1-adamantyl-(4-nitrophenyl)methanol | 1245928-26-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-adamantyl-(4-nitrophenyl)methanol
• 英文别名: 1-Adamantyl-(4-nitrophenyl)methanol
• CAS: 1245928-26-0
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: DGOYRCXSFYLKIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-adamantyl-(4-nitrophenyl)methanol 在 氢气 作用下， 以 乙醇 为溶剂， 以98%的产率得到(1-adamantyl)(4-aminophenyl)methanol
  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：

  adamantan-1-yl(4-nitrophenyl)methanone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以96%的产率得到1-adamantyl-(4-nitrophenyl)methanol
  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

文献信息

• Novel adamantane-bearing anilines and properties of their supramolecular complexes with β-cyclodextrin
  作者：Robert Vícha、Michal Rouchal、Zuzana Kozubková、Ivo Kuřitka、Radek Marek、Petra Branná、Richard Čmelík

  DOI：10.1080/10610278.2011.593628

  日期：2011.10.1

  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.