3-ethyl-4-hydroxy-8-methoxyquinolin-2(1H)-one | 88636-78-6

• 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-hydroxy-8-methoxyquinolin-2(1H)-one
• 英文别名: 3-ethyl-4-hydroxy-8-methoxy-1H-quinolin-2-one
• CAS: 88636-78-6
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: RZCMNUYMYCJZJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-ethyl-4-hydroxy-8-methoxyquinolin-2(1H)-one 在 过氧乙酸 、 sodium hydroxide 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 0.5h， 以83%的产率得到3-ethyl-3-hydroxy-8-methoxyquinoline-2,4(1H,3H)-dione
  参考文献：
  名称：

  3-羟基喹啉-2,4（1 H，3 H）-二酮向N-（α-酮酰基）邻氨基苯甲酸的氧化性开环

  摘要：

  使用对二碘酸（H 5 IO 6）或高碘酸钠（NaIO 4），通过3-羟基喹啉-2,4（1 H，3 H）-二酮的氧化开环来制备N-（α-酮酰基）邻氨基苯甲酸。描述了反应条件的优化以及在邻氨基苯甲酸盐酸盐的制备中N-（α-酮酰基）邻氨基苯甲酸的利用。

  DOI：

  10.1016/j.tet.2013.10.092
• 作为产物：
  描述：

  3-ethyl-8-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)quinolin-2(1H)-one 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 38.0h， 以78%的产率得到3-ethyl-8-methoxy-4-(β-D-glucopyranosyloxy)quinolin-2(1H)-one
  参考文献：
  名称：

  Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones

  摘要：

  A comparative study for selective glucosylation of N-unsubstituted 4-hydroxyquinolin-2(1H)-ones into 4-(tetra-O-acetyl-beta-D-glucopyranosyloxy)quinolin-2(1H)-ones is reported. Four glycosyl donors including tetra-O-acetyl-alpha-D-glucopyranosyl bromide, beta-D-glucose pentaacetate, glucose tetraacetate and tetra-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate were tested, along with different promoters and reaction conditions. The best results were obtained with tetra-O-acetyl-alpha-D-glucopyranosyl bromide with Cs(2)CO(3) in CH(3)CN. In some cases the 4-O-glucosylation of the quinolinone ring was accompanied by 2-O-glucosylation yielding the corresponding 2,4-bis(tetra-O-acetyl-beta-D-glucopyranosyloxy)quinoline. Next, 4-(tetra-O-acetyl-beta-D-glucopyranosyloxy)quinolin-2(1H)-ones were deacetylated into 4-(beta-D-glucopyranosyloxy)quinolin-2(1H)-ones with Et(3)N in MeOH. In some instances the deacetylation was accompanied by the sugar-aglycone bond cleavage. Structure elucidation, complete assignment of proton and carbon resonances as well as assignment of anomeric configuration for all the products under investigation were performed by 1D and 2D NMR spectroscopy. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.01.023

文献信息

• Design, synthesis and antitubercular potency of 4-hydroxyquinolin-2(1H)-ones
  作者：Maíra Bidart de Macedo、Roman Kimmel、Damijana Urankar、Martin Gazvoda、Antonio Peixoto、Freya Cools、Eveline Torfs、Luc Verschaeve、Emerson Silva Lima、Antonín Lyčka、David Milićević、Antonín Klásek、Paul Cos、Stanislav Kafka、Janez Košmrlj、Davie Cappoen

  DOI：10.1016/j.ejmech.2017.06.061

  日期：2017.9

  None of these selected derivatives showed significant acute toxicity against MRC-5 cells or early signs of genotoxicity in the Vitotox™ assay at the active concentration range. The structure activity study relation provided some insight in the further favourable substitution pattern at the 4-hydroxyquinolin-2(1H)-one scaffold and finally 6-fluoro-4-hydroxy-3-phenylquinolin-2(1H)-one (38) was selected as

