1-acetyl-3-adamantanol oxime | 90812-23-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-acetyl-3-adamantanol oxime
• 英文别名: 3-(N-hydroxy-C-methylcarbonimidoyl)adamantan-1-ol
• CAS: 90812-23-0
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: IQPYQLZGOSVXSE-UHFFFAOYSA-N

物化性质

• 熔点：
  177-179 °C
• 沸点：
  363.6±21.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.916
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-acetyl-3-adamantanol oxime 在 sodium 作用下， 以 various solvent(s) 为溶剂， 生成 3-氨乙基-1-金刚烷醇盐酸盐
  参考文献：
  名称：

  摘要：

  A general procedure was proposed for synthesizing 3-R-1-adamantyl methyl ketones from the corresponding adamantanecarbonyl chlorides and dimethyl malonate in toluene (benzene) in the presence of sodium hydroxide. Intermediate dimethyl (3-R-1-adamantylcarbonyl)malonates can also be isolated. The resulting ketones were brought into reactions with hydroxylamine and formamide in the presence of formic acid to obtain the corresponding oximes and 1-(3-R-1-adamantyl)ethylamines. Dimethyl (3-R-1-adamantylcarbonyl)malonates reacted with phenylhydrazine to give adamantyl-substituted 4,5-dihydropyrazol-5-one derivatives.

  DOI：

  10.1023/a:1013154831862
• 作为产物：
  描述：

  1-(3-羟基金刚烷-1-基)乙酮 在 盐酸羟胺 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以60%的产率得到1-acetyl-3-adamantanol oxime
  参考文献：
  名称：

  摘要：

  A general procedure was proposed for synthesizing 3-R-1-adamantyl methyl ketones from the corresponding adamantanecarbonyl chlorides and dimethyl malonate in toluene (benzene) in the presence of sodium hydroxide. Intermediate dimethyl (3-R-1-adamantylcarbonyl)malonates can also be isolated. The resulting ketones were brought into reactions with hydroxylamine and formamide in the presence of formic acid to obtain the corresponding oximes and 1-(3-R-1-adamantyl)ethylamines. Dimethyl (3-R-1-adamantylcarbonyl)malonates reacted with phenylhydrazine to give adamantyl-substituted 4,5-dihydropyrazol-5-one derivatives.

  DOI：

  10.1023/a:1013154831862

文献信息

• Synthesis and antiviral activity of metabolites of rimantadine
  作者：Percy S. Manchand、Richard L. Cerruti、Joseph A. Martin、Christopher H. Hill、John H. Merrett、Elizabeth Keech、Robert B. Belshe、Edward V. Connell、Iain S. Sim

  DOI：10.1021/jm00169a029

  日期：1990.7

  The hydroxy metabolites of rimantadine (3-5) were synthesized and compared to amantadine (1) and rimantadine (2) for their ability to inhibit the replication of influenza viruses in vitro. All three metabolites were inhibitory to wild-type influenza A viruses (H3N2 and H1N1). In particular, 2-hydroxyrimantadine (3) showed similar activity to amantadine, but the 3- and 4-hydroxy metabolites (4 and 5, respectively), both of which are found in rimantadine-treated patients, showed only modest inhibitory activity. A rimantadine-resistant isolate of influenza A virus exhibited cross-resistance to amantadine and to each of the metabolites 3-5. None of the compounds were effective against influenza B virus.
• ——
  作者：N. V. Makarova、I. K. Moiseev、M. N. Zemtsova

  DOI：10.1023/a:1013404128654

  日期：——

  Along Iffland's reactions from 1-adamantyl methyl ketone, (1-adamantyl)acetone, 3-hydroxy-1-adamantyl methyl ketone and N-bromosuccinimide were obtained the corresponding bromonitro derivatives that on reduction with sodium borohydride afforded 1-(1-adamantyl)-1-nitroethane, 1-(1-adamantyl)-2nitropropane, and 1-(3-hydroxy-1-adamantyl)-1-nitroethane.
• ——
  作者：V. V. Pozdnyakov、N. V. Makarova、I. K. Moiseev

  DOI：10.1023/a:1013154831862

  日期：——

  A general procedure was proposed for synthesizing 3-R-1-adamantyl methyl ketones from the corresponding adamantanecarbonyl chlorides and dimethyl malonate in toluene (benzene) in the presence of sodium hydroxide. Intermediate dimethyl (3-R-1-adamantylcarbonyl)malonates can also be isolated. The resulting ketones were brought into reactions with hydroxylamine and formamide in the presence of formic acid to obtain the corresponding oximes and 1-(3-R-1-adamantyl)ethylamines. Dimethyl (3-R-1-adamantylcarbonyl)malonates reacted with phenylhydrazine to give adamantyl-substituted 4,5-dihydropyrazol-5-one derivatives.