率显著提高。已经成功合成了有丝分裂动力蛋白Eg5抑制剂monastrol，分离产率高达95%。
• Green Chemistry Approaches to the Synthesis of 5-Alkoxycarbonyl-4-aryl-3,4- dihydropyrimidin-2(1<i>H</i>)-ones by a Three-Component Coupling of One-Pot Condensation Reaction:  Comparison of Ethanol, Water, and Solvent-free Conditions
  作者：D. Subhas Bose、Liyakat Fatima、Hari Babu Mereyala

  DOI：10.1021/jo0205199

  日期：2003.1.1

  A general and practical green chemistry route to the Biginelli cyclocondensation reaction using cerium(III) chloride as the catalyst (25% mol) is described under three different sets of reaction conditions. This method provides an efficient and much improved modification of original Biginelli reaction reported in 1893, in terms of high yields, short reaction times, and simple work-up procedure, and

  在三组不同的反应条件下，描述了使用氯化铈（III）作为催化剂（25％摩尔）进行Biginelli环缩合反应的一般和实用的绿色化学路线。该方法在高收率，较短的反应时间和简单的后处理方面，提供了有效且大大改进了1893年报道的Biginelli反应的修饰，并且能够耐受所有这三种组分的多种取代，这是现有程序所缺乏的。