  在这项研究中，设计了一个由50个成员组成的，由4-羟基喹啉2（1 H）-取代基和两个密切相关的类似物组成的文库，对该文进行了计算机模拟评分，随后进行了合成。共有13个共有3-苯基取代基的13种衍生物对10μM以下的结核分枝杆菌H37Ra和牛分枝杆菌的抑制作用最小低于15μM的AN5A对快速生长的分枝杆菌物种无活性。在活性浓度范围内，在Vitotox™分析中，这些选择的衍生物均未显示出对MRC-5细胞具有明显的急性毒性或遗传毒性的早期迹象。结构活性研究的关系为4-羟基喹啉-2（1 H）-one支架和6-氟-4-羟基-3-苯基喹啉-2（1 H）-one（1 ）的进一步有利的取代方式提供了一些见识。38）被选为库中最有前途的成员，MIC为3.2μM，针对MRC-5的CC 50为67.4μM。
• Isolation of Alkaloids from Balfourodendron riedelianum. The Structure of Balfourodine
  作者：Henry Rapoport、Kenneth G. Holden

  DOI：10.1021/ja01523a062

  日期：1959.7
• Oxidative ring opening of 3-hydroxyquinoline-2,4(1H,3H)-diones into N-(α-ketoacyl)anthranilic acids
  作者：Stanislav Kafka、Karel Proisl、Věra Kašpárková、Damijana Urankar、Roman Kimmel、Janez Košmrlj

  DOI：10.1016/j.tet.2013.10.092

  日期：2013.12

  N-(α-Ketoacyl)anthranilic acids were prepared by oxidative ring opening of 3-hydroxyquinoline-2,4(1H,3H)-diones by using paraperiodic acid (H5IO6) or sodium periodate (NaIO4). The optimisation of the reaction conditions is described as well as the utilisation of N-(α-ketoacyl)anthranilic acids in the preparation of anthranilic acid hydrochlorides.

  使用对二碘酸（H 5 IO 6）或高碘酸钠（NaIO 4），通过3-羟基喹啉-2,4（1 H，3 H）-二酮的氧化开环来制备N-（α-酮酰基）邻氨基苯甲酸。描述了反应条件的优化以及在邻氨基苯甲酸盐酸盐的制备中N-（α-酮酰基）邻氨基苯甲酸的利用。
• Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones
  作者：Roman Kimmel、Stanislav Kafka、Janez Košmrlj

  DOI：10.1016/j.carres.2010.01.023

  日期：2010.4

  A comparative study for selective glucosylation of N-unsubstituted 4-hydroxyquinolin-2(1H)-ones into 4-(tetra-O-acetyl-beta-D-glucopyranosyloxy)quinolin-2(1H)-ones is reported. Four glycosyl donors including tetra-O-acetyl-alpha-D-glucopyranosyl bromide, beta-D-glucose pentaacetate, glucose tetraacetate and tetra-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate were tested, along with different promoters and reaction conditions. The best results were obtained with tetra-O-acetyl-alpha-D-glucopyranosyl bromide with Cs(2)CO(3) in CH(3)CN. In some cases the 4-O-glucosylation of the quinolinone ring was accompanied by 2-O-glucosylation yielding the corresponding 2,4-bis(tetra-O-acetyl-beta-D-glucopyranosyloxy)quinoline. Next, 4-(tetra-O-acetyl-beta-D-glucopyranosyloxy)quinolin-2(1H)-ones were deacetylated into 4-(beta-D-glucopyranosyloxy)quinolin-2(1H)-ones with Et(3)N in MeOH. In some instances the deacetylation was accompanied by the sugar-aglycone bond cleavage. Structure elucidation, complete assignment of proton and carbon resonances as well as assignment of anomeric configuration for all the products under investigation were performed by 1D and 2D NMR spectroscopy. (C) 2010 Elsevier Ltd. All rights reserved.