4-Hydroxy-8-methoxy-3-phenyl-2(1H)-chinolon | 103929-50-6

• 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: 4-Hydroxy-8-methoxy-3-phenyl-2(1H)-chinolon
• 英文别名: 4-hydroxy-8-methoxy-3-phenyl-2(1H)-quinolinone；4-hydroxy-8-methoxy-3-phenylquinolin-2(1H)-one；2-hydroxy-8-methoxy-3-phenyl-1H-quinolin-4-one；4-hydroxy-8-methoxy-3-phenyl-1H-quinolin-2-one
• CAS: 103929-50-6
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: SPRCUPYOSOLXHB-UHFFFAOYSA-N

物化性质

• 溶解度：
  >40.1 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  4-Hydroxy-8-methoxy-3-phenyl-2(1H)-chinolon 在 氢溴酸 作用下， 反应 17.0h， 以83%的产率得到4,8-dihydroxy-3-phenylquinolin-2(1H)-one
  参考文献：
  名称：

  4-羟基喹啉-2（1 H）-ones的设计，合成及抗结核功效

  摘要：

  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。

  DOI：

  10.1016/j.ejmech.2017.06.061
• 作为产物：
  描述：

  甲氧苯胺 、 苯基丙二酸二乙酯 反应 0.25h， 以45%的产率得到4-Hydroxy-8-methoxy-3-phenyl-2(1H)-chinolon
  参考文献：
  名称：

  在无溶剂条件下快速微波增强4-羟基喹啉酮的合成

  摘要：

  3-Aryl-4-hydroxyquinolin-2（1 H）-ones是有效的，选择性的，具有药用价值的甘氨酸位点NMDA受体拮抗剂。已经开发了在无溶剂条件下这种喹啉酮的新型微波增强合成方法。由于丙二酸酯衍生物与苯胺的正式酰胺化反应和随后的中间体丙二烯环化反应，可以通过一锅法轻松获得喹啉酮。

  DOI：

  10.1016/s0040-4039(00)02244-9

文献信息

• Substituent effects on absorption and fluorescence spectra of carbostyrils
  作者：Walter M.F. Fabian、Karlheinz S. Niederreiter、Georg Uray、Wolfgang Stadlbauer

  DOI：10.1016/s0022-2860(98)00616-4

  日期：1999.3

  Abstract Absorption and fluorescence spectra as well as quantum yields of a series of differently substituted carbostyrils (quinolin-2(1H)-ones) are reported. Especially for compounds containing donor substituents in position 6, substantial bathochromic shifts (comparable to analogous coumarins) of both absorption as well as fluorescence transitions are obtained. High absorption intensities and quantum

  摘要 报告了一系列不同取代的喹诺酮 (quinolin-2(1H)-ones) 的吸收光谱和荧光光谱以及量子产率。特别是对于在 6 位含有供体取代基的化合物，获得了吸收和荧光跃迁的显着红移（与类似香豆素相当）。7 供体取代异构体具有高吸收强度和量子产率。半经验分子轨道计算（AM1 表示结构，ZINDO 表示电子跃迁能）被证明是预测这些化合物的吸收和荧光特性的合适工具。从头算和密度泛函计算确定内酰胺形式作为母体喹啉-2(1H)-one 的主要互变异构体。
• Halogenation reactions in position 3 of quinoline-2,4-dione systems by electrophilic substitution and halogen exchange
  作者：Wolfgang Stadlbauer、Rita Laschober、Herbert Lutschouig、Gerda Schindler、Thomas Kappe

  DOI：10.1007/bf00816857

  日期：——

  3-Substituted 4-hydroxy-2(1 H)-quinolones 3, 5, 7 are halogenated with bromine or sulfuryl chloride to yield the quinolinediones 9 or 10. Reaction of 3, 5, 7 with chloroform gives the dichloromethyl quinolinediones 11. Halogen exchange leads from the chloro quinolinediones 10 to fluoro quinolinedones 12 and to azido quinolinediones 13. Similarly the dichloro quinolinedione 10 an reacts to the difluoro quinolinedione 14, which is reduced to the 3-fluoro-4-hydroxyquinolone 16 and reacts again with sulfuryl chloride to give the mixed 3-chloro-3-fluoroquinolinedione 15.
• Oxidative Hydroxylierung von heterocyclischen ?-Dicarbonylberbindungen
  作者：Wolfgang Stadlbauer、Thomas Kappe

  DOI：10.1007/bf00809193

  日期：——
• 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.
• STADLBAUER, W.;KAPPE, TH., MONATSH. CHEM., 1985, 116, N 8-9, 1005-1015
  作者：STADLBAUER, W.、KAPPE, TH.

  DOI：——

  日期：——