1-(1-phenylcyclooctyl)piperidine | 83385-89-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(1-phenylcyclooctyl)piperidine
• CAS: 83385-89-1
• 化学式: C₁₉H₂₉N
• 分子量: 271.446
• InChiKey: NYYQZXFXBPABFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-苯基-1-环辛醇 在 lithium aluminium tetrahydride 、 sodium azide 、 potassium carbonate 、 三氯乙酸 作用下， 以 乙醚 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-(1-phenylcyclooctyl)piperidine
  参考文献：
  名称：

  Structure-activity relationships of the cycloalkyl ring of phencyclidine

  摘要：

  In order to investigate the structural requirements for a cycloalkyl moiety in the potent hallucinogen 1-(1-phenylcyclohexyl)piperidine (PCP, 1), a series of structural analogues was synthesized in which the size of the cycloalkyl ring was varied from three carbons to eight carbons. Biological activities of these compounds were assessed in an in vitro assay (phencyclidine binding assay) and an in vivo assay (discriminative stimulus assay). As the cycloalkyl ring size decreased from that of cyclohexane (PCP), PCP-like activity declined in both assays, but as the cycloalkyl ring size became larger than cyclohexane, a sharp decline in PCP-like activity was observed in the in vivo assay, while activity in the in vitro assay was only slightly less than that of PCP. 1-(1-Phenylcyclooctyl)piperidine (8) had potent competitive binding properties in the in vitro binding assay but produced no observable PCP-like effects in the in vivo assay. The importance of the cycloalkyl ring in the structure of PCP was demonstrated by testing benzylpiperidine (2), which had almost no measurable activity in either assay.

  DOI：

  10.1021/jm00144a011

文献信息

• MCQUINN, R. L.;CONE, E. J.;SHANNON, H. E.;SU, TSUNG-PING, J. MED. CHEM., 1981, 24, N 12, 1429-1432
  作者：MCQUINN, R. L.、CONE, E. J.、SHANNON, H. E.、SU, TSUNG-PING

  DOI：——

  日期：——
• Structure-activity relationships of the cycloalkyl ring of phencyclidine
  作者：Roy L. McQuinn、Edward J. Cone、Harlan E. Shannon、Tsung-Ping Su

  DOI：10.1021/jm00144a011

  日期：1981.12

  In order to investigate the structural requirements for a cycloalkyl moiety in the potent hallucinogen 1-(1-phenylcyclohexyl)piperidine (PCP, 1), a series of structural analogues was synthesized in which the size of the cycloalkyl ring was varied from three carbons to eight carbons. Biological activities of these compounds were assessed in an in vitro assay (phencyclidine binding assay) and an in vivo assay (discriminative stimulus assay). As the cycloalkyl ring size decreased from that of cyclohexane (PCP), PCP-like activity declined in both assays, but as the cycloalkyl ring size became larger than cyclohexane, a sharp decline in PCP-like activity was observed in the in vivo assay, while activity in the in vitro assay was only slightly less than that of PCP. 1-(1-Phenylcyclooctyl)piperidine (8) had potent competitive binding properties in the in vitro binding assay but produced no observable PCP-like effects in the in vivo assay. The importance of the cycloalkyl ring in the structure of PCP was demonstrated by testing benzylpiperidine (2), which had almost no measurable activity in either assay.