6-甲基-2-氧代-4-噻吩-3-基-3,4-二氢-1H-嘧啶-5-羧酸乙酯 | 352692-70-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 6-甲基-2-氧代-4-噻吩-3-基-3,4-二氢-1H-嘧啶-5-羧酸乙酯
• 英文名称: (±)-ethyl 6-methyl-2-oxo-4-(thiophen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: ethyl 6-methyl-2-oxo-4-(thiophen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate；5-ethoxycarbonyl-4-(thiophen-3-yl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one；SY1AF080；SYAF080；ethyl 6-methyl-2-oxo-4-thiophen-3-yl-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 352692-70-7
• 化学式: C₁₂H₁₄N₂O₃S
• 分子量: 266.321
• InChiKey: YDPAVIZFYHAEHR-UHFFFAOYSA-N

物化性质

• 熔点：
  231-232 °C
• 沸点：
  394.0±42.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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 、 乙酰乙酸乙酯 、 尿素 在 三苯基锑 作用下， 以 neat (no solvent) 为溶剂， 以90 %的产率得到6-甲基-2-氧代-4-噻吩-3-基-3,4-二氢-1H-嘧啶-5-羧酸乙酯
  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

• Concentrated solar radiation as a renewable heat source for a preparative-scale and solvent-free Biginelli reaction
  作者：Yatin U. Gadkari、Navnath T. Hatvate、Balaram S. Takale、Vikas N. Telvekar

  DOI：10.1039/d0nj01351j

  日期：——

  A well-known Biginelli reaction for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones was performed in an environmentally responsible manner. Large numbers of substrates were screened, and found to give excellent yields of the desired products. In addition to the synthesis of drug molecules, the reaction was easily scaled up to 50 mmol. The present method was also energy efficient and saved

  以对环境负责的方式进行了众所周知的Biginelli反应，该反应用于合成3,4-二氢嘧啶-2（1 H）-酮/硫酮。筛选了大量的底物，发现得到所需产物的优异产率。除了合成药物分子外，该反应还容易扩大到50 mmol。与传统方法相比，本方法还具有能源效率，并节省了95％以上的能量。
• One Pot Synthesis of Micromolar BACE-1 Inhibitors Based on the Dihydropyrimidinone Scaffold and Their Thia and Imino Analogues
  作者：Jessica Bais、Fabio Benedetti、Federico Berti、Iole Cerminara、Sara Drioli、Maria Funicello、Giorgia Regini、Mattia Vidali、Fulvia Felluga

  DOI：10.3390/molecules25184152

  日期：——

  A library of dihydropyrimidinones was synthesized via a “one-pot” three component Biginelli reaction using different aldehydes in combination with β-dicarbonyl compounds and urea. Selected 2-thiooxo and 2-imino analogs were also obtained with the Biginelli reaction from thiourea and guanidine hydrochloride, respectively. The products were screened in vitro for their β-secretase inhibitory activity. The majority of the compounds resulted to be active, with IC50 in the range 100 nM–50 μM.

  通过使用不同的醛与β-二羰基化合物和尿素的“一锅法”三组分Biginelli反应合成了一系列二氢嘧啶酮类化合物。选择性地，也从硫脲和盐酸胍得到了2-硫氧代和2-亚氨基类似物。这些产物在体外被筛选，用于评估它们的β-分泌酶抑制活性。大多数化合物表现出活性，IC50在100 nM至50 μM范围内。
• 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。
• SUBSTITUTED HETEROCYCLIC COMPOUNDS
  申请人：Abelman Matthew

  公开号：US20090012103A1

  公开（公告）日：2009-01-08

  The present invention relates to novel heterocyclic compounds and to their use in the treatment of various disease states, including cardiovascular diseases and diabetes. In particular embodiments, the structure of the compounds is given by Formula (I): wherein Q1, Q2, R2, R3, R4, R5, and R6 are as described herein. The invention also relates to methods for the preparation of the compounds, and to pharmaceutical compositions containing such compounds.

  本发明涉及新颖的杂环化合物及其在治疗各种疾病状态中的应用，包括心血管疾病和糖尿病。在特定实施例中，化合物的结构由公式（I）给出：其中Q1、Q2、R2、R3、R4、R5和R6如本文所述。该发明还涉及制备这些化合物的方法，以及含有这些化合物的药物组合物。
• Grindstone chemistry: a highly efficient and green method for synthesis of 3,4-dihydropyrimidin-2-(1H)-ones by<scp>l</scp>-tyrosine as an organocatalyst: a combined experimental and DFT study
  作者：Anamika Khaskel、Prasanta Gogoi、Pranjit Barman、Biman Bandyopadhyay

  DOI：10.1039/c4ra05244g

  日期：——

  A single step, mild, environmentally friendly green method has been developed for the synthesis of physiologically active 3,4-dihydropyrimidin-2-(1H)-ones employing L-tyrosine as catalyst under solvent-free conditions at room temperature via grinding. The procedure is efficient, time saving and gives high-yields. The structures and purity of these compounds were confirmed by FT-IR, NMR (1H and 13C) and HRMS spectral analysis. DFT calculations have been used to show the effectiveness of L-tyrosine as a suitable catalyst for the above reaction.

  已开发出一种单步、温和、环保的绿色方法，在常温下无溶剂条件下，通过研磨法以L-酪氨酸作为催化剂合成生理活性的3,4-二氢嘧啶-2-(1H)-酮。该过程高效、节省时间，并且产率较高。这些化合物的结构和纯度通过FT-IR、NMR（1H和13C）以及HRMS光谱分析得到确认。DFT计算被用来展示L-酪氨酸作为上述反应适宜催化剂的有效性。