N-(1-adamantyl)-2-amino-1-(p-nitrophenyl)ethyl p-nitrobenzoate | 737005-16-2

• 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: N-(1-adamantyl)-2-amino-1-(p-nitrophenyl)ethyl p-nitrobenzoate
• 英文别名: N-(1-adamantyl)-2-amino-1-(p-nitrophenyl)-ethyl p-nitrobenzoate；[2-(1-adamantylamino)-1-(4-nitrophenyl)ethyl] 4-nitrobenzoate
• CAS: 737005-16-2
• 化学式: C₂₅H₂₇N₃O₆
• 分子量: 465.506
• InChiKey: WALQHCCBNFHVFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  对甲基苯甲酰氯 、 N-(1-adamantyl)-2-amino-1-(p-nitrophenyl)ethyl p-nitrobenzoate 在 三乙胺 作用下， 以 氯仿 为溶剂， 以80%的产率得到N-(1-adamantyl)-2-amino-N-(p-toluoyl)-1-(p-nitrophenyl)ethyl p-nitrobenzoate
  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 在 六甲基二硅氮烷 作用下， 以 氯仿 、 异丙醇 、 甲苯 为溶剂， 生成 N-(1-adamantyl)-2-amino-1-(p-nitrophenyl)ethyl p-nitrobenzoate
  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