5-aceto-4-(4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine

• 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-aceto-4-(4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine
• 英文别名: 5-acetyl-4-(4-hydroxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one；5-acetyl-6-methyl-4-(4-hydroxyphenyl)-3,4-dihydropyrimidin-2(1H)-one；5-acetyl-4-(4-hydroxyphenyl)-6-methyl-3,4-dihydro-1H-pyrimidin-2-one
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: VQXHIBPXHJPGJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-aceto-4-(4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine 在 copper(l) iodide 、 sodium azide 、 potassium tert-butylate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.47h， 生成 5-acetyl-4-{4-[(1-benzyl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}-6-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：

  对羟基苯甲醇 、 尿素 、 乙酰丙酮 在 bismuth(III) nitrate 作用下， 以 乙腈 为溶剂， 以72%的产率得到5-aceto-4-(4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine
  参考文献：
  名称：

  Bi(NO3)3·5H2O在两种不同介质：有机溶剂和离子液体中一锅法合成3,4-二氢嘧啶-2-(1H)-酮

  摘要：

  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。

  DOI：

  10.3987/com-04-10257

文献信息

• BiVO4-NPs: an efficient nano-catalyst for the synthesis of biscoumarins, bis(indolyl)methanes and 3,4-dihydropyrimidin-2(1H)-ones (thiones) derivatives
  作者：Farhad Shirini、Monireh Pourghasemi Lati

  DOI：10.1007/s13738-016-0959-y

  日期：2017.1

  4-dihydropyrimidin-2(1H)-ones (thiones) derivatives. The structures of the products were characterized by IR, 1H NMR and 13C NMR spectroscopy and comparison with the authentic samples. Easy work-up procedure, excellent yields, short reaction times and reusability of the catalyst are some advantages of this work. In addition, in this article and for the first time, the preparation of 3,4-dihydropyrimidin-2(1H)-ones

  BiVO 4 -NPs可用作促进双香豆素，双（吲哚基）甲烷和3,4-二氢嘧啶-2（1 H）-ones（thiones）衍生物合成的有效且可重复使用的纳米催化剂。产物的结构通过IR，1 H NMR和13 C NMR光谱表征，并与真实样品进行比较。简便的后处理程序，优异的收率，较短的反应时间和催化剂的可重复使用性是这项工作的一些优势。另外，在本文中并且首次报道了从醛的被保护的衍生物包括肟，半咔唑酮和1,1-二乙酸酯制备3,4-二氢嘧啶-2（1 H）-酮和-硫酮的报道。
• The development of an ecofriendly procedure for alkaline metal (II) sulfate promoted synthesis of<i>N</i>,<i>N</i>′-dimethyl substituted (unsubstituted)-4-aryl-3,4-dihydropyrimidones (thiones) and corresponding bis-analogues in aqueous medium: Evaluation by green chemistry metrics
  作者：Chhanda Mukhopadhyay、Arup Datta

  DOI：10.1002/jhet.283

  日期：——

  Different alkaline metal (II) sulfates were used as catalysts for the N,N′-dimethyl substituted as well as unsubstituted 4-aryl-3,4-dihydropyrimidones (thiones) and their corresponding bis-analogues in aqueous medium. Among the various salts, MgSO4·7H2O (Epsom salt) proved to be the best catalyst giving the desired products in good to excellent yields. This catalyst enables the construction of a series

  在水性介质中，将不同的碱金属（II）硫酸盐用作N，N'-二甲基取代的和未取代的4-芳基-3,4-二氢嘧啶酮（硫酮）及其相应的双类似物的催化剂。在各种盐中，MgSO 4 ·7H 2 O（泻盐）被证明是最好的催化剂，以良好至极佳的收率提供了所需的产物。该催化剂能够构建一系列化合物库，特别是对于N，N'-二甲基取代的DHPM，其合成在文献中非常罕见。通过绿色化学的应用评估了在多种底物上的反应指标和非常好的相关性。J.杂环化​​学.2010。
• General solvent-free ionic liquid catalyzed C–N/C–C coupled cyclization to diverse dihydropyrimidinones and new organic materials: Langmuir–Blodgett film study
  作者：Swapan Majumdar、Jhinuk De、Ajitesh Pal、Indra Ghosh、Ranendu K. Nath、Sandip Chowdhury、Dipanwita Roy、Dilip K. Maiti

  DOI：10.1039/c5ra01618e

  日期：——

  An ionic liquid catalyzed dual C–N/C–C coupled cyclization under solvent-free green conditions to DHPMs and their innovative new organic materials by LB film study are demonstrated.

  一种离子液体催化的双C-N/C-C偶联环化反应在无溶剂绿色条件下合成了DHPMs及其创新的新有机材料，通过LB膜研究进行了展示。
• Solvent-free efficient one-pot synthesis of Biginelli and Hantzsch compounds catalyzed by potassium phthalimide as a green and reusable organocatalyst
  作者：Hamzeh Kiyani、Maryam Ghiasi

  DOI：10.1007/s11164-014-1621-x

  日期：2015.8

  The usage of potassium phthalimide (PPI) for the simple and green one-step multicomponent synthesis of Hantzsch 1,4-dihydropyridines, polyhydroquinolines, 3,4-dihydropyrimidin-2(1H)-ones/thiones, and octahydroquinazolinones under solventless conditions at 120 °C is reported. The method is operationally simple, environmentally benign, and has relatively high yields. The other merits of this method include efficient, clean, green, and catalyst reusability.

  本文报道了在无溶剂条件下，于120°C下使用邻苯二甲酰亚胺钾（PPI）进行Hantzsch 1,4-二氢吡啶、多氢喹啉、3,4-二氢嘧啶-2(1H)-酮/硫酮以及八氢喹唑啉酮的一步多组分简单绿色合成。该方法操作简便，环境友好，且产率相对较高。此外，该方法还具有高效、清洁、绿色以及催化剂可重复使用的优点。
• 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。