N-methyl-8-tosyloxyquinolin-4-one | 927833-22-5

• 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: N-methyl-8-tosyloxyquinolin-4-one
• 英文别名: 1-Methyl-4-oxo-1,4-dihydroquinolin-8-yl 4-methylbenzene-1-sulfonate；(1-methyl-4-oxoquinolin-8-yl) 4-methylbenzenesulfonate
• CAS: 927833-22-5
• 化学式: C₁₇H₁₅NO₄S
• 分子量: 329.376
• InChiKey: UDJAQAIEDYUUTR-UHFFFAOYSA-N

物化性质

• 熔点：
  156 °C
• 沸点：
  503.2±50.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,8-二羟基喹啉 在 sodium hydroxide 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 5.0h， 生成 N-methyl-8-tosyloxyquinolin-4-one
  参考文献：
  名称：

  Synthesis of 4-Alkoxy-8-hydroxyquinolines

  摘要：

  Quinolines with a hydroxyl group at the 8-position and an alkoxy group at the 4-position are rare compounds. In this paper the synthesis of five 4-alkoxy-8-hydroxyquinolines is reported. The key reaction in the synthetic route is a selective protection of the hydroxyl group at C-atom 8 in 4,8-dihydroxyquinoline with a tosyl group and the hydrolytic removal of the protective group after the alkylation. The tosyl group is stable during the alkylations with various alkylating agents in the presence of sodium hydride.

  DOI：

  10.1021/jo062175i

文献信息

• Synthesis of 4-Alkoxy-8-hydroxyquinolines
  作者：Juha P. Heiskanen、Walaa A. E. Omar、Mari K. Ylikunnari、Kirsi M. Haavisto、Maria J. Juan、Osmo E. O. Hormi

  DOI：10.1021/jo062175i

  日期：2007.2.1

  Quinolines with a hydroxyl group at the 8-position and an alkoxy group at the 4-position are rare compounds. In this paper the synthesis of five 4-alkoxy-8-hydroxyquinolines is reported. The key reaction in the synthetic route is a selective protection of the hydroxyl group at C-atom 8 in 4,8-dihydroxyquinoline with a tosyl group and the hydrolytic removal of the protective group after the alkylation. The tosyl group is stable during the alkylations with various alkylating agents in the presence of sodium hydride.