(±)-methyl 6-methyl-2-oxo-4-(thiophen-3-yl)-1,2,3,4-tetrahydropyrimidine-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: (±)-methyl 6-methyl-2-oxo-4-(thiophen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: methyl 6-methyl-2-oxo-4-(thiophen-3'-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate；methyl 6-methyl-2-oxo-4-(thiophen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate；Methyl 6-methyl-2-oxo-4-(3-thienyl)-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate；methyl 6-methyl-2-oxo-4-thiophen-3-yl-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₁H₁₂N₂O₃S
• 分子量: 252.294
• InChiKey: QJKNCYMVAPBLOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  95.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-噻吩甲醛 、 乙酰乙酸甲酯 、 尿素 在 三苯基锑 作用下， 以 neat (no solvent) 为溶剂， 以95 %的产率得到(±)-methyl 6-methyl-2-oxo-4-(thiophen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  SbPh3：利用 Biginelli 反应合成二氢嘧啶酮和二氢嘧啶-5-甲酰胺的高效催化剂

  摘要：

  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）

  DOI：

  10.1080/00304948.2023.2190711

文献信息

• 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。
• Dihydropyrimidones: As novel class of β-glucuronidase inhibitors
  作者：Farman Ali、Khalid Mohammed Khan、Uzma Salar、Sarosh Iqbal、Muhammad Taha、Nor Hadiani Ismail、Shahnaz Perveen、Abdul Wadood、Mehreen Ghufran、Basharat Ali

  DOI：10.1016/j.bmc.2016.06.002

  日期：2016.8

  Dihydropyrimidones 1–37 were synthesized via a ‘one-pot’ three component reaction according to well-known Biginelli reaction by utilizing Cu(NO3)2·3H2O as catalyst, and screened for their in vitro β-glucuronidase inhibitory activity. It is worth mentioning that amongst the active molecules, compounds 8 (IC50 = 28.16 ± .056 μM), 9 (IC50 = 18.16 ± 0.41 μM), 10 (IC50 = 22.14 ± 0.43 μM), 13 (IC50 = 34.16 ± 0

  Dihydropyrimidones 1 - 37分别经由“一锅”根据通过利用铜公知的Biginelli反应三个组分反应而合成（NO 3）2 ·3H 2 O作为催化剂，并筛选它们的体外β葡萄糖醛酸酶抑制活性。值得一提的是，在活性分子中，化合物8（IC 50  = 28.16±.056μM），9（IC 50  = 18.16± 0.41μM ），10（IC 50  = 22.14±0.43μM），13（IC 50  = 34.16±0.65μM），14（IC 50  = 17.60±0.35μM），15（IC 50  = 15.19±0.30μM），16（IC 50  = 27.16±0.48μM），17（IC 50  = 48.16±1.06μM），22（IC 50  = 40.16±0.85μM），23（IC 50  = 44.16） ±  0.86μM ），24（IC 50 = 47.16±0
• 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones as Antagonists of the Human A_2B Adenosine Receptor: Optimization, Structure–Activity Relationship Studies, and Enantiospecific Recognition
  作者：María Majellaro、Willem Jespers、Abel Crespo、María J. Núñez、Silvia Novio、Jhonny Azuaje、Rubén Prieto-Díaz、Claudia Gioé、Belma Alispahic、José Brea、María I. Loza、Manuel Freire-Garabal、Carlota Garcia-Santiago、Carlos Rodríguez-García、Xerardo García-Mera、Olga Caamaño、Christian Fernandez-Masaguer、Javier F. Sardina、Angela Stefanachi、Abdelaziz El Maatougui、Ana Mallo-Abreu、Johan Åqvist、Hugo Gutiérrez-de-Terán、Eddy Sotelo

  DOI：10.1021/acs.jmedchem.0c01431

  日期：2021.1.14
• Zn2+/MCM-41 catalyzed Biginelli reaction of heteroaryl aldehydes and evaluation of the antimicrobial activity and cytotoxicity of the pyrimidone products
  作者：Zarrin Ghasemi、Farzaneh Farshbaf Orafa、Mahtab Pirouzmand、Gholamreza Zarrini、Behnaz Nikzad Kojanag、Roya Salehi

  DOI：10.1016/j.tetlet.2015.09.143

  日期：2015.11

  The three component Biginelli condensation of various aryl aldehydes, 1,3-dicarbonyls and urea was investigated in the presence of free or MCM-41 supported ZnNO3. The pyrimidone products, which were obtained under solvent-free conditions, were evaluated for antibacterial and antifungal activities as well as their cytotoxicities. (C) 2015 Elsevier Ltd. All rights reserved.