5-ethoxycarbonyl-6-methyl-3-benzoyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one | 526224-44-2

• 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-methyl-3-benzoyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: Ethyl 3-benzoyl-6-methyl-2-oxo-4-phenyl-1,4-dihydropyrimidine-5-carboxylate
• CAS: 526224-44-2
• 化学式: C₂₁H₂₀N₂O₄
• 分子量: 364.401
• InChiKey: GNOMCEUHZWAVCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 5-ethoxycarbonyl-6-methyl-3-benzoyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.25h， 生成 5-ethoxycarbonyl-6-methyl-1,3-dibenzoyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  High-Throughput Synthesis of N3-Acylated Dihydropyrimidines Combining Microwave-Assisted Synthesis and Scavenging Techniques

  摘要：

  The solution-phase synthesis of N3-acylated dihydropyrimidines was achieved utilizing microwave flash heating both in the synthesis (acylation) and purification (scavenging) steps. Quenching times for excess anhydrides using polystyrene or silica-supported diamine sequestration reagents were reduced from several hours to minutes utilizing microwave irradiation. The use of water as sequestration agent, coupled with an efficient solid-phase extraction workup technique allowed the rapid generation of a 20-member library of N3-acylated dihydropyrimidines.

  DOI：

  10.1021/ol034085v
• 作为产物：
  描述：

  6-甲基-2-氧代-4-苯基-1,2,3,4-四氢-5-嘧啶羧酸乙酯 在 三甲基氯硅烷 、 三乙胺 、 potassium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 5-ethoxycarbonyl-6-methyl-3-benzoyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  Efficient and Convenient Synthesis of N3-(Acyloxymethyl)dihydropyrimidinones by a One-Pot Two-Step Method

  摘要：

  通过3,4-二氢嘧啶酮与多聚甲醛和取代苯甲酸/乙酸的反应，通过一锅两步反应，可以以良好的收率区域选择性地获得用N3-(乙酰氧基甲基)和(芳酰氧基甲基)基团修饰的3,4-二氢嘧啶酮。在三甲基氯硅烷存在下的策略。该方法的优点是流程简单、产物区域选择性高、反应时间短、反应条件温和。另外，该方法直接使用酸作为酰化试剂，不需要酸酐或酰氯。

  DOI：

  10.2174/157017811795038458

文献信息

• A mild and practical method for the regioselective synthesis of N-acylated 3,4-dihydropyrimidin-2-ones. New acyl transfer reagents
  作者：Kamaljit Singh、Sukhdeep Singh

  DOI：10.1016/j.tetlet.2006.09.039

  日期：2006.11

  The treatment of 3,4-dihydropyrimidin-2-ones with n-BuLi at −78 °C, followed by quenching with various electrophiles furnished N3-substituted derivatives, regioselectively. Further, N1,N3-diacyl derivatives were found to transfer N1-acyl groups to nucleophilic sites.

  在-78°C下用正丁基锂处理3,4-二氢嘧啶-2-酮，然后用区域选择性选择性提供的N 3取代衍生物的各种亲电试剂淬灭。此外，发现N 1，N 3-二酰基衍生物将N 1-酰基转移至亲核位点。
• A Domino Desulfitative Coupling/Acylation/Hydration Process Cocatalyzed by Copper(I) and Palladium(II): Synthesis of Highly Substituted and Functionalized Pyrimidines
  作者：Zheng-Jun Quan、Wang-Hua Hu、Xiao-Dong Jia、Zhang Zhang、Yu-Xia Da、Xi-Cun Wang

  DOI：10.1002/adsc.201200402

  日期：2012.11.12

  A domino desulfitative coupling/acylation/hydration process to synthesize C-2-(2-oxo-2-phenylethylidene)- and N-3-carbonyl-substituted pyrimidines by unprecedented CC and CN cross-coupling reactions is described. This methodology couples 3,4-dihydropyrimidine-2-thiones and alkynes under modified Liebeskind–Srogl conditions using palladium acetate and copper(I) carboxylate. Remarkably the copper(I)

  描述了通过空前的CC和CN交叉偶联反应合成C-2-（2-氧代-2-苯基亚乙基）-和N-3-羰基取代的嘧啶的多米诺脱硫偶联/酰化/水合方法。这种方法在改良的Liebeskind-Srogl条件下使用乙酸钯和羧酸铜（I）偶联3,4-二氢嘧啶-2-硫酮和炔烃。值得注意的是，羧酸铜（I）同时在反应中充当脱硫剂和酰化剂。
• N1,N3-Diacyl-3,4-dihydropyrimidin-2(1H)-ones: neutral acyl group transfer reagents
  作者：Kamaljit Singh、Kawaljit Singh

  DOI：10.1016/j.tet.2009.10.037

  日期：2009.12

  Readily available N1,N3-diacyl-3,4-dihydropyrimidin-2(1H)-ones efficiently acylate ammonia, primary and secondary amines to furnish primary, secondary and tertiary amides in good to excellent yields. The wide applicability of the procedure is demonstrated by running the reactions in a neutral medium, easy isolation of products, recycling of the innocuous by-product and chemoselectivity of the transformation

  易于获得的N 1，N 3-二酰基3,4-二氢嘧啶-2（1 H）-一有效地酰化氨，伯胺和仲胺，从而以良好或优异的收率提供伯，仲和叔酰胺。通过在中性介质中进行反应，易于分离产物，回收无害副产物和进行转化的化学选择性，证明了该方法的广泛适用性。
• QSAR analysis of 2-oxo-1,2,3,4-tetrahydropyrimidine analogues of antibacterials
  作者：Ramesh L. Sawant、Manish S. Bhatia

  DOI：10.1135/cccc2009054

  日期：——

  QSAR analysis of two sets of analogues of 2-oxo-1,2,3,4-tetrahydropyrimidine was performed to investigate the relationship between their physicochemical parameters and antibacterial activity. Predictive and statistically significant models were generated. On the basis of these models new compounds were synthesized, structurally characterized and evaluated for their antibacterial potential. The potential of newly synthesized compounds was higher than the training set of compounds, in close agreement with QSAR prediction.

  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。