4-(4-fluorophenyl)-3-hydroxyquinolin-2(1H)-one | 1434103-17-9

• 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: 4-(4-fluorophenyl)-3-hydroxyquinolin-2(1H)-one
• 英文别名: 4-(4-fluorophenyl)-3-hydroxy-1H-quinolin-2-one
• CAS: 1434103-17-9
• 化学式: C₁₅H₁₀FNO₂
• 分子量: 255.248
• InChiKey: HWLFFZSGMUOCNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,2-二氢-3-羟基-2-氧代喹啉-4-羧酸乙酯 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 水 、 sodium carbonate 、 sodium hydroxide 作用下， 以 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 4-(4-fluorophenyl)-3-hydroxyquinolin-2(1H)-one
  参考文献：
  名称：

  Dirhodium(II)/DBU 金属-有机体系催化靛红与重氮乙酸乙酯的扩环反应：获得 Viridicatin 生物碱的途径

  摘要：

  我们在此介绍了 NHC-二铑 (II)/DBU 催化的靛红与重氮乙酸乙酯的扩环反应。这种新的一锅法产生了 3-羟基-2(1H)-oxoquinoline-4-carboxylate 核心，区域选择性和良好的产率。DFT 机理研究表明，3-羟基吲哚-重氮中间体和二铑 (II) 络合物之间的金属卡宾形成是反应的限速步骤。合成的 3-羟基-2(1H)-氧喹啉-4-羧酸乙酯核心可以很容易地转化为绿色生物碱，通过微波辅助的 3-羟基-4-Suzuki-Miyaura 交叉偶联，产率高达 80%。溴喹啉-2(1H)-一种与芳基硼酸。

  DOI：

  10.1002/ejoc.201300796

文献信息

• [EN] THERAPEUTIC HYDROXYQUINOLONES<br/>[FR] HYDROXYQUINOLONES THÉRAPEUTIQUES
  申请人：UNIV RUTGERS

  公开号：WO2014074926A1

  公开（公告）日：2014-05-15

  The invention provides compounds of formula (I) and salts thereof wherein R4-R8 have any of the meanings defined in the specification, as well as pharmaceutical compositions comprising the compounds or salts and methods for their use in therapy. The compounds have useful antiviral properties.

  该发明提供了式(I)的化合物及其盐，其中R4-R8具有规范中定义的任何含义，以及包含这些化合物或盐的药物组合物以及其在治疗中的使用方法。这些化合物具有有用的抗病毒特性。
• THERAPEUTIC HYDROXYQUINOLONES
  申请人：LAVOIE Edmond J.

  公开号：US20150291531A1

  公开（公告）日：2015-10-15

  The invention provides compounds of formula (I) and salts thereof wherein R 4 -R 8 have any of the meanings defined in the specification, as well as pharmaceutical compositions comprising the compounds or salts and methods for their use in therapy. The compounds have useful antiviral properties.

  该发明提供了公式(I)的化合物及其盐，其中R4-R8具有规范中定义的任何含义，以及包含该化合物或盐的药物组合物和它们在治疗中的使用方法。这些化合物具有有用的抗病毒特性。
• One-Pot Synthesis of 3-Hydroxyquinolin-2(1<i>H</i>)-ones from <i>N-</i>Phenylacetoacetamide via PhI(OCOCF₃)₂-Mediated α-Hydroxylation and H₂SO₄-Promoted Intramolecular Cyclization
  作者：Yucheng Yuan、Rui Yang、Daisy Zhang-Negrerie、Junwei Wang、Yunfei Du、Kang Zhao

  DOI：10.1021/jo400541s

  日期：2013.6.7

  A clean, one-pot synthesis of the biologically important 3-hydroxyquinolin-2(1H)-one compounds has been realized from the readily available N-phenylacetoacetamide derivatives through a PhI(OCOCF3)(2)-mediated alpha-hydroxylation and a H2SO4-promoted intramolecular condensation. The hydroxyl group in the generated alpha-hydroxylated intermediate can be well tolerated in the second H2SO4-promoted cyclization step.
• 3-Hydroxyquinolin-2(1<i>H</i>)-ones As Inhibitors of Influenza A Endonuclease
  作者：Hye Yeon Sagong、Ajit Parhi、Joseph D. Bauman、Disha Patel、R. S. K. Vijayan、Kalyan Das、Eddy Arnold、Edmond J. LaVoie

  DOI：10.1021/ml4001112

  日期：2013.6.13

  Several 3-hydroxyquinolin-2(1H)-ones. derivatives were synthesized and evaluated as inhibitors of 2009 pandemic H1N1 influenza A endonuclease. All five of the monobrominated 3-hydroxyquinolin (1H)-2-ones derivatives were synthesized. Suzuki-coupling of p-fluorophenylboronic acid with each of these brominated derivatives provided the respective p-fluorophenyl hydroxyquinolin (1H)-2-ones. In addition to 3-hydroxyquinolin-2 (1H)-one, its 4-methyl, 4-phenyl, 4-methyl-7-(p-fluorophenyl), and 4-phenyl-7-(p-fluorophenyl) derivatives were also synthesized. Comparative studies on their relative activity revealed that both 6- and 7-(p-fluorophenyl)-3- hydroxyquinolin-2(1H)-one are among the more potent inhibitors of H1N1 influenza A endonuclease. An X-ray crystal structure of 7-(p-fluorophenyl)-3-hydroxyquinolin-2(1H)-one complexed to the influenza endonuclease revealed that this molecule chelates to two metal ions at the active site of the enzyme.
• US9701638B2
  申请人：——

  公开号：US9701638B2

  公开（公告）日：2017-07-11