4-hydroxy-tricyclo[4.3.1.0(3,8)]decan-4-acetonitrile | 1257334-37-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-tricyclo[4.3.1.0(3,8)]decan-4-acetonitrile
• 英文别名: 2-(4-hydroxy-4-tricyclo[4.3.1.03,8]decanyl)acetonitrile
• CAS: 1257334-37-4
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: IWQJGTFDGIJQFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.02
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-tricyclo[4.3.1.0(3,8)]decan-4-acetonitrile 在 lithium aluminium tetrahydride 、 水 、 sodium hydroxide 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 20.0h， 以95%的产率得到4-(2-aminoethyl)tricyclo[4.3.1.0(3,8)]decan-4-ol
  参考文献：
  名称：

  Design and synthesis of bioactive adamantanaminoalcohols and adamantanamines

  摘要：

  Adamantanamines 16, 18, 21, 24, 27, 28, 30, 32, 35, 36, 37, 40, 46 and 48 were synthesized and tested for anti-influenza A virus and trypanocidal activity. The stereoelectronic requirements for optimal antiviral and trypanocidal potency were investigated. The effect of introducing a hydroxyl group close to the amino group on this class of compounds was examined for the first time. Aminoalcohol 24 proved to be the most active of the compounds tested against influenza A virus, being 6-fold more active than amantadine, equipotent to rimantadine and 26-fold more potent than ribavirin. Aminoalcohols 36 and 37 were found to have considerable activity against bloodstream forms of the African trypanosome, Trypanosoma brucei, being almost 10 times more potent than rimantadine. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.009
• 作为产物：
  描述：

  金刚烷酮 、 乙腈 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.4h， 以95%的产率得到4-hydroxy-tricyclo[4.3.1.0(3,8)]decan-4-acetonitrile
  参考文献：
  名称：

  Design and synthesis of bioactive adamantanaminoalcohols and adamantanamines

  摘要：

  Adamantanamines 16, 18, 21, 24, 27, 28, 30, 32, 35, 36, 37, 40, 46 and 48 were synthesized and tested for anti-influenza A virus and trypanocidal activity. The stereoelectronic requirements for optimal antiviral and trypanocidal potency were investigated. The effect of introducing a hydroxyl group close to the amino group on this class of compounds was examined for the first time. Aminoalcohol 24 proved to be the most active of the compounds tested against influenza A virus, being 6-fold more active than amantadine, equipotent to rimantadine and 26-fold more potent than ribavirin. Aminoalcohols 36 and 37 were found to have considerable activity against bloodstream forms of the African trypanosome, Trypanosoma brucei, being almost 10 times more potent than rimantadine. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.009