N-<9-(10-hydroxyanthryl)>-N-methylpiperidinium iodide | 132178-10-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-<9-(10-hydroxyanthryl)>-N-methylpiperidinium iodide
• CAS: 132178-10-0
• 化学式: C₂₀H₂₂NO*I
• 分子量: 419.305
• InChiKey: RODOGYOOOPLMOC-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  N-<9-(10-hydroxyanthryl)>-N-methylpiperidinium iodide 、 碘甲烷 在 potassium tert-butylate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以48%的产率得到N-<9-(10-methoxyanthryl)>-N-methylpiperidinium iodide
  参考文献：
  名称：

  Rapid intermolecular electron transfer specific to the Zwitterionic form of N-(9-(10-hydroxyanthryl))piperidine (HAP)

  摘要：

  The acid-catalyzed condensation of anthrone with excess piperidine affords both N-anthrylpiperidine (80-85%) and HAP (5-10%). The H-1 and C-13 NMR spectra of N-(9-anthryl)piperidine are unexceptional and consistent with the structure assignment. However, the NMR spectra of HAP in DMSO-d6 reveal, except for impurities, only resonances for the aliphatic protons or carbons. Treatment of the DMSO-d6 solution with either strong acid or base results in appearance of the expected aromatic protons or carbons, with integrations and/or chemical shifts as expected for the predicted ionic forms of HAP produced under these conditions. We have interpreted the unusual NMR behavior of HAP in DMSO-d6 in terms of intermolecular electron transfer with an impurity of the corresponding O-centered radical, observable by ESR. Of the four ionization states available to 10-N-piperidinylanthranol, only the zwitterionic form exhibits electron transfer that is rapid and reversible. The results of NMR studies on the N-methylated derivative of HAP are consistent with this interpretation.

  DOI：

  10.1021/ja00005a009