4-(3,4-dimethylphenyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one | 1262394-26-2

• 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: 4-(3,4-dimethylphenyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: ethyl 4-(3,4-dimethylphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 4-(3,4-dimethylphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 1262394-26-2
• 化学式: C₁₆H₂₀N₂O₃
• 分子量: 288.346
• InChiKey: CQCDAPSSZCQFLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,4-二甲基苯甲醛 、 乙酰乙酸乙酯 、 尿素 在 ZAF-16/16 作用下， 以 乙二醇 为溶剂， 反应 5.0h， 以71.5%的产率得到4-(3,4-dimethylphenyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  New magnetic nanocomposites of ZrO₂–Al₂O₃–Fe₃O₄as green solid acid catalysts in organic reactions

  摘要：

  通过简便的共沉淀方法设计并制备了一系列磁性固体酸纳米催化剂。原始纳米复合材料ZrO2–Al2O3–Fe3O4通过ICP-AES、BET、XRD、TEM、HRTEM、VSM、FT-IR、NH3-TPD和TG进行了表征。通过酯化反应、双吲哚甲烷合成、Hantzsch反应、Biginelli反应和Pechmann反应研究了它们的催化行为。在所有这些有机反应中，获得了相应产品的中等至优良产率。最佳催化剂是ZAF-16/16，经过多次循环后仍保持催化活性。

  DOI：

  10.1039/c3cy00572k

文献信息

• Synthesis of Polyacrylonitrile Fiber-Supported Poly(ammonium methanesulfonate)s as Active and Recyclable Heterogeneous Brønsted Acid Catalysts
  作者：Xian-Lei Shi、Xiaoli Xing、Huikun Lin、Wenqin Zhang

  DOI：10.1002/adsc.201400048

  日期：2014.7.7

  new polyacrylonitrile fiber‐supported Brønsted acid catalyst has been developed and verified to efficiently (high yield, 10 cycles) mediate Biginelli reactions in ethanol, Pechmann condensations in toluene, Friedel–Crafts alkylations of indoles in water and conversion of fructose in dimethyl sulfoxide (DMSO) and mixed‐aqueous system.

  已开发并验证了一种新型的聚丙烯腈纤维负载的布朗斯台德酸催化剂，该催化剂可有效（高产率，10个循环）介导乙醇中的Biginelli反应，甲苯中的Pechmann缩合，水中吲哚的Friedel-Crafts烷基化反应以及果糖在二甲亚砜中的转化（ DMSO）和混合水系统。
• Sulfonic acid-functionalized polypropylene fiber: highly efficient and recyclable heterogeneous Brønsted acid catalyst
  作者：Xian-Lei Shi、Huixiao Yang、Minli Tao、Wenqin Zhang

  DOI：10.1039/c3ra23187a

  日期：——

  A sulfonic acid-functionalized polypropylene fiber, capable of acting as a supported catalyst in the accomplishment of the Biginelli reaction, is presented. Excellent results, in terms of chemical yields, catalyst dosage, work-up procedure and catalytic recyclability, are reported for the metal-free catalyzed one-pot synthesis of a number of substituted 3,4-dihydropyrimidin-2-(1H)-ones/-thiones (DHPMs). The catalyst can be prepared by a simple process from inexpensive and readily available polypropylene fiber, after completion of the catalytic reaction, the catalyst was simply recovered with common tweezers and recycled with excellent stability and activity even after 11 runs, which in turn is very attractive for economic interest and industrial safety. This is the first report about the application of the polypropylene fiber as a new support for heterogeneous catalysis in the practice of organic synthesis in an environmentally friendly manner.

  本研究介绍了一种磺酸官能化聚丙烯纤维，它能够在完成比吉内利反应的过程中充当支撑催化剂。在化学收率、催化剂用量、操作步骤和催化可回收性方面，报告了无金属催化一锅合成多种取代的 3,4-二氢嘧啶-2-(1H)-酮/硫酮（DHPMs）的优异结果。催化剂的制备过程非常简单，只需利用廉价易得的聚丙烯纤维，完成催化反应后，用普通镊子即可回收催化剂并循环使用，即使经过 11 次运行，催化剂仍具有极佳的稳定性和活性，这在经济利益和工业安全方面具有极大的吸引力。这是首次报道将聚丙烯纤维作为一种新的异相催化支持物，以环境友好的方式应用于有机合成实践中。
• A microwave-assisted, copper-catalyzed three-component synthesis of dihydropyrimidinones under mild conditions
  作者：Kalyan Kumar Pasunooti、Hua Chai、Chantel Nixon Jensen、Bala Kishan Gorityala、Siming Wang、Xue-Wei Liu

  DOI：10.1016/j.tetlet.2010.10.150

  日期：2011.1

  The synthesis of dihydropyrimidinones via a clean multi-component Biginelli reaction under microwave irradiation is reported. The copper-catalyzed process proved to be simple, efficient, economical, and environmentally friendly. (C) 2010 Elsevier Ltd. All rights reserved.