2-(2-苯基乙基)-1H-喹唑啉-4-酮 | 4765-57-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 2-(2-苯基乙基)-1H-喹唑啉-4-酮
• 英文名称: 2-phenethylquinazolin-4(3H)-one
• 英文别名: 2-phenethylquinazolin-4(3Η)-one；2-(2-phenylethyl)quinazolin-4(3H)-one；2-(2-Phenylethyl)-4(3H)-quinazolinone；2-(2-phenylethyl)-3H-quinazolin-4-one
• CAS: 4765-57-5
• 化学式: C₁₆H₁₄N₂O
• 分子量: 250.3
• InChiKey: AUEZMLBIHNUTTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-苯基乙基)-1H-喹唑啉-4-酮 在 劳森试剂 作用下， 以 1,4-二氧六环 为溶剂， 以89%的产率得到2-phenethyl-3H-quinazoline-4-thione
  参考文献：
  名称：

  2-Alkyl(aryl)-quinazolin-4(3H)-thiones, 2-R-(quinazolin-4(3H)-ylthio)carboxylic acids and amides: synthesis, molecular docking, antimicrobial and anticancer properties

  摘要：

  In this study, a series of novel 2-alkyl(aryl)-quinazolin-4(3H)-thiones, 2-R-(quinazolin-4(3H)-ylthio)carboxylic acids and amides were synthesized and evaluated for antimicrobial and anticancer activities. Their structure was confirmed by elemental analysis and spectral data (FT-IR, LC-MS, H-1-NMR). Antimicrobial activity was tested in vitro against Staphylococcus aureus, Enterococcus faecalis, Enterobacter aerogenes, Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumonia, Candida albicans and NCI in vitro preliminary anticancer activity against nine different cancer types. The most active antibacterial and antifungal compounds were: 2.1, 2.2 and 2.4. The introduction of the carboxylic acid or amide residue into the fourth position of quinazolin-4(3H)-thione resulted in the absence of antimicrobial activity. Substance 3.8 inhibited renal cancer UO-31 line and 2.18 - leukemia CCRF-CEM. The results of in silico molecular docking for DHFR and CK2 kinase had no correlation with in vitro properties, proposing the presence of other biological activity pathways.

  DOI：

  10.3109/14756366.2015.1018243
• 作为产物：
  描述：

  (E)-2-styrylquinazolin-4(3H)-one 在 sodium amalgam 、 乙醇 作用下， 生成 2-(2-苯基乙基)-1H-喹唑啉-4-酮
  参考文献：
  名称：

  Researches on Quinazolines. XXXIX. The Synthesis of Quinazoline Derivatives Structurally Analogous to the Angostura Alkaloids Galiopine and Galipine¹

  摘要：

  DOI：

  10.1021/ja01307a041

文献信息

• Photoredox-mediated Minisci C–H alkylation of N-heteroarenes using boronic acids and hypervalent iodine
  作者：Guo-Xing Li、Christian A. Morales-Rivera、Yaxin Wang、Fang Gao、Gang He、Peng Liu、Gong Chen

  DOI：10.1039/c6sc02653b

  日期：——

  A photoredox-mediated Minisci C–H alkylation reaction of N-heteroarenes with alkyl boronic acids is reported. A broad range of primary and secondary alkyl groups can be efficiently incorporated into various N-heteroarenes using [Ru(bpy)3]Cl2 as photocatalyst and acetoxybenziodoxole as oxidant under mild conditions. The reaction exhibits excellent substrate scope and functional group tolerance, and

  报道了N-杂芳烃与烷基硼酸的光氧化还原介导的 Minisci C-H 烷基化反应。在温和条件下，使用[Ru(bpy) 3 ]Cl 2作为光催化剂和乙酰氧基苯并氧杂环戊烯作为氧化剂，可以将广泛的伯烷基和仲烷基有效地引入各种N-杂芳烃中。该反应表现出优异的底物范围和官能团耐受性，为复杂底物的后期功能化提供了广泛适用的方法。机理实验和计算研究表明，分子内稳定的邻碘苯甲酰氧基自由基中间体可能在该反应体系中发挥关键作用。
• Linear-Organic-Polymer-Supported Iridium Complex as a Recyclable Auto-Tandem Catalyst for the Synthesis of Quinazolinones via Selective Hydration/Acceptorless Dehydrogenative Coupling from <i>o</i>-Aminobenzonitriles
  作者：Shushu Hao、Jiazhi Yang、Peng Liu、Jing Xu、Chenchen Yang、Feng Li

