1-(RS)-(2-furanyl)-2-(RS)-methylcyclohexan-1-azide | 247151-94-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(RS)-(2-furanyl)-2-(RS)-methylcyclohexan-1-azide
• 英文别名: 2-(1-Azido-2-methylcyclohexyl)furan
• CAS: 247151-94-6
• 化学式: C₁₁H₁₅N₃O
• 分子量: 205.26
• InChiKey: YQHALYSGAJVRRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  27.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(RS)-(2-furanyl)-2-(RS)-methylcyclohexan-1-azide 在 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 水 为溶剂， 反应 168.0h， 生成 (+)-cis-1-<1-(2-furanyl)-2-methylcyclohexyl>piperidine
  参考文献：
  名称：

  Homochiral structures derived from 1-[1-(2-thienyl)cyclohexyl]piperidine (TCP) are potent non-competitive antagonists of glutamate at NMDA receptor sites

  摘要：

  The racemates of cis (pip/Me) 1-[1-(2-thienyl)-2-methylcyclohexyl]pipe and cis (pip/Me) 1-[1-(2-furanyl)-2-methylcyclohexyl]piperidine, 2 derivatives of the noncompetitive N-methyl-D-aspartate (NMDA) antagonist 1-[1-(2-thienyl)cyclohexyl]piperidine (TCP) have been synthesized. The corresponding isomers were resolved by a crystallization procedure, via the diastereoisomeric salts formed with (+)- and (-)-di-O,O'-4-toluoyltartaric acid. The absolute configuration was determined by single-crystal X-ray analysis and by comparison with previously published data in related series. The 4 homochiral structures obtained were tested for their affinity for the PCP receptor sites labelled with [H-3]TCP. Their neuroprotective potency was assessed in primary cultured neuronal cells against neurotoxicity induced by glutamate. The 2(-)-1S, 2R-isomers displayed the highest affinity for the PCP receptor sites and the highest efficacy for neuronal protection in comparison with the (+)-1R, 2S-isomers.

  DOI：

  10.1016/0223-5234(94)90109-0
• 作为产物：
  描述：

  2-甲基环己酮 在 正丁基锂 、 sodium azide 、 四甲基乙二胺 、 三氯乙酸 作用下， 以 氯仿 为溶剂， 反应 72.5h， 生成 1-(RS)-(2-furanyl)-2-(RS)-methylcyclohexan-1-azide
  参考文献：
  名称：

  Homochiral structures derived from 1-[1-(2-thienyl)cyclohexyl]piperidine (TCP) are potent non-competitive antagonists of glutamate at NMDA receptor sites

  摘要：

  The racemates of cis (pip/Me) 1-[1-(2-thienyl)-2-methylcyclohexyl]pipe and cis (pip/Me) 1-[1-(2-furanyl)-2-methylcyclohexyl]piperidine, 2 derivatives of the noncompetitive N-methyl-D-aspartate (NMDA) antagonist 1-[1-(2-thienyl)cyclohexyl]piperidine (TCP) have been synthesized. The corresponding isomers were resolved by a crystallization procedure, via the diastereoisomeric salts formed with (+)- and (-)-di-O,O'-4-toluoyltartaric acid. The absolute configuration was determined by single-crystal X-ray analysis and by comparison with previously published data in related series. The 4 homochiral structures obtained were tested for their affinity for the PCP receptor sites labelled with [H-3]TCP. Their neuroprotective potency was assessed in primary cultured neuronal cells against neurotoxicity induced by glutamate. The 2(-)-1S, 2R-isomers displayed the highest affinity for the PCP receptor sites and the highest efficacy for neuronal protection in comparison with the (+)-1R, 2S-isomers.

  DOI：

  10.1016/0223-5234(94)90109-0

文献信息

• US5972952A
  申请人：——

  公开号：US5972952A

  公开（公告）日：1999-10-26