4-bromo-3-hydroxyquinolin-2(1H)-one | 176170-14-2

• 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: 4-bromo-3-hydroxyquinolin-2(1H)-one
• 英文别名: 4-bromo-3-hydroxy-1H-quinolin-2-one
• CAS: 176170-14-2
• 化学式: C₉H₆BrNO₂
• 分子量: 240.056
• InChiKey: BSYFERFWIZPSKL-UHFFFAOYSA-N

物化性质

• 沸点：
  416.1±45.0 °C(Predicted)
• 密度：
  1.854±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• 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：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-3-hydroxyquinolin-2(1H)-one 在 palladium on activated charcoal sodium hydroxide 、 四(三苯基膦)钯 、 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 3-(3-hydroxy-2-oxo-1H-quinolin-4-yl)propanoic acid
  参考文献：
  名称：

  3-Hydroxy-quinolin-2-ones: Inhibitors of [3H]-glycine binding to the site associated with the NMDA receptor

  摘要：

  A series of substituted 3-hydroxy-quinolin-2-one derivatives 6 was synthesized and evaluated as inhibitors of [H-3]-glycine and [H-3]-AMPA binding to rat cortical membranes. These compounds were generally found to be more potent ligands for the NMDA-associated glycine binding site than the AMPA receptor. Affinity for the glycine site was found to be influenced by both the electronic and steric properties associated with the C-4 substituent and the nature and pattern of substitution of the aromatic ring. The most active compound in this series, 6y, displaces [H-3]-glycine with an IC50 of 29 nM.

  DOI：

  10.1016/0960-894x(96)00031-5
• 作为产物：
  描述：

  3-羟基喹啉-2-酮 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4-bromo-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

• Ring-Expansion Reaction of Isatins with Ethyl Diazoacetate Catalyzed by Dirhodium(II)/DBU Metal-Organic System: En Route to Viridicatin Alkaloids
  作者：Roberta Paterna、Vânia André、M. Teresa Duarte、Luis F. Veiros、Nuno R. Candeias、Pedro M. P. Gois

  DOI：10.1002/ejoc.201300796

  日期：2013.10

  present here the NHC-dirhodium(II)/DBU-catalyzed ring expansion reaction of isatins with ethyl diazoacetate. This new one-pot protocol yields the ethyl 3-hydroxy-2(1H)-oxoquinoline-4-carboxylate core, regioselectively and in good to excellent yields. A DFT mechanistic study indicates metallocarbene formation between the 3-hydroxyindole-diazo intermediate and the dirhodium(II) complex to be the rate-limiting

  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。
• [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。
• US9701638B2
  申请人：——

  公开号：US9701638B2

  公开（公告）日：2017-07-11
• 3-Hydroxy-quinolin-2-ones: Inhibitors of [3H]-glycine binding to the site associated with the NMDA receptor
  作者：Sing-Yuen Sit、Frederick J. Ehrgott、Jinnian Gao、Nicholas A. Meanwell

  DOI：10.1016/0960-894x(96)00031-5

  日期：1996.3

  A series of substituted 3-hydroxy-quinolin-2-one derivatives 6 was synthesized and evaluated as inhibitors of [H-3]-glycine and [H-3]-AMPA binding to rat cortical membranes. These compounds were generally found to be more potent ligands for the NMDA-associated glycine binding site than the AMPA receptor. Affinity for the glycine site was found to be influenced by both the electronic and steric properties associated with the C-4 substituent and the nature and pattern of substitution of the aromatic ring. The most active compound in this series, 6y, displaces [H-3]-glycine with an IC50 of 29 nM.