2-phenyl-3-(n-propyl)-2,3-dihydro-4(1H)-quinazolinone | 1326009-54-4

• 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-phenyl-3-(n-propyl)-2,3-dihydro-4(1H)-quinazolinone
• 英文别名: 2-phenyl-3-propyl-2,3-dihydroquinazolin-4(1H)-one；2,3-dihydro-2-phenyl-3-n-propyl-quinazolin-4(1H)-one；2,3-dihydro-2-phenyl-3-propylquinazolin-4(1H)-one；2-phenyl-3-propyl-1,2-dihydroquinazolin-4-one
• CAS: 1326009-54-4
• 化学式: C₁₇H₁₈N₂O
• 分子量: 266.343
• InChiKey: NTOCTBPOLIYTBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻氨基苯甲酸 在 copper diacetate 、 palladium diacetate 、 溶剂黄146 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 9.0h， 生成 2-phenyl-3-(n-propyl)-2,3-dihydro-4(1H)-quinazolinone
  参考文献：
  名称：

  Pd(II)-Catalyzed Cascade Annulation of o-Aminobenzoic Acids with CO, Amines, and Aldehydes to N3-/N1,N3-Substituted 2,3-Dihydroquinazolin-4(1H)-ones

  摘要：

  DOI：

  10.1021/acs.joc.3c00802

文献信息

• Crosslinked chitosan nanoparticle-anchored magnetic multi-wall carbon nanotubes: a bio-nanoreactor with extremely high activity toward click-multi-component reactions
  作者：Ahmad Shaabani、Ronak Afshari、Seyyed Emad Hooshmand

  DOI：10.1039/c7nj01150d

  日期：——

  have designed a procedure for the synthesis of a bio-nanoreactor catalyst, crosslinked chitosan nanoparticle-anchored magnetic multi-wall carbon nanotubes (CS NPs/MWCNT@Fe3O4), via an in situ ionotropic gelation method. The synthesized robust nanoreactor was fully characterized. Moreover, the catalytic activity was investigated towards the click-based multi-component reactions for the synthesis of 2

  在本研究中，我们设计了一种通过原位电离凝胶法合成生物纳米反应器催化剂，交联壳聚糖纳米粒子锚定的磁性多壁碳纳米管（CS NPs / MWCNT @ Fe 3 O 4）的程序。。合成的坚固的纳米反应器已得到充分表征。此外，研究了催化活性对基于点击的多组分反应合成2,3-二氢喹唑啉-4（1 H）-，三取代的咪唑和1,2,3-三唑在绿色介质中。由于可以通过施加外部磁场来回收纳米催化剂，这使得无需过滤即可轻松分离，并且可以在不损失其显着活性的情况下进行多次回收，因此在可重复使用的催化方面显示出令人钦佩的潜力。
• Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones using aluminum methanesulfonate as a reusable catalyst
  作者：Zhiguo Song、Lianli Liu、Yang Wang、Xiaohu Sun

  DOI：10.1007/s11164-011-0445-1

  日期：2012.3

  A wide range of mono- and disubstituted 2,3-dihydroquinazolin-4(1 H )-ones were synthesized via a one-pot three components condensation of isatoic anhydride, aldehydes, and ammonium salts or primary amines in the presence of aluminum methanesulfonate in EtOH/H2O solution. The catalyst is reusable and could be recycled for several runs without any distinct decrease in its efficiency. A plausible mechanism

  在甲磺酸铝的存在下，通过一锅三组分的ISA酸酐，醛，铵盐或伯胺的缩合反应合成了广泛的单和二取代的2,3-二氢喹唑啉-4（1 H ）-。 EtOH / H 2 O溶液。该催化剂是可重复使用的，并且可以循环使用几次，而不会明显降低其效率。提出了这种一锅三组分反应的合理机制。
• Metal-Free Oxidative C(sp3)–N Coupling by HBr and DMSO: A Novel Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones
  作者：Parviz Ranjbar、Narjes Rezaei、Ehsan Sheikhi

  DOI：10.1055/s-0036-1591544

  日期：2018.4

  A metal-free oxidative C(sp3)–N coupling process has been developed for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones. The reaction between primary amines, isatoic anhydride, and benzylic alcohols in the presence of HBr in DMSO at 80 °C affords 2,3-dihydroquinazolin-4(1H)-ones in excellent yields. Under these reaction conditions, benzylic alcohols react with in situ generated bromodimethylsulfonium

  已开发出一种无金属氧化 C(sp3)-N 偶联工艺来合成 2,3-二氢喹唑啉-4(1H)-酮。在 DMSO 中，在 80 °C 下，在 HBr 存在下，伯胺、靛红酸酐和苄醇之间的反应以极好的收率提供了 2,3-二氢喹唑啉-4(1H)-酮。在这些反应条件下，苄醇与原位生成的溴化二甲基锍反应形成烷氧基锍中间体。这些中间体与伯胺和靛红酸酐发生氧化环化反应，生成标题产物。
• Cation-exchange resin as an efficient hetero-geneous catalyst for one-pot three-component synthesis of 2,3-dihydro-4(1H)-quinazolinones
  作者：M. Wang、T. T. Zhang、J. J. Gao、Y. Liang

  DOI：10.1007/s10593-012-1073-4

  日期：2012.9

  Various mono- and disubstituted 2,3-dihydro-4(1H)-quinazolinones were synthesized efficiently by a one-pot three-component condensation of isatoic anhydride, aromatic aldehydes, and ammonium salts or primary amines using a strong acidic cation-exchange resin as the catalyst in EtOH-H2O solution. The catalyst is cheap, efficient, stable, and reusable under the reaction conditions. The novel method offers several advantages, such as excellent yields, environmentally friendly reaction media, and simple procedure.
• Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones using copper benzenesulfonate as a reusable catalyst in aqueous solution
  作者：Min Wang、Ting T. Zhang、Yan Liang、Jing J. Gao

  DOI：10.1007/s00706-011-0648-6

  日期：2012.5

  Copper benzenesulfonate was found to be an effective catalyst for one-pot three-component cyclocondensation of isatoic anhydride, aromatic aldehydes, and ammonium salts or primary amines in aqueous solution to afford the corresponding mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones in good yields. The catalyst is reusable and could be recycled for several times without distinct decrease in its efficiency.