N-(4-methoxyphenyl)-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide | 333767-81-0

• 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: N-(4-methoxyphenyl)-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide
• 英文别名: N-(4-methoxyphenyl)-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydro-5-pyrimidinecarboxamide；N-(4-methoxyphenyl)-6-methyl-2-oxo-4-phenyl-3,4-dihydro-1H-pyrimidine-5-carboxamide
• CAS: 333767-81-0
• 化学式: C₁₉H₁₉N₃O₃
• 分子量: 337.378
• InChiKey: ZNRQABQUHMHPRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  79.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-methoxyphenyl)-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide 、 苯甲醛 在 iron(III) chloride hexahydrate 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以85%的产率得到(E)-N-(4-methoxyphenyl)-2-oxo-4-phenyl-6-styryl-1,2,3,4-tetrahydropyrimidine-5-carboxamide
  参考文献：
  名称：

  铁催化的比格内利产物的乙烯基醛醇缩合反应及其在吡喃并[4,3- d ]嘧啶酮中的应用

  摘要：

  已经开发了一种新型的铁催化的比格内利产物与芳基醛基的乙烯基醇醛醇醛缩合反应，用于合成潜在的生物活性（E）-6-芳基乙烯基-二氢嘧啶-2（1 H）-ones。这些材料是药物样吡啶并[4,3- d ]嘧啶衍生物的有价值的合成前体。二氢嘧啶-2（1 H）-的5-位的酰胺基在乙烯基醇醛缩合反应中起重要作用。

  DOI：

  10.1021/jo402773r
• 作为产物：
  描述：

  N-(4-methoxyphenyl)-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carbothioamide 在 溶剂黄146 、 sodium nitrite 作用下， 反应 8.0h， 以42%的产率得到N-(4-methoxyphenyl)-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide
  参考文献：
  名称：

  2-Acylthioacetamides in the Biginelli Reaction

  摘要：

  We have demonstrated for the first time a Biginelli reaction of 2-acylthioacetamides with aromatic aldehydes and ureas or thioureas, leading to N-Ar-1-4-Ar-2-6-R-1-1-R-2-2-oxo(thioxo)-1,2,3,4-tetrahydro-pyrimidine-5-carbothioamides. The regioselectivity of this process matched the concept of hard/soft Lewis acids and bases. It was established that nitrous acid or other oxidants converted the synthesized compounds into N-Ar-1-4-Ar-2-6-R-1-1-R-2-2-oxo(thioxo)-1,2,3,4-tetrahydropyrimidine-5-carboxamides, and not the expected 4-Ar-2-6-R-1-1-R-2-5-(1,3-benzothiazol-2-yl)-1,2,3,4-tetrahydropyrimidin-2-ones(thiones).

  DOI：

  10.1007/s10593-014-1429-z

文献信息

• α-Zirconium Sulfophenylphosphonate as a Catalyst for the Synthesis of 3,4-Dihydropyrimidin-2(1H)-One Derivatives Under Solvent Free Conditions
  作者：Ornelio Rosati、Massimo Curini、Francesca Montanari、Morena Nocchetti、Salvatore Genovese

  DOI：10.1007/s10562-011-0604-4

  日期：2011.6

  4-Dihydropyrimidin-2(1H)-one derivatives were synthesized using layered α-zirconium sulfophenylphosphonate as a recyclable heterogeneous catalyst. Several classes of reagents, such as functionalized aromatic and aliphatic aldehydes, β-dicarbonyl derivatives and 2-aminobenzimidazole, were used to synthesize different 3,4-dihydropyrimidin-2(1H)-one derivatives under solvent free conditions.Graphical Abstract

  摘要 以层状 α-磺基苯基膦酸锆为可回收的多相催化剂，合成了 3,4-二氢嘧啶-2(1H)-one 衍生物。几类试剂，如官能化的芳香醛和脂肪醛、β-二羰基衍生物和 2-氨基苯并咪唑，用于在无溶剂条件下合成不同的 3,4-二氢嘧啶-2(1H)-one 衍生物。图形摘要
• Synthesis of 3,4-Dihydropyrimidin-2(1H)-one-5-carboxamides
  作者：Mousa Soleymani、Hamid Reza Memarian

  DOI：10.1515/znb-2010-0408

  日期：2010.4.1

  The synthesis of various dihydropyrimidinone derivatives bearing carbamoyl moieties in 5-position under reflux conditions and microwave irradiation is described. An efficient three-component Biginelli reaction using catalytic amounts of zirconium(IV) chloride as an efficient catalyst leads to the formation of these compounds.

