7-amino-6-cyano-5-(4-trifluoromethylphenyl)-4-oxo-5H-pyrano[2,3-d]pyrimidinone | 1135579-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃嘧啶类
• 英文名称: 7-amino-6-cyano-5-(4-trifluoromethylphenyl)-4-oxo-5H-pyrano[2,3-d]pyrimidinone
• 英文别名: 7-amino-2,4-dioxo-5-[4-(trifluoromethyl)phenyl]-1,5-dihydropyrano[2,3-d]pyrimidine-6-carbonitrile
• CAS: 1135579-47-3
• 化学式: C₁₅H₉F₃N₄O₃
• 分子量: 350.257
• InChiKey: QSJSJRHKOKLKJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 巴比妥酸 、 丙二腈 在 Zn(L-proline)₂ 作用下， 以 乙醇 为溶剂， 反应 0.67h， 以88%的产率得到7-amino-6-cyano-5-(4-trifluoromethylphenyl)-4-oxo-5H-pyrano[2,3-d]pyrimidinone
  参考文献：
  名称：

  Zn[(L)proline]2：一种合成生物活性吡喃并[2,3-d]嘧啶衍生物的高效催化剂

  摘要：

  通过丙二腈、苯甲醛和巴比妥酸的三组分、一锅缩合反应，使用催化量的 Zn[(L) 脯氨酸]，以优异的收率高效合成了具有生物活性的吡喃并 [2,3-d] 嘧啶衍生物。

  DOI：

  10.1080/00397910903174390

文献信息

• 4,4’-trimethylenedipiperidine as a nitrogen heterocycle solvent and/or catalyst: Liquid phase tandem Knoevenagel–Michael condensation
  作者：Lia ZAHARANI、Nader GHAFFARI KHALIGH、Hayede GORJIAN、Mohd RAFIE JOHAN

  DOI：10.3906/kim-2010-41

  日期：——

  Liquid phase tandem Knoevenagel-Michael condensation of various aromatic and heteroaromatic aldehydes with barbituric acid or 2-thiobarbituric acid and malononitrile was studied in a one-pot three-component reaction. For the first time, TMDP was employed as a safe and efficient solvent and/or catalyst in the liquid and aqueous ethanol medium, respectively, for the practical and eco-friendly Knoevenagel-Michael

  在一锅三组分反应中研究了各种芳香醛和杂芳香醛与巴比妥酸或2-硫代巴比妥酸和丙二腈的液相串联Knoevenagel-Michael缩合反应。TMDP 首次分别在液体和水性乙醇介质中用作安全高效的溶剂和/或催化剂，用于实用且环保的 Knoevenagel-Michael 缩合反应。反应是通过使用更绿色的程序进行的，包括a）在回流温度下使用TMDP作为N-杂环有机催化剂，在包括水和乙醇（1:1 v/v）的绿色介质中，以及b）使用TMDP在 65 °C、无任何溶剂的情况下作为双溶剂-催化剂。在前面提到的两种条件下获得了所需吡喃并[2,3-d]嘧啶酮的高至优异产率。目前的方法具有优点，包括（a）避免危险、有毒、挥发性和易燃材料和溶剂，（b）避免繁琐的过程、恶劣的条件和制备催化剂的多个步骤，（c）使用毒性较小和非腐蚀性催化剂，(d) 最大限度地减少危险废物的产生和简单的后处理过程，以及 (e) TMDP
• SO₃H-functionalized nano-MGO-D-NH₂: Synthesis, characterization and application for one-pot synthesis of pyrano[2,3-<i>d</i>]pyrimidinone and tetrahydrobenzo[<i>b</i>]pyran derivatives in aqueous media
  作者：Heshmatollah Alinezhad、Mehrasa Tarahomi、Behrooz Maleki、Amirhassan Amiri

  DOI：10.1002/aoc.4661

  日期：2019.3

  of a magnetic graphene oxide (GO) nanohybrid and evaluated in the synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3‐d]pyrimidinone derivatives. The GO/Fe3O4 (MGO) hybrid was prepared via an improved Hummers method followed by the covalent attachment of 1,4‐butanesultone with the amino group of the as‐prepared polyamidoamine‐functionalized MGO (MGO‐D‐NH2) to give double‐functionalized magnetic nanoparticles

  SO 3 H-官能化的纳米MGO-D-NH 2催化剂是通过磁性氧化石墨烯（GO）纳米杂化物的多官能化制备的，并在四氢苯并[ b ]吡喃和吡喃[2,3- d ]嘧啶酮衍生物。通过改进的Hummers方法制备GO / Fe 3 O 4（MGO）杂化物，然后将1,4-丁磺酸内酯与已制备的聚酰胺型胺官能化MGO（MGO-D-NH 2）得到双功能化的磁性纳米粒子作为催化剂。表征所制备的纳米颗粒以确认其合成并精确确定其理化性质。总之，就反应时间和产物产率而言，制备的催化剂显示出显着的可循环性和催化性能。希望这项研究的结果有助于开发新型的非均相催化剂，以显示出高性能并作为工业应用的优秀候选者。
• Nano-ZnO Impregnated on Starch—A Highly Efficient Heterogeneous Bio-Based Catalyst for One-Pot Synthesis of Pyranopyrimidinone and Xanthene Derivatives as Potential Antibacterial Agents
  作者：A. Amininia、K. Pourshamsian、B. Sadeghi

  DOI：10.1134/s1070428020070234

  日期：2020.7

  A new method has been proposed for the synthesis of pyranopyrimidinone and xanthene derivatives using zinc oxide-starch nanocomposite as catalyst under microwave irradiation. The ZnO-starch nanocomposite was characterized by X-ray diffraction and scanning electron microscopy data, and the size of the ZnO-starch nanocomposite particles was estimated at 70-90 nm. The catalyst was used in the three-component condensation of aromatic aldehydes with barbituric acid and malononitrile and the 1:2 condensation of aromatic aldehydes with naphthalen-2-ol to obtain pyranopyrimidinone and xanthene derivatives, respectively. The catalyst can be reused several times without loss of catalytic activity. The proposed procedure utilizes affordable and inexpensive materials, provides excellent yields in short reaction time, and is eco-friendly, which makes it more economic than conventional methods. The antibacterial activity of the synthesized compounds was evaluated againstM. luteusandP. aeruginosa.