cis-4-(4-fluorophenyl)-1-methylpiperidine-3-carboxylic acid methyl ester

• 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: cis-4-(4-fluorophenyl)-1-methylpiperidine-3-carboxylic acid methyl ester
• 英文别名: (+/-)-cis-4-(4'-Fluorophenyl)-3-methoxycarbonyl-1-methyl-piperidine；methyl (3S,4S)-4-(4-fluorophenyl)-1-methylpiperidine-3-carboxylate
• 化学式: C₁₄H₁₈FNO₂
• 分子量: 251.301
• InChiKey: NTYATEQGMUSJQM-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-4-(4-fluorophenyl)-1-methylpiperidine-3-carboxylic acid methyl ester 、 sodium methylate 以 甲苯 为溶剂， 反应 7.0h， 以gave the title compound as an oil (1.97 g, 99%), purity 85-90%的产率得到(-)-(3S,4R)-4-(4-fluoro-phenyl)-1-methyl-piperidine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Chemical process

  摘要：

  公开了一种制备式(I)化合物的过程：##STR1## 其中Ar是芳基或取代芳基，R.sup.3和R.sup.4相同或不同，且每个都是烷基，该过程包括加氢化式(II)的化合物：##STR2## 其中Ar，R.sup.3和R.sup.4与式(I)相对应定义，Hal是卤素原子。式(I)化合物可用作化学中间体。

  公开号：

  US04861893A1
• 作为产物：
  描述：

  4-(4'-fluorophenyl)-3-methoxycarbonyl-1-methylpyridinium bromide 在 氧化铂 disodium;carbonate 、 二氯甲烷 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 45.0 ℃ 、13.51 MPa 条件下， 反应 24.0h， 以to give an off-white solid (12.1 g)的产率得到cis-4-(4-fluorophenyl)-1-methylpiperidine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Chemical process

  摘要：

  公开了一种制备式(I)化合物的过程：##STR1## 其中Ar是芳基或取代芳基，R.sup.3和R.sup.4相同或不同，且每个都是烷基，该过程包括加氢化式(II)的化合物：##STR2## 其中Ar，R.sup.3和R.sup.4与式(I)相对应定义，Hal是卤素原子。式(I)化合物可用作化学中间体。

  公开号：

  US04861893A1

文献信息

• Radical fluoroarylation in radiochemical synthesis
  作者：Christina Hultsch、Olga Blank、Hans-Jürgen Wester、Markus R. Heinrich

  DOI：10.1016/j.tetlet.2007.12.128

  日期：2008.3

  In this study, we report on the radical [F-18]fluoroarylation of different olefins using 4-[F-18]fluorobenzenediazonium ions to provide a new route to radiopharmaceuticals containing a deactivated, 4-[F-18]fluoro substituted phenyl group. This new methodology was shown to be well suited for the synthesis of F-18-labelled stilbenes. Stilbene 7 is now accessible within 80 min in 30-45% overall radiochemical yield starting from [F-18]fluoride. (C) 2008 Elsevier Ltd. All rights reserved.
• Syntheses of 3-carbomethoxy-4-(aryl)piperidines and In vitro and In vivo pharmacological evaluation: identification of inhibitors of the human dopamine transporter
  作者：Xianqi Feng、Keith Fandrick、Robert Johnson、Aaron Janowsky、John R Cashman

  DOI：10.1016/s0968-0896(02)00528-x

  日期：2003.3

  A series of 3-carbomethoxy-4-(aryl-substituted)piperidines with various aryl groups were synthesized and examined for binding and reuptake inhibition at the human dopamine transporter, the human serotonin transporter, and the human norepinephrine transporter. The binding potency and reuptake inhibition efficacy was compared with that of (-)-cocaine to determine the significance of removing the two-carbon bridge of the cocaine nucleus on the inhibition of transporter binding and reuptake. Of the transporters examined, the substituted piperidines were relatively selective for the human dopamine transporter. In all cases examined, the cis-diastereomer of the 3-carbomethoxy-4-(aryl-substituted)piperidine was observed to be a more potent inhibitor of the human dopamine transporter than the trans diastereomer. Based on the K-i (binding) and IC50 (reuptake inhibition) values obtained, the most potent inhibitor of the series was cis-3-carbomethoxy-4-(4'-chlorophenyl)piperidine,and this compound suppressed spontaneous- and cocaine-induced stimulation in non-habituated male Swiss-Webster mice. The conclusion is that substantial portions of the cocaine structure can be dissected away to provide compounds with significant binding and reuptake inhibition of the human dopamine transporter. (C) 2002 Elsevier Science Ltd. All rights reserved.