2-(1H-pyrrol-2-yl)-2,3-dihydroquinazolin-4(1H)-one  | 930566-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(1H-pyrrol-2-yl)-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: ^{2-(1H-pyrrol-2-yl)-2,3-dihydroquinazolin-4(1H)-one}；2-(1H-pyrrol-2-yl)-2,3-dihydroquinazoline-4(1H)-one；2-(1H-pyrrol-2-yl)-2,3-dihydro-1H-quinazolin-4-one
• CAS: 930566-47-5
• 化学式: C₁₂H₁₁N₃O
• 分子量: 213.239
• InChiKey: ZMJQUGLFXCSRKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  56.9
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-吡咯甲醛 、 靛红酸酐 在 ammonium acetate 、 β-环糊精 作用下， 以 水 为溶剂， 以81%的产率得到2-(1H-pyrrol-2-yl)-2,3-dihydroquinazolin-4(1H)-one 
  参考文献：
  名称：

  Tandem supramolecular synthesis of substituted 2-aryl-2,3-dihydroquinazolin-4(1H)-ones in the presence of β-cyclodextrin in water

  摘要：

  Substituted 2-aryl-2,3-dihydroquinazolin-4(1H)-ones were prepared for the first time in water under neutral conditions by the reaction of aniline, isatoic anhydride, and aldehyde mediated by beta-cyclodextrin in good yields. beta-Cyclodextrin can be recovered and reused with a little loss of catalytic activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.141

文献信息

• Stabilization and anchoring of palladium‐copper alloy on murexide modified carbon nanotube as a superb nanocatalyst: Excellent performance in coupling and synthetic reactions
  作者：Samane Mohammadlou、Nader Noroozi Pesyan

  DOI：10.1002/aoc.7237

  日期：2023.10

  in the catalytic field. Herein, an environmentally benign approach was developed for immobilizing and anchoring Pd-Cu alloy nanoparticles on murexide (MX)-functionalized carbon nanotubes (CNTs). Afterward, the catalytic activity of Pd2-Cu3@MX/CNT was studied in synthesizing 2,3-dihydro quinazoline-4(1H)-ones and carbon–carbon coupling reactions at sustainable reaction conditions under ultrasound irradiation

  勾勒出具有补充属性的适当催化系统，包括易于分离、宽表面积、最高的负载能力和奇妙的电子属性，为有效地将纳米结构用于各种应用提供了令人鼓舞的方向。然而，调整纳米级双金属粒子的能力是为了在催化领域获得优异性能而进行的调整。在此，开发了一种环境友好的方法，用于将 Pd-Cu 合金纳米颗粒固定和锚定在螺脲 (MX) 功能化碳纳米管 (CNT) 上。随后研究了Pd 2 -Cu 3 @MX/CNT在合成2,3-二氢喹唑啉-4(1 H)-酮和碳-碳偶联反应在超声波照射下可持续反应条件下的反应。结果表明，高亲和力MX配体和多孔CNT结构比Pd-Cu吸附在合金纳米颗粒的高范围稳定性和后续催化活性方面具有独特的设计。此外，超声波照射使Pd-Cu合金纳米颗粒的电子受到搅动，在Cu和Pd金属之间构建了合成和偶联反应的协同效应。我们的研究表明，设计的催化剂是绿色、可回收且最合适的，为双金属纳米粒子的广泛应用的高范围稳定性提供了新的直觉。
• Evaluation of the antioxidant activity for 2,3-dihydroquinazolin-4(1H)-one and derivatives. An experimental and theoretical study
  作者：Diego Durango、Benjamín Rojano、Astrid Sanchez

  DOI：10.1016/j.molstruc.2024.138072

  日期：2024.7

  2,3-dihydroquinazoline-4(1H)-one (DHQ) is an important building block in drug design with several biological properties. The antioxidant activity of three DHQ-derivatives was assessed using ABTS (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)) and ORAC (oxygen radical absorbance capacity) tests, indicating that these compounds have antioxidant properties. Theoretical calculations were carried

  2,3-二氢喹唑啉-4(1H)-酮 (DHQ) 是药物设计中的重要组成部分，具有多种生物学特性。使用ABTS（2,2'-连氮基-双（3-乙基苯并噻唑啉-6-磺酸））和ORAC（氧自由基吸收能力）测试评估了三种DHQ衍生物的抗氧化活性，表明这些化合物具有抗氧化特性。通过热力学参数和分子结构特征进行理论计算，以建立抗氧化性能的可能解释。电离能、键解离焓、电子亲和力和亲电子指数表明 DHQ 具有与多酚相似的抗氧化特性。确定的活性可以通过前线轨道的能量值来阐明，因为两种测定中抗氧化活性较低的分子具有正电子亲和力和最高的亲电子指数，表明它更有可能吸引电子而不是捐赠电子用于自由基清除。
• A concise aqueous phase supramolecular synthesis of 2-phenyl-2,3-dihydroquinazolin-4(1H)-one derivatives
  作者：K. Ramesh、K. Karnakar、G. Satish、B.S.P. Anil Kumar、Y.V.D. Nageswar

  DOI：10.1016/j.tetlet.2012.10.029

  日期：2012.12

  2-Phenyl-2,3-dihydroquinazolin-4(1H)-one derivatives were synthesized for the first time in water under neutral conditions by the reaction of aldehyde, and anthranilamide mediated by beta-cyclodextrin in high yields. beta-Cyclodextrin can be recovered and reused with a small loss of catalytic activity. (C) 2012 Elsevier Ltd. All rights reserved.
• Immobilization of nickel on Kryptofix 222 modified Fe3O4@PEG core‐shell nanosphere for the clean synthesis of 2‐Aryl‐2,3‐dihydroquinazolin‐4(1H)‐ones
  作者：Akram Taghizadeh、Nader Noroozi Pesyan、Hassan Alamgholiloo、Golaleh Sheykhaghaei

  DOI：10.1002/aoc.6787

  日期：2022.9

  The development of green‐based nanostructures is extremely compelling for their implementation in the catalytic arena. In this study, a new type of magnetically core‐shell nanocomposite was successfully designed to be used as a green catalyst for the synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones under ultrasonic irradiation. Initially, magnetic Fe3O4 nanoparticle (NP) cores were fabricated via the co‐operation method and subsequently coated with polyethylene glycol (PEG). After that, the macro‐bicyclic Kryptofix 222 (KP222) functionalized on the surface of Fe3O4@PEG for graft and stabilization of nickel metal. The obtained Ni@KP222/Fe3O4@PEG nanocomposite was characterized by FT‐IR (Fourier Transform Infrared), wide‐angle XRD (X‐ray Powder Difraction), FESEM (Field Emiossion Scanning Electron Microscopy), TEM (Transmission Electron Microscopy), VSM (Vibrating‐Sample Magnetometer), TGA‐DTA (Thermogravimetrtic Analysis‐ Differential Thermal Analysis), DLS (Dynamic Light Scattering), and BET (Brunauer–Emmett–Teller) spectroscopy and technique. The findings indicated that high‐affinity KP222 ligand in the stabilization of Ni2+ and ultrasound irradiation catalyzed synergistically the formation of the 2,3‐dihydroquinazolin‐4(1H)‐ones. The benzaldehydes with electron‐withdrawing and electron donor groups could react well with the amino benzamide under ultrasound irradiation in 5 min, indicating that the reaction was not sensitive to the electronic effects. Furthermore, the reusability test for the Ni@KP222/Fe3O4@PEG catalyst revealed successful recyclability for six runs. The current study provided a rational design and synthesis of multifunctional catalysts for catalytic applications.