6,6,7,7-tetramethyl-2-quinuclidone | 28526-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 英文名称: 6,6,7,7-tetramethyl-2-quinuclidone
• 英文别名: 6,6,8,8-Tetramethylchinuclidin-2-on；6,6,7,7-Tetramethyl-2-chinuclidon；6,6,7,7-Tetramethyl-2-quinuclidon；6,6,7,7-tetramethyl-1-aza-bicyclo[2.2.2]octan-2-one；6,6,8,8-Tetramethylquinuclidine-2-one；6,6,7,7-tetramethyl-1-azabicyclo[2.2.2]octan-2-one
• CAS: 28526-65-0
• 化学式: C₁₁H₁₉NO
• 分子量: 181.278
• InChiKey: LKLXQFNENOWZPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6,6,7,7-tetramethyl-2-quinuclidone 在 tetrafluoroboric acid 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以86%的产率得到6,6,7,7-tetramethyl-2-quinuclidine tetrafluoroboric acid salt
  参考文献：
  名称：

  Synthesis of 2-Quinuclidonium by Eliminating Water:  Experimental Quantification of the High Basicity of Extremely Twisted Amides

  摘要：

  The chemical properties of an extremely twisted amide are examined quantitatively for the first time. The predicted high basicity of 2-quinuclidonium is confirmed experimentally by measuring the gas-phase proton affinity using the extended kinetic method. Fragmentation of this molecule further reveals that the lack of resonance stabilization weakens the amide bond. Furthermore, a new route for synthesizing 2-quinuclidonium by eliminating water is demonstrated in the gas phase.

  DOI：

  10.1021/ja067703m

文献信息

• Synthesis of 2-Quinuclidonium by Eliminating Water:  Experimental Quantification of the High Basicity of Extremely Twisted Amides
  作者：Tony Ly、Michael Krout、Don K. Pham、Kousuke Tani、Brian M. Stoltz、Ryan R. Julian

  DOI：10.1021/ja067703m

  日期：2007.2.1

  The chemical properties of an extremely twisted amide are examined quantitatively for the first time. The predicted high basicity of 2-quinuclidonium is confirmed experimentally by measuring the gas-phase proton affinity using the extended kinetic method. Fragmentation of this molecule further reveals that the lack of resonance stabilization weakens the amide bond. Furthermore, a new route for synthesizing 2-quinuclidonium by eliminating water is demonstrated in the gas phase.