3-phenylcyclopentane-1,1-dicarboxylic acid | 115340-09-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-phenylcyclopentane-1,1-dicarboxylic acid
• 英文别名: 3-Phenyl-1,1-cyclopentanedicarboxylic acid
• CAS: 115340-09-5
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: XZZNOUXZAKNTRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-phenylcyclopentane-1,1-dicarboxylic acid 在 sodium hydroxide 、 甲烷磺酸 、 偶氮二异丁腈 、 碘苯二乙酸 、 碘 、 phosphorus pentoxide 作用下， 以 苯 为溶剂， 反应 76.0h， 生成 1,2,3,4-tetrahydro-1,4-methanonaphthalene-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：

  dimethyl 3-phenylcyclopentane-1,1-dicarboxylate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以91.5%的产率得到3-phenylcyclopentane-1,1-dicarboxylic acid
  参考文献：
  名称：

  Conformationally defined adrenergic agents. Part 13. Synthesis of benzobicyclo[3.2.1]octanes involving inversion of configuration via an N-to-O acetyl migration

  摘要：

  DOI：

  10.1021/jo00252a026

文献信息

• Conformationally defined adrenergic agents. Part 13. Synthesis of benzobicyclo[3.2.1]octanes involving inversion of configuration via an N-to-O acetyl migration
  作者：Gary L. Grunewald、Qizhuang Ye

  DOI：10.1021/jo00252a026

  日期：1988.8
• GRUNEWALD, GARY L.;YE, QIZHUANG, J. ORG. CHEM., 53,(1988) N 17, 4021-4026
  作者：GRUNEWALD, GARY L.、YE, QIZHUANG

  DOI：——

  日期：——
• 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.