(+)-cis-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)piperidine hydrochloride

• 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)-3-(3,4-methylenedioxyphenoxymethyl)piperidine hydrochloride
• 英文别名: (3R,4R)-3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine;hydron;chloride
• 化学式: C₁₉H₂₀FNO₃*ClH
• 分子量: 365.832
• InChiKey: GELRVIPPMNMYGS-CVLQQERVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  39.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(4-fluorophenyl)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydropyridine 在 palladium on activated charcoal 盐酸 、 lithium aluminium tetrahydride 、 溴化氰 、 氢气 、 sodium 、 三乙胺 、 苯磺酰氯 作用下， 反应 76.0h， 生成 (+)-cis-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)piperidine hydrochloride
  参考文献：
  名称：

  Synthesis and 5HT Modulating Activity of Stereoisomers of 3-Phenoxymethyl-4-phenylpiperidines.

  摘要：

  A series of pairs of enantiomers of substituted 3-phenoxymethyl-4-phenylpiperidines has been prepared from arecoline or alpha-methylstyrene by a combination of stereospecific reactions and optical resolutions. The ability of the compounds to modulate serotonin (5HT) neurotransmission in vitro was determined. Several derivatives, among which is the antidepressant paroxetine, are very potent inhibitors of 5HT reuptake. These compounds exhibit a pronounced steric requirement for inhibition of 5HT reuptake and binding to 5HT(2A) and 5HT(2C) receptors.

  DOI：

  10.3891/acta.chem.scand.50-0164

文献信息

• Piperidine compounds and their preparation and use
  申请人：NOVO NORDISK A/S

  公开号：EP0266574B1

  公开（公告）日：1994-01-05
• US4877799A
  申请人：——

  公开号：US4877799A

  公开（公告）日：1989-10-31
• US4985446A
  申请人：——

  公开号：US4985446A

  公开（公告）日：1991-01-15
• US5019582A
  申请人：——

  公开号：US5019582A

  公开（公告）日：1991-05-28
• Synthesis and 5HT Modulating Activity of Stereoisomers of 3-Phenoxymethyl-4-phenylpiperidines.
  作者：Mogens Engelstoft、John Bondo Hansen、Tore Vulpius、Peter Moldt、S. Brøgger Christensen

  DOI：10.3891/acta.chem.scand.50-0164

  日期：——

  A series of pairs of enantiomers of substituted 3-phenoxymethyl-4-phenylpiperidines has been prepared from arecoline or alpha-methylstyrene by a combination of stereospecific reactions and optical resolutions. The ability of the compounds to modulate serotonin (5HT) neurotransmission in vitro was determined. Several derivatives, among which is the antidepressant paroxetine, are very potent inhibitors of 5HT reuptake. These compounds exhibit a pronounced steric requirement for inhibition of 5HT reuptake and binding to 5HT(2A) and 5HT(2C) receptors.