1-(2-hydroxy-2-adamantyl)-4-methoxynaphthalene | 1443991-99-8

• 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)-4-methoxynaphthalene
• CAS: 1443991-99-8
• 化学式: C₂₁H₂₄O₂
• 分子量: 308.42
• InChiKey: UTQQSNPDBWNCPY-UHFFFAOYSA-N

物化性质

• 沸点：
  486.7±28.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

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-4-甲氧基萘酚 以68%的产率得到1-(2-hydroxy-2-adamantyl)-4-methoxynaphthalene
  参考文献：
  名称：

  一系列亲脂性酚和萘酚的抗菌活性的体外研究

  摘要：

  合成了五组酚/萘酚（总共42种化合物），并针对革兰氏阳性金黄色葡萄球菌和枯草芽孢杆菌，革兰氏阴性大肠杆菌和肺炎克雷伯菌以及白色念珠菌进行了筛选。尽管发现化合物对革兰氏阴性细菌无活性，但观察到对革兰氏阳性细菌有效的活性。该活性与分子形成醌甲基化物的能力相关，表明潜在的新作用方式。关键词抗菌活性，酚，萘，醌甲基化物。

  DOI：

  10.17159/0379-4350/2016/v69a6

文献信息

• Atropisomerism in 1-(2-adamantyl)naphthalene Derivatives
  作者：Jelena Veljković、Ivana Antol、Nikola Basarić、Vilko Smrečki、Krešimir Molčanov、Norbert Müller、Kata Mlinarić-Majerski

  DOI：10.1016/j.molstruc.2013.04.027

  日期：2013.8

  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.