Adamantan-2-spiro-2'-azetidin | 59591-93-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: Adamantan-2-spiro-2'-azetidin
• 英文别名: Spiro[adamantane-2,2'-azetidine]
• CAS: 59591-93-4
• 化学式: C₁₂H₁₉N
• 分子量: 177.29
• InChiKey: STEZQPFDOUTCHF-UHFFFAOYSA-N

物化性质

• 熔点：
  53-56 °C
• 沸点：
  264.7±8.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Adamantan-2-spiro-2'-azetidin 、 氯甲酸乙酯 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以98%的产率得到
  参考文献：
  名称：

  Design and synthesis of bioactive adamantane spiro heterocycles

  摘要：

  Spiro[aziridine-2,2'-adamantanes] I and 2, spiro[azetidine-2,2'-adamantanes] 3 and 5, spiro[azetidine-3,2'-adamantane] 13, spiro[piperidine-4,2'-adamantanes] 25 and 27, and spiro barbituric analog 18 were synthesized and tested for their anti-influenza A virus properties and for trypanocidal activity. The effect of ring size on potency was investigated. Piperidine 25 showed significant anti-influenza A virus activity, being 12-fold more active than amantadine, about 2-fold more active than rimantadine, and 54-fold more potent than ribavirin. It also proved to be the most active of the compounds tested against bloodstream forms of the African trypanosome, Trypanosoma brucei, being 1.5 times more potent than rimantadine and at least 25 times more active than amantadine. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.108
• 作为产物：
  描述：

  spiro3,7>decane> 、 氢化铝锂 以55%的产率得到
  参考文献：
  名称：

  SASAKI T.; EGUCHI S.; HIRAKO Y., TETRAHEDRON , 1976, 32, NO 4, 437-440

  摘要：

  DOI：

文献信息

• Design and synthesis of bioactive adamantane spiro heterocycles
  作者：Nicolas Kolocouris、Grigoris Zoidis、George B. Foscolos、George Fytas、S. Radhika Prathalingham、John M. Kelly、Lieve Naesens、Erik De Clercq

  DOI：10.1016/j.bmcl.2007.04.108

  日期：2007.8

  Spiro[aziridine-2,2'-adamantanes] I and 2, spiro[azetidine-2,2'-adamantanes] 3 and 5, spiro[azetidine-3,2'-adamantane] 13, spiro[piperidine-4,2'-adamantanes] 25 and 27, and spiro barbituric analog 18 were synthesized and tested for their anti-influenza A virus properties and for trypanocidal activity. The effect of ring size on potency was investigated. Piperidine 25 showed significant anti-influenza A virus activity, being 12-fold more active than amantadine, about 2-fold more active than rimantadine, and 54-fold more potent than ribavirin. It also proved to be the most active of the compounds tested against bloodstream forms of the African trypanosome, Trypanosoma brucei, being 1.5 times more potent than rimantadine and at least 25 times more active than amantadine. (c) 2007 Elsevier Ltd. All rights reserved.
• SASAKI T.; EGUCHI S.; HIRAKO Y., TETRAHEDRON <TETR-AB>, 1976, 32, NO 4, 437-440
  作者：SASAKI T.、 EGUCHI S.、 HIRAKO Y.

  DOI：——

  日期：——