benzyl 4-(3,4-dichlorophenyl)-1-methyl-piperidine-4-carboxylate

• 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: benzyl 4-(3,4-dichlorophenyl)-1-methyl-piperidine-4-carboxylate
• 英文别名: Benzyl 4-(3,4-dichlorophenyl)-1-methylpiperidine-4-carboxylate hydrochloride；benzyl 4-(3,4-dichlorophenyl)-1-methylpiperidine-4-carboxylate
• 化学式: C₂₀H₂₁Cl₂NO₂
• 分子量: 378.298
• InChiKey: RDKSWLZDHPEDCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 4-(3,4-dichlorophenyl)-1-methyl-piperidine-4-carboxylate 在 1-氯乙基氯甲酸酯 、 碳酸氢钠 、 甲醇 、 sodium hydroxide 作用下， 以 1,2-二氯乙烷 、 氯仿 为溶剂， 反应 51.0h， 以57%的产率得到benzyl 4-(3,4-dichlorophenyl)piperidine-4-carboxylate
  参考文献：
  名称：

  Synthesis and structure–activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands

  摘要：

  A series of benzyl esters of meperidine and normeperidine were synthesized and evaluated for binding affinity at serotonin, dopamine and norepinephrine transporters. The 4-methoxybenzyl ester 8b and 4-nitrobenzyl ester 8c in the meperidine series and 4-methoxybenzyl ester 14a in the normeperidine series exhibited low nanomolar binding affinities at the SERT (K-i values <2 nM) and high SERT selectivity (DAT/SERT > 1500 and NET/SERT > 1500). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.060
• 作为产物：
  描述：

  4-(3,4-二氯苯基)-1-甲基哌啶-4-甲腈 在 4 A molecular sieve 、 硫酸 、 potassium tert-butylate 、 1,3-二均三甲苯基咪唑-2-叉 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 benzyl 4-(3,4-dichlorophenyl)-1-methyl-piperidine-4-carboxylate
  参考文献：
  名称：

  Structure–activity studies of 3′-4′-dichloro-meperidine analogues at dopamine and serotonin transporters

  摘要：

  The structure-activity relationships of 3',4'-dichloro-meperidine were investigated at dopamine (DAT) and serotonin transporters (SERT). Large ester substituents and lipophilic groups at the 4-position favored molecular recognition at the SERT. The benzyl ester of 3',4'-dichloro-meperidine exhibited high potency and high selectivity for the SERT (DAT/SERT = 760). Chemical modification of the ester group and N-substitution generally led to compounds with decreased DAT affinity. Only small esters and alkyl groups were tolerated at the 4-position of the meperidine ring system by the DAT. Overall, the meperidine analogues were generally more selective for the SERT than for the DAT. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.025