4-{2-[bis-(4-fluorophenyl)methoxy]ethyl}-1-naphthalen-1-ylmethylpiperidine

• 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: 4-{2-[bis-(4-fluorophenyl)methoxy]ethyl}-1-naphthalen-1-ylmethylpiperidine
• 英文别名: 4-(2-(Bis(4-fluorophenyl)methoxy)ethyl)-1-(naphthalen-1-ylmethyl)piperidine；4-[2-[bis(4-fluorophenyl)methoxy]ethyl]-1-(naphthalen-1-ylmethyl)piperidine
• 化学式: C₃₁H₃₁F₂NO
• 分子量: 471.59
• InChiKey: HXSHKIDYCUOFFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-哌啶乙醇 在 sodium hydroxide 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 、 sodium iodide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 36.0h， 生成 4-{2-[bis-(4-fluorophenyl)methoxy]ethyl}-1-naphthalen-1-ylmethylpiperidine
  参考文献：
  名称：

  Piperidine Analogues of 1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (GBR 12909):  High Affinity Ligands for the Dopamine Transporter

  摘要：

  A series of 4-[2-[bis(4-fluorophenyl)methoxy]ethylpiperidines were examined for their ability to bind to the dopamine transporter (DAT), the norepinephrine transporter, and the serotonin transporter (SERT). In particular, the role of the N-substituent on affinity and selectivity for the DAT was probed. 4-[2-[Bis(4-fluorophenyl)methoxy]ethyl-1-(2-naphthylmethyl)piperidine was found to possess subnanomolar affinity (K-i = 0.7 nM) and good selectivity for the DAT (SERT/DAT = 323).

  DOI：

  10.1021/jm020264r

文献信息

• Piperidine Analogues of 1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (GBR 12909):  High Affinity Ligands for the Dopamine Transporter
  作者：Thomas Prisinzano、Elisabeth Greiner、Edward M. Johnson、Christina M. Dersch、Jamila Marcus、John S. Partilla、Richard B. Rothman、Arthur E. Jacobson、Kenner C. Rice

  DOI：10.1021/jm020264r

  日期：2002.9.1

  A series of 4-[2-[bis(4-fluorophenyl)methoxy]ethylpiperidines were examined for their ability to bind to the dopamine transporter (DAT), the norepinephrine transporter, and the serotonin transporter (SERT). In particular, the role of the N-substituent on affinity and selectivity for the DAT was probed. 4-[2-[Bis(4-fluorophenyl)methoxy]ethyl-1-(2-naphthylmethyl)piperidine was found to possess subnanomolar affinity (K-i = 0.7 nM) and good selectivity for the DAT (SERT/DAT = 323).