2-(1-adamantylmethylamino)-1-(4-nitrophenyl)ethanol | 737005-18-4

• 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: 2-(1-adamantylmethylamino)-1-(4-nitrophenyl)ethanol
• CAS: 737005-18-4
• 化学式: C₁₉H₂₆N₂O₃
• 分子量: 330.427
• InChiKey: LQJUEQPDGKRFSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  75.4
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(1-adamantylmethylamino)-1-(4-nitrophenyl)ethanol 在 六甲基二硅氮烷 作用下， 以 氯仿 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Adamantyl-Substituted Amino Alcohols. Synthesis and Functionalization at the Nitrogen and Oxygen Nucleophilic Centers

  摘要：

  1-Aminoadamantanes and 1-aminomethyladamantanes were brought into reactions with p-nitrophenyloxirane and 9-carbazolylmethyloxirane. The reactions occurred in a regioselective fashion according to the Krasusky rule, which was confirmed by the H-1 and C-13 NMR data. The resulting amino alcohols having a p-nitrophenyl moiety were subjected to functionalization at the nitrogen and oxygen nucleophilic centers using p-nitrobenzenesulfonyl chloride, p-nitrobenzoyl chloride, and hexamethyldisilazane, and N,O-bisacyl derivative was synthesized. The structure of the products was proved by IR and H-1 NMR spectroscopy.

  DOI：

  10.1023/b:rujo.0000010210.89695.79
• 作为产物：
  描述：

  (P-硝基苯基)环氧乙烷 、 1-金刚烷甲胺 以 异丙醇 为溶剂， 以73.5%的产率得到2-(1-adamantylmethylamino)-1-(4-nitrophenyl)ethanol
  参考文献：
  名称：

  Adamantyl-Substituted Amino Alcohols. Synthesis and Functionalization at the Nitrogen and Oxygen Nucleophilic Centers

  摘要：

  1-Aminoadamantanes and 1-aminomethyladamantanes were brought into reactions with p-nitrophenyloxirane and 9-carbazolylmethyloxirane. The reactions occurred in a regioselective fashion according to the Krasusky rule, which was confirmed by the H-1 and C-13 NMR data. The resulting amino alcohols having a p-nitrophenyl moiety were subjected to functionalization at the nitrogen and oxygen nucleophilic centers using p-nitrobenzenesulfonyl chloride, p-nitrobenzoyl chloride, and hexamethyldisilazane, and N,O-bisacyl derivative was synthesized. The structure of the products was proved by IR and H-1 NMR spectroscopy.

  DOI：

  10.1023/b:rujo.0000010210.89695.79

文献信息

• Adamantyl-Substituted Amino Alcohols. Synthesis and Functionalization at the Nitrogen and Oxygen Nucleophilic Centers
  作者：L. I. Kas'yan、E. A. Golodaeva、A. O. Kas'yan

  DOI：10.1023/b:rujo.0000010210.89695.79

  日期：2003.9

  1-Aminoadamantanes and 1-aminomethyladamantanes were brought into reactions with p-nitrophenyloxirane and 9-carbazolylmethyloxirane. The reactions occurred in a regioselective fashion according to the Krasusky rule, which was confirmed by the H-1 and C-13 NMR data. The resulting amino alcohols having a p-nitrophenyl moiety were subjected to functionalization at the nitrogen and oxygen nucleophilic centers using p-nitrobenzenesulfonyl chloride, p-nitrobenzoyl chloride, and hexamethyldisilazane, and N,O-bisacyl derivative was synthesized. The structure of the products was proved by IR and H-1 NMR spectroscopy.