cis-8a-phenyldecahydroquinoline | 131556-11-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: cis-8a-phenyldecahydroquinoline
• 英文别名: 8a-phenyldecahydroquinoline；(4aS,8aS)-8a-phenyl-2,3,4,4a,5,6,7,8-octahydro-1H-quinoline
• CAS: 131556-11-1
• 化学式: C₁₅H₂₁N
• 分子量: 215.338
• InChiKey: QEXADSRMRUUCQJ-LSDHHAIUSA-N

物化性质

• 沸点：
  324.1±11.0 °C(Predicted)
• 密度：
  1.009±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  cis-8a-phenyldecahydroquinoline 在 吡啶 、 potassium tert-butylate 、 水 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 75.0h， 生成 (4aS,8aS)-cis-N-formyl-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-pyrrolidino-cyclohex-1-enyl)-propionitrile 在 sodium hydroxide 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.5h， 生成 cis-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

文献信息

• An unusual fragmentation process discovered during the course of cleavage of a camphanic acid amide
  作者：Alan P. Kozikowski、Chinpiao Chen、Richard G. Ball

  DOI：10.1016/s0040-4039(00)97981-4

  日期：1990.1

  An unusual fragmentation reaction that affords a carbamoyl anion discovered during the course of the synthesis of rigidified PCP analogues is reported.

  报道了一种不寻常的断裂反应，该反应会在合成刚性PCP类似物的过程中发现氨基甲酰基阴离子。
• Synthesis and biological activity of 8a-phenyldecahydroquinolines as probes of PCP's binding conformation. A new PCP-like compound with increased in vivo potency
  作者：Chinpiao Chen、Alan P. Kozikowski、Paul L. Wood、Ian J. Reynolds、Richard G. Ball、Yuan Ping Pang

  DOI：10.1021/jm00087a020

  日期：1992.5

  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.