3-butyl-2-(4-nitrophenyl)-2,3-dihydroquinazolin-4(1H)-one | 1341123-66-7

• 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-butyl-2-(4-nitrophenyl)-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: 3-Butyl-2-(4-nitrophenyl)-1,2-dihydroquinazolin-4-one
• CAS: 1341123-66-7
• 化学式: C₁₈H₁₉N₃O₃
• 分子量: 325.367
• InChiKey: UTSUNZWBXRNHPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-butyl-2-(4-nitrophenyl)-2,3-dihydroquinazolin-4(1H)-one 在 bismuth (III) nitrate pentahydrate 作用下， 反应 3.0h， 生成 3-butyl-2-(4-nitro-phenyl)-3H-quinazolin-4-one
  参考文献：
  名称：

  从芳香醛高效一锅合成 2,3-二氢喹唑啉-4(1H)-酮及其在 Bi(NO3)3·5H2O 催化下一锅氧化为喹唑啉-4(3H)-酮：研究其作用催化剂

  摘要：

  摘要 在 Bi(NO 3 ) 催化下，通过靛红酸酐、伯胺和芳香醛的一锅三组分反应高效、新颖地合成 2,3-二取代的 2,3-二氢喹唑啉-4(1 H )-酮描述了在无溶剂条件下的 3 ·5H 2 O。在 Bi(NO 3 ) 3 ·5H 2 O 存在下，这些 2,3-二氢喹唑啉-4(1 H )-酮也被成功地氧化为它们的喹唑啉-4(3 H )-酮。这种新方法具有操作方便、反应时间短、收率高、后处理非常容易，以及使用市售、低成本和相对无毒的催化剂等优点。还研究了 Bi(NO 3 ) 3 ·5H 2 O 在这些转化中的作用。

  DOI：

  10.1016/j.crci.2011.05.003
• 作为产物：
  描述：

  对硝基苯甲醛 、 2-氨基-n-丁基苯甲酰胺 在 aluminum oxide 、 柠檬酸 作用下， 反应 0.17h， 以95%的产率得到3-butyl-2-(4-nitrophenyl)-2,3-dihydroquinazolin-4(1H)-one
  参考文献：
  名称：

  Tandem synthesis of 2,3-dihydroquinazolin-4(1H)-ones on grinding under solvent-free conditions

  摘要：

  AbstractCitric acid promoted synthesis of a mini‐library 2,3‐dihydroquinazolin‐4(1H)‐ones with good to excellent yields is achieved by tandem reaction of anthranilamides (or anthranilhydrazides) with aldehydes on grinding at room temperature under solvent‐free conditions. This method has notable advantages in terms of simple workup, short reaction time, cost‐effective, and environmentally benign. J. Heterocyclic Chem., (2012).

  DOI：

  10.1002/jhet.759

文献信息

• One-pot synthesis of 2,3-disubstituted-2,3-dihydroquinazolin-4(1H)-ones using [Hmim][NO3]: An eco-friendly protocol
  作者：Iraj Mohammadpoor-Baltork、Ahmad Reza Khosropour、Majid Moghadam、Shahram Tangestaninejad、Valiollah Mirkhani、Mohammad Soltani、Arsalan Mirjafari

  DOI：10.1002/jhet.721

  日期：2011.11

  An efficient method for the synthesis of a series of 2,3‐disubstituted‐2,3‐dihydroquinazolin‐4(1H)‐ones is described via one‐pot condensation reaction of isatoic anhydride, aryl aldehydes, and primary amines using a Brønsted acidic ionic liquid, [Hmim][NO3], as a catalyst and medium. The present protocol enjoys convenient reaction and simple work‐up, greenness, short reaction times, and reusable catalyst