  在回流条件和微波辐射下合成了带有5位羰基基团的各种二氢嘧啶酮衍生物。使用催化量的四氯化锆作为高效催化剂进行高效的三组分Biginelli反应，导致这些化合物的形成。
• Synthesis of Biginelli Compounds Using Cobalt Hydrogen Sulfate
  作者：Hamid Reza Memarian、Mahnaz Ranjbar

  DOI：10.1002/jccs.201190016

  日期：2011.8

  Efficient synthesis of various 2‐oxo(thioxo)‐1,2,3,4‐tetrahydropyrimidines containing acetyl, carboethoxy, carbomethoxy and carboxamide groups on 5‐position of the N1‐substituted and N1‐unsubstituted heterocyclic ring was achieved using cobalt hydrogen sulfate Co(HSO4)2 under thermal conditions. Good to high yield, shorter reaction times, easy work up and simple preparation of Co(HSO4)2 are the advantages

  使用钴实现了在N 1-取代和N 1-未取代的杂环的5位上含有乙酰基，碳乙氧基，碳甲氧基和羧酰胺基团的各种2-氧代（thioxo）-1、2、3、4-四氢嘧啶的高效合成在热条件下产生硫酸氢Co（HSO 4）2。该合成方法的优点是产率高至高，反应时间短，易于后处理和制备Co（HSO 4）2简便。
• Synthesis of novel Hantzsch dihydropyridines and Biginelli dihydropyrimidines of biological interest: a 3D-QSAR study on their cytotoxicity
  作者：B. R. Prashantha Kumar、Pankaj Masih、E. Karthikeyan、Ankur Bansal、Suja、Pottekad Vijayan

  DOI：10.1007/s00044-009-9195-7

  日期：2010.5

  We report a library consisting of some novel Hantzsch dihydropyridines and Biginelli dihydropyrimidines of biological interest as well as their synthesis and analysis. The important steps in the synthetic part were found to be Hantzsch and Biginelli multicomponent reactions. The synthesized compounds were screened for their in vitro antibacterial activity against two gram-positive bacteria: Staphylococcus

  我们报告由一些新型的Hantzsch dihydropyridines和Biginelli dihydropyrimidines具有生物学意义以及它们的合成和分析组成的库。发现合成部分中的重要步骤是Hantzsch和Biginelli多组分反应。筛选合成的化合物对两种革兰氏阳性细菌：金黄色葡萄球菌和枯草芽孢杆菌的体外抗菌活性。标题化合物没有显示出潜在的抗菌活性。此外，化合物对Vero细胞具有体外细胞毒性作用。化合物表现出弱，中度或高细胞毒性。化合物4a，4b，4c，4f，4g，4h，4i，7i，7l，7m和7r表现出潜在的细胞毒性。CoMFA研究已鉴定出有助于其细胞毒性的结构特征。
• Design, Synthesis, Analysis, Evaluation of Cytotoxicity Against MCF-7 Breast Cancer Cells, 3D QSAR Studies and EGFR, HER2 Inhibition Studies on Novel Biginelli 1,4-Dihydropyrimidines
  作者：Namburu Lalitha Naishima、Syed Faizan、Ruby Mariam Raju、Aki Satya Venkata Lakshmi Sruthi、Veena NG、Gyanedra Kumar Sharma、Kumar S Vasanth、Vasanth Kumar Shivaraju、Ramith Ramu、BR Prashantha Kumar

  DOI：10.1016/j.molstruc.2022.134848

  日期：2023.4