5-Hydroxy-2-oxatricyclo<3.3.1.1^3,7>decan | 94053-17-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 5-Hydroxy-2-oxatricyclo<3.3.1.1^3,7>decan
• 英文别名: (1R,3S,5s,7s)-2-oxaadamantan-5-ol；5-hydroksy-2-oxaadamantane；2-oxaadamantan-5-ol；2-oxatricyclo[3.3.1.13,7]decan-5-ol
• CAS: 94053-17-5
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: NYNSDHIHRUKTBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Hydroxy-2-oxatricyclo<3.3.1.1^3,7>decan 、 氯乙腈 在 硫酸 、 溶剂黄146 作用下， 反应 70.0h， 以86.5%的产率得到N-(2-oxaadamantan-5-yl)-2-chloroacetamide
  参考文献：
  名称：

  Ritter reaction-mediated syntheses of 2-oxaadamantan-5-amine, a novel amantadine analog

  摘要：

  Two alternative syntheses of 2-oxaadamantan-5-amine, a novel analog of the clinically approved drug amantadine, are reported. The compound has been tested as an anti-influenza A virus agent and as an NMDA receptor antagonist. While the compound was not antivirally active, it displayed moderate activity as an NMDA receptor antagonist. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.01.160
• 作为产物：
  描述：

  2-oxaadamantane 在 硫酸 、 硝酸 作用下， 生成 5-Hydroxy-2-oxatricyclo<3.3.1.1^3,7>decan
  参考文献：
  名称：

  Bromination and oxidation of 2-oxaadamantane

  摘要：

  DOI：

  10.1007/bf01169827

文献信息

• Duddeck, Helmut; Wagner, Petra, Liebigs Annalen der Chemie, 1984, # 12, p. 1981 - 1988
  作者：Duddeck, Helmut、Wagner, Petra

  DOI：——

  日期：——
• Bromination and oxidation of 2-oxaadamantane
  作者：N. S. Zefirov、N. V. Averina、O. A. Fomicheva

  DOI：10.1007/bf01169827

  日期：1994.5
• Ritter reaction-mediated syntheses of 2-oxaadamantan-5-amine, a novel amantadine analog
  作者：Rosana Leiva、Sabrina Gazzarrini、Roser Esplugas、Anna Moroni、Lieve Naesens、Francesc X. Sureda、Santiago Vázquez

  DOI：10.1016/j.tetlet.2015.01.160

  日期：2015.3

  Two alternative syntheses of 2-oxaadamantan-5-amine, a novel analog of the clinically approved drug amantadine, are reported. The compound has been tested as an anti-influenza A virus agent and as an NMDA receptor antagonist. While the compound was not antivirally active, it displayed moderate activity as an NMDA receptor antagonist. (C) 2015 Elsevier Ltd. All rights reserved.