5-acetyl-6-methyl-4-(4-dimethylaminophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine | 100950-24-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-acetyl-6-methyl-4-(4-dimethylaminophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine
• 英文别名: 5-acetyl-4-(4-dimethylaminophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one；5-acetyl-4-(4-dimethylamino-phenyl)-6-methyl-3,4-dihydro-1H-pyrimidin-2-one；5-Acetyl-4-(4-dimethylamino-phenyl)-6-methyl-3,4-dihydro-1H-pyrimidin-2-on；4-[4-(Dimethylamino)phenyl]-5-acetyl-6-methyl-3,4-dihydropyrimidine-2(1H)-one；5-acetyl-4-[4-(dimethylamino)phenyl]-6-methyl-3,4-dihydro-1H-pyrimidin-2-one
• CAS: 100950-24-1
• 化学式: C₁₅H₁₉N₃O₂
• 分子量: 273.335
• InChiKey: TZRKQWCTEMXXAM-UHFFFAOYSA-N

物化性质

• 熔点：
  213-214 °C(Solv: ethanol (64-17-5))
• 沸点：
  440.3±45.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-acetyl-6-methyl-4-(4-dimethylaminophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine 在 copper(l) iodide 、 sodium azide 、 sodium hydride 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.41h， 生成 5-acetyl-4-[4-(dimethylamino)phenyl]-6-methyl-1,3-bis{[1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl]methyl}-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  Dihydropyrimidinone/1,2,3-triazole hybrid molecules: Synthesis and anti-varicella-zoster virus (VZV) evaluation

  摘要：

  By combining the structural features of dihydropyrimidinone and 1,2,3-triazole heterocycles, novel hybrid compounds were synthesized using a simple and convenient method. A series of novel mono and bis 1,2,3-triazole was synthesized via copper-catalyzed Huisgen azide-alkyne cycloadditions (CuAAC) under microwave irradiation. The newly synthesized compounds were evaluated for their antiviral activity against varicella-zoster virus (VZV). Compounds 6aa, lab, 6ba and 6da showed valuable antiviral activities, with EC50 values ranging from 3.6 to 11.3 mu M against TK+ and TK- VZV and without measurable cell-growth inhibition. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.06.028
• 作为产物：
  描述：

  对二甲氨基苯甲醛 、 尿素 、 乙酰丙酮 以 四氢呋喃 为溶剂， 反应 3.0h， 以86%的产率得到5-acetyl-6-methyl-4-(4-dimethylaminophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine
  参考文献：
  名称：

  使用光化学方法在溶剂介质中合成一些 Biginelli 化合物

  摘要：

  一些 Biginelli 化合物是通过使用光化学方法合成的。Biginell 三组分环缩合反应在 THF 介质中使用 g-酮酯或 g-二酮、芳醛和（硫代）脲的混合物在 Wolframe 灯光照射下得到 1,4-二氢嘧啶-2（1H）-酮、DHPM、后处理后的产率为 70-95%。

  DOI：

  10.1080/10426500307928

文献信息

• 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。
• Light-induced Free Radical Oxidation of 2-Oxo-1,2,3,4-tetrahydropyrimidines
  作者：Hamid Reza Memarian、Leila Hejazi、Asadallah Farhadi

  DOI：10.1515/znb-2012-0313

  日期：2012.3.1

  A variety of 4-substituted 5-acetyl- and 5-carboethoxy-2-oxo-1,2,3,4-tetrahydropyrimidines were oxidized under UV irradiation in the presence or absence of benzoyl peroxide. The nature of the substituents on the 4- and 5-positions of the heterocyclic ring affects the rate of photo-oxidation, and irradiation of these compounds in the presence of benzoyl peroxide decreases the time of reaction drastically. Removal of 4-H by a benzoyloxy radical under formation of a trihydropyrimidinoyl radical intermediate occurs in the rate-determining step. The stability of this benzylic and allylic radical intermediate is affected by the nature and the position of the additional substituent on the phenyl group located at C-4.

  一系列4-取代的5-乙酰基和5-羧乙酯基-2-氧代-1,2,3,4-四氢嘧啶在紫外辐射下在有或无苯甲酰过氧化物存在下被氧化。杂环环上4-和5-位置的取代基的性质影响光氧化的速率，这些化合物在有苯甲酰过氧化物存在下的照射显著减少了反应时间。在速率决定步骤中，苯甲酰氧自由基去除4-H形成三氢嘧啶基自由基中间体。这种苄基和烯丙基自由基中间体的稳定性受到苯基团上附加取代基的性质和位置的影响，该苯基团位于C-4。
• 10.1002/aoc.7535
  作者：Bakr, Eman A.、Hamada, Wafaa M.、Noser, Ahmed A.、Fayed, Tarek A.、El-Nahass, Marwa N.

  DOI：10.1002/aoc.7535

  日期：——

  binding constants and limit of detection (LOD) have been calculated. Cu2+ is the strongest binded one with both NS1 and NS2, while Al3+ and Fe3+ are the strongest binded metal ions with NS3 and NS4, respectively. The obtained results confirmed the high ability of the nanosensors to detect heavy metals ions at environmentally relevant concentrations using simple and low-cost experimental studies with good

  荧光纳米传感器是用于检测有毒金属离子的最有效技术之一，其基于嵌入介孔材料中的配体。本研究通过将含有二氢吡啶和二氢嘧啶酮片段的荧光探针掺入氨基功能化的可控纳米传感器（Ba 0.8 Sr 0.2 ）中，合成了四种不同的新型纳米传感器NS1、NS2、NS3和NS4。 )CO 3 @介孔硅酸盐核/壳纳米复合材料。设计的纳米传感器通过 FT-IR（傅里叶变换红外光谱）、X 射线衍射、透射电子显微镜（TEM）和氮气吸附-解吸等温线进行表征。采用目视肉眼观察和发射技术研究了所研究的纳米传感器对各种金属离子（Al 3+ 、Cr 3+ 、Mn 2+ 、Co 2+ 、Ni 2+ 和 Cu 2+ ）。对于所有纳米传感器，大多数研究的金属离子都清楚地观察到荧光强度的大幅猝灭。计算了结合常数和检测限 (LOD)。 Cu 2+ 是与 NS1 和 NS2 结合最强的金属离子，而 Al 3+ 和 Fe 3+ 分别是与 NS3
• Free-radical oxidation of 1,2,3,4-tetrahydro-2-oxopyrimidines
  作者：Hamid Reza Memarian、Nazanin Jafarpour、Asadallah Farhadi

  DOI：10.1007/s00706-011-0573-8

  日期：2012.2

  Free-radical oxidation of 4-substituted 5-acetyl- and 5-carboethoxy-1,2,3,4-tetrahydro-2-oxopyrimidines using benzoyl peroxide under thermal conditions has been investigated to elucidate the effects of the nature of the substituents in the 4- and 5-positions on the rate of reaction. Whereas the presence of the acetyl group instead of the carboethoxy group in position 5 decreases the rate of oxidation, the nature of the additional substituent (electron-releasing or electron-withdrawing group) and also its location on the phenyl ring attached to C-4 of the tetrahydropyrimidinone ring effectively influence the rate of reaction. The latter observation supports the proposal that the removal of the 4-hydrogen on the heterocyclic ring occurs in the rate-determining step.
• Chi; Ling, Scientia Sinica (English Edition), 1957, vol. 6, p. 247,250
  作者：Chi、Ling

  DOI：——

  日期：——