  DOI：10.1021/acs.orglett.1c00475

  日期：2021.4.2

  coordinative immobilization of [Cp*IrCl2]2 on poly(4-vinylpyridine), was proven to be an efficient heterogeneous autotandem catalyst for synthesizing quinazolinones via selective hydration/acceptorless dehydrogenative coupling from o-aminobenzonitriles. Furthermore, the synthesized catalyst was recycled five times without an obvious decrease in the catalytic activity.

  通过将[Cp * IrCl 2 ] 2配位固定在聚（4-乙烯基吡啶）上设计和合成的线性有机聚合物负载的铱络合物Cp * Ir @ P4VP被证明是一种有效的异质串联催化剂通过邻氨基苄腈的选择性水合/无受体脱氢偶联合成喹唑啉酮。此外，将合成的催化剂循环使用五次，而催化活性没有明显降低。
• Quinazolinones from <i>o</i> -Aminobenzonitriles by One-Pot Sequential Selective Hydration/Condensation/Acceptorless Dehydrogenation Catalyzed by an Iridium Complex
  作者：Wei Zhao、Pengcheng Liu、Feng Li

  DOI：10.1002/cctc.201501385

  日期：2016.4.20

  A new strategy for the direct synthesis of quinazolinones from o‐aminobenzonitriles was proposed and accomplished. In the presence of [Cp*IrCl2]2 (Cp*=pentamethylcyclopentadienyl), a variety of desirable products was obtained easily through the one‐pot sequential selective hydration/condensation/acceptorless dehydrogenation. This protocol is highly attractive because it uses readily available starting

  提出并完成了由邻氨基苯甲腈直接合成喹唑啉酮的新策略。在[Cp * IrCl 2 ] 2（Cp * =五甲基环戊二烯基）的存在下，通过一锅顺序选择性水合/缩合/无受体脱氢可以轻松获得各种所需产物。该协议具有很高的吸引力，因为它使用了容易获得的起始原料，原子效率高，产率高到优，化学药品和能源的消耗最少。值得注意的是，这项研究显示出开发涉及无受体脱氢的过渡金属催化单锅顺序反应的新潜力。
• 一种合成喹唑酮的方法
  申请人：南京理工大学

  公开号：CN106478525A

  公开（公告）日：2017-03-08

  本发明公开了一种合成喹唑酮的方法，具体包括如下步骤：在反应容器中，加入邻氨基苯腈，过渡金属催化剂，肟，溶剂对二甲苯；反应混合物在60-70℃下反应8-12小时后，冷却到室温；再加入化合物醛，反应混合物在100-110℃下反应2-4小时后，然后通过分离，得到目标化合物。本发明从商品化、经济化的邻氨基苯腈衍生物出发，在过渡金属催化剂的参与下,使用肟作为水源在中性条件下发生水解，生成酰胺中间体，然后和醛发生脱氢偶联反应，得到喹唑酮，反应展现出三个显著的优点：1)使用商品化、经济化的邻氨基苯腈衍生物为起始原料；2)串联反应无需分离中间产物；3)反应原子经济性高；因此，该反应符合绿色化学的要求，具有广阔的发展前景。
• Ruthenium-catalysed oxidative synthesis of heterocycles from alcohols
  作者：Andrew J. A. Watson、Aoife C. Maxwell、Jonathan M. J. Williams

  DOI：10.1039/c1ob06516e

  日期：——

  Ruthenium-catalysed hydrogen transfer has been successfully used for the conversion of alcohols into either 2,3-dihydroquinazolines or quinazolines. The choice of reaction conditions allows for the selective formation of either heterocycle and the methodology can also be applied to the sulfonamide analogue.

  钌催化的氢转移已被成功用于将醇转化为2,3-二氢喹唑啉或喹唑啉。反应条件的选择能够选择性地形成任一杂环，并且该方法也可以应用于磺酰胺类似物。