ethyl 4-benzyl-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-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: ethyl 4-benzyl-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 英文别名: 4-benzyl-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester；4-Benzyl-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidin-5-carbonsaeure-aethylester
• 化学式: C₁₅H₁₈N₂O₃
• 分子量: 274.32
• InChiKey: LLTQNXREPMMKBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-benzyl-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate 在 硝酸 作用下， 反应 0.58h， 以92%的产率得到ethyl 4-benzyl-6-methyl-2-oxo-1H-pyrimidine-5-carboxylate
  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：

  苯乙醛 、 乙酰乙酸乙酯 、 尿素 在 yttria-zirconia-based Lewis acid catalyst 作用下， 以 水 、 乙腈 为溶剂， 反应 10.0h， 以86%的产率得到ethyl 4-benzyl-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
  参考文献：
  名称：

  Biginelli 反应的氧化钇-氧化锆基路易斯酸催化：3,4-二氢嘧啶-2-(1H)-酮的高效一锅法合成

  摘要：

  摘要 氧化钇-氧化锆基路易斯酸在乙腈回流中高效催化醛、β-酮酯和尿素或硫脲的三组分环缩合反应，以高产率制备相应的二氢嘧啶酮。

  DOI：

  10.1080/00397910802519174

文献信息

• Samarium Triflate–Catalyzed Biginelli Condensation: An Improved Method for the Synthesis of 3,4-Dihydropyrimidin-2(<i>1H</i>)-ones
  作者：A. Venkat Narsaiah、A. Ramesh Reddy、J. S. Yadav

  DOI：10.1080/00397911.2010.515355

  日期：2011.9.15

  Abstract A simple and efficient method for multicomponant synthesis of 3,4-dihydropyrimidinones has been reported. All the reactions were carried out using samarium triflate as catalyst (10 mol%) at acetonitrile reflux. This procedure is applicable to a variety of substrates such as aliphatic, aromatic, and heterocyclic aldehydes.

  摘要 报道了一种简单有效的多组分合成 3,4-二氢嘧啶酮的方法。所有反应均使用三氟甲磺酸钐作为催化剂（10 mol%）在乙腈回流下进行。此程序适用于各种底物，如脂肪族、芳香族和杂环醛。
• Ultrasound-accelerated synthesis of 3,4-dihydropyrimidin-2(1H)-ones with ceric ammonium nitrate†
  作者：Jhillu S. Yadav、Basi V. Subba Reddy、Kasireddy Bhaskar Reddy、Kavuda Sarita Raj、Attaluri R. Prasad

  DOI：10.1039/b102565c

  日期：——

  Ceric ammonium nitrate efficiently catalyzes the three component condensation of an aldehyde, β-ketoester and urea in methanol to afford the corresponding dihydropyrimidinones in excellent yields under sonication. Other oxidants such as manganese triacetate and Oxone were also found to catalyze this transformation under similar conditions.

  铈铵硝酸盐有效催化醛、β-酮酯和尿素在甲醇中的三组分缩合反应，生成相应的二氢嘧啶酮，产率优秀，并在超声条件下进行。其他氧化剂，如醋酸锰三乙酯和Oxone，也在类似条件下催化了这一转化反应。
• Green Synthesis of Copper Oxide Nanoparticles with an Extract of <i>Euphorbia maculata</i> and Their Use in the Biginelli Reaction
  作者：Heshmatollah Alinezhad、Khatereh Pakzad

  DOI：10.1080/00304948.2020.1764819

  日期：2020.7.3

  biological method because it can produce nanoparticles on a large scale with no need for culture. Copper, of course, is abundantly found in numerous salts in nature and these serve as the primary sources for copper oxide nanoparticles. CuO NPs are used to improve the viscosity of energy transferring fluids, in addition to raising thermal conductivity. Industrially, CuO NPs are broadly applied as p-type semiconductors

  最近，纳米技术因其卓越的生产用途而在科学中获得了巨大的认可。一些金属纳米粒子 (NPs) 在医疗应用中的应用受到限制，因为它们的制备涉及有毒和危险物质、高压、环境和生物风险以及高成本。在纳米粒子中，铜纳米粒子因其成本低、获取方便而受到重视，应用广泛，尤其是在催化剂领域。它们有用的物理特性包括高温超导性。铜催化被认为是各种有机反应最有效的系统之一。通过植物和植物化学物质绿色合成金属和金属氧化物 NPs 是非常有益的，因为它获取简单、成本效益高、使用安全化学品、环境友好、产量高；它不需要严格保存实验室培养物。因此，使用植物提取物合成纳米颗粒是一种有效的生物方法，因为它可以大规模生产纳米颗粒而无需培养。当然，铜在自然界中大量存在于许多盐中，这些盐是氧化铜纳米颗粒的主要来源。除了提高热导率之外，CuO NPs 还用于提高能量传输流体的粘度。在工业上，CuO NPs 被广泛用作 p 型半导体和晶体管
• Researches on Pyrimidines. CXXXIV. The Reaction of Phenylacetaldehyde and Acetophenone with Urea
  作者：Karl Folkers、Treat B. Johnson

  DOI：10.1021/ja01335a053

  日期：1933.8