5-acetyl-6-methyl-2-oxo-4-(3',4',5'-trimethoxyphenyl)-1,2,3,4-tetrahydropyrimidine | 315240-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-acetyl-6-methyl-2-oxo-4-(3',4',5'-trimethoxyphenyl)-1,2,3,4-tetrahydropyrimidine
• 英文别名: 5-acetyl-6-methyl-4-(3,4,5-trimethoxyphenyl)-3,4-dihydropyrimidin-2(1H)-one；5-aceto-6-methyl-4-(3,4,5-trimethoxyphenyl)-3,4-dihydropyrimidin-2(1H)-one；5-acetyl-6-methyl-4-(3,4,5-trimethoxyphenyl)-3,4-dihydro-1H-pyrimidin-2-one
• CAS: 315240-35-8
• 化学式: C₁₆H₂₀N₂O₅
• 分子量: 320.345
• InChiKey: GUVROHMRMDARPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  85.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-acetyl-6-methyl-2-oxo-4-(3',4',5'-trimethoxyphenyl)-1,2,3,4-tetrahydropyrimidine 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 以89%的产率得到
  参考文献：
  名称：

  El-Hamouly, Wageeh S.; El-Khamry, Abdel-Momen A.; Abbas, Eman M. H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 9, p. 2091 - 2098

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 尿素 、 乙酰丙酮 在 盐酸 、 aluminum (III) chloride 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 5-acetyl-6-methyl-2-oxo-4-(3',4',5'-trimethoxyphenyl)-1,2,3,4-tetrahydropyrimidine
  参考文献：
  名称：

  QSAR analysis of 2-oxo-1,2,3,4-tetrahydropyrimidine analogues of antibacterials

  摘要：

  对两组2-氧代-1,2,3,4-四氢嘧啶类似物进行QSAR分析，以研究它们的理化参数与抗菌活性之间的关系。生成了具有预测性和统计显著性的模型。基于这些模型，合成了新化合物，进行了结构表征，并评估了它们的抗菌潜力。新合成化合物的潜力高于训练集中的化合物，与QSAR预测结果密切一致。

  DOI：

  10.1135/cccc2009054

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。
• QSAR analysis of 2-oxo-1,2,3,4-tetrahydropyrimidine analogues of antibacterials
  作者：Ramesh L. Sawant、Manish S. Bhatia

  DOI：10.1135/cccc2009054

  日期：——

  QSAR analysis of two sets of analogues of 2-oxo-1,2,3,4-tetrahydropyrimidine was performed to investigate the relationship between their physicochemical parameters and antibacterial activity. Predictive and statistically significant models were generated. On the basis of these models new compounds were synthesized, structurally characterized and evaluated for their antibacterial potential. The potential of newly synthesized compounds was higher than the training set of compounds, in close agreement with QSAR prediction.

  对两组2-氧代-1,2,3,4-四氢嘧啶类似物进行QSAR分析，以研究它们的理化参数与抗菌活性之间的关系。生成了具有预测性和统计显著性的模型。基于这些模型，合成了新化合物，进行了结构表征，并评估了它们的抗菌潜力。新合成化合物的潜力高于训练集中的化合物，与QSAR预测结果密切一致。
• New Procedure for One‐Pot Synthesis of 3,4‐Dihydropyrimidin‐2(1<i>H</i>)‐ones by Biginelli Reaction
  作者：Feng Xu、Jian‐Jun Wang、You‐Ping Tian

  DOI：10.1080/00397910701873524

  日期：2008.3.28

  Abstract A practical green chemistry procedure for synthesis of 3,4‐dihydropyrimidin‐2(1H);‐ones in good yields was successfully carried out in micellar systems according to the Biginelli reaction using β‐ketoester, urea and appropriate aromatic aldehyde in the presence of CuCl2 · H2O as catalyst. The advantages of this method involved the broader application scope of substrates, the more environmental

  摘要 根据 Biginelli 反应，在胶束体系中使用 β-酮酯、尿素和适当的芳香醛在胶束体系中成功地合成了 3,4-二氢嘧啶-2(1H);-ones 的实用绿色化学程序。 CuCl2·H2O作为催化剂。该方法的优点包括底物适用范围更广、工艺更环保、路易斯酸催化剂成本低。
• Yttria-Zirconia–Based Lewis Acid Catalysis of the Biginelli Reaction: An Efficient One-Pot Synthesis of 3,4-Dihydropyrimidin-2-(1<i>H</i>)-ones
  作者：S. Ramalingam、Pradeep Kumar

  DOI：10.1080/00397910802519174

  日期：2009.3.10

  Abstract Yttria-zirconia–based Lewis acid efficiently catalyzes the three-component cyclocondensation reaction of aldehyde, β-keto ester, and urea or thiourea in refluxing acetonitrile to produce the corresponding dihydropyrimidones in high yields.

  摘要 氧化钇-氧化锆基路易斯酸在乙腈回流中高效催化醛、β-酮酯和尿素或硫脲的三组分环缩合反应，以高产率制备相应的二氢嘧啶酮。
• El-Hamouly, Wageeh S.; El-Khamry, Abdel-Momen A.; Abbas, Eman M. H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 9, p. 2091 - 2098
  作者：El-Hamouly, Wageeh S.、El-Khamry, Abdel-Momen A.、Abbas, Eman M. H.

  DOI：——

  日期：——