2H,3H,5H-1,4-oxazino[6,5,4-i,j]quinolin-5-one

• 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: 2H,3H,5H-1,4-oxazino[6,5,4-i,j]quinolin-5-one
• 英文别名: Oxazinoquinolone；4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13),10-tetraen-12-one
• 化学式: C₁₁H₉NO₂
• 分子量: 187.198
• InChiKey: QJJKSMRAKSECFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  8-(2-chloro-ethoxy)-2-methyl-quinoline 在 air 作用下， 生成 2H,3H,5H-1,4-oxazino[6,5,4-i,j]quinolin-5-one
  参考文献：
  名称：

  General methodology for synthesis of fused tricyclic oxazino-2-quinolones under phase-transfer catalyzed conditions

  摘要：

  A one-pot synthesis of substituted oxazino-2-quinolones is described. The cornerstone of this methodology involves PTC catalyzed addition of an ethylene dihalide to a quinol to generate the corresponding O-alkylated intermediate in situ followed by ring closing and subsequent formation of a carbonyl group in the oxazinoquinolone in a one-pot sequence. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.134

文献信息

• Synthesis of 2,3-Dihydro[1,4]oxazino[2,3,4-ij]quinolinium Bromide and Its Reaction with Sodium Hydroxide
  作者：D. G. Kim、A. V. Vasilenko、A. B. Melent’ev

  DOI：10.1134/s1070363218010218

  日期：2018.1

  The reaction of quinolin-8-ol with 1,2-dibromoethane in dimethylformamide gave 2,3-dihydro[1,4]-oxazino[2,3,4-ij]quinolinium bromide which reacted with aqueous sodium hydroxide to afford 2,3,4,5-tetrahydro[1,4]oxazino[2,3,4-ij]quinoline, 2,3,4,5-tetrahydro[1,4]oxazino[2,3,4-ij]quinolin-5-ol, and 2,3,4,5-tetrahydro[1,4]oxazino[2,3,4-ij]quinolin-5-one.

  喹啉-8-醇与1,2-二溴乙烷在二甲基甲酰胺中的反应生成2,3-二氢[1,4]-恶嗪基[2,3,4- ij ]溴化喹啉鎓，与氢氧化钠水溶液反应得到2， 3,4,5-四氢[1,4]恶嗪[2,3,4- ij ]喹啉，2,3,4,5-四氢[1,4]恶嗪[2,3,4- ij ]喹啉- 5-醇和2,3,4,5-四氢[1,4]恶嗪基[2,3,4- ij ]喹啉-5-酮。
• Synthesis of polycyclic fused 2-quinolones in aqueous micellar system
  作者：Subhendu Naskar、Pritam Saha、Rupankar Paira、Abhijit Hazra、Priyankar Paira、Shyamal Mondal、Arindam Maity、Krishnendu B. Sahu、Sukdeb Banerjee、Nirup B. Mondal

  DOI：10.1016/j.tetlet.2010.01.030

  日期：2010.3

  A high yielding green protocol has been developed for the synthesis of tri-, tetra-, and pentacyclic fused 2-quinolones in micellar medium. The method is more effective compared to phase-transfer catalytic (PTC) method in terms of the yield of the product as well as the reaction time. It is operationally simple as well as environmentally benign. (C) 2010 Elsevier Ltd. All rights reserved.
• Phase transfer catalyzed synthesis of bis-quinolines: Antileishmanial activity in experimental visceral leishmaniasis and in vitro antibacterial evaluation
  作者：Partha Palit、Priyankar Paira、Abhijit Hazra、Sukdeb Banerjee、Asish Das Gupta、Sujata G. Dastidar、Nirup B. Mondal

  DOI：10.1016/j.ejmech.2008.04.014

  日期：2009.2

  A one-pot synthesis of some novel bis-quinolines has been achieved under phase transfer catalyzed conditions using 8-hydroxy quinoline derivatives as substrates. The synthesized analogues were evaluated for antileishmanial activity against Leishmania donovani promastigotes and amastigotes. The entire bis-quinolines showed efficacy in both in vitro and in vivo studies. Compound 5 (1,1-bis-[(5-chloro-8-quinolyl)oxy] methane) exhibited the most significant activity. Compounds 4 (1,1-bis-[(8-quinolyl)oxylmethane) and 9 (1,5-bis-[(2-methyl-8-quinolyl)oxy] pentane) also demonstrated significant leishmanicidal efficacy against established visceral leishmaniasis in BALB/c model. Ultrastructural studies of promastigotes treated with compound 5, demonstrated membrane blebbing, chromatin condensation and vacuolization in the parasites and the flagellated parasites became round shaped after treatment. Moreover, in vitro antibacterial activity of compound 5 against several bacterial strains revealed its promising efficacy. The findings suggested that 1,1-bis-[(5-chloro-8-quinolyl)oxy] methane (5) is a bright candidate to be considered as lead compound for leishmanicidal drug. (c) 2008 Elsevier Masson SAS. All rights reserved.
• General methodology for synthesis of fused tricyclic oxazino-2-quinolones under phase-transfer catalyzed conditions
  作者：Rajat Dutta、Debayan Mandal、Nilendu Panda、Nirup B. Mondal、Sukdeb Banerjee、Shrabanti Kumar、Manuela Weber、Peter Luger、Niranjan P. Sahu

  DOI：10.1016/j.tetlet.2004.10.134

  日期：2004.12

  A one-pot synthesis of substituted oxazino-2-quinolones is described. The cornerstone of this methodology involves PTC catalyzed addition of an ethylene dihalide to a quinol to generate the corresponding O-alkylated intermediate in situ followed by ring closing and subsequent formation of a carbonyl group in the oxazinoquinolone in a one-pot sequence. (C) 2004 Elsevier Ltd. All rights reserved.