methyl 4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine 5-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: methyl 4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine 5-carboxylate
• 英文别名: methyl 4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；5-methoxycarbonyl-6-methyl-4-(4-hydroxy-3-methoxyphenyl)-3,4-dihydropyrimidin-2-(1H)-one；5-Methoxycarbonyl-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one；methyl 4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₄H₁₆N₂O₅
• 分子量: 292.291
• InChiKey: JZPXSMURKIJDAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  香草醛 、 乙酰乙酸甲酯 、 尿素 在 高氯酸 作用下， 反应 0.02h， 以95%的产率得到methyl 4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine 5-carboxylate
  参考文献：
  名称：

  微波诱导的高氯酸通过比奇内利缩合催化新型无溶剂合成4-芳基-3,4-二氢嘧啶酮

  摘要：

  我们在这里首次报道了家用微波诱导的高氯酸催化的各种4-芳基-3,4-二氢嘧啶酮的无溶剂合成。在所有情况下，收率都非常好，其机理遵循简单的Biginelli缩合反应，可在几秒钟内产生二氢嘧啶酮。该程序已成功用于合成有丝分裂驱动蛋白EG5抑制剂Monastrol（图I）。

  DOI：

  10.1002/jhet.5570440439

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。
• Methods and compositions for treating pain
  申请人：Moran M. Magdalene

  公开号：US20070219222A1

  公开（公告）日：2007-09-20

  The present application relates to compounds and methods for treating pain, incontinence and other conditions.

  本申请涉及化合物和治疗疼痛、失禁和其他疾病的方法。
• An efficient and clean one-pot synthesis of 3,4-dihydropyrimidine-2(1<i>H</i>)-ones catalyzed by tungstate sulfuric acid in solvent-free conditions
  作者：Masoud Nasr-Esfahani、Bahador Karami、Morteza Montazerozohori、Karim Abdi

  DOI：10.1002/jhet.5570450438

  日期：2008.7

  Tungstate sulfuric acid catalyzes the three component condensation reaction of an aromatic aldehyde, urea and a β-ketoester under solvent-free conditions to afford the corresponding dihydropyrimidinones in high to excellent yields at room temperature.

  钨酸硫酸盐在无溶剂条件下催化芳族醛，尿素和β-酮酸酯的三组分缩合反应，从而在室温下以高收率或优异的收率提供相应的二氢嘧啶酮。
• Double catalytic effect of (PhNH3)2CuCl4 in a novel, highly efficient synthesis of 2-oxo and thioxo-1,2,3,4-tetra-hydopyrimidines
  作者：Nenad Jankovic、Zorica Bugarcic、Svetlana Markovic

  DOI：10.2298/jsc141028011j

  日期：——

  An innovative route for the construction of 2-oxo and thioxo-1,2,3,4-tetrahydropyrimidines was delineated through a multicomponent reaction under Biginelli conditions, starting from different aromatic aldehydes, ?-ketoesters and urea or thiourea. Proper choice of copper complex (PhNH3)2CuCl4, as a novel homogeneous catalyst, enables facile, efficient, and inexpensive reaction under mild experimental conditions. Moreover, we present the first application of this complex salts in organic synthesis ever. The obtained products are of high purity, and can be easily isolated from the reaction mixture in good to excellent yields. Also, compared to the classical Biginelli reaction conditions, the present method has the advantages in higher yields and experimental and work-up simplicity. To illustrate the joint catalytic action of the Cu2+ and phenylammonium ions, two key steps of Biginelli reaction were examined using the M06 functional.

  通过多组分方法，为构建 2-氧代和硫代-1,2,3,4-四氢嘧啶的 和硫代-1,2,3,4-四氢嘧啶的创新路线。 在Biginelli条件下，通过多组分反应，从不同的芳香 醛、酮酯和脲或硫脲为起点，在 Biginelli 条件下通过多组分反应进行了研究。正确选择铜络合物 (PhNH3)2CuCl4 作为新型均相催化剂，可以在温和的实验条件下进行简便、高效和廉价的反应、 而且成本低廉。此外，我们 此外，我们还首次将这种复合盐应用于有机合成中。 我们还首次将这种复盐应用于有机合成。所得到的产物纯度很高，可以很容易地从反应混合物中分离出 从反应混合物中分离出来，而且产量极高。此外，与 比吉内利反应条件相比，本方法具有 而且，与传统的 Biginelli 反应条件相比，本方法具有产率高、实验和操作简单等优点。为了 Cu2+ 和苯基铵离子的联合催化作用、 使用 M06 功能对 Biginelli 反应的两个关键步骤进行了研究。
• Copper(II) Sulfamate: An Efficient Catalyst for the One-Pot Synthesis of 3,4-Dihydropyrimidine-2(1H)-ones and thiones
  作者：Chen-Jiang Liu、Ji-De Wang

  DOI：10.3390/molecules14020763

  日期：——

  A simple, efficient procedure for the one-pot Biginelli condensation reaction of aldehydes, β-ketoesters and urea or thiourea employing copper(II) sulfamate as a novel catalyst is described. Compared to the classical Biginelli reaction conditions, the present method has the advantages of good yields, short reaction times and experimental simplicity.

  描述了使用氨基磺酸铜 (II) 作为新型催化剂进行醛、β-酮酯和尿素或硫脲的一锅 Biginelli 缩合反应的简单、有效的程序。与经典的 Biginelli 反应条件相比，本方法具有收率好、反应时间短、实验简单等优点。