Tricyclo[6.2.2.0^2,7]dodeca-2(7),3,5-triene-1-carboxylic acid methyl ester | 201275-19-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Tricyclo[6.2.2.0^2,7]dodeca-2(7),3,5-triene-1-carboxylic acid methyl ester
• 英文别名: Methyl tricyclo[6.2.2.02,7]dodeca-2,4,6-triene-1-carboxylate
• CAS: 201275-19-6
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: SHVGEUQJYZLYOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Tricyclo[6.2.2.0^2,7]dodeca-2(7),3,5-triene-1-carboxylic acid methyl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 2,3-benzobicyclo[2.2.2]oct-2-ene-1-carboxylic acid
  参考文献：
  名称：

  Rigid Phencyclidine Analogues. Binding to the Phencyclidine and σ₁ Receptors

  摘要：

  Three phencyclidine (PCP) analogues possessing a highly rigid carbocyclic structure and an attached piperidine ring which is free to rotate were synthesized. Each analogue has a specific fixed orientation of the ammonium center of the piperidinium ring to the centrum of the phenyl ring. The binding affinities of the rigid analogues 1-piperidino-7,8-benzobicyclo[4.2.0]octene (14), 1-piperidinobenzobicyclo[2.2.1]heptene (16), and 1-piperidinobenzobicyclo[2.2.2]octene (13) for the PCP receptor ([H-3]TCP) and sigma-receptor (NANM) were determined. The three analogues show low to no affinity for the PCP receptor but good affinity for the sigma-receptor and can be considered sigma-receptor selective ligands with PCP/sigma ratios of 13, 293, and 368, respectively. The binding affinities for the sigma-receptor are rationalized in terms of a model for the sigma-pharmacophore.

  DOI：

  10.1021/jm970059p
• 作为产物：
  描述：

  methyl cyclohexa-1,3-diene-1-carboxylate 在 palladium on activated charcoal 氢气 、 亚硝酸异戊酯 作用下， 以 甲醇 为溶剂， 70.0 ℃ 、206.84 kPa 条件下， 反应 15.0h， 生成 Tricyclo[6.2.2.0^2,7]dodeca-2(7),3,5-triene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Rigid Phencyclidine Analogues. Binding to the Phencyclidine and σ₁ Receptors

  摘要：

  Three phencyclidine (PCP) analogues possessing a highly rigid carbocyclic structure and an attached piperidine ring which is free to rotate were synthesized. Each analogue has a specific fixed orientation of the ammonium center of the piperidinium ring to the centrum of the phenyl ring. The binding affinities of the rigid analogues 1-piperidino-7,8-benzobicyclo[4.2.0]octene (14), 1-piperidinobenzobicyclo[2.2.1]heptene (16), and 1-piperidinobenzobicyclo[2.2.2]octene (13) for the PCP receptor ([H-3]TCP) and sigma-receptor (NANM) were determined. The three analogues show low to no affinity for the PCP receptor but good affinity for the sigma-receptor and can be considered sigma-receptor selective ligands with PCP/sigma ratios of 13, 293, and 368, respectively. The binding affinities for the sigma-receptor are rationalized in terms of a model for the sigma-pharmacophore.

  DOI：

  10.1021/jm970059p

文献信息

• Rigid Phencyclidine Analogues. Binding to the Phencyclidine and σ₁ Receptors
  作者：Robert M. Moriarty、Livia A. Enache、Lei Zhao、Richard Gilardi、Mariena V. Mattson、Om Prakash

  DOI：10.1021/jm970059p

  日期：1998.2.1

  Three phencyclidine (PCP) analogues possessing a highly rigid carbocyclic structure and an attached piperidine ring which is free to rotate were synthesized. Each analogue has a specific fixed orientation of the ammonium center of the piperidinium ring to the centrum of the phenyl ring. The binding affinities of the rigid analogues 1-piperidino-7,8-benzobicyclo[4.2.0]octene (14), 1-piperidinobenzobicyclo[2.2.1]heptene (16), and 1-piperidinobenzobicyclo[2.2.2]octene (13) for the PCP receptor ([H-3]TCP) and sigma-receptor (NANM) were determined. The three analogues show low to no affinity for the PCP receptor but good affinity for the sigma-receptor and can be considered sigma-receptor selective ligands with PCP/sigma ratios of 13, 293, and 368, respectively. The binding affinities for the sigma-receptor are rationalized in terms of a model for the sigma-pharmacophore.