naphthalen-2-ylmethyl (13)C2-acetate | 929642-78-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalen-2-ylmethyl (13)C2-acetate
• CAS: 929642-78-4
• 化学式: C₁₃H₁₂O₂
• 分子量: 202.215
• InChiKey: HKBNQGIZBGLLAL-WUACOMEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  naphthalen-2-ylmethyl (13)C2-acetate 在 2,6-二叔丁基吡啶 、 叔丁基二甲硅基三氟甲磺酸酯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 naphthalen-2-ylmethyl 2-(3-oxocyclopentyl)-(13)C2-ethanoate
  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
• 作为产物：
  描述：

  乙酸-13C2 、 2-萘甲醇 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到naphthalen-2-ylmethyl (13)C2-acetate
  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