4,5,8-trimethoxy-1-methyl-1H-quinolin-2-one | 479682-18-3

• 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: 4,5,8-trimethoxy-1-methyl-1H-quinolin-2-one
• 英文别名: 4,5,8-Trimethoxy-1-methylquinolin-2-one
• CAS: 479682-18-3
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: JXQLITNAAXDTJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5,8-trimethoxy-1-methyl-1H-quinolin-2-one 在 ammonium cerium(IV) nitrate 、 silica gel 作用下， 以 水 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 20.75h， 生成 7-acetoxy-2-methyl-4-methoxy-1H-benzo[g]quinoline-2,5,10-trione
  参考文献：
  名称：

  A Synthesis of Oxygenated 1-Azaanthra- quinones via Diels-Alder Reaction of 2,4-Dioxygenated Quinoline-5,8-diones with 1-Methoxy-3-trimethylsilyloxy- 1,3-butadiene

  摘要：

  Diels-Alder reaction of 2,4-dioxygenated quinoline-5,8-diones (7a, b and 8) with 1-methoxy-3-trimethylsilyloxy-1,3-butadiene (11) proceeded in a regio- and stereoselctive manner to give 2,4,6,8-tetraoxygenated 1-azaanthraquinoes (12a, b and 18) in good to moderate yields, respectively. The results demonstrated that Diels-Alder reaction of the 2,4-dioxygenated quinolone-5,8-diones with the activated diene provides a useful method for synthesizing highly oxygenated 1-azaanthraquinones.

  DOI：

  10.3987/com-02-9502
• 作为产物：
  描述：

  4-hydroxy-5,8-dimethoxy-1H-quinolin-2-one 在 sodium hydroxide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 27.5h， 生成 4,5,8-trimethoxy-1-methyl-1H-quinolin-2-one
  参考文献：
  名称：

  A Synthesis of Oxygenated 1-Azaanthra- quinones via Diels-Alder Reaction of 2,4-Dioxygenated Quinoline-5,8-diones with 1-Methoxy-3-trimethylsilyloxy- 1,3-butadiene

  摘要：

  Diels-Alder reaction of 2,4-dioxygenated quinoline-5,8-diones (7a, b and 8) with 1-methoxy-3-trimethylsilyloxy-1,3-butadiene (11) proceeded in a regio- and stereoselctive manner to give 2,4,6,8-tetraoxygenated 1-azaanthraquinoes (12a, b and 18) in good to moderate yields, respectively. The results demonstrated that Diels-Alder reaction of the 2,4-dioxygenated quinolone-5,8-diones with the activated diene provides a useful method for synthesizing highly oxygenated 1-azaanthraquinones.

  DOI：

  10.3987/com-02-9502

文献信息

• A Synthesis of Oxygenated 1-Azaanthra- quinones via Diels-Alder Reaction of 2,4-Dioxygenated Quinoline-5,8-diones with 1-Methoxy-3-trimethylsilyloxy- 1,3-butadiene
  作者：Yoshie Horiguchi、Noriko Fukuda、Mutsumi Takada、Takehiro Sano

  DOI：10.3987/com-02-9502

  日期：——

  Diels-Alder reaction of 2,4-dioxygenated quinoline-5,8-diones (7a, b and 8) with 1-methoxy-3-trimethylsilyloxy-1,3-butadiene (11) proceeded in a regio- and stereoselctive manner to give 2,4,6,8-tetraoxygenated 1-azaanthraquinoes (12a, b and 18) in good to moderate yields, respectively. The results demonstrated that Diels-Alder reaction of the 2,4-dioxygenated quinolone-5,8-diones with the activated diene provides a useful method for synthesizing highly oxygenated 1-azaanthraquinones.