3-(3,4-dimethylphenyl)-N-n-propylpiperidine | 219704-16-2

• 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: 3-(3,4-dimethylphenyl)-N-n-propylpiperidine
• 英文别名: 3-(3,4-Dimethyl-phenyl)-1-propyl-piperidine；3-(3,4-dimethylphenyl)-1-propylpiperidine
• CAS: 219704-16-2
• 化学式: C₁₆H₂₅N
• 分子量: 231.381
• InChiKey: WKCUEEXFTZSNLI-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933399090

反应信息

• 作为产物：
  描述：

  丙醛 、 3-(3,4-dimethylphenyl)piperidine 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 3-(3,4-dimethylphenyl)-N-n-propylpiperidine
  参考文献：
  名称：

  Synthesis and dopaminergic properties of the two enantiomers of 3-(3,4-dimethylphenyl)-1-propylpiperidine, a potent and selective dopamine D4 receptor ligand

  摘要：

  The synthesis of the two enantiomers of 3-(3,4-dimethylphenyl)-1-propylpiperidine 1, a potent and selective D4 dopaminergic ligand, was performed. The 3-(3,4-dimethylpheny1)-l-propylpiperidine with the R configuration showed an affinity for the D4 receptors 6-fold higher than the corresponding enantiomer with the S configuration. Furthermore, the (R)-1 enantiomer proved to be highly selective for D4 receptors with respect to D2-D3 receptors, with a K-i ratio higher than 25,000, while the (S)-1 enantiomer was about 100-fold less selective than the (R)-1 one (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00633-8

文献信息

• <i>N</i>-<i>n</i>-Propyl-Substituted 3-(Dimethylphenyl)piperidines Display Novel Discriminative Properties between Dopamine Receptor Subtypes:  Synthesis and Receptor Binding Studies
  作者：Luigi Cervetto、Gian Carlo Demontis、Gino Giannaccini、Biancamaria Longoni、Bruno Macchia、Marco Macchia、Adriano Martinelli、Elisabetta Orlandini

  DOI：10.1021/jm9708700

  日期：1998.12.1

  substituted on the phenyl ring. In previous studies, we found that the dimethyl substitution on the phenyl ring of N-unsubstituted PPEs provided compounds active toward alpha2-adrenergic receptors (alpha2-ARs), which proved to possess interesting selectivity properties. The high degree of homology between the binding domains of alpha2-ARs and D4-dopaminergic receptors (D4-DARs) prompted us to verify whether

  鉴于3-苯基哌啶（PPE）具有令人感兴趣的多巴胺能活性，已经对其进行了彻底的研究，并且Nn-丙基取代被认为是在苯环上不同取代的几种PPE中最有效的。在先前的研究中，我们发现N-未取代的PPE的苯环上的二甲基取代提供了对α2-肾上腺素能受体（alpha2-ARs）具有活性的化合物，事实证明该化合物具有令人感兴趣的选择性。α2-ARs与D4-多巴胺能受体（D4-DARs）的结合域之间的高度同源性促使我们验证芳环上的这种取代是否可能被证明对D4亚型的视网膜DAR具有活性。在这些前提的基础上，我们合成了二甲基苯基取代的PPE 4a-f，其中正丙基链存在于胺氮上。在D1样和D2样DAR的牛视网膜和纹状体膜上进行放射性配体结合测定表明，PPE 4a，4b和4f对D4-DAR亚型的牛视网膜具有很高的亲和力和选择性。
• Synthesis and dopaminergic properties of the two enantiomers of 3-(3,4-dimethylphenyl)-1-propylpiperidine, a potent and selective dopamine D4 receptor ligand
  作者：Bruno Macchia、Luigi Cervetto、Gian Carlo Demontis、Paolo Domiano、Biancamaria Longoni、Marco Macchia、Filippo Minutolo、Elisabetta Orlandini、Gabriella Ortore、Chiara Papi

  DOI：10.1016/s0960-894x(00)00633-8

  日期：2001.1

  The synthesis of the two enantiomers of 3-(3,4-dimethylphenyl)-1-propylpiperidine 1, a potent and selective D4 dopaminergic ligand, was performed. The 3-(3,4-dimethylpheny1)-l-propylpiperidine with the R configuration showed an affinity for the D4 receptors 6-fold higher than the corresponding enantiomer with the S configuration. Furthermore, the (R)-1 enantiomer proved to be highly selective for D4 receptors with respect to D2-D3 receptors, with a K-i ratio higher than 25,000, while the (S)-1 enantiomer was about 100-fold less selective than the (R)-1 one (C) 2001 Elsevier Science Ltd. All rights reserved.