ethyl 1,2,3,4-tetrahydro-6-methyl-2-oxo-4-(pyridine-3-yl)pyrimidine-5-carboxylate

• 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: ethyl 1,2,3,4-tetrahydro-6-methyl-2-oxo-4-(pyridine-3-yl)pyrimidine-5-carboxylate
• 英文别名: ethyl 6-methyl-2-oxo-4-(pyridin-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate；5-(ethoxycarbonyl)-6-methyl-4-(3-pyridyl)-3,4-dihydropyrimidin-2(1H)-one；ethyl 6-methyl-2-oxo-4-(pyridine-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 6-methyl-2-oxo-4-pyridin-3-yl-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₃H₁₅N₃O₃
• 分子量: 261.28
• InChiKey: YPGGWPBGMSAMJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  80.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1,2,3,4-tetrahydro-6-methyl-2-oxo-4-(pyridine-3-yl)pyrimidine-5-carboxylate 在 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.5h， 以84%的产率得到ethyl 6-methyl-4-(3-pyridyl)-pyrimidin-2(1H)-one-5-carboxylate
  参考文献：
  名称：

  4-Bis(triphenylphosphonium)-2-butene peroxodisulfate as an efficient oxidizing agent for one-pot synthesis of ethyl pyrimidin-2(1H)-one-5-carboxylates

  摘要：

  An efficient one-pot synthesis of pyrimidin-2(1H)-ones via three-component condensation of aldehyde, ethyl acetoacetate and urea using 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate [BTPBPDS] as an oxidant is described.

  DOI：

  10.1134/s1070363217040284
• 作为产物：
  描述：

  3-吡啶甲醇 、 乙酰乙酸乙酯 、 尿素 在 T₃P 、 二甲基亚砜 作用下， 以 乙酸乙酯 为溶剂， 以75%的产率得到ethyl 1,2,3,4-tetrahydro-6-methyl-2-oxo-4-(pyridine-3-yl)pyrimidine-5-carboxylate
  参考文献：
  名称：

  Propylphosphonic Anhydride-catalyzed Tandem Approach for Biginelli Reaction Starting from Alcohols

  摘要：

  在 T3P®/DMSO 的存在下，通过对多种醇、β-酮酯/β-二硫代氧杂环酯和脲进行单锅三组分氧化环缩合，开发出了一种高效、高度收敛的二氢嘧啶酮（DHPMs）路线。这种新方法始终具有串联和高产率（65-88%）的优势。

  DOI：

  10.1246/cl.130732

文献信息

• One-Pot synthesis of dihydropyrimidinones by dodecylphosphonic acid as solid Bronsted Acid Catalyst under Solvent-Free Conditions via Biginelli condensation
  作者：S. Ghassamipour、A. R. Sardarian

  DOI：10.1007/bf03245884

  日期：2010.3

  Dodecylphosphonic acid is a solid Bronsted acid that catalyzes efficiently the preparation of dihydropyrimidinones by Biginelli condensation under solvent-free conditions. This protocol offers several advantages including high yields, short reaction times, easy work-up, and use of cheap, relatively moderate acidic and safe catalyst.

  十二烷基膦酸是一种固体布朗斯台德酸，可在无溶剂条件下通过Biginelli缩合有效催化制备二氢嘧啶酮。该方案具有许多优点，包括产率高，反应时间短，易于后处理以及使用廉价，相对中等酸性和安全的催化剂。
• Copper-doped mesoporous silica supported dual acidic ionic liquid as an efficient and cooperative reusability catalyst for Biginelli reaction
  作者：Nan Yao、Ming Lu、Xiao Bing Liu、Jin Tan、Yu Lin Hu

  DOI：10.1016/j.molliq.2018.04.121

  日期：2018.7

  A series of MCM-41 supported functionalized ionic liquids doped with copper species were prepared, characterized and evaluated as catalysts in the Biginelli reaction. Most of these supported ionic liquids perform well in the reaction, especially the multifunctional copper coordinated MCM-41 supported heterogeneous catalysts (0.5)IL-TiCl5@[email protected](15) and (0.5)IL-HSO4@[email protected](15)

  制备了一系列掺杂有铜物质的MCM-41负载型官能化离子液体，对其进行了表征和评估，作为Biginelli反应的催化剂。这些负载型离子液体大多数在反应中表现良好，尤其是多官能铜配位的MCM-41负载型多相催化剂（0.5）IL-TiCl 5 @ [受电子邮件保护]（15）和（0.5）IL-HSO 4 @ [受电子邮件保护] ]（15）。催化试验表明，（0.5）IL-HSO 4@ [受电子邮件保护]（15）是Biginelli反应中最好的和强大的催化剂，用于制备3,4-二氢嘧啶酮，产率高至优异。通过过滤可以很容易地将催化剂从反应混合物中分离出来，并在六个连续的循环中重复使用，而不会明显降低催化活性。
• Sulfonic Acid and Ionic Liquid Functionalized Covalent Organic Framework for Efficient Catalysis of the Biginelli Reaction
  作者：Bing-Jian Yao、Wen-Xiu Wu、Luo-Gang Ding、Yu-Bin Dong

  DOI：10.1021/acs.joc.0c02423

  日期：2021.2.5

  quinoline-linked and ionic liquid-decorated covalent organic framework was prepared by incorporation of a multicomponent Povarov reaction and postsynthetic modification. The imidazolium and sulfonic acid-decorated COF-IM-SO3H can be a highly efficient Brønsted acid catalyst to promote the Biginelli reaction under solvent-free conditions in a heterogeneous way. In addition, a scaled-up Biginelli reaction has been

  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。
• Structure based virtual screening-driven identification of monastrol as a potent urease inhibitor
  作者：Umer Rashid、Iram Batool、Abdul Wadood、Ajmal Khan、Zaheer ul-Haq、Muhammad Iqbal Chaudhary、Farzana Latif Ansari

  DOI：10.1016/j.jmgm.2013.04.006

  日期：2013.6

  Virtual screening uses computer based methods to discover new ligands on the basis of biological structures. Among all virtual screening methods structure based docking has received considerable attention. In an attempt to identify new ligands as urease inhibitors, structure-based virtual screening (SBVS) of an in-house database of 10,000 organic compounds was carried out. The X-ray crystallographic structure of Bacillus pasteurii (BP) in complex with acetohydroxamic acid (PDB Code 4UBP) was used as a protein structure. As a starting point, similar to 10,000 compounds of our in-house database were analyzed to check redundancy and the compounds found repeated were removed from the database. Finally 6993 compounds were docked into the active site of BP urease using GOLD and MOE-Dock software. A remarkable feature of this study was the identification of monastrol, a well-known KSP inhibitor already in clinical trials, as a novel urease inhibitor. The hits identified were further evaluated by molecular docking and on examination of the affinity predictions, twenty-seven analogs of monastrol were synthesized by a multicomponent Biginelli reaction followed by their in vitro screening as urease inhibitors. Finally twelve compounds were identified as new urease inhibitors. The excellent in vitro activity suggested that these compounds may serve as viable lead compounds for the treatment of urease related problems. (c) 2013 Elsevier Inc. All rights reserved.
• 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.