4-羟基-6-甲氧基-1-甲基-2(1H)-喹啉酮 | 223668-09-5

• 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
• 中文名称: 4-羟基-6-甲氧基-1-甲基-2(1H)-喹啉酮
• 英文名称: 4-hydroxy-6-methoxy-1-methylquinolin-2(1H)-one
• 英文别名: 4-Hydroxy-6-methoxy-1-methyl-1H-quinolin-2-one；4-hydroxy-6-methoxy-1-methylquinolin-2-one
• CAS: 223668-09-5
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: DYEJJCQLQRUPRP-UHFFFAOYSA-N

物化性质

• 熔点：
  278-279℃
• 沸点：
  366℃
• 密度：
  1.314
• 闪点：
  175℃

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  4-羟基-6-甲氧基-1-甲基-2(1H)-喹啉酮 在 rhodium(II) pivalate 、 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 乙醇 为溶剂， 反应 60.0h， 生成 2-acetoxy-8-methoxy-5-methyl-2,3-dihydrofuro[3,4-d]quinolin-4-one
  参考文献：
  名称：

  Rhodium-Mediated Dipolar Cycloaddition of Diazoquinolinediones

  摘要：

  As an entry to furoquinoline structures of natural origin, the rhodium-mediated dipolar cycloaddition of diazoquinolinediones with alkenes and alkynes has been examined. Because of the unsymmetrical nature of the diazo compounds, both linear and angular furoquinoline products are possible. For the most part, a mixture of regioisomers is generated in moderate to good yields, though in a few cases dominant products are obtained in high yields. The products can be further converted to naturally occurring alkaloids such as isodictamnine. A novel observation in this work is that catalytic quantities of acid enhance the yield and regiochemical control in the cycloaddition.

  DOI：

  10.1021/jo982503h
• 作为产物：
  描述：

  6-甲氧基-9-甲基呋喃并[2,3-B]喹啉-4(9H)-酮 在 potassium permanganate 、 丙酮 作用下， 生成 4-羟基-6-甲氧基-1-甲基-2(1H)-喹啉酮
  参考文献：
  名称：

  Lamberton; Price, Australian Journal of Chemistry, 1953, vol. 6, p. 173,178

  摘要：

  DOI：

文献信息

• Copper-Mediated Direct Sulfenylation of 4-Hydroxyquinolinones and 4-Hydroxypyridones with Aryl Thiols via a C−H Functionalization Process
  作者：Tao Guo、Hongyan Wang

  DOI：10.1055/s-0036-1588829

  日期：2017.9

  An efficient approach for the direct sulfanylation of 4-hydroxyquinolinones and 4-hydroxypyridones with aryl thiols in the presence of CuI/DMSO has been developed. The substrate scope is broad, allowing facile synthesis of a range of structurally diverse 3-sulfanyl-4-hydroxyquinolinones and 3-sulfanyl-4-hydroxypyridones in good efficiency.

  一种在CuI/DMSO存在下，利用芳基硫醇直接对4-羟基喹啉酮和4-羟基吡啶酮进行砜化的高效方法已经开发出来。底物范围广泛，能够轻松合成一系列结构多样的3-砜基-4-羟基喹啉酮和3-砜基-4-羟基吡啶酮，效率良好。
• Identification and characterization of amino-piperidinequinolones and quinazolinones as MCHr1 antagonists
  作者：Christopher Blackburn、Matthew J. LaMarche、James Brown、Jennifer Lee Che、Courtney A. Cullis、Sujen Lai、Martin Maguire、Thomas Marsilje、Bradley Geddes、Elizabeth Govek、Vivek Kadambi、Colleen Doherty、Brian Dayton、Sevan Brodjian、Kennan C. Marsh、Christine A. Collins、Philip R. Kym

  DOI：10.1016/j.bmcl.2006.02.044

  日期：2006.5

  Several potent, functionally active MCHr1 antagonists derived from quinolin-2(1H)-ones and quinazoline-2(1H)-ones have been synthesized and evaluated. Pyridylmethyl substitution at the quinolone 1-position results in derivatives with low-nM binding potency and good selectivity with respect to hERG binding.

