2,3-dihydro-2-(5-methylfuran-2-yl)-quinazolin-4(1H)-one | 380204-04-6

• 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-(5-methylfuran-2-yl)-quinazolin-4(1H)-one
• 英文别名: 2-(5-methyl-2-furyl)-2,3-dihydroquinazolin-4(1H)-one；2-(5-methylfuran-2-yl)-2,3-dihydroquinazolin-4(1H)-one；2-(5-methylfuran-2-yl)-2,3-dihydro-1H-quinazolin-4-one
• CAS: 380204-04-6
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: HTIWQIPVCIRJKO-UHFFFAOYSA-N

物化性质

• 沸点：
  498.4±45.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  54.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-2-(5-methylfuran-2-yl)-quinazolin-4(1H)-one 在 air 作用下， 以 氯仿 为溶剂， 反应 0.33h， 以40%的产率得到2-(5-methylfuran-2-yl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Light induced oxidation of 2,3-dihydroquinazolin-4(1H)-ones

  摘要：

  Light induced oxidation of various of 2-substituted 2,3-dihydroquinazolin-4(1H)-ones (DHQZs) results smoothly the formation of quinazolin-4(3H)-ones (QZs) product. The electronic nature of the substituent on the 2-position and also the nature of solvent affect the rate of reaction, which supports the proposed mechanism based on the electron-transfer induced photo-oxidation. Analysis of the computational results obtained at the DFT-B3LYP/6-31++G** level of theory supports the mechanism in which the first electron removal occurs preferably from the N1 atom of the heterocyclic ring. In contrast to the solution photochemistry, no changes have been observed by irradiation in the solid state. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2013.07.008
• 作为产物：
  描述：

  5-甲基呋喃醛 、 2-氨基苯甲酰胺 以 乙醇 为溶剂， 反应 72.0h， 以68%的产率得到2,3-dihydro-2-(5-methylfuran-2-yl)-quinazolin-4(1H)-one
  参考文献：
  名称：

  呋喃基-、呋喃基乙烯基-、噻吩基-、吡咯啉基喹唑啉和异吲哚并[2,1-a]喹唑啉的合成

  摘要：

  开发了一种合成氢化呋喃基-、呋喃基乙烯基-、噻吩基-和吡咯啉基-取代的喹唑啉-4-酮的方法。证明了 2-呋喃基喹唑啉与马来酸酐反应的可能性。对获得的许多喹唑啉进行了乙酰胆碱酯酶抑制的初步生物筛选。

  DOI：

  10.1007/s11172-015-1016-1

文献信息

• Synthesis of furyl-, furylvinyl-, thienyl-, pyrrolinylquinazolines and isoindolo[2,1-a]quinazolines
  作者：V. P. Zaytsev、E. L. Revutskaya、M. G. Kuz´menko、R. A. Novikov、F. I. Zubkov、E. A. Sorokina、E. V. Nikitina、F. A. A. Toze、A. V. Varlamov

  DOI：10.1007/s11172-015-1016-1

  日期：2015.6

  A method for the synthesis of hydrogenated furyl-, furylvinyl-, thienyl-, and pyrrolinyl-substituted quinazolin-4-ones was developed. A possibility of the reaction of 2-furylquinazolines with maleic anhydride was demonstrated. A number of quinazolines obtained were subjected to a primary bioscreening on inhibition of acetylcholinesterase.

  开发了一种合成氢化呋喃基-、呋喃基乙烯基-、噻吩基-和吡咯啉基-取代的喹唑啉-4-酮的方法。证明了 2-呋喃基喹唑啉与马来酸酐反应的可能性。对获得的许多喹唑啉进行了乙酰胆碱酯酶抑制的初步生物筛选。
• Application of SBA-Pr-SO3H in the synthesis of 2,3-dihydroquinazoline-4(1H)-ones: characterization, UV–Vis investigations and DFT studies
  作者：Seyedeh Yasaman Afsar、Ghodsi Mohammadi Ziarani、Hoda Mollabagher、Parisa Gholamzadeh、Alireza Badiei、Ali Abolhasani Soorki

  DOI：10.1007/s13738-016-1006-8

  日期：2017.3

  An efficient one-pot synthesis of 2,3-dihydroquinazoline-4(1H)-one derivatives 4a–l is described using SBA-Pr-SO3H as a heterogeneous acid catalyst. The present methodology resulted in various derivatives of 2,3-dihydroquinazoline-4(1H)-one in good yield via a three-component reaction of isatoic anhydride, aldehydes and ammonium acetate. SBA-Pr-SO3H played a significant role as an efficient mesoporous

  使用SBA-Pr-SO 3 H作为非均相酸催化剂描述了有效的一锅合成2,3-二氢喹唑啉-4（1 H）-一衍生物4a-1。本方法学通过二酸酐，醛和乙酸铵的三组分反应以高收率得到了2,3-二氢喹唑啉-4（1 H）-one的各种衍生物。SBA-Pr-SO 3 H由于其孔径为6 nm而在有效的介孔催化剂中起着重要作用。此外，还研究了产品的UV-Vis光谱，以研究其作为UV吸收剂的应用。
• Light induced oxidation of 2,3-dihydroquinazolin-4(1H)-ones
  作者：Hamid R. Memarian、Saeid Ebrahimi

  DOI：10.1016/j.jphotochem.2013.07.008

  日期：2013.11

  Light induced oxidation of various of 2-substituted 2,3-dihydroquinazolin-4(1H)-ones (DHQZs) results smoothly the formation of quinazolin-4(3H)-ones (QZs) product. The electronic nature of the substituent on the 2-position and also the nature of solvent affect the rate of reaction, which supports the proposed mechanism based on the electron-transfer induced photo-oxidation. Analysis of the computational results obtained at the DFT-B3LYP/6-31++G** level of theory supports the mechanism in which the first electron removal occurs preferably from the N1 atom of the heterocyclic ring. In contrast to the solution photochemistry, no changes have been observed by irradiation in the solid state. (C) 2013 Elsevier B.V. All rights reserved.