4,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one | 4113-79-5

• 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: 4,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: 3,4-dihydro-4,6-diphenylpyrimidin-2(1H)-one；4.6-Diphenyl-2-oxo-1.2.3.4-tetrahydro-pyrimidin；4,6-diphenyl-3,4-dihydro-1H-pyrimidin-2-one
• CAS: 4113-79-5
• 化学式: C₁₆H₁₄N₂O
• 分子量: 250.3
• InChiKey: DFTAAYUSFSEGNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 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：
  41.1
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  4,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one 在 劳森试剂 、 甲烷 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 苯 为溶剂， 反应 3.0h， 生成 4-(3-溴苯基)-6-苯基-2-羟基嘧啶
  参考文献：
  名称：

  Synthesis of novel nucleosides and stereoselectivity of N-glycosidation

  摘要：

  An efficient synthetic route for novel nucleosides has been realized. We report the formation of alpha-isomers in spite of neighboring group participation by the benzoyl group at the 2-position in N-glycosidation as well as discuss the stereoselectivity observed. We also found that non-silylated pyrimidin-2(1H)-ones and pyrimidin-2(1H)-thiones having aromatic structures reacted with 1-fluororibose in the presence of a Lewis acid to give the corresponding nucleosides in good to high yield. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.017
• 作为产物：
  描述：

  苯甲醛 在 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 18.17h， 生成 4,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  Synergistic antifungal effect of cyclized chalcone derivatives and fluconazole against Candida albicans

  摘要：

  环化的双差烯酮衍生物与氟康唑表现出协同的抗真菌作用，通过抑制麦角固醇生物合成来证明，进而下调ERG11基因表达。

  DOI：

  10.1039/c7md00440k

文献信息

• Synthesis of 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones using Sodium Bisulfate as a Catalyst under Solvent-free Conditions
  作者：Min Wang、Ji-Lei Song、Shuang Zhao、Xin Wan

  DOI：10.1080/00304948.2014.944407

  日期：2014.9.3

  the preparation of 5-unsubstituted 3,4-dihydropyrimidin2(1H)-ones via the one-pot condensation of aromatic aldehydes, acetophenones and urea in the presence of NaHSO4 at 90◦C without solvent and promoter (Scheme 1). We initiated our study with 2-nitrobenzaldehyde, acetophenone, and urea as a model reaction to determine the best experimental conditions. Solvent, the amount of catalyst and suitable reaction

  嘧啶酮或二氢嘧啶酮 (DHPM) 是重要的杂环化合物，因其生物学 1 和药理 2 作用以及强效的钙通道阻断活性而备受关注。 3-5 因此，近年来，这些化合物的合成引起了相当大的兴趣。 6多组分反应 (MCR) 是高度灵活、化学选择性、收敛和原子效率高的过程。在过去的十年中，使用 MCR 是获取杂环的一种非常有效的方法。2004 年，Wang 等人。首次报道了在 CH3CN 中 FeCl3·6H2O/TMSCl 存在下，由芳香醛、芳香酮和尿素合成 5-未取代的 3,4-二氢嘧啶-2(1H)-酮的 MCR 制备方法。后来，其他催化剂如 NaI/TMSCl、8 Co(OAc)2/TMSCl、tBuONa/MWI、10 PTSA/MWI、11 AlCl3 或 AlBr3 in CH3CN、I2、ZnI2/MWI、Fe(NO3)3·9H2O 和 N2 气氛下的 AlCl3/KI16 等也已被使用。然
• PPh₃/I₂-catalyzed one-pot synthesis of 4,6-diarylpyrimidin-2(1<i>H</i>)-ones
  作者：Yanzhi Zhang、Min Lei、Kangsheng Xue、Guoxiang Sun、Yang Zhou、Jinjun Hou、Huali Long、Zijia Zhang、Xubing Chen、Wanying Wu

