2-(anthracen-9-yl)-2,3-dihydroquinazolin-4(1H)-one | 359779-36-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(anthracen-9-yl)-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: 2-anthracen-9-yl-2,3-dihydro-1H-quinazolin-4-one
• CAS: 359779-36-5
• 化学式: C₂₂H₁₆N₂O
• 分子量: 324.382
• InChiKey: AMSIZMCDFZQNRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  靛红酸酐 、 9-蒽甲醛 在 ammonium acetate 、 β-环糊精 作用下， 以 水 为溶剂， 以83%的产率得到2-(anthracen-9-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

• BF₃-grafted Fe₃O₄@Sucrose nanoparticles as a highly-efficient acid catalyst for syntheses of Dihydroquinazolinones (DHQZs) and Bis 3-Indolyl Methanes (BIMs)
  作者：Iman Radfar、Maryam Kazemi Miraki、Leila Ghandi、Naghmeh Esfandiary、Sepideh Abbasi、Meghdad Karimi、Akbar Heydari

  DOI：10.1002/aoc.4431

  日期：2018.8

  core and grafting of boron trifluoride (BF3) onto the new surface. The catalytic activity of these nanoparticles was tested in syntheses of Dihydroquinazolinones (DHQZs) and Bis (3‐Indolyl) Methanes (BIMs) as two fruitful pharmaceutical structures. Acidic capacity, FT‐IR, XRD, VSM, TGA and SEM–EDX tests are carried out on such novel nanoparticles (NPs). Catalyst has shown more acidic capacity per one

  当前的论文表示将蔗糖固定在Fe 3 O 4核上并将三氟化硼（BF 3）接枝到新表面上。在二氢喹唑啉酮（DHQZs）和双（3-吲哚基）甲烷（BIM）的合成中，作为两种卓有成效的药物结构，测试了这些纳米颗粒的催化活性。对这种新型纳米颗粒（NP）进行了酸性容量，FT-IR，XRD，VSM，TGA和SEM-EDX测试。与以前报道的磺化同系物相比，催化剂每1克NP的酸容量更高。
• Recyclable [Ce(l-Pro)2]2 (Oxa) used as Heterogeneous Catalyst: One-Pot Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones in Ethanol
  作者：Ramesh Katla、Rakhi Chowrasia、Caren da Silva、Aline de Oliveira、Beatriz dos Santos、Nelson Domingues

  DOI：10.1055/s-0036-1590886

  日期：2017.12

  (Oxa) was used as a recyclable heterogeneous catalyst under mild conditions for the preparation of 2-aryl-2,3-dihydroquinazolin-4(1H)-one derivatives. The one-pot protocol proceeds in ethanol using anthranilamide with several aldehydes at 50–55 °C. The catalyst can be recycled and reused three cycles without significant loss of catalytic activity. [Ce(l-Pro)2]2 (Oxa) was used as a recyclable heterogeneous

  摘要 [Ce（1- Pro）2 ] 2（Oxa）在温和条件下用作可回收的多相催化剂，用于制备2-芳基-2,3-二氢喹唑啉-4（1 H）-一衍生物。一锅法在乙醇中使用邻氨基苯甲酰胺和几种醛在50–55°C下进行。该催化剂可以循环使用和再利用三个循环，而不会显着降低催化活性。 [Ce（1- Pro）2 ] 2（Oxa）在温和条件下用作可回收的多相催化剂，用于制备2-芳基-2,3-二氢喹唑啉-4（1 H）-一衍生物。一锅法在乙醇中使用邻氨基苯甲酰胺和几种醛在50–55°C下进行。该催化剂可以循环使用和再利用三个循环，而不会显着降低催化活性。
• Amino Acid Catalyzed Synthesis of 2,3-Dihydroquinazolin-4(1H)-One Derivatives
  作者：K. Mohammed Mustaque、A. Subramani、T.K. Shabeer、H. Thajudeen、V.S. Jamal Ahamed

  DOI：10.2174/1570178614666171130154814

  日期：2018.3.9

  A simple, convenient and facile approach for the synthesis of a series of 2,3- dihydroquinazolin-4(1H)-ones in an environmentally benign method has been developed. This method involves a direct cyclocondensation of 2-aminobenzamide with aromatic aldehydes and ketones using aspartic acid as a catalyst in water.

