4a-hydroperoxy-Δ^8,8a-octahydroquinoline | 139870-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: 4a-hydroperoxy-Δ^8,8a-octahydroquinoline
• 英文别名: 2,3,4,5,6,7-hexahydro-1H-quinolin-4a-ol
• CAS: 139870-93-2
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: MUGHHZHSBZVRNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4a-hydroperoxy-Δ^8,8a-octahydroquinoline 在 platinum(IV) oxide 硫酸 、 氢气 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 47.0h， 生成 trans-8a-phenyldecahydroquinoline
  参考文献：
  名称：

  Synthesis and biological activity of 8a-phenyldecahydroquinolines as probes of PCP's binding conformation. A new PCP-like compound with increased in vivo potency

  摘要：

  The synthesis and chemical resolution of cis- and trans-fused 8a-phenyldecahydroquinolines 3 and 4 are described together with the affinity of the four optically pure compounds for the PCP recognition site of the NMDA receptor complex. These compounds were also evaluated for their antagonistic effects on cGMP levels in male Swiss Webster mice, and (-)-4 was found to exhibit in vivo potency comparable to that of MK-801. The results of the binding studies are interpreted in terms of a preferred orientation of PCP's N-H bond in binding to its NMDA receptor-associated recognition site.

  DOI：

  10.1021/jm00087a020
• 作为产物：
  描述：

  3-(2-Pyrrolidin-1-yl-cyclohex-1-enyl)-propylamine 在 sodium hydroxide 、 氧气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 4a-hydroperoxy-Δ^8,8a-octahydroquinoline
  参考文献：
  名称：

  Synthesis and biological activity of 8a-phenyldecahydroquinolines as probes of PCP's binding conformation. A new PCP-like compound with increased in vivo potency

  摘要：

  The synthesis and chemical resolution of cis- and trans-fused 8a-phenyldecahydroquinolines 3 and 4 are described together with the affinity of the four optically pure compounds for the PCP recognition site of the NMDA receptor complex. These compounds were also evaluated for their antagonistic effects on cGMP levels in male Swiss Webster mice, and (-)-4 was found to exhibit in vivo potency comparable to that of MK-801. The results of the binding studies are interpreted in terms of a preferred orientation of PCP's N-H bond in binding to its NMDA receptor-associated recognition site.

  DOI：

  10.1021/jm00087a020