5-(ethoxycarbonyl)-6-methyl-4-(4-biphenylyl)-3,4-dihydro-pyrimidin-2(1H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(ethoxycarbonyl)-6-methyl-4-(4-biphenylyl)-3,4-dihydro-pyrimidin-2(1H)-one
• 英文别名: ethyl 1,2,3,4-tetrahydro-6-methyl-2-oxo-4-biphenylpyrimidine-5-carboxylate；ethyl 4-(biphenyl-4-yl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 6-methyl-2-oxo-4-(4-phenylphenyl)-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₂₀H₂₀N₂O₃
• 分子量: 336.39
• InChiKey: OVDBCSFTRVIBHF-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：

  5-(ethoxycarbonyl)-6-methyl-4-(4-biphenylyl)-3,4-dihydro-pyrimidin-2(1H)-one 在 ammonium cerium(IV) nitrate 、 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 1.5h， 以79%的产率得到ethyl 6-methyl-4-biphenyl-pyrimidin-2(1H)-one-5-carboxylate
  参考文献：
  名称：

  Regioselective dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones mediated by ceric ammonium nitrate

  摘要：

  Ceric ammonium nitrate (CAN) has been explored for the regioselective oxidation of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs). Interestingly, we obtained ethyl 2,4-dioxo-6-phenyl-tetrahydropyrimidin-5-carboxylates as the major products during the oxidation of DHPMs by CAN/AcOH at 80 degrees C. The reaction afforded a mixture of products while employing CAN in organic solvents without additives. However, the regioselective dehydrogenated product, ethyl 6-methyl-4-aryl(alkyl)-pyrimidin-2(1H)-one-5-carboxylate was obtained by performing the reaction with NaHCO3. The single crystal X-ray crystallography of ethyl 6-methyl-4-(2-phenyl)-pyrimidin-2(1H)-one-5-carboxylate revealed that the oxidized product existed in amidic form rather than aromatized enol form of pyrimidines. The efficiency of the present protocol enabled the synthesis of structurally diverse pyrimidines in moderate to good yields under milder reaction conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.063
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 对苯基苯甲醛 、 尿素 在 sulfonic acid and ionic liquid functionalized covalent organic framework 作用下， 反应 2.5h， 以60%的产率得到5-(ethoxycarbonyl)-6-methyl-4-(4-biphenylyl)-3,4-dihydro-pyrimidin-2(1H)-one
  参考文献：
  名称：

  磺酸和离子液体官能化的共价有机骨架，可有效催化Biginelli反应

  摘要：

  通过并入多组分Povarov反应和合成后修饰，制备了喹啉连接和离子液体装饰的共价有机骨架。咪唑鎓和磺酸修饰的COF-IM-SO 3 H可以是高效的布朗斯台德酸催化剂，以无溶剂方式以非均相方式促进Biginelli反应。另外，在基于COF-IM-SO 3 H壳聚糖气凝胶的杯形反应器上已经容易实现放大的Biginelli反应。

  DOI：

  10.1021/acs.joc.0c02423

文献信息

• (C₅H₆N₄O)(C₅H₅N₄O)₃(C₅H₄N₄O)[Bi₂Cl₁₁]Cl₂as a simple and efficient catalyst in Biginelli reaction
  作者：Xiang Zhang、Xiaoyu Gu、Yuhua Gao、Shipeng Nie、Hongfei Lu

  DOI：10.1002/aoc.3590

  日期：2017.4

  A highly efficient and facile procedure for the one‐pot three‐component synthesis of 3,4‐dihydropyrimidin‐2‐(1H)ones/thiones from the one‐pot condensation of aldehyde, β‐dicarbonyl compound and urea/thiourea was developed. The methodology is applicable to a wide range of substrates with high yield in the presence of (C5H6N4O)(C5H5N4O)3(C5H4N4O)[Bi2Cl11]Cl2. The complex is an air‐stable, environmentally

  开发了一种高效，简便的方法，该方法可通过醛，β-二羰基化合物和尿素/硫脲的一锅缩合反应一锅三组分合成3,4-二氢嘧啶-2-（1 H）酮/硫酮。该方法适用于（C 5 H 6 N 4 O）（C 5 H 5 N 4 O）3（C 5 H 4 N 4 O）[Bi 2 Cl 11 ] Cl 2。该络合物是一种对空气稳定，对环境友好且可回收的催化剂，可以有效催化Biginelli反应。该催化剂具有高催化效率和低催化剂载量，并且可以循环十次而活性损失很小。
• Revisit to the Biginelli reaction: a novel and recyclable bioglycerol-based sulfonic acid functionalized carbon catalyst for one-pot synthesis of substituted 3,4-dihydropyrimidin-2-(1H)-ones
  作者：Karnakar Konkala、Narayana Murthy Sabbavarapu、Ramesh Katla、Nageswar Yadavalli Venkata Durga、Vijai Kumar Reddy T、Prabhavathi Devi Bethala L.A.、Prasad Rachapudi B.N.