  开发了一种简单、方便且容易的方法，以环保的方式合成一系列2,3-二氢喹唑啉-4(1H)-酮。该方法涉及在水中使用天冬氨酸作为催化剂，将2-氨基苯酰胺与芳香醛和酮进行直接环缩合。
• Potassium <i>tert</i>-Butoxide Promoted Synthesis of Dihydroquinazolinones
  作者：Tridev Ghosh、Indradip Mandal、Soumya Jyoti Basak、Jyotirmayee Dash

  DOI：10.1021/acs.joc.1c01510

  日期：2021.11.5

  protocol to access heterocyclic dihydroquinazolinones by a transition-metal-free process, involving the reaction of 2-aminobenzonitriles with aldehydes in the presence of KOtBu. The method is compatible with aromatic ketones providing 2,2-disubstituted dihydroquinazolinones in high yields. This reaction proceeds feasibly at room temperature and features a broad substrate scope and tolerance to a range

  我们在此报告了一种通过无过渡金属工艺获得杂环二氢喹唑啉酮的有效合成方案，包括在 KO t Bu存在下 2-氨基苯甲腈与醛的反应。该方法与芳族酮兼容，以高产率提供 2,2-二取代二氢喹唑啉酮。该反应在室温下可行，具有广泛的底物范围和对一系列官能团的耐受性。该机制遵循激进的途径。
• Anthracene Based AIE Active Probe for Colorimetric and Fluorimetric Detection of Cu²⁺ Ions
  作者：Abdullah G. Al-Sehemi、Ahmad Irfan、Mehboobali Pannipara、Mohammed A. Assiri、Abul Kalam

  DOI：10.1515/zpch-2018-1215

  日期：2019.7.26

  A novel aggregation induced emission (AIE) active anthracene based dihydroquinazolinone derivative (probe 1) has been synthesized and characterized by means of spectroscopic methods. The photophysical properties of this probe have been investigated in solvents of different polarity display that fluorescence states are of intramolecular charge transfer (ICT) character. Probe 1 show clear AIE behavior in water/THF mixture on reaching water fraction 95%. The AIE behavior of probe 1 have been exploited for the detection of metal ions in aqueous solution which reveals high selectivity and sensitivity towards Cu²⁺ ions by colorimetrically and function as a chemosensor in a remarkable turn-off fluorescence manner. Further, the experimental results were investigated by computational means by optimizing the ground state geometries of probe 1 and probe 1-Cu complex using density functional theory (DFT) at B3LYP/6-31G^∗∗ and B3LYP/6-31G^∗∗(LANL2DZ) levels of theory. Intra-molecular charge transfer was observed in probe 1 while ligand to metal charge transfer (LMCT) for probe 1-Cu complex.

  摘要：已合成并通过光谱方法表征了一种新型聚集诱导发光（AIE）活性蒽基二氢喹唑啉酮衍生物（探针1）。该探针的光物理性质在不同极性溶剂中的研究显示，荧光状态具有分子内电荷转移（ICT）特性。在水/THF混合物中，当水分数达到95%时，探针1显示出明显的AIE行为。探针1的AIE行为已被利用于检测水溶液中的金属离子，通过比色法显示对Cu2+离子具有高选择性和敏感性，并作为一种化学传感器以引人注目的熄灭荧光方式。此外，实验结果通过计算手段进行了研究，通过密度泛函理论（DFT）在B3LYP/6-31G**和B3LYP/6-31G**(LANL2DZ)理论水平上优化了探针1和探针1-Cu复合物的基态几何结构。在探针1中观察到分子内电荷转移，而在探针1-Cu复合物中观察到配体到金属的电荷转移（LMCT）。