(+/-)-quinuclidin-3-ol; picrate | 100611-34-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (+/-)-quinuclidin-3-ol; picrate
• 英文别名: (+/-)-Chinuclidin-3-ol; Picrat
• CAS: 100611-34-5
• 化学式: C₆H₃N₃O₇*C₇H₁₃NO
• 分子量: 356.292
• InChiKey: KKZWJQSSARMOSD-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  2,4,6-三硝基氯苯 、 奎宁环-3-醇 以 水 为溶剂， 生成 (+/-)-quinuclidin-3-ol; picrate
  参考文献：
  名称：

  Nucleophilic reactivity: nucleophilic aromatic substitution reactions of 2,4-dinitrochlorobenzene and picryl chloride in aqueous and methanol solutions

  摘要：

  Rate constants for nucleophilic aromatic substitution reactions of picryl chloride, I, with acetate ion and a series of amine nucleophiles, including primary, secondary, tertiary (quinuclidines), and amines which show the alpha-effect, in aqueous and methanol solutions have been measured. Rate constants have also been measured, in water, for the reactions of 2,4-dinitrochlorobenzene, II, with trifluoroethylamine and semicarbazide. Reactions of picryl chloride with 3-quinuclidinol and DABCO yield picrate ion via general base catalyzed hydrolysis. On the other hand, reaction with quinuclidine proceeds at least in part via a mechanism in which N-picrylquinuclidinium ion is formed and then converted into a N-picrylpiperidine derivative. When the kinetic data are combined with data previously reported in the literature, the slopes of plots of log of the second-order rate constants against Ritchie's N+ parameter are 0.95 +/- 0.13 and 0.79 +/- 0.11 for the reactions of 2,4-dinitrochlorobenzene and picryl chloride, respectively (the reported error limits are the 95% confidence intervals). Steric effects may be important in these reactions, but these effects do not significantly change the slopes of the N+ correlation lines. The slope smaller than one for the reactions of picryl chloride is consistent with decreased selectivity towards nucleophilic attack, and with the modified form of Ritchie's equation, log k = S+N+ + log k0, in which relative nucleophilic reactivities are substrate dependent.

  DOI：

  10.1021/jo00041a021