3-ethyl-2,3-dihydro-2-(4-hydroxyphenyl)quinazolin-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: 3-ethyl-2,3-dihydro-2-(4-hydroxyphenyl)quinazolin-4(1H)-one
• 英文别名: 3-Ethyl-2-(4-hydroxyphenyl)-1,2-dihydroquinazolin-4-one
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: WCNZWDFCVYZPIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  靛红酸酐 、 对羟基苯甲醛 、 乙胺 在 gallium(III) triflate 作用下， 以 乙醇 为溶剂， 反应 0.83h， 以87%的产率得到3-ethyl-2,3-dihydro-2-(4-hydroxyphenyl)quinazolin-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

• Gallium(III) triflate-catalyzed one-pot selective synthesis of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones
  作者：Jiuxi Chen、Dengze Wu、Fei He、Miaochang Liu、Huayue Wu、Jinchang Ding、Weike Su

  DOI：10.1016/j.tetlet.2008.03.127

  日期：2008.6

  A series of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones have been synthesized in good to excellent yields and high selectivity by one-pot reaction using isatoic anhydride, ammonium acetate (or amines), and aldehydes in ethanol or in DMSO under mild conditions, respectively. The reaction was efficiently promoted by 1 mol % Ga(OTf)3 and the catalyst could be recovered easily after the

  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。
• 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.
• One-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones by Fe3O4@SiO2-imid-PMAn nano-catalyst under ultrasonic irradiation and reflux conditions
  作者：Mohsen Esmaeilpour、Jaber Javidi、Saeed Zahmatkesh、Nafiseh Fahimi

  DOI：10.1007/s00706-016-1832-5

  日期：2017.5

  corresponding 2,3-dihydroquinazolin-4(1H)-one derivatives under ultrasonic irradiation or reflux conditions. This method gives notable advantages such as operational simplicity, excellent yields, short reaction times, and absence of any tedious workup or purification. In addition, the excellent catalytic performance and the easy preparation, thermal stability, and separation of the catalyst make it

  摘要Fe 3 O 4 @SiO 2-亚胺基-PMA n有效催化异戊酸酐，醛，伯胺或铵盐的缩合反应，得到相应的2,3-二氢喹唑啉-4（1 H）-在超声波辐射或回流条件下的一种衍生物。该方法具有显着的优点，例如操作简便，产率高，反应时间短以及无需任何繁琐的后处理或纯化。另外，优异的催化性能以及催化剂的易于制备，热稳定性和分离使其成为良好的非均相体系，并且是其他非均相催化剂的有用替代品。同样，上述纳米催化剂可以容易地通过磁场回收，并且至少在六次后用于后续反应而不会明显降低催化活性和反应产率。 图形概要