4-羟基-3-丙基-1H-喹啉-2-酮 | 1873-61-6

• 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
• 中文名称: 4-羟基-3-丙基-1H-喹啉-2-酮
• 英文名称: 4-hydroxy-3-propyl-2(1H)-quinolinone
• 英文别名: 3-propyl-4-hydroxy-2-quinolone；4-hydroxy-3-propyl-1H-quinolin-2-one；3-Propyl-4-hydroxy-chinolon-(2)；4-Hydroxy-3-propyl-2-chinolon；4-Hydroxy-3-propyl-1H-quinolin-2-one
• CAS: 1873-61-6
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: CKETYLIKMVJPGC-UHFFFAOYSA-N

物化性质

• 熔点：
  228 °C
• 沸点：
  412.1±45.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-羟基-3-丙基-1H-喹啉-2-酮 在 溴 、 sodium methylate 、 溶剂黄146 作用下， 反应 1.17h， 生成 3-methoxy-3-propyl-2,4-dioxoquinoline
  参考文献：
  名称：

  4-Hydroxy-2-quinolones. 26. Bromination of 3-substituted 2-oxo-4-hydroxyquinolones

  摘要：

  DOI：

  10.1007/bf01169675
• 作为产物：
  描述：

  Ethyl 2-(2-ethoxycarbonylpentanoylamino)benzoate 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 4-羟基-3-丙基-1H-喹啉-2-酮
  参考文献：
  名称：

  4-Hydroxy-2-quinolones. 1. Efficient method for obtaining 3-alkyl-4-hydroxy-2-quinolones

  摘要：

  DOI：

  10.1007/bf00471752

文献信息

• CONVENIENT ROUTE TO 2H-FURO[3,2-c]QUINOLIN-4-ONE FRAMEWORK USING Mn(III)-BASED OXIDATIVE RADICAL CYCLIZATION
  作者：Ryoukou Kumabe、Hiroshi Nishino

  DOI：10.1515/hc.2004.10.2-3.135

  日期：2004.1

  The oxidation of a mixture of 1.1-disubstituted ethenes 1 with 4-hydroxy-2-quinolinone derivatives 2 with manganese(III) acetate in boiling glacial acetic acid was investigated. The reaction of 3-substituted quinolinones 2 gave 9b-hydroxy-3,3a,5,9b-tetrahydro-2//-furo[3,2-c]quinolin-4-ones 3 and 3-(2.2-diarvlethenyl)quinoline-2,4-diones 4 in moderate to good yields. On the other hand, 3,5-dihydro-2//-furo[3

  研究了 1.1-二取代的乙烯 1 与 4-羟基-2-喹啉酮衍生物 2 与乙酸锰 (III) 在沸腾冰醋酸中的氧化反应。3-取代喹啉酮2反应得到9b-羟基-3,3a,5,9b-四氢-2//-呋喃[3,2-c]喹啉-4-酮3和3-(2.2-二亚乙烯基)喹啉-2,4-二酮 4 中等至良好的收率。另一方面，3,5-dihydro-2//-furo[3,2-c]quinolin-4-ones 5 主要在 3-位无取代基的喹啉酮 2 反应过程中产生。讨论了反应途径和反应的应用。喹啉酮是一类非常重要的杂环化合物。喹啉酮环存在于许多天然产物中，大量喹啉酮衍生物显示出令人感兴趣的生物活性。最近，我们发现了一种独特的过氧化物形成，使用锰 (III) 催化的 4-羟基喹啉-2-酮在烯烃存在下的有氧氧化。有氧氧化产生 3,3-双（2 氢过氧乙基）喹啉二酮和 [4.4.3] 丙烷型环状过氧化物。从抗疟活性的角度来看
• Quinolone compounds for use in treating viral infections
  申请人：——

  公开号：US20030069271A1

  公开（公告）日：2003-04-10

  The present invention relates to quinolone compounds and their use in the treatment of viral infections.

