5-methoxycarbonyl-6-methyl-4-isopropyl-3,4-dihydropyrimidin-2(1H)-one

• 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-methoxycarbonyl-6-methyl-4-isopropyl-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: Methyl 4-isopropyl-6-methyl-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate；methyl 6-methyl-2-oxo-4-propan-2-yl-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₀H₁₆N₂O₃
• 分子量: 212.249
• InChiKey: KSRYGGDNUAFIJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  乙酰乙酸甲酯 、 异丁醛 、 尿素 在 [MeC(OH)2]ClO₄ 作用下， 以 neat (no solvent) 为溶剂， 反应 0.5h， 以85%的产率得到5-methoxycarbonyl-6-methyl-4-isopropyl-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  无溶剂条件下超酸性离子液体催化的 Biginelli 型反应

  摘要：

  [MeC(OH)2]+ClO4- 作为一种超酸性离子液体，是一种非常活跃的 Biginelli 型反应催化剂。本方法对惰性脂肪醛特别有效。无溶剂条件、高催化活性、广泛的底物耐受性和方便的产品分离使该协议更具优势。

  DOI：

  10.3184/174751912x13518654161237

文献信息

• An Efficient Synthesis of Multi-Substituted 3,4-Dihydropyrimidin-2(1H)-ones/thiones Under Solvent-Free Microwave Irradiation Using Alumina Sulfuric Acid
  作者：Hamid Reza Shaterian、Asghar Hosseinian、Majid Ghashang

  DOI：10.1080/10426500802083182

  日期：2008.12.23

  A new and efficient method for the synthesis of multi-substituted dihydropyrimidinone derivatives or their sulfur analogs has been developed under solvent-free microwave irradiation conditions in the presence of alumina sulfuric acid (Al2O3-SO3H) as an environmentally friendly heterogeneous recyclable catalyst, in high yields and short reaction time.

  在无溶剂微波辐射条件下，在硫酸铝 (Al2O3-SO3H) 作为环境友好的多相可回收催化剂存在下，开发了一种新的高效合成多取代二氢嘧啶酮衍生物或其硫类似物的方法。产率高，反应时间短。
• Ferric chloride/tetraethyl orthosilicate as an efficient system for synthesis of dihydropyrimidinones by Biginelli reaction
  作者：Ivica Cepanec、Mladen Litvić、Anamarija Bartolinčić、Marija Lovrić

  DOI：10.1016/j.tet.2005.02.059

  日期：2005.4

  efficient method for the Biginelli reaction of aldehydes, acetoacetate esters and urea employing tetraethyl orthosilicate in the presence of ferric chloride is described. These improved reaction conditions allow the preparation of a wide variety of substituted dihydropyrimidinones (including sterically encumbered ones) in high yields and purity under mild reaction conditions.

  描述了在氯化铁存在下使用原硅酸四乙酯进行醛，乙酰乙酸酯和脲的Biginelli反应的有效方法。这些改进的反应条件允许在温和的反应条件下以高收率和纯度制备多种取代的二氢嘧啶酮（包括空间受限的二氢嘧啶酮）。
• Wang, Min; Jiang, Heng; Wang, Zhichang, Journal of Chemical Research, 2005, # 11, p. 691 - 693
  作者：Wang, Min、Jiang, Heng、Wang, Zhichang

  DOI：——

  日期：——
• One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using chloroacetic acid as catalyst
  作者：Yang Yu、Di Liu、Chunsheng Liu、Genxiang Luo

  DOI：10.1016/j.bmcl.2006.12.068

  日期：2007.6

  A simple and effective synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives from aldehydes, 1,3-dicarbonyl compounds and urea or thiourea using chloroacetic acid as catalyst under solvent-free conditions is described. Compared with the classical Biginelli reaction conditions, this new method has the advantage of good to excellent yields and short reaction time. (c) 2006 Elsevier Ltd. All rights reserved.