3-chloro-1-methyl-4-quinolone | 64965-20-4

• 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: 3-chloro-1-methyl-4-quinolone
• 英文别名: 3-chloro-1-methyl-1H-quinolin-4-one；3-Chloro-1-methylquinolin-4-one
• CAS: 64965-20-4
• 化学式: C₁₀H₈ClNO
• 分子量: 193.633
• InChiKey: XXGPWJQUCCFUDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基甲酰苯胺 在 sodium hydroxide 、 ammonium hexafluorophosphate 、 三氯氧磷 作用下， 以 甲醇 、 水 为溶剂， 反应 4.75h， 生成 3-chloro-1-methyl-4-quinolone
  参考文献：
  名称：

  The reverse vilsmeier approach to the synthesis of quinolines, quinolinium salts and quinolones

  摘要：

  N-Methylformanilide(MFA) reacts with various electron-rich alkenes in POCl3 solution to give N-methylquinolinium salts generally in good yield. The alkenes can be vinyl acetate, an aldehyde or ketone enamine (preferably the morpholine enamine), a methyl aryl ketone (reacting as its enol) or it may be generated from an alkanoamide bearing alpha-protons (which produces an alpha-chloroenamine in situ). The reaction is effective for a variety of other alkyl-, aryl- and benzyl- formanilides as well as ring substituted anilides though electron-withdrawing groups tend to inhibit cyclisation. The mechanism of the cyclisation has been elucidated and shown to involve an electrocyclic ak process. The reactions of MFA with amides in POCl3 gives 4-quinolones on alkaline workup.

  DOI：

  10.1016/0040-4020(95)00729-r

文献信息

• A novel one-step synthesis of quinolinium salts and 4-quinolones from formanilides
  作者：Otto Meth-Cohn、David L Taylor

  DOI：10.1016/s0040-4039(00)73654-9

  日期：1993.5

  N-Methylformanilide in POCl3 reacts readily at 80°C with alkanoamides(RCH2CONR'2) to give 3-R-4-chloroquinolinium salts in good yields. The arylamide reacts as its Vilsmeier salt and the alkanoamide as an α-chloroenamine. High yields of 4-quinolones are easily obtained by base treatment.

  N-甲基甲酰苯胺在将POCl 3下进行反应容易地在80℃下用alkanoamides（RCH 2 CONR” 2），得到良好的收率3-R-4-chloroquinolinium盐。芳基酰胺以其维斯迈尔盐形式反应，而链烷酰胺以α-氯烯胺形式反应。通过碱处理容易获得高产率的4-喹诺酮。