4-(3-bromophenyl)-3,4-dihydro-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: 4-(3-bromophenyl)-3,4-dihydro-6-phenylpyrimidin-2(1H)-one
• 英文别名: 4-(3-bromophenyl)-6-phenyl-3,4-dihydro-1H-pyrimidin-2-one
• 化学式: C₁₆H₁₃BrN₂O
• 分子量: 329.196
• InChiKey: RFFJVAJERCYECG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  41.1
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  间溴苯甲醛 、 苯乙酮 、 尿素 在 TiO₂ supported multi walled carbon nanotube 作用下， 以 neat (no solvent) 为溶剂， 反应 0.17h， 以92%的产率得到4-(3-bromophenyl)-3,4-dihydro-6-phenylpyrimidin-2(1H)-one
  参考文献：
  名称：

  金属氧化物-MWCNTs纳米复合材料催化无溶剂合成4,6-二芳基-3,4-二氢嘧啶-2(1H)-ones的新方案

  摘要：

  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。

  DOI：

  10.1016/j.molstruc.2014.05.012

文献信息

• 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。
• 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。
• MnO2–MWCNT nanocomposites as efficient catalyst in the synthesis of Biginelli-type compounds under microwave radiation
  作者：Javad Safari、Soheila Gandomi-Ravandi

  DOI：10.1016/j.molcata.2013.02.021

  日期：2013.7

  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.
• 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.