adamantan-1-yl(4-nitrophenyl)methanone | 1207682-36-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: adamantan-1-yl(4-nitrophenyl)methanone
• CAS: 1207682-36-7
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: VHNQSKJOONVXLH-UHFFFAOYSA-N

物化性质

• 熔点：
  122-123 °C
• 沸点：
  423.0±18.0 °C(predicted)
• 密度：
  1.279±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  60.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  adamantan-1-yl(4-nitrophenyl)methanone 在 盐酸 、 sodium tetrahydroborate 、 铁粉 作用下， 以 乙醇 、 水 为溶剂， 生成 4-[1-adamantyl(methoxy)methyl]aniline
  参考文献：
  名称：

  Novel adamantane-bearing anilines and properties of their supramolecular complexes with β-cyclodextrin

  摘要：

  Several novel anilines bearing 1-adamantyl substituents that are useful for drug modification were synthesised from the corresponding 1-adamantyl (nitrophenyl) ketones. The host-guest systems of these prepared ligands with beta-cyclodextrin (beta-CD) were studied using electrospray ionisation mass spectrometry, NMR spectroscopy, titration calorimetry and semi-empirical calculations. The complexes with 1: 1 stoichiometry were found to predominantly exist as pseudorotaxane-like threaded structures with the adamantane cage sitting deep in the cavity of beta-CD close to the wider rim. Such geometry was observed for all examined amines and is independent of their structure and/or presence of protic substituents.

  DOI：

  10.1080/10610278.2011.593628
• 作为产物：
  描述：

  金刚烷酰氯 在 硝酸乙酸酐 、 乙酸酐 、 copper(l) chloride 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 adamantan-1-yl(4-nitrophenyl)methanone
  参考文献：
  名称：

  Novel adamantane-bearing anilines and properties of their supramolecular complexes with β-cyclodextrin

  摘要：

  Several novel anilines bearing 1-adamantyl substituents that are useful for drug modification were synthesised from the corresponding 1-adamantyl (nitrophenyl) ketones. The host-guest systems of these prepared ligands with beta-cyclodextrin (beta-CD) were studied using electrospray ionisation mass spectrometry, NMR spectroscopy, titration calorimetry and semi-empirical calculations. The complexes with 1: 1 stoichiometry were found to predominantly exist as pseudorotaxane-like threaded structures with the adamantane cage sitting deep in the cavity of beta-CD close to the wider rim. Such geometry was observed for all examined amines and is independent of their structure and/or presence of protic substituents.

  DOI：

  10.1080/10610278.2011.593628