3,4-dihydro-4-(4-hydroxyphenyl)-6-phenylpyrimidin-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: 3,4-dihydro-4-(4-hydroxyphenyl)-6-phenylpyrimidin-2(1H)-one
• 英文别名: 4-(p-Hydroxyphenyl)-6-phenyldihydro-pyrimidin-2-one；4-(4-hydroxyphenyl)-6-phenyl-3,4-dihydro-1H-pyrimidin-2-one
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: ATFGBNGFVUMEOR-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：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  61.4
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-4-(4-hydroxyphenyl)-6-phenylpyrimidin-2(1H)-one 、 聚合甲醛 、 二甲胺 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.06h， 以79%的产率得到4-(4-hydroxyphenyl)-6-(phenyl)-1,4-dihydropyrimidine-2-yloxy-N,N-dimethylmethanamine
  参考文献：
  名称：

  二氢嘧啶酮类曼尼希碱的构效关系、药物相似性及抗氧化活性评价

  摘要：

  采用微波辐射技术，通过多组分反应分两步合成了一系列21个O-和N-曼尼希碱的3,4-二氢嘧啶酮（2a-j和3a-k）。通过四种方法评估所有化合物的自由基清除活性。结构活性关系研究表明，与标准抗坏血酸相比，化合物 2h、2g、3h 和 3g 表现出深厚的抗氧化特性。在O-和N-曼尼希碱中，N-曼尼希碱被发现在清除自由基方面更有效。这些化合物的结构和活性之间的相关性与药物可能性曲线和其他物理化学参数有关，并通过实验进行了描述和验证。

  DOI：

  10.14233/ajchem.2019.22008
• 作为产物：
  描述：

  苯甲醛 、 对羟基苯乙酮 在 MnO₂ supported on multiwalled carbon nanocomposites 作用下， 以 neat (no solvent) 为溶剂， 反应 0.42h， 以87%的产率得到3,4-dihydro-4-(4-hydroxyphenyl)-6-phenylpyrimidin-2(1H)-one
  参考文献：
  名称：

  MnO2–MWCNT nanocomposites as efficient catalyst in the synthesis of Biginelli-type compounds under microwave radiation

  摘要：

  A novel Biginelli-like cyclocondensation reaction is efficiently catalyzed by MnO2-CNT nanocomposites as a new catalyst under microwave irradiation and solvent-free conditions in excellent yields. The major advantages of the present method are high yields, short reaction times and solvent-free reaction conditions, reducing reaction steps and purification of products by non-chromatographic methods. The activity, recovery and reusability of the catalyst are found to be good. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2013.02.021

文献信息

• A novel protocol for solvent-free synthesis of 4,6-diaryl-3,4-dihydropyrimidine-2(1H)-ones catalyzed by metal oxide–MWCNTs nanocomposites
  作者：Javad Safari、Soheila Gandomi-Ravandi

  DOI：10.1016/j.molstruc.2014.05.012

  日期：2014.9

  cost and long lifetime. The application of solvent-free conditions and transition metal oxides decorated–MWCNTs (MOx–MWCNTs) nanocomposites as attractive, effective and reusable catalysts leads to the efficient synthesis of 4,6-diaryl-3,4-dihydropyrimidin-2-(1H)-ones. This recyclable heterogeneous catalytic system provides a simple strategy to generate a variety of pyrimidinones under solvent-free conditions

  Biginelli 样缩合被描述为使用苯乙酮作为活性亚甲基化合物与醛和尿素在无溶剂条件下提供嘧啶酮类似物。在本文中，除了制备基于多壁碳纳米管的纳米复合材料外，我们的研究还集中在金属氧化物-多壁碳纳米管复合材料的催化效率上。好的催化剂的必要条件是高活性、选择性、可重复使用性、合理的成本和长寿命。无溶剂条件和过渡金属氧化物装饰的多壁碳纳米管（MOx-MWCNTs）纳米复合材料作为有吸引力、有效和可重复使用的催化剂的应用导致4,6-二芳基-3,4-二氢嘧啶-2-(1H)的有效合成-那些。这种可回收的多相催化系统提供了一种在无溶剂条件下生成各种嘧啶酮的简单策略。
• Fe₃O₄–CNTs nanocomposites: a novel and excellent catalyst in the synthesis of diarylpyrimidinones using grindstone chemistry
  作者：Javad Safari、Soheila Gandomi-Ravandi

  DOI：10.1039/c3ra47827k

  日期：——

  The Fe₃O₄–CNTs in conjunction with grindstone chemistry have been used in this report to synthesize 5-unsubstituted pyrimidinones.

  本报告使用磁性纳米颗粒Fe3O4和碳纳米管（CNTs）结合研磨化学方法来合成5-未取代嘧啶酮。
• Three-components condensation catalyzed by molecular iodine for the synthesis of 2,4,6-triarylpyridines and 5-unsubstituted-3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions
  作者：Yi-Ming Ren、Chun Cai

  DOI：10.1007/s00706-008-0011-8

  日期：2009.1

  One-pot, three-components synthesis of 2,4,6-triarylpyridines and 5-unsubstituted-3,4-dihydropyrimidin-2(1H)-ones was performed under solvent-free conditions using molecular iodine as the catalyst in moderate to good product yields.
• New three-component cyclocondensation reaction: microwave-assisted one-pot synthesis of 5-unsubstituted-3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions
  作者：Bing Liang、Xitian Wang、Jin-Xian Wang、Zhengyin Du

  DOI：10.1016/j.tet.2006.12.062

  日期：2007.2

  Sixteen 5-unsubstituted-3,4-dihydropyrimidin-2(1H)-ones have been synthesized by microwave-assisted Biginelli reactions in a short and concise manner employing ZnI2 as a catalyst under solvent-free conditions. All products were identified by IR, NMR, elemental analysis and HRMS. The advantages of this novel protocol include the excellent yield, operational simplicity, short time and the avoidance of the use of organic solvents and expensive catalysts. (c) 2007 Elsevier Ltd. All rights reserved.
• H₆P₂W₁₈O₆₂-18H₂O, a Green and Reusable Catalyst for the Three-Component, One-Pot Synthesis of 4,6-Diarylpyrimidin-2(1<i>H</i>)-ones Under Solvent-Free Conditions
  作者：Majid M. Heravi、Fatemeh Derikvand、Leila Ranjbar、Fatemeh F. Bamoharram

  DOI：10.1080/00397910903062272

  日期：2010.4.12