(+/-)-cis-3-(4-methoxyphenoxymethyl)-1-methyl-4-phenylpiperidine | 54088-07-2

• 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: (+/-)-cis-3-(4-methoxyphenoxymethyl)-1-methyl-4-phenylpiperidine
• 英文别名: (3S,4S)-3-[(4-methoxyphenoxy)methyl]-1-methyl-4-phenylpiperidine
• CAS: 54088-07-2；57775-23-2；59859-58-4；85610-75-9；89615-16-7；109361-00-4；112137-04-9；112137-05-0
• 化学式: C₂₀H₂₅NO₂
• 分子量: 311.424
• InChiKey: OJSFTALXCYKKFQ-FXAWDEMLSA-N

物化性质

• 沸点：
  437.9±35.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-cis-3-(4-methoxyphenoxymethyl)-1-methyl-4-phenylpiperidine 在 lithium aluminium tetrahydride 、 溴化氰 作用下， 生成 (-)-cis-3-(4-methoxyphenoxymethyl)-4-phenylpiperidine hydrochloride 、 (+)-cis-3-(4-methoxyphenoxymethyl)-4-phenylpiperidine 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
• 作为产物：
  描述：

  3-(4-methoxyphenoxymethyl)-1-methyl-4-phenyl-1,2,3,4-tetrahydropyridine hydrochloride 在 palladium on activated charcoal 氢气 作用下， 生成 (+/-)-cis-3-(4-methoxyphenoxymethyl)-1-methyl-4-phenylpiperidine
  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

• On the formation of the 1-aza-[3.1.1]-bicycloheptane ring system
  作者：J.A. Christensen、M. Engelstoft、K. Schaumburg、H. Schou、F. Wätjen

  DOI：10.1016/s0040-4039(00)94067-x

  日期：1983.1
• 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.