4-hydroxy-2-oxo-1-propyl-1,2-dihydroquinoline | 296759-12-1

• 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-2-oxo-1-propyl-1,2-dihydroquinoline
• 英文别名: 1-propyl-2-oxo-4-hydroxyquinoline；4-hydroxy-1-propylquinolin-2(1H)-one；4-hydroxy-1-propylquinolin-2-one
• CAS: 296759-12-1
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: SQWCUOUPRCFSGG-UHFFFAOYSA-N

物化性质

• 沸点：
  325.4±42.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1-二苯乙烯 、 4-hydroxy-2-oxo-1-propyl-1,2-dihydroquinoline 在 manganese triacetate 、 溶剂黄146 作用下， 反应 0.03h， 以76%的产率得到3,5-dihydro-2,2-diphenyl-5-propylfuro[3,2-c]quinolin-4(2H)-one
  参考文献：
  名称：

  使用基于 Mn(III) 的氧化自由基环化制备 2H-FURO[3,2-c]QUINOLIN-4-ONE 框架的便捷途径

  摘要：

  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

  DOI：

  10.1515/hc.2004.10.2-3.135
• 作为产物：
  描述：

  1-propyl-2,4-dioxo-1,2,3,4-tetrahydroquinoline-3-carboxylic acid 以90%的产率得到4-hydroxy-2-oxo-1-propyl-1,2-dihydroquinoline
  参考文献：
  名称：

  4-hydroxy-2-quinolones. 42. Synthesis and biological activity of 1-R-2-oxo-3-(2H-1,2,4-benzothiadiazine-1,1-dioxid-3-yl)-4-hydroxyquinolines

  摘要：

  DOI：

  10.1007/bf02256875

文献信息

• COMPOSITIONS FOR PREVENTING AND TREATING TYPE I ALLERGY
  申请人：Sunstar Inc.

  公开号：EP1172109A1

  公开（公告）日：2002-01-16

  A method for screening a cysteine protease inhibitor of which cysteine protease inhibitory activity is enhanced in the presence of endogenous polyvalent metal ion, which comprises treating a cysteine protease with a test compound in the presence of the polyvalent metal ion, and a pharmaceutical composition for treating apoptosis-associated diseases, which contains as the active ingredient a cysteine protease inhibitor of which cysteine protease inhibitory activity is enhanced in the presence of endogenous polyvalent metal ion.

  一种筛选半胱氨酸蛋白酶抑制剂的方法，其半胱氨酸蛋白酶抑制活性在内源性多价金属离子存在下得到增强，该方法包括在多价金属离子存在下用测试化合物处理半胱氨酸蛋白酶，以及一种治疗细胞凋亡相关疾病的药物组合物，其活性成分含有半胱氨酸蛋白酶抑制剂，其半胱氨酸蛋白酶抑制活性在内源性多价金属离子存在下得到增强。
• METHOD FOR SCREENING CYSTEINE PROTEASE INHIBITOR
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：EP1172443A1

  公开（公告）日：2002-01-16

  A method for screening a cysteine protease inhibitor of which cysteine protease inhibitory activity is enhanced in the presence of endogenous polyvalent metal ion, which comprises treating a cysteine protease with a test compound in the presence of the polyvalent metal ion, and a pharmaceutical composition for treating apoptosis-associated diseases, which contains as the active ingredient a cysteine protease inhibitor of which cysteine protease inhibitory activity is enhanced in the presence of endogenous polyvalent metal ion.

  一种筛选半胱氨酸蛋白酶抑制剂的方法，其半胱氨酸蛋白酶抑制活性在内源性多价金属离子存在下得到增强，该方法包括在多价金属离子存在下用测试化合物处理半胱氨酸蛋白酶，以及一种治疗细胞凋亡相关疾病的药物组合物，其活性成分含有半胱氨酸蛋白酶抑制剂，其半胱氨酸蛋白酶抑制活性在内源性多价金属离子存在下得到增强。
• 4-hydroxy-2-quinolones. 149*. Synthesis, chemical transformations, and biological properties of β-N-acylhydrazides of 1-R-4-hydroxy-2-oxo-1,2-dihydro-quinoline-4-carboxylic acids
  作者：I. V. Ukrainets、A. A. Tkach、Liu Yang Yang

  DOI：10.1007/s10593-009-0198-6

  日期：2008.11

  Two methods of preparation have been proposed and the synthesis has been effected of a large series of beta-N-acylhydrazides of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids. The possibility of using various condensing agents for converting them into the corresponding 1,3,4-oxa-diazoloquinolines has been studied. Results are given of an investigation of the antitubercular activity of the synthesized compounds.
• 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.