N-<9-(10-hydroxyanthryl)>piperidine | 132178-09-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-<9-(10-hydroxyanthryl)>piperidine
• CAS: 132178-09-7
• 化学式: C₁₉H₁₉NO
• 分子量: 277.366
• InChiKey: FGPXIABBSOUIDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  23.47
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  哌啶 、 蒽酮 在 蒽醌 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 20.0h， 生成 N-(9-anthryl)piperidine 、 蒽醌 、 N-<9-(10-hydroxyanthryl)>piperidine
  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