  DOI：10.1080/00397911.2020.1815784

  日期：2020.12.1

  6-diarylpyrimidin-2-(1H)-ones is described. Under the experimental conditions, the main reaction products are 4,6-diarylpyrimidin-2-(1H)-ones not 4,6-diaryl-3,4-dihydropyrimidin-2(1H)-ones. The advantage of this method is to achieve improved product yields with an inexpensive and readily available catalyst, and easy experimental set-up, which provides a good method to synthesize 4,6-diarylpyrimidin-2-(1H)-ones. Graphical

  摘要 介绍了一种利用PPh3/I2催化芳香酮、芳香醛和尿素三组分Biginelli反应合成4,6-二芳基嘧啶-2-(1H)-酮的方法。在实验条件下，主要反应产物是 4,6-二芳基嘧啶-2-(1H)-ones 而不是 4,6-diaryl-3,4-dihydropyrimidin-2(1H)-ones。这种方法的优点是使用廉价易得的催化剂和简单的实验装置实现了更高的产品收率，这为合成 4,6-二芳基嘧啶-2-(1H)-酮提供了一种很好的方法。图形概要
• Synthesis and in vitro and in vivo antitumor/anticancer activity of novel O-Mannich bases of 4,6-diaryl-3,4-dihydropyrimidine-2(1H)-ones
  作者：K. Venkateshwarlu、G. Chakradar Rao、V. M. Reddy、Y. Narasimha Reddy

  DOI：10.1007/s13738-014-0438-2

  日期：2014.12

  A new series of [4,6 substituted diaryl-1,6-dihydropyrimidin-2-yl-oxymethyl]-amines 5a–o have been synthesized by the Mannich condensation on the respective 4,6-diaryl-3,4-dihydropyrimidine-2(1H)-ones 4, in basic medium using formaldehyde along with three secondary amines, viz., dimethylamine, piperidine and morpholine. The dihydropyrimidinones 4 in turn were synthesized by the cyclocondensation of chalcones 3 with urea. Alternatively, compounds 4 were also prepared directly by one-pot 3-component cyclocondensation reaction starting from acetophenone, benzaldehyde and urea. The structures of all the newly synthesized compounds have been confirmed by their spectral and analytical data. All the O-Mannich bases 5 have been evaluated for their in vitro cytotoxic and antitumor activities, and based on the results, the potent compounds were selected for in vivo activity, as well. Only one compound 5m of the series has been found to be relatively more effective.

  新系列的[4,6取代的二芳基-1,6-二氢嘧啶-2-基-氧甲基]-胺类化合物5a–o是通过在碱性介质中对各自的4,6-二芳基-3,4-二氢嘧啶-2(1H)-酮4进行曼尼希缩合反应合成的，使用了甲醛与三种二级胺，即二甲胺、哌啶和吗啉。这些二氢嘧啶酮4又是通过查尔酮3与尿素的环状缩合反应合成的。或者，化合物4也可以通过从乙酮、苯甲醛和尿素出发的三组分一锅合成反应直接制备。所有新合成化合物的结构已通过其光谱和分析数据得到确认。所有的O-曼尼希碱基5都被评估了体外细胞毒性和抗肿瘤活性，并根据结果选出了有效的化合物进行体内活性测试。在该系列中，仅发现化合物5m相对更有效。
• Facile Biginelli-Type Reactions Catalysed by Super Acidic Ionic Liquid under Solvent-Free Conditions
  作者：Liang Wang、Min Zhou、Qun Chen、Ming-Yang He

  DOI：10.3184/174751912x13518654161237

  日期：2012.12

  [MeC(OH)2]+ClO4- as a super acidic ionic liquid is an extremely active catalyst for Biginelli-type reactions. The present method is especially effective for the inactive aliphatic aldehydes. The solvent-free conditions, high catalytic activity, wide substrates tolerance and convenient product isolation make the protocol more advantageous.

  [MeC(OH)2]+ClO4- 作为一种超酸性离子液体，是一种非常活跃的 Biginelli 型反应催化剂。本方法对惰性脂肪醛特别有效。无溶剂条件、高催化活性、广泛的底物耐受性和方便的产品分离使该协议更具优势。
• 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。