4-(4-hydroxyphenyl)-6-phenylpyrimidin-2(1H)-one | 161200-20-0

• 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: 4-(4-hydroxyphenyl)-6-phenylpyrimidin-2(1H)-one
• 英文别名: 6-(4-hydroxyphenyl)-4-phenyl-1H-pyrimidin-2-one
• CAS: 161200-20-0
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: WLYWOBKVNWZXBL-UHFFFAOYSA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-二甲基甲酰胺 、 4-(4-hydroxyphenyl)-6-phenylpyrimidin-2(1H)-one 在 三氯氧磷 作用下， 反应 2.0h， 生成 2-chloro-4-(p-hydroxyphenyl)-6-phenylpyrimidine 、 2-chloro-4-(p-formyloxyphenyl)-6-phenylpyrimidine
  参考文献：
  名称：

  Synthesis of 2- and 4-chloropyrimidines with hydroxyphenyl substituents by the interaction of Vilsmeier-Haack reagents with (hydroxyphenyl)dihydropyrimidin-2- and -4-ones

  摘要：

  The reaction of 2- and 4-hydroxypyrimidines containing ortho- and para-hydroxyphenyl substituents with Vilsmeier-Haack reagents generated in situ from DMF and SOCl2 or POCl3 results in the chemoselective replacement of the heterocyclic hydroxyl group by chlorine and formylation of the phenolic hydroxyl group. Aryl formates are hydrolyzed under the conditions of their isolation to give the corresponding phenols, especially if the pyrimidyl fragment is ortho to the formyloxy group.

  DOI：

  10.1007/bf00704199
• 作为产物：
  描述：

  对羟基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.17h， 生成 4-(4-hydroxyphenyl)-6-phenylpyrimidin-2(1H)-one
  参考文献：
  名称：

  固相微波法对查耳酮类新嘧啶-2（1H）-醇/硫醇衍生物的生物学评价和合成

  摘要：

  通过以下反应合成了二十五个新的羟基和甲氧基取代的4,6-二芳基嘧啶-2（1H）-醇（20-34）和4,6-二芳基嘧啶-2（1H）-硫醇衍生物（35-44）。使用固相微波方法，将相应的1,3-二芳基-2-丙烯-1酮化合物（1-19）与尿素或硫脲一起使用。对所有新的合成化合物（20-44）的α-葡萄糖苷酶活性进行了评估。但是，只有化合物22–25、27、31、34、35、37和40表现出比标准阿卡波糖更大的抑制作用。活性化合物的IC50值在2.36和13.34μM之间。还筛选了25种新化合物的体外胰腺脂肪酶活性，发现化合物20–27和35–39具有活性。在这些化合物中，26、27和39在0.40±0.06、0.26±0.07，和0.29±0.026μM。对所有新化合物（20-44）的九种测试微生物的体外抗菌活性进行了评估。经测定，化合物20-24和35-39在检测的细菌病原菌中对革兰氏阳性粪便

  DOI：

  10.3906/kim-1711-9

文献信息

• Synthesis, fluorescence properties and Zn²⁺ recognition of 4-Aryl-6-phenylpyrimidin-2(1H)-one
  作者：Hui Wu、Xiu-mei Chen、Yu Wan、Ling Ye、Hai-qiang Xin、Hua-hong Xu、Li-ling Pang、Rui Ma、Cai-hui Yue

  DOI：10.3184/030823408x389958

  日期：2008.12

  4-Aryl-6-phenylpyrimidin-2(1H)-ones were synthesised via a three-component one-pot cyclocondensation of aromatic aldehyde, acetophenone and urea catalysed by 0.2 ml (0.024 mol%) of concentration HCI in ionic liquid [BMIM][BF₄]. The fluorescence properties of product and partial products’ efficient sensing of zinc ion were studied in detail. The structure of 4,6-diphenylpyrimidin-2(1H)-one was confirmed by X-ray analysis.

