8-phenylquinolin-4(1H)-one | 92724-47-5

• 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: 8-phenylquinolin-4(1H)-one
• 英文别名: 8-phenyl-1H-quinolin-4-one
• CAS: 92724-47-5
• 化学式: C₁₅H₁₁NO
• mdl: MFCD12427475
• 分子量: 221.258
• InChiKey: WVJYDVLLMGZLPZ-UHFFFAOYSA-N

物化性质

• 熔点：
  201 °C
• 沸点：
  406.4±30.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-phenylquinolin-4(1H)-one 在 三氯氧磷 作用下， 生成 4-chloro-8-phenyl-quinoline
  参考文献：
  名称：

  92.衍生自2-氨基联苯的一些内消旋-氨基-啶和喹啉

  摘要：

  DOI：

  10.1039/jr9500000464
• 作为产物：
  描述：

  diethyl 2-((biphenyl-2-ylamino)methylene)malonate 在 sodium hydroxide 作用下， 以 二苯醚 、 水 为溶剂， 反应 24.08h， 生成 8-phenylquinolin-4(1H)-one
  参考文献：
  名称：

  Synthesis and antiplatelet activity of phenyl quinolones

  摘要：

  In our search for novel antiplatelet agents, seven positional phenyl quinolone isomers were synthesized. Preliminary screening confirmed their inhibitory effects against arachidonic acid (AA)-induced platelet aggregation. Varying the substitutional position of the phenyl group had a profound effect on the antiplatelet activity of these isomers. 3-Phenyl-4-quinolone showed the greatest potency and was superior to indomethacin, although the two structures are quite different. The mechanism and pharmacological action of 3-phenyl-4-quinolone are currently under investigation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00141-2

文献信息

• Synthesis of Novel Halogenated 4(1H)-Quinolones by Thermolysis of Arylaminomethylene-1,3-dioxane-4,6-diones
  作者：Peter Langer、Sven Rotzoll、Helmut Reinke、Christine Fischer

  DOI：10.1055/s-0028-1083237

  日期：2009.1

  A variety of novel 4(1H)-quinolone derivatives were prepared by thermolysis of aminomethylene Meldrum’s acid derivatives. N-heterocycles - quinolones - cyclizations

  通过氨基亚甲基梅德鲁姆酸衍生物的热解制备了多种新颖的4（1 H）-喹诺酮衍生物。 N-杂环-喹诺酮-环化
• Tautomeric Switching and Metal-Cation Sensing of Ligand-Equipped 4-Hydroxy-/4-oxo-1,4-dihydroquinolines
  作者：Aleksandar R. Todorov、Martin Nieger、Juho Helaja

  DOI：10.1002/chem.201103868

  日期：2012.6.4

  or aprotic media. This change is accompanied by selective and highly sensitive fluorometric sensing of Zn2+ ions. In the case of the bidentate 8‐(quinolin‐8‐ylimino)methyl side arm, NMR studies in CD3OD indicated that both Cd2+ and Zn2+ ions afford N chelation for 4HQ, coexisting with tautomeric switching from quinolin‐4(1H)‐one to quinolin‐4‐olate. In corroboration, UV/Vis‐monitored metal‐ion titrations

  报告了新型的基于4-羟基喹啉（4HQ）的互变异构开关。配备有协调侧臂（8-芳基亚氨基和3-哌啶-1-基甲基团）4HQs合成到址O -或Zn氮选择性螯合2+和Cd 2+离子通过4HQ。在单齿芳基氨基的情况下，金属离子的O螯合可在非极性或非质子介质中诱导苯酚互变异构体同时转换为酮形式。这种变化伴随着对Zn 2+离子的选择性和高度灵敏的荧光检测。对于双齿8-（喹啉-8-ylimino）甲基侧臂，CD 3 OD中的NMR研究表明，Cd 2+和Zn 2+离子为4HQ提供了N螯合，并与互变异构体从quinolin-4（1 H）-1转变为quinolin-4-olate并存。为了证实这一点，在甲苯和甲醇中用UV / Vis监测的金属离子滴定法也暗示了类似的结构变化。此外，荧光测量表明，金属触发的互变异构转换与化合物的信号传导特性有关。B3LYP 6-31G *级别的DFT计算支持该结果。提出了几种无金属
• A one-pot, two-step synthesis of 3-deazacanthin-4-ones via sequential Pd-catalyzed Suzuki-Miyaura and Cu-catalyzed Buchwald-Hartwig reactions
  作者：Emmanouil Broumidis、Panayiotis A. Koutentis

  DOI：10.1016/j.tetlet.2017.05.076

  日期：2017.7

  yields from 8-iodoquinolones and 2-chloro(het)arylboronic acids. The strategy involves construction of the central B ring via concomitant Pd-catalyzed Suzuki-Miyaura CC and Cu-catalyzed Buchwald-Hartwig CN coupling reactions.

  从8-碘喹诺酮和2-氯（杂）芳基硼酸快速制备了3-Deazantanthin-4-one和9个类似物，包括8-aza类似物。该策略涉及通过伴随的Pd催化的Suzuki-Miyaura C C和Cu催化的Buchwald-Hartwig C N偶联反应来构建中心B环。
• Phenylquinolines¹
  作者：C. E. Kaslow、Mason Hayek

  DOI：10.1021/ja01154a525

  日期：1951.10
• Synthesis and antiplatelet activity of phenyl quinolones
  作者：Li-Jiau Huang、Ming-Chieh Hsieh、Che-Ming Teng、Kuo-Hsiung Lee、Sheng-Chu Kuo

  DOI：10.1016/s0968-0896(98)00141-2

  日期：1998.10

  In our search for novel antiplatelet agents, seven positional phenyl quinolone isomers were synthesized. Preliminary screening confirmed their inhibitory effects against arachidonic acid (AA)-induced platelet aggregation. Varying the substitutional position of the phenyl group had a profound effect on the antiplatelet activity of these isomers. 3-Phenyl-4-quinolone showed the greatest potency and was superior to indomethacin, although the two structures are quite different. The mechanism and pharmacological action of 3-phenyl-4-quinolone are currently under investigation. (C) 1998 Elsevier Science Ltd. All rights reserved.