ethyl 4-(4-methylphenyl)-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl 4-(4-methylphenyl)-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: 1,2,3,4-tetrahydro-4-(4-methylphenyl)-2-oxo-6-phenyl-5-pyrimidinecarboxylic acid ethyl ester；ethyl 4-(4-methylphenyl)-2-oxo-6-phenyl-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₂₀H₂₀N₂O₃
• 分子量: 336.39
• InChiKey: RFIQBKDJQPTXCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-(4-methylphenyl)-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 四氯化碳 、 [Re(CO)₃(phen)Br] 、 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 12.0h， 以91%的产率得到ethyl 2-oxo-6-phenyl-4-(p-tolyl)-1,2-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  hen（I）配合物在可见光下光化学制备嘧啶丁2（1 H）-ones

  摘要：

  与铼的可见光照射（λ> 400nm）的（I）配合物（P1 - P4）由3,4-二氢嘧啶2，光化学转化（1 ħ） -酮向嘧啶-2-（1 ħ） -酮在在含有CCl 4和K 2 CO 3的CH 3 CN-H 2 O溶液中，室温可以达到良好或极好的收率。发光猝灭研究和产物分析表明rh（I）配合物P和3,4-dihydropyrimidin-2（1 H）-ones之间的光诱导电子转移在初始事件中起重要作用。

  DOI：

  10.1021/jo102062u
• 作为产物：
  描述：

  2-Benzoyl-3-phenoxycarbonylamino-3-p-tolyl-propionic acid ethyl ester 在 ammonium hydroxide 、 对甲苯磺酸 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 ethyl 4-(4-methylphenyl)-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  A new approach to the synthesis of Biginelli compounds

  摘要：

  A new synthesis of 4-aryl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid esters is based on the reactions of alpha-tosyl-substituted phenyl carbamates with the enolates of beta-oxoesters followed by treatment with ammonia and dehydration of the resulting 4-hydroxyhexahydropyrimidin-2-ones.

  DOI：

  10.1070/mc2005v015n02abeh002022

文献信息

• Synthesis of Biginelli dihydropyrimidinone derivatives with various substituents on aluminium-planted mesoporous silica catalyst
  作者：Hiroaki Murata、Haruro Ishitani、Masakazu Iwamoto

  DOI：10.1039/b920821f

  日期：——

  Biginelli reactions were well catalyzed on mesoporous silica MCM-41 (M41) whose activity was much greater than that of amorphous silica. Octane was the most suitable among 6 kinds of solvents examined. The addition of metal ions on M41 enhanced the catalytic activity in the order Al > Ti > Fe = In. Al-planted M41s with Si/Al ratios of 45–35 showed the highest catalytic activity and could be used repeatedly though a small loss of the activity was observed. The catalysis could widely be applied to obtain various substituted dihydropyrimidinones (DHPMs) with high yields, some of which were very difficult to prepare until now. In addition, Biginelli reactions were combined with formyl C–H insertion reactions of diazoester on mesoporous silica; that is, a tandem one-pot four-component DHPM synthesis was attempted. Acetaldehyde, ethyl diazoacetate, p-tolualdehyde, and urea could be condensed and the corresponding DHPM derivative was obtained with 50% yield on Al-planted M41.

  介孔二氧化硅 MCM-41 (M41) 能很好地催化 Biginelli 反应，其活性远远高于无定形二氧化硅。在所考察的 6 种溶剂中，辛烷是最合适的溶剂。在 M41 上添加金属离子可提高催化活性，其顺序为 Al > Ti > Fe = In。硅/铝比为 45-35 的铝植入 M41 显示出最高的催化活性，虽然活性略有下降，但仍可重复使用。该催化反应可广泛应用于高产率获得各种取代的二氢嘧啶酮（DHPM），其中一些到目前为止还很难制备。此外，还在介孔二氧化硅上将 Biginelli 反应与重氮酯的甲酰基 C-H 插入反应相结合，即尝试了串联式一锅四组份 DHPM 合成。乙醛、重氮乙酸乙酯、对甲苯酚和尿素可以缩合，并在 Al-planted M41 上得到相应的 DHPM 衍生物，收率为 50%。
• An electrochemical off–on method for pyrimidin-2(1<i>H</i>)-one synthesis <i>via</i> three-component cyclization
  作者：Yanyan Kong、Yabo Li、Mengmeng Huang、Jung Keun Kim、Yangjie Wu

  DOI：10.1039/c9gc02005e

  日期：——

  A green and simple ‘one-pot’ electrochemical off–on approach to synthesize pyrimidin-2(1H)-ones was realized without any catalyst, oxidant and toxic reagent. The desired products were obtained in moderate to good yields after the stepwise ‘one-pot’ reaction. The results of control experiments and cyclic voltammetry indicated that the electrooxidation of DHPMs might proceed via two steps process losing

  在没有任何催化剂，氧化剂和有毒试剂的情况下，实现了一种绿色且简单的“一锅法”电化学关闭法，以合成嘧啶2-2 （1 H）-酮。在逐步的“一锅法”反应之后，以中等至良好的产率获得了所需的产物。控制实验和循环伏安法的结果表明，通过自由基中间体的吸收控制，DHPMs的电氧化可通过两步过程损失两个电子和两个质子来进行。