2,3-dihydro-2-(4-nitrophenyl)-3-propylquinazolin-4(1H)-one

• 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: 2,3-dihydro-2-(4-nitrophenyl)-3-propylquinazolin-4(1H)-one
• 英文别名: 2-(4-Nitrophenyl)-3-propyl-1,2-dihydroquinazolin-4-one
• 化学式: C₁₇H₁₇N₃O₃
• 分子量: 311.34
• InChiKey: LAKQZQWDTBLVNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 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：
  78.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  正丙胺 、 靛红酸酐 、 对硝基苯甲醛 在 gallium(III) triflate 作用下， 以 乙醇 为溶剂， 反应 0.83h， 以87%的产率得到2,3-dihydro-2-(4-nitrophenyl)-3-propylquinazolin-4(1H)-one
  参考文献：
  名称：

  三氟甲磺酸镓（III）催化一锅选择性合成2,3-二氢喹唑啉-4（1 H）-one和喹唑啉-4（3 H）-one

  摘要：

  一系列的2,3-二氢喹唑啉-4（1 H）-和喹唑啉-4（3 H）-已通过使用等位酸酐，乙酸铵（或胺和乙醛分别在温和条件下的乙醇或DMSO中。通过1mol％的Ga（OTf）3有效地促进了反应，并且反应后催化剂可以容易地回收并重复使用而没有明显的反应性损失。

  DOI：

  10.1016/j.tetlet.2008.03.127

文献信息

• Water-Accelerated Synthesis of Novel Bis-2,3-dihydroquinazolin-4(1<i>H</i>)-one Derivatives
  作者：Peyman Salehi、Mostafa Baghbanzadeh、Minoo Dabiri、Gholamreza Kozehgary

  DOI：10.1055/s-2005-924766

  日期：——

  Bisdihydroquinazolinones were synthesized for the first time by a novel pseudo five-component condensation of isatoic anhydride, a primary amine, and a dialdehyde in water. Several solvents were examined for this reaction; however, in terms of reaction yield and time, water was found to be the optimum solvent.

  双氢喹喔啉酮首次通过一种新型的伪五组分缩合反应合成，该反应涉及邻苯二甲酸酐、一级胺和双醛在水中的反应。对该反应进行了多种溶剂的考察；然而，从反应产率和时间来看，水被发现是最佳溶剂。
• Ionic Liquid Promoted Eco-friendly and Efficient Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones
  作者：Minoo Dabiri、Peyman Salehi、Mostafa Baghbanzadeh

  DOI：10.1007/s00706-007-0635-0

  日期：2007.11

  2,3-Dihydroquinazolin-4(1H)-ones were efficiently synthesised by the reaction of isatoic anhydride, a primary amine or ammonium acetate, and different aromatic aldehydes in 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF4) without using any acidic catalyst. Also a bis-derivative of the title compound as a polyheterocyclic system was synthesised successfully in high yield.
• Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones using KAl(SO4)2·12H2O as a reusable catalyst in water and ethanol
  作者：Minoo Dabiri、Peyman Salehi、Somayeh Otokesh、Mostafa Baghbanzadeh、Gholamreza Kozehgary、Ali A. Mohammadi

  DOI：10.1016/j.tetlet.2005.06.157

  日期：2005.9

  KAI(SO4)(2)(.)l2H(2)O was found to catalyze efficiently a one-pot three-component cyclocondensation of isatoic anhydride and primary amines or ammonia sources such as (NH4)(2)CO3, NH4OAc and NH4Cl with aromatic aldehydes under mild conditions to afford the corresponding mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones in good yields. (c) 2005 Elsevier Ltd. All rights reserved.
• Expeditious One‐Pot and Solvent‐Free Synthesis of Dihydroquinazolin‐4(1H)‐ones in the Presence of Microwaves
  作者：Mandar P. Surpur、Pankajkumar R. Singh、Sachin B. Patil、Shriniwas D. Samant

  DOI：10.1080/00397910701354699

  日期：2007.6
• An Efficient One-Pot Synthesis of 2,3-dihydroquinazolin-4(1H)-ones in Green Media
  作者：Mohammad Ali Bodaghi Fard、Akbar Mobinikhaledi、Mahdia Hamidinasab

  DOI：10.1080/15533174.2013.776605

  日期：2014.4.21

  A series of mono- and disubstituted 2,3-dihydroquinazoline-4(1H)-ones have been synthesized in good yields by one-pot reaction using isatoic anhydride, ammonium acetate or amines and aldehydes in green and mild reaction conditions. The effects of various parameters such as the solvent, catalyst amount, reaction time, and temperature were examined. The protocol is simple, efficient, and environmentally benign and the catalyst can be recovered and reused without evident loss of reactivity.