1-(2-hydroxy-2-adamantyl)-5-methoxynaphthalene | 1443992-00-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-hydroxy-2-adamantyl)-5-methoxynaphthalene
• CAS: 1443992-00-4
• 化学式: C₂₁H₂₄O₂
• 分子量: 308.42
• InChiKey: RHHBEOQMVRRAGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  金刚烷酮 、 1-溴-5-甲氧基萘 在 碘 、 magnesium 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以42%的产率得到1-(2-hydroxy-2-adamantyl)-5-methoxynaphthalene
  参考文献：
  名称：

  Atropisomerism in 1-(2-adamantyl)naphthalene Derivatives

  摘要：

  Two new adamantylnaphthalene derivatives 1-(2-hydroxy-2-adamantyl)-4-methoxynaphthalene (5) and 1-(2-hydroxy-2-adamantyl)-5-methoxynaphthalene (6) were synthesized and characterized by NMR spectroscopy. In addition, 5 was characterized by single crystal X-ray structural analysis and DFT calculations. For both derivatives, 5 and 6, dynamic NMR of diastereotopic spins revealed atropisomerism due to hindered rotation around the C-C bond between the adamantyl and the naphthyl moieties, giving rise to intermediate conformational exchange on the NMR timescale at room temperature. Upon decrease of the temperature to 223 K the existence of two enantiomerically related conformers in slow exchange was observed. The free energy of activation for the conformer exchange calculated using the coalescence temperature method amounts to 56.4 +/- 0.3 kJ mol(-1) for both derivatives. The experimental findings are corroborated by DFT calculations. The calculated NMR chemical shifts and the energy of activation for the conformer exchange are in excellent agreement with the measured values. (c) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.04.027