4-hydroxy-3-(5-isoxazolyl)-1-methyl-2(1H)-quinolinone | 875126-05-9

• 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-3-(5-isoxazolyl)-1-methyl-2(1H)-quinolinone
• 英文别名: 4-hydroxy-3-(5-isoxazolyl)-1-methylquinolin-2(1H)-one；4-Hydroxy-1-methyl-3-(1,2-oxazol-5-yl)quinolin-2-one；4-hydroxy-1-methyl-3-(1,2-oxazol-5-yl)quinolin-2-one
• CAS: 875126-05-9
• 化学式: C₁₃H₁₀N₂O₃
• 分子量: 242.234
• InChiKey: IMSUVZBCBKJHAL-UHFFFAOYSA-N

物化性质

• 熔点：
  280-282 °C(Solv: ethanol (64-17-5))
• 沸点：
  426.5±45.0 °C(Predicted)
• 密度：
  1.422±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-(5-isoxazolyl)-1-methyl-2(1H)-quinolinone 、 硫酸二甲酯 生成 1-methyl-3-(2-methyl-2H-1,2-oxazol-2-ium-5-ylidene)quinoline-2,4-dione
  参考文献：
  名称：

  Synthesis, structural determination and photo-antiproliferative activity of new 3-pyrazolyl or -isoxazolyl substituted 4-hydroxy-2(1H)-quinolinones

  摘要：

  A convenient route to new 3-quinolinonyl-pyrazoles and isoxazoles is described through cyclization of 3-[(E)-3(di methylamino)-2-propenoyl]-4-hydroxy-1-methyl-2(1H)-quinolinone. The phototoxicity as well as the cytotoxic activities of the title compounds are evaluated against leukemia- and adenocarcinoma-derived cell lines in comparison to the normal human keratinocytes. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.135
• 作为产物：
  描述：

  3-[(E)-3-(dimethylamino)-2-propenoyl]-4-hydroxy-1-methyl-2(1H)-quinolinone 在 羟胺 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以84%的产率得到4-hydroxy-3-(5-isoxazolyl)-1-methyl-2(1H)-quinolinone
  参考文献：
  名称：

  Synthesis, structural determination and photo-antiproliferative activity of new 3-pyrazolyl or -isoxazolyl substituted 4-hydroxy-2(1H)-quinolinones

  摘要：

  A convenient route to new 3-quinolinonyl-pyrazoles and isoxazoles is described through cyclization of 3-[(E)-3(di methylamino)-2-propenoyl]-4-hydroxy-1-methyl-2(1H)-quinolinone. The phototoxicity as well as the cytotoxic activities of the title compounds are evaluated against leukemia- and adenocarcinoma-derived cell lines in comparison to the normal human keratinocytes. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.135

文献信息

• An Efficient New Route for the Synthesis of Some 3-Hterocyclylquinolinones <i>via</i> Novel 3-(1,2-Dihydro-4-hydroxy-1-methyl-2-oxoquinolin-3-yl)-3-oxopropanal and Their Antioxidant Screening
  作者：Mohamed M. Hassan、Hany M. Hassanin

  DOI：10.1002/jhet.2952

  日期：2017.11

  3‐(4‐hydroxy‐1‐methylquinoline‐3‐yl)‐3‐oxoproponal (5) was synthesized from 3‐[(E)‐3‐(dimethylamino)‐2‐propenoyl]‐4‐hydroxy‐1‐methyl‐2(1H)‐quinolinone (3) and was utilized as a starting precursor material. A convenient new route to functionalized 3‐heterocyclyl 4‐hydroxy‐2(1H)‐quinolinones such as pyrazolyl, isoxazolyl, pyrimidinyl, azepineyl, pyridonyl, and pyranyl heterocycles was described via cyclization

  3-（4-羟基-1-甲基喹啉-3-基）-3-氧代丙醛（5）由3-[（（E）-3-（二甲基氨基）-2-丙烯酰基] -4-羟基-1-甲基）合成-2（1 H）-喹啉酮（3）用作起始前体材料。官能化3-杂环基-4-羟基- 2（1一种方便新路线ħ）-quinolinones如吡唑基，异恶唑基，嘧啶基，azepineyl ，吡啶酮和吡喃基的杂环经由化合物环化描述5与一些Ñ和Ç -nucleophiles。新合成的醛5显示使用化合物与最大产率只有一个环闭合可能性，而不是3表现出不同的区域选择性闭环途径，且收率最低。根据相关光谱数据和元素微量分析，对所有新合成的产物进行了结构阐明。在一系列体外测试中筛选了产品的抗氧化活性。