  DOI：10.1016/j.tetlet.2012.02.018

  日期：2012.4

  synthetic protocol has been developed for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones by using a novel bioglycerol-based sulfonic acid functionalized carbon catalyst, devoid of moisture sensitive metal catalysts and corrosive acidic reagents. The developed method has the advantages of good to excellent yields, short reaction times, operational simplicity, and a recyclable catalyst. The catalyst can be

  通过使用新型的基于生物甘油的磺酸官能化的碳催化剂，开发了一种简单高效的合成方案，用于合成3,4-二氢嘧啶-2-（1 H）-一，该方法缺少对水分敏感的金属催化剂和腐蚀性酸性试剂。所开发的方法具有良好至优异的产率，短的反应时间，操作简单和可回收的催化剂的优点。该催化剂可以通过简单的方法由廉价且容易获得的甘油制备，并且已显示出可回收和可重复使用多达四个循环而没有任何活性损失。
• Synthesis, Characterization, and Anticancer Activities Evaluation of Compounds Derived from 3,4-Dihydropyrimidin-2(1H)-one
  作者：Ye Liu、Jiaqi Liu、Renmei Zhang、Yan Guo、Hongbo Wang、Qingguo Meng、Yuan Sun、Zongliang Liu

  DOI：10.3390/molecules24050891

  日期：——

  antitumor activity. The results from in vivo study indicated the great potential of compound 3d to serve as a lead compound for novel anti-tumor drugs to treat glioma. Pharmacophore study regarding the structure-activity relations of DHPMs were also conducted. Our results here could provide a guide for the design of novel bioactive 3,4-dihydropyrimidin-2(1H)-one compounds.

  3,4-二氢嘧啶-2（1H）-one化合物（DHPMs）具有广泛的生物学活性，主要通过Biginelli反应和N-烷基化制备。在本研究中，使用氢氧化四丁铵研究了N 1的选择性烷基化。对所有合成化合物的体外细胞毒性研究表明，在DHPMs的R 3中引入芳基链以及在R 1中引入低电子给体基团有助于抗增殖能力。发现较大的分配系数（Log P）值和合适的极性表面积（PSA）值对于维持抗肿瘤活性都是重要的。体内研究的结果表明，化合物3d有望作为新型抗肿瘤药物治疗神经胶质瘤的先导化合物。还进行了有关DHPMs构效关系的药理学研究。我们的研究结果可为新型生物活性3,4-二氢嘧啶-2（1H）-one化合物的设计提供指导。
• 一种3,4-二氢嘧啶-2(1H)-酮类化合物的制备方法
  申请人：宁夏大学

  公开号：CN111675658B

  公开（公告）日：2023-06-23

  本发明公开了一种3,4‑二氢嘧啶‑2(1H)‑酮类化合物的制备方法，包括以下步骤：(1)将反应底物原料芳香醛类、1,3‑二酮酯、尿素和微量的水分别加入到反应器内；(2)在密闭状态下加热到110‑160℃，保持一定的时间；(3)停止加热，使反应器冷却到室温至40℃，加入有机溶剂冲洗物料到收集槽中；(4)进行固液分离、洗涤和再结晶操作，获得目标产物3,4‑二氢嘧啶‑2(1H))酮类化合物；(5)溶剂母液收集并回收产物、回收溶剂套用。本发明与现有技术相比的优点在于：成本低、环保。
• Trifluoroethanol as a Metal-Free, Homogeneous, and Recyclable Medium for the Efficient One-Pot Synthesis of Dihydropyrimidones
  作者：S. V. Rashmi、N. C. Sandhya、B. Raghava、M. N. Kumara、K. Mantelingu、K. S. Rangappa

  DOI：10.1080/00397911.2010.525335

  日期：2012.2.1

  Trifluoroethanol is an efficient and recyclable medium in promoting one-pot, three-component condensation reactions of beta-ketoesters, aldehydes, and urea (or thiourea) to afford the corresponding dihydropyrimidones in good yields. This protocol does not require the use of an acid or base catalyst.