3-ethyl-4-phenyl-2(1H)-quinolinone | 93315-31-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-ethyl-4-phenyl-2(1H)-quinolinone
• 英文别名: 3-ethyl-4-phenylquinolin-2(1H)-one；3-ethyl-4-phenyl-1H-quinolin-2-one；3-Ethyl-4-phenyl-carbostyril；3-Ethyl-4-phenyl-carbostyryl；3-ethyl-4-phenyl-1H-quinolin-2-one
• CAS: 93315-31-2
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: HBGJLOGXBUITLP-UHFFFAOYSA-N

物化性质

• 熔点：
  234.3-235.7 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  438.9±45.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-(2-benzoylphenyl)butyramide 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以31%的产率得到3-ethyl-4-phenyl-2(1H)-quinolinone
  参考文献：
  名称：

  Synthesis of 3-O-methylviridicatin analogues with improved anti-TNF-α properties

  摘要：

  We synthesized 3-O-methylviridicatin 1 and several analogues of this fungal metabolite. We showed that replacement of the methoxy moiety by a thiomethyl enhanced dramatically its ability to inhibit TNF-alpha secretion. These results strongly suggest that 4-phenyl-3-methylthioquinolinone 3 may provide the basis for the development of new anti-inflammatory agents. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.08.036

文献信息

• Synthesis of 2-Quinolones via Palladium-Catalyzed Carbonylative Annulation of Internal Alkynes by <i>N</i>-Substituted <i>o</i>-Iodoanilines
  作者：Dmitry V. Kadnikov、Richard C. Larock

  DOI：10.1021/jo049149+

  日期：2004.10.1

  The palladium-catalyzed annulation of internal alkynes by N-substituted o-iodoanilines under 1 atm of carbon monoxide results in the formation of 3,4-disubstituted 2-quinolones. The nature of the substituent on the nitrogen is crucial to obtaining high yields of 2-quinolones. The best results are obtained using alkoxycarbonyl, p-tolylsulfonyl, and trifluoroacetyl substituents. The nitrogen substituent

  在1个大气压的一氧化碳下，N-取代的邻碘苯胺在钯催化的内部炔烃的环化反应中形成3,4-二取代的2-喹诺酮。氮上取代基的性质对于获得高产率的2-喹诺酮至关重要。使用烷氧羰基，对甲苯磺酰基和三氟乙酰基取代基可获得最佳结果。氮取代基在反应过程中丢失，导致形成N-未取代的2-喹诺酮。带有烷基，芳基，杂芳基，羟基和烷氧基取代基的多种内部炔烃在该方法中是有效的。富电子和贫电子的N取代的o碘苯胺以及杂环类似物可以用作成环剂。
• Intramolecular cyclization of diarylmethanols and α,β-unsaturated amides promoted by KOt-Bu/DMF: a metal-free approach towards 3,4-disubstituted quinolinones
  作者：Jia-hua Chen、Zi-cong Chen、Hong Zhao、Yong Zou、Xue-jing Zhang、Ming Yan

  DOI：10.1039/c6ob02119k

  日期：——

  A facile synthesis of quinolinones through intramolecular addition of diarylmethanols to α,β-unsaturated amides promoted by KOt-Bu/DMF is reported. A series of 3,4-disubstituted quinolinones were obtained in moderate to good yields. A reaction pathway via the ketyl radical is proposed.

  据报道，通过将二芳基甲醇分子内加到由KO t -Bu / DMF促进的α，β-不饱和酰胺上，可以容易地合成喹啉酮。以中等至良好的产率获得了一系列的3，4-二取代的喹啉酮。提出了通过酮基的反应途径。
• Alkylation and Cyclization of Benzoylacetanilides¹
  作者：A. Langley Searles、Daniel Ressler

  DOI：10.1021/ja01547a047

  日期：1958.7
• Synthesis of 3-O-methylviridicatin analogues with improved anti-TNF-α properties
  作者：Nigel Ribeiro、Helena Tabaka、Jean Peluso、Ludivine Fetzer、Can Nebigil、Serge Dumont、Christian D. Muller、Laurent Désaubry

  DOI：10.1016/j.bmcl.2007.08.036

  日期：2007.10

  We synthesized 3-O-methylviridicatin 1 and several analogues of this fungal metabolite. We showed that replacement of the methoxy moiety by a thiomethyl enhanced dramatically its ability to inhibit TNF-alpha secretion. These results strongly suggest that 4-phenyl-3-methylthioquinolinone 3 may provide the basis for the development of new anti-inflammatory agents. (c) 2007 Elsevier Ltd. All rights reserved.