5-aceto-6-methyl-4-styryl-3,4-dihydropyrimidin-2(1H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-aceto-6-methyl-4-styryl-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: 5-acetyl-6-methyl-4-(2-phenylethenyl)-3,4-dihydro-1H-pyrimidin-2-one
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: MVHFVTXGXFBZDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  肉桂醛 、 尿素 、 乙酰丙酮 在 magnesium sulfate 作用下， 反应 0.67h， 以79%的产率得到5-aceto-6-methyl-4-styryl-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  Anhydrous Magnesium Sulfate Mediated Solvent-Free Synthesis of Dihydropyrimidin-2(1H)-ones at Ambient Temperature

  摘要：

  本文介绍了一种以无水硫酸镁为介质的无溶剂方案，用于在常温下合成二氢嘧啶酮（Biginelli 化合物）。

  DOI：

  10.1071/ch07097

文献信息

• Nebivolol nanoparticles: a first catalytic use in Biginelli and Biginelli-like reactions
  作者：Anamika Khaskel、Pranjit Barman、Subir Kumar Maiti、Utpal Jana

  DOI：10.1139/cjc-2017-0621

  日期：2018.12

  Herein, we report the catalytic activity of nebivolol nanoparticles a novel organocatalyst for the synthesis of DHPMs and DHPM-5-carboxamides. The nanoparticles are confirmed by DSC, TEM, AFM, and IR spectroscopy. The catalyst can be readily recovered and reused for the next four runs without any significant impact on the yields of the products. The products are fully characterized by FTIR, ¹H NMR, ¹³C NMR, and distortionless enhanced polarization transfer (DEPT) NMR. The methodology adopted here offers several advantages such as solvent-free reaction, low loading of catalyst, short reaction times, and quantifiable yields.

  在这里，我们报道了尼比地尔纳米颗粒作为合成DHPMs和DHPM-5-羧酰胺的新型有机催化剂的催化活性。通过DSC、TEM、AFM和IR光谱确认了这些纳米颗粒。该催化剂可以轻松回收并在接下来的四次运行中重复使用，对产物的产率没有显著影响。产物通过FTIR、1H NMR、13C NMR和无畸变增强极化转移（DEPT）NMR进行了全面表征。这里采用的方法具有多种优点，如免溶剂反应、催化剂负载量低、反应时间短和产率可量化。
• A Highly Efficient Solvent-Free Synthesis of Dihydropyrimidinones Catalyzed by Zinc Chloride
  作者：Run-tao Li、Qi Sun、Yi-qiang Wang、Ze-mei Ge、Tie-ming Cheng

  DOI：10.1055/s-2004-822331

  日期：——

  Dihydropyrimidinones are prepared from zinc chloride (20 mol%) catalyzed Biginelli condensation of an aldehyde, 1,3-dicarbonyl compounds and urea or thiourea at 80 °C for short time under solvent-free conditions in high yields.

  二氢嘧啶酮是通过锌氯化物（20 mol%）催化的Biginelli缩合反应，在无溶剂条件下，在80 °C的短时间内，将醛、1,3-二酮化合物和尿素或硫脲反应制备而成，产率很高。
• SbPh ₃ : An Efficient Catalyst for Dihydropyrimidinone and Dihydropyrimidin-5-carboxamide Synthesis Using the Biginelli Reaction
  作者：Anamika Khaskel、Santosh Kumari Bajiya、Suman Lata、Rakesh Kumar Sharma、Shatabdi Basu

  DOI：10.1080/00304948.2023.2190711

  日期：2023.11.2

  Published in Organic Preparations and Procedures International: The New Journal for Organic Synthesis (Vol. 55, No. 6, 2023)

  发表于《国际有机制备和程序：有机合成新期刊》（第 55 卷，第 6 期，2023 年）
• Ultrasound-Mediated Synthesis of 3,4-Dihydropyrimidin-2-(<i>1H</i>)-Ones (or Thiones) with NaHSO₄·H₂O
  作者：Karim Akbari Dilmaghani、Behzad Zeynizadeh、Maryam Amirpoor

  DOI：10.1080/10426507.2013.777725

  日期：2013.11.1

  A fast and efficient Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)-ones (or thiones) by the reaction of aromatic aldehydes, -dicarbonyls, and urea/thiourea using NaHSO4H2O/ultrasound system is presented. The reactions were carried out in refluxing n-hexane/CH3CN (2.5:0.5mL) to afford the products in excellent yields.
• Trimethylsilyl Chloride: A Facile and Efficient Reagent for One‐Pot Synthesis of 3,4‐Dihydropyrimidin‐2(1<i>H</i>)‐ones
  作者：Yulin Zhu、Yuanjiang Pan、Shenlin Huang

  DOI：10.1081/scc-200028607

  日期：2004.1

  Trimethylsilyl chloride (TMSCl) was used as a Lewis acid to efficiently perform one-pot, three-components, Biginelli condensation reactions of aldehydes, 1,3-dicarbonyl compounds, and urea or thiourea. This resulted in simple one-pot synthesis of the corresponding 3,4-dihydropyrimidin-2(1H)-ones at room temperature with excellent yield.