5-methoxycarbonyl-4-(2,4-dichlorophenyl)-6-methyl-3,4-dihydropyrimidine-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-4-(2,4-dichlorophenyl)-6-methyl-3,4-dihydropyrimidine-2(1H)-one
• 英文别名: methyl 4-(2,4-dichlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；4-(2,4-dichlorophenyl)-5-(methoxycarbonyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one；5-(methoxycarbonyl)-4-(2,4-dichlorophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one；5-(methoxycarbonyl)-6-methyl-4-(2,4-dichlorophenyl)-3,4-dihydropyrimidin-2(1H)-one；5-methoxycarbonyl-4-(2,4-dichlorophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one；5-methoxycarbonyl-6-methyl-4-(2,4-dichlorophenyl)-3,4-dihydropyrimidin-2(1H)-one；methyl 4-(2,4-dichlorophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₃H₁₂Cl₂N₂O₃
• 分子量: 315.156
• InChiKey: UPVGHMMSSMAUAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 四氯化硅 作用下， 反应 6.0h， 生成 5-methoxycarbonyl-4-(2,4-dichlorophenyl)-6-methyl-3,4-dihydropyrimidine-2(1H)-one
  参考文献：
  名称：

  Synthesis of 4-Aryl Substituted 3,4-Dihydropyrimidinones Using Silica-chloride Under Solvent Free Conditions

  摘要：

  本文描述了一种改进的程序，用于在温和反应条件下，以优良的产率高效、简便地合成4-芳基取代的3, 4-二氢吡咯啶酮，采用廉价的氯化硅，并在无溶剂条件下进行。

  DOI：

  10.3390/12071341

文献信息

• A One-Pot Synthesis of 3,4-Dihydropyrimidin-2-(1H)-ones from Primary Alcohols Promoted by Bi(NO3)3·5H2O in Two Different Media: Organic Solvent and Ionic Liquid
  作者：Ahmad Reza Khosropour、Ahmad R. Khosropour、Mohammd M. Khodaei、Mojtaba Beygzadeh、Mahbubeh Jokar

  DOI：10.3987/com-04-10257

  日期：——

  A new, simple and efficient procedure for the one-pot conversion of alcohols instead of aldehydes to the corresponding 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) with Bi(NO 3 ) 3 .5H 2 O as a commercially available, inexpensive, stable and non-toxic reagent in two media, acetonitrile (as an organic solvent) and tetrabutylammonium bromide (as an ionic liquid) is described. This one-pot oxidation-cyclocondensation

  一种新的、简单且有效的方法，用于将醇而不是醛一锅转化为相应的 3,4-二氢嘧啶-2(1H)-酮 (DHPM)，其中 Bi(NO 3 ) 3 .5H 2 O 作为商业应用描述了在乙腈（作为有机溶剂）和四丁基溴化铵（作为离子液体）这两种介质中可获得、廉价、稳定和无毒的试剂。这种一锅氧化-环缩合反应无需分离任何中间体（醛）即可进行，从而缩短了时间，节省了能源和原材料。另一方面，用这种新的一锅法处理伯醇产生的脱氢嘧啶酮的产率高于传统方法中的产率。
• Silica sulfuric acid: an efficient and reusable catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones
  作者：Peyman Salehi、Minoo Dabiri、Mohammad Ali Zolfigol、Mohammad Ali Bodaghi Fard

  DOI：10.1016/s0040-4039(03)00436-2

  日期：2003.3

  Silica sulfuric acid efficiently catalyzes the three-component Biginelli reaction between an aldehyde, a β-dicarbonyl compound and urea or thiourea in refluxing ethanol to afford the corresponding dihydropyrimidinones in high yields. The catalyst is reusable and can be applied several times without any decrease in the yield of the reactions.

  二氧化硅硫酸在回流的乙醇中有效催化醛，β-二羰基化合物与脲或硫脲之间的三组分Biginelli反应，以高收率提供相应的二氢嘧啶酮。该催化剂是可重复使用的，并且可以多次使用而不会降低反应的产率。
• 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。
• 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。
• Efficient Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones over Silica Sulfuric Acid as a Reusable Catalyst under Solvent-free Conditions
  作者：Peyman Salehi、Minoo Dabiri、Mohammad Ali Zolfigol、Mohammad Ali Bodaghi Fard

  DOI：10.3987/com-03-9837

  日期：——

  3,4-Dihydropyrimidin-2(1H)-ones and their sulfur analogues are efficiently synthesized by the three-component condensation of β-dicarbonyl compounds, aromatic and aliphatic aldehydes, and urea or thiourea in the presence of catalytic amounts of silica sulfuric acid under solvent-free conditions in high yields. The catalyst is recyclable and can be used several times without any decrease in the products

  3,4-Dihydropyrimidin-2(1H)-ones 及其硫类似物是在催化量的二氧化硅硫酸存在下，通过 β-二羰基化合物、芳香醛和脂肪醛以及脲或硫脲的三组分缩合有效合成的在无溶剂条件下以高产率。该催化剂可循环使用，可多次使用，不会降低产品收率。