hexafluoro-l6-phosphane, 3-formyl-1-methyl-4-(p-tolyl)quinolin-1-ium salt | 98888-86-9

• 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: hexafluoro-l6-phosphane, 3-formyl-1-methyl-4-(p-tolyl)quinolin-1-ium salt
• CAS: 98888-86-9
• 化学式: C₁₈H₁₆NO*F₆P
• 分子量: 407.295
• InChiKey: HMAPSLLDTDXOBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.83
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.95
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  对甲基苯乙酮 、 N-甲基甲酰苯胺 在 ammonium hexafluorophosphate 、 三氯氧磷 作用下， 生成 hexafluoro-l6-phosphane, 3-formyl-1-methyl-4-(p-tolyl)quinolin-1-ium salt
  参考文献：
  名称：

  The synthesis of quinolines from N-alkylformanilides and electron-rich alkenes

  摘要：

  DOI：

  10.1016/s0040-4039(00)94769-5

文献信息

• The reverse vilsmeier approach to the synthesis of quinolines, quinolinium salts and quinolones
  作者：Otto Meth-Cohn、David L Taylor

  DOI：10.1016/0040-4020(95)00729-r

  日期：1995.11

  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.