  已合成和评估了几种衍生自喹啉2（1H）-和喹唑啉-2（1H）-的功能强大的功能性MCHr1拮抗剂。喹诺酮1位上的吡啶基甲基取代导致衍生物具有较低的nM结合力和相对于hERG结合的良好选择性。
• Palladium-catalyzed facile synthesis of furoquinolinones and furopyridinones
  作者：Tao Guo、Xu-Ning Wei、Hong-Yan Wang、Bing Zhao

  DOI：10.1080/00397911.2017.1422519

  日期：2018.4.3

  ABSTRACT This work is focused on the development of a convenient and efficient approach for the synthesis of furoquinolinones and furopyridinones through palladium-catalyzed cyclization reactions between styrenes and 4-hydroxyquinolinones/4-hydroxypyridinones under air conditions. Studies conducted to evaluate the antitumoral potential of the resulted compounds revealed that some of the obtained furoquinolinones

  摘要这项工作的重点是开发一种方便有效的方法，通过钯催化苯乙烯和 4-羟基喹啉酮/4-羟基吡啶酮在空气条件下的环化反应合成呋喃喹啉酮和呋喃吡啶酮。为评估所得化合物的抗肿瘤潜力而进行的研究表明，一些获得的呋喃喹啉酮在体外对人源胃癌细胞系具有抗增殖活性。图形概要
• Symmetrical Bisquinolones via Metal-Catalyzed Cross-Coupling and Homocoupling Reactions
  作者：Jamshed Hashim、Toma N. Glasnov、Jennifer M. Kremsner、C. Oliver Kappe

  DOI：10.1021/jo052283p

  日期：2006.2.1

  Functionalized 4,4‘-bisquinolones can be efficiently synthesized by microwave-assisted palladium(0)-catalyzed one-pot borylation/Suzuki cross-coupling reactions or via nickel(0)-mediated homocouplings of 4-chloroquinolin-2(1H)-one precursors. Both methods are also applicable to other types of symmetrical biaryls.

  可以通过微波辅助钯（0）催化的一锅硼化/ Suzuki交叉偶联反应或通过镍（0）介导的4-氯喹啉2（1 H）介导的有效偶联来有效合成功能化的4,4'-双喹啉酮。一前体。两种方法也适用于其他类型的对称联芳基。
• Syntheses and Fluorescent Properties of 6-Methoxy-2-oxoquinoline-3,4-dicarbonitriles and 6,7-Dimethoxy-2-oxoquinoline-3,4-dicarbonitriles
  作者：Guy Crépin Enoua、Günther Lahm、Georg Uray、Wolfgang Stadlbauer

  DOI：10.1002/jhet.1865

  日期：2014.8

  4-Chlorocarbostyrils , , , , with methoxy substituents in 6, 7, or 6,7-position react with potassium cyanide in a p-toluenesulfinate mediated reaction either to the highly fluorescent and stable 2-oxoquinoline-3,4-dicarbonitriles , , , or at slightly lower temperatures to 4-monocarbonitriles , , . 4-Chlorocarbostyril and lithium p-toluenesulfinate gave pure 4-toluenesulfonylquinolone , which reacted

  4-氯咔啉 ， ， ， ， 在6、7或6,7位的甲氧基取代基与 对甲苯磺酸酯介导的对高荧光和稳定的2-氧代喹啉-3,4-二腈的反应中的氰化钾， ， ， 或在较低的温度下生成4-单腈 ， ， 。4-氯卡巴斯蒂利 和 对甲苯磺酸锂得到纯的4-甲苯磺酰基喹诺酮与氰化钾反应生成单腈 或二腈 ，取决于反应条件。4-三氟甲基喹诺酮类 和 由合适的甲氧基苯胺和4,4,4-三氟乙酰乙酸制备用于荧光比较的样品。