  本发明涉及喹诺酮化合物及其在治疗病毒感染中的应用。
• A unique peroxide formation based on the Mn(III)-catalyzed aerobic oxidation
  作者：Ryoukou Kumabe、Hiroshi Nishino

  DOI：10.1016/j.tetlet.2003.11.054

  日期：2004.1

  1-diarylsubstituted alkenes 4 and 4-hydroxy-1H-quinolin-2-ones 5 in the presence of a catalytic amount of manganese(III) acetate dihydrate in air gave 3,3-bis(2-hydroperoxyethyl)-1H-quinoline-2,4-diones 6 in 31–91% yields together with [4.4.3]propellane-type cyclic peroxides 7 (10–34%). A similar aerobic oxidation of 3-substituted quinolinones 8 yielded cyclic peroxide derivatives 9 and/or 3-hydroperoxyethylated

  在催化量的乙酸锰（III）二水合物存在下，在空气中将1,1-二芳基取代的烯烃4和4-羟基-1 H-喹啉-2-酮5的混合物进行自氧化，得到3,3-bis（ 2-氢过氧乙基）-1 H-喹啉-2,4-二酮6的产率为31-91％，与[4.4.3]丙炔型环状过氧化物7（10-34％）一起产生。3-取代的喹啉酮8的类似的需氧氧化产生环过氧化物衍生物9和/或3-氢过氧乙基化的喹啉二酮10，这取决于取代基。双（氢过氧化物）6（R 1 = Me，Ar = 4-ClC通过X射线晶体学证实了6 H 4）和[4.4.3]丙炔7（R 1 = Me，Ar = Ph）。
• Design of Non-nucleoside Inhibitors of HIV-1 Reverse Transcriptase with Improved Drug Resistance Properties. 2.
  作者：George A. Freeman、C. Webster Andrews、Andrew L. Hopkins、Gina S. Lowell、Lee T. Schaller、Jill R. Cowan、Stephen S. Gonzales、George W. Koszalka、Richard J. Hazen、Lawrence R. Boone、Rob G. Ferris、Katrina L. Creech、Grace B. Roberts、Steven A. Short、Kurt Weaver、David J. Reynolds、John Milton、Jingshan Ren、David I. Stuart、David K. Stammers、Joseph H. Chan

  DOI：10.1021/jm040072r

  日期：2004.11.1

  HIV-1 nonnucleoside reverse transcriptase inhibitors (NNRTIs) are part of the combination therapy currently used to treat HIV infection. The features of a new NNRTI drug for HIV treatment must include selective potent activity against both wild-type virus as well as against mutant virus that have been selected by use of current antiretroviral treatment regimens. Based on analogy with known HIV-1 NNRTI inhibitors and modeling studies utilizing the X-ray crystal structure of inhibitors bound in the HIV-1 RT, a series of substituted 2-quinolones was synthesized and evaluated as HIV-1 inhibitors.
• Mn(III)-based reaction of alkenes with quinolinones. Formation of peroxyquinolinones and quinoline-related derivatives
  作者：Hiroshi Nishino、Ryoukou Kumabe、Ryoichi Hamada、Mehtap Yakut

  DOI：10.1016/j.tet.2014.01.013

  日期：2014.2

  The reactions of 1,1-disubstituted alkenes with 4-hydroxyquinolin-2(1H)-ones under both Mn(III)-catalyzed aerobic oxidation conditions at room temperature and Mn(III)-mediated oxidation conditions at reflux temperature are described. The Mn(III)-catalyzed aerobic oxidation afforded bis(hydroperoxyethyl)quinolinones and azatrioxa[4.431propellanes, while the oxidation with Mn(OAc)(3)center dot 2H(2)O produced furo[3,2-c]quinolin-4-one analogues. The existence of a substituent at the 3-position of the 4-hydroxyquinolin-2(1H)-ones prevented a double reaction with the alkenes, and (endoperoxy)quinolinones and/or (hydroperoxyethyl)quinolinones were obtained under the Mn(III)-catalyzed aerobic conditions, while furo[3,2-c]quinolinone hemiacetals and vinylquinolinones were selectively produced under the Mn(III)-mediated oxidation conditions depending on the reaction temperature and times. Cyclic assembly of quinolinone-related 1,3-dicarbonyl compounds such as dihydropyridinones, pyranones, and dimedone derivatives was also examined under elevated temperature conditions. (C) 2014 Elsevier Ltd. All rights reserved.