  描述了通过使用布朗斯台德酸的苯磺酸酐，芳基醛和伯胺的一锅缩合反应，合成一系列2,3-二取代-2,3-二氢喹唑啉-4（1H）-酮的有效方法。离子液体[Hmim] [NO 3 ]，作为催化剂和介质。本方案具有反应方便，后处理简单，绿色，反应时间短，催化剂可重复使用以及反应条件温和的特点。J.杂环化​​学。（2011）。
• Zeolite-Catalyzed Method for the Preparation of 2,3-Dihydroquinazolin-4(1H)-ones
  作者：Anna Takács、Anna Fodor、János Németh、Zoltán Hell

  DOI：10.1080/00397911.2014.894525

  日期：2014.8.3

  The reaction of isatoic anhydride, amines, and aldehydes in the presence of a microporous zeolite gave 2,3-dihydroquinazolin-4(1H)-one derivatives with good to excellent yield. The yield depends on the structure of the aldehyde and/or amine compound.
• A Greener Protocol for Accessing 2,3-Dihydro/spiroquinazolin-4(1H)-ones: Natural Acid-SDS Catalyzed Three-Component Reaction
  作者：Prem Chauhan、Rashmi Sharma、Anand Pandey

  DOI：10.1055/s-0032-1317014

  日期：——

  A novel green and energy-efficient synthesis of 2,3-dihydro/spiroquinazolin-4(1H)-ones via three-component cyclo-condensation reaction involving isatoic anhydride, amines and aldehydes/ketones utilizing recyclable tartaric acid-SDS catalyst system has been achieved. With simple requirements of mechanical stirring or mechanochemical activation at room temperature and one of the shortest reported times as of yet, it is a significant improvement on previously described methods for the synthesis of such compounds. Moreover the catalyst system can also be efficiently applied in large-scale reactions which indicates the potential for applications in industry.
• Tandem synthesis of 2,3-dihydroquinazolin-4(1H)-ones on grinding under solvent-free conditions
  作者：Quan-Sheng Ding、Ji-Lei Zhang、Jiu-Xi Chen、Miao-Chang Liu、Jin-Chang Ding、Hua-Yue Wu

  DOI：10.1002/jhet.759

  日期：2012.3

  AbstractCitric acid promoted synthesis of a mini‐library 2,3‐dihydroquinazolin‐4(1H)‐ones with good to excellent yields is achieved by tandem reaction of anthranilamides (or anthranilhydrazides) with aldehydes on grinding at room temperature under solvent‐free conditions. This method has notable advantages in terms of simple workup, short reaction time, cost‐effective, and environmentally benign. J. Heterocyclic Chem., (2012).
• Efficient one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones from aromatic aldehydes and their one-pot oxidation to quinazolin-4(3H)-ones catalyzed by Bi(NO3)3·5H2O: Investigating the role of the catalyst
  作者：Iraj Mohammadpoor-Baltork、Ahmad R. Khosropour、Majid Moghadam、Shahram Tangestaninejad、Valiollah Mirkhani、Saeid Baghersad、Arsalan Mirjafari

  DOI：10.1016/j.crci.2011.05.003

  日期：2011.10

  three-component reaction of isatoic anhydride, primary amines and aromatic aldehydes catalyzed by Bi(NO 3 ) 3 ·5H 2 O under solvent-free conditions is described. Oxidation of these 2,3-dihydroquinazolin-4(1 H )-ones to their quinazolin-4(3 H )-ones was also successfully performed in the presence of Bi(NO 3 ) 3 ·5H 2 O. This new method has the advantages of convenient manipulation, short reaction times, excellent

  摘要 在 Bi(NO 3 ) 催化下，通过靛红酸酐、伯胺和芳香醛的一锅三组分反应高效、新颖地合成 2,3-二取代的 2,3-二氢喹唑啉-4(1 H )-酮描述了在无溶剂条件下的 3 ·5H 2 O。在 Bi(NO 3 ) 3 ·5H 2 O 存在下，这些 2,3-二氢喹唑啉-4(1 H )-酮也被成功地氧化为它们的喹唑啉-4(3 H )-酮。这种新方法具有操作方便、反应时间短、收率高、后处理非常容易，以及使用市售、低成本和相对无毒的催化剂等优点。还研究了 Bi(NO 3 ) 3 ·5H 2 O 在这些转化中的作用。