  在离子液体[BMIM][BF4]中以 0.2 ml（0.024 mol%）浓度的 HCI 催化下，通过芳香醛、苯乙酮和脲的三组分一锅环缩合合成了 4-芳基-6-苯基嘧啶-2(1H)-酮。详细研究了产物和部分产物高效感应锌离子的荧光特性。X 射线分析证实了 4,6-二苯基嘧啶-2(1H)-酮的结构。
• Highly effectual synthesis of 4,6-diarylpyrimidin-2(1<i>H</i>)-ones using <i>N</i>,<i>N</i>,<i>N</i>′,<i>N</i>′-tetramethylethylenediaminium-<i>N</i>,<i>N</i>′-disulfonic acid hydrogen sulfate as a dual-functional catalyst
  作者：Roghayyeh Khanivar、Abdolkarim Zare

  DOI：10.1515/znb-2018-0075

  日期：2018.9.25

  Abstract The highly effectual synthesis of 4,6-diarylpyrimidin-2(1H)-ones via the one-pot multicomponent reaction of acetophenones with arylaldehydes and urea in the presence of trimethylsilyl chloride and a catalytic amount of the ionic liquid N,N,N′,N′-tetramethylethylenediaminium-N,N′-disulfonic acid hydrogen sulfate ([TMEDSA][HSO4]2) under solvent-free conditions has been described. The reaction

  摘要 在三甲基氯硅烷和催化量的离子液体 N,N,N 存在下，通过苯乙酮与芳醛和尿素的一锅多组分反应高效合成 4,6-二芳基嘧啶-2(1H)-酮。 ',N'-四甲基乙二胺-N,N'-二磺酸硫酸氢盐 ([TMEDSA][HSO4]2) 在无溶剂条件下已有描述。该催化体系的反应结果和条件已与先前报道的催化剂进行了比较。[TMEDSA][HSO4]2 与报道的催化剂相比，在以下一个或多个因素方面提供了更好的结果：收率、温度、反应介质、时间和通用性。此外，还提出了一种基于催化剂双重功能的合理反应机制。
• Iodine-Catalyzed Versatile Synthesis of 4,6-Diarylpyrimidin-2(1<i>H</i>)-ones (DAPMs) via One-Pot, Multicomponent Reaction
  作者：M. B. Madhusudana Reddy、M. A. Pasha

  DOI：10.1080/00397911.2010.493263

  日期：2011.7.1

  [image omitted] An efficient, solvent-free, one-pot, three-component cyclocondensation reaction between aldehyde, ketone, and urea to give 4,6-diarylpyrimidin-2(1H)-ones (DAPMs) using iodine as catalyst is described. This new protocol provides a simple and environmentally benign route along with the associated advantages of good to excellent yield of the products (90-96%) and short reaction times (5-15min) at 80 degrees C.
• Synthesis of diarylpyrimidinones (DAPMs) using large pore zeolites
  作者：Sunil R. Mistry、Kalpana C. Maheria

  DOI：10.1016/j.molcata.2011.12.019

  日期：2012.3

  A series of diarylpyrymidin-2(1H)-one (DAPM) belongs to one of the important class of therapeutic and pharmacological active hetrocycles, were synthesized through the multicomponent reactions (MCRs) of aldehydes, ketone and urea, followed by the heterogeneous catalysis. The synthetic utility of this method is well demonstrated by avoiding expensive reagent TMSCI, using large pore zeolites (H-MOR, HY and H-BEA) as potential solid acid catalyst. Key role of textural properties such as surface acidity, hydrophobicity and porosity on catalytic activity of the zeolites on the synthesis of DAPMs has also been described. (C) 2011 Elsevier B.V. All rights reserved.
• A one-pot three-component synthesis of 4,6-diarylpyrimidin-2(1H)-ones (DAPMs) using atomized sodium in THF under sonic condition
  作者：Mohamed Afzal Pasha、Shrivatsa Nagashree

  DOI：10.1016/j.ultsonch.2013.12.021

  日期：2014.7

  A simple and an efficient procedure for the synthesis of 4,6-diarylpyrimidin-2(1H)-ones using atomized sodium/THF via a one-pot three-component Biginelli-like cyclocondensation of an aldehyde, a methyl ketone and urea under ultrasonic condition is developed. The method is mild and inexpensive; yields are high and the reactions go to completion within 10-15 min. (C) 2013 Elsevier B.V. All rights reserved.