4-(4-methoxyphenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide | 361481-55-2

• 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: 4-(4-methoxyphenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide
• 英文别名: 6-methyl-2-oxo-N-phenyl-4-(4-methoxyphenyl)-1,2,3,4-tetrahydropyrimidin-5-carboxamide；4-(4-methoxyphenyl)-6-methyl-2-oxo-N-phenyl-3,4-dihydro-1H-pyrimidine-5-carboxamide
• CAS: 361481-55-2
• 化学式: C₁₉H₁₉N₃O₃
• 分子量: 337.378
• InChiKey: UJGHNWNCMHNLTI-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：

  4-(4-methoxyphenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide 、 4-甲氧基苯甲醛 在 iron(III) chloride hexahydrate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以73%的产率得到(E)-4-(4-methoxyphenyl)-6-(4-methoxystyryl)-2-oxo-N-phenyl-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：

  4-(4-methoxyphenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carbothioamide 在 溶剂黄146 、 sodium nitrite 作用下， 反应 8.0h， 以45%的产率得到4-(4-methoxyphenyl)-6-methyl-2-oxo-N-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

• Iron-catalyzed four-member multicomponent reaction for assembly of (E)-6-arylvinyl-3,4-dihydropyrimidin-2(1H)-ones
  作者：Zhiguo Zhang、Lianqiang Zhang、Xinyu Duan、Xiangqian Yan、Yan Yan、Qingfeng Liu、Tongxin Liu、Guisheng Zhang

  DOI：10.1016/j.tet.2015.07.039

  日期：2015.10

  A novel iron-catalyzed one-pot multi-component tandem reaction of acetoacetamide, urea, and two molecules of aryl aldehydes has been developed. This reaction provides a general, straightforward, practical and useful method for the preparation of potential bioactive (E)-6-arylvinyl-3,4-dihydropyrimidin-2(1H)-ones. They are also versatile precursors leading to diverse drug-like dihydropyrimidin-2(1H)-one

  已开发出一种新的铁催化的乙酰乙酰胺，尿素和两分子芳基醛的单锅多组分串联反应。该反应为制备潜在的生物活性（E）-6-芳基乙烯基-3,4-二氢嘧啶-2（1 H）-酮提供了一种通用，直接，实用和有用的方法。它们还是通用的前体，可产生多种药物样的二氢嘧啶-2（1 H）-一衍生物。避免质子酸并使用单一廉价且对环境无害的催化剂的特征使该方法更有价值。
• An efficient green protocol for the preparation of acetoacetamides and application of the methodology to a one-pot synthesis of Biginelli dihydropyrimidines. Expansion of dihydropyrimidine topological chemical space
  作者：Fernando H. S. Gama、Rodrigo O. M. A. de Souza、Simon J. Garden

  DOI：10.1039/c5ra14355a

  日期：——

  A one pot synthesis of Biginelli dihydropyrimidines. The novel use of the amino acids allows topological diversification of the chemical space.

  一锅法合成Biginelli双氢嘧啶化合物。氨基酸的新颖应用使化学空间具有拓扑多样性。
• A General, Effcient and Green Procedure for Synthesis of Dihydropyrimidine-5-carboxamides in Low Melting Betaine Hydrochloride/Urea Mixture
  作者：Peng Liu、Jianwu Hao、Zhanhui Zhang

  DOI：10.1002/cjoc.201500862

  日期：2016.6

  A simple, facile and convenient strategy has been developed for the synthesis of dihydropyrimidine‐5‐carboxamides in low melting mixture of betaine hydrochloride/urea. In this procedure, the low melting mixture of betaine hydrochloride/urea plays a triple role: as a catalyst, solvent and reactant. The present green protocol has advantages such as high yield of products, short reaction times, operational

  已经开发了一种简单，简便，方便的策略，用于在甜菜碱盐酸盐/尿素的低熔点混合物中合成二氢嘧啶-5-羧酰胺。在此过程中，甜菜碱盐酸盐/尿素的低熔点混合物起着三重作用：作为催化剂，溶剂和反应物。当前的绿色方案具有以下优点：产品产量高，反应时间短，操作简便，无需色谱分离，生态友好以及适用于大规模合成。
• Nebivolol nanoparticles: a first catalytic use in Biginelli and Biginelli-like reactions
  作者：Anamika Khaskel、Pranjit Barman、Subir Kumar Maiti、Utpal Jana

  DOI：10.1139/cjc-2017-0621

  日期：2018.12

  Herein, we report the catalytic activity of nebivolol nanoparticles a novel organocatalyst for the synthesis of DHPMs and DHPM-5-carboxamides. The nanoparticles are confirmed by DSC, TEM, AFM, and IR spectroscopy. The catalyst can be readily recovered and reused for the next four runs without any significant impact on the yields of the products. The products are fully characterized by FTIR, ¹H NMR, ¹³C NMR, and distortionless enhanced polarization transfer (DEPT) NMR. The methodology adopted here offers several advantages such as solvent-free reaction, low loading of catalyst, short reaction times, and quantifiable yields.

  在这里，我们报道了尼比地尔纳米颗粒作为合成DHPMs和DHPM-5-羧酰胺的新型有机催化剂的催化活性。通过DSC、TEM、AFM和IR光谱确认了这些纳米颗粒。该催化剂可以轻松回收并在接下来的四次运行中重复使用，对产物的产率没有显著影响。产物通过FTIR、1H NMR、13C NMR和无畸变增强极化转移（DEPT）NMR进行了全面表征。这里采用的方法具有多种优点，如免溶剂反应、催化剂负载量低、反应时间短和产率可量化。
• SbPh ₃ : An Efficient Catalyst for Dihydropyrimidinone and Dihydropyrimidin-5-carboxamide Synthesis Using the Biginelli Reaction
  作者：Anamika Khaskel、Santosh Kumari Bajiya、Suman Lata、Rakesh Kumar Sharma、Shatabdi Basu

  DOI：10.1080/00304948.2023.2190711

  日期：2023.11.2

  Published in Organic Preparations and Procedures International: The New Journal for Organic Synthesis (Vol. 55, No. 6, 2023)

  发表于《国际有机制备和程序：有机合成新期刊》（第 55 卷，第 6 期，2023 年）