(R)-(-)-1-(1,2-diphenylethyl)piperidine | 127529-17-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (R)-(-)-1-(1,2-diphenylethyl)piperidine
• 英文别名: 1-(1,2-Diphenylethyl)piperidine-(+/-)；1-[(1R)-1,2-diphenylethyl]piperidine
• CAS: 127529-17-3
• 化学式: C₁₉H₂₃N
• 分子量: 265.398
• InChiKey: JQWJJJYHVHNXJH-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-(-)-1-(1,2-diphenylethyl)piperidine 在 盐酸 、 水 作用下， 以85%的产率得到(-)-DEP hydrochloride
  参考文献：
  名称：

  NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds

  摘要：

  We resolved 1,2-diphenylethylamine (DPEA) into its (S)- and (R)- enantiomer and used them as precursors for synthesis of (S)- and (R)-1-(1,2-diphenylethyl)piperidine,flexible homeomorphs of the NMDA channel blocker MK-801. We also describe the synthesis of the dicyclohexyl analogues of DPEA. These and related compounds were tested as inhibitors of [(3)H]MK-801 binding to rat brain membranes. Stereospecificity ranged between factors of 0.5 and 50. Some blockers exhibited stereospecific sensitivity to the modulator spermine. Our results may help to elucidate in more detail the NMDA channel pharmacophore. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.025
• 作为产物：
  描述：

  1,5-二溴戊烷 、 (R)-(-)-1,2-diphenylethylamine 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以64%的产率得到(R)-(-)-1-(1,2-diphenylethyl)piperidine
  参考文献：
  名称：

  NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds

  摘要：

  We resolved 1,2-diphenylethylamine (DPEA) into its (S)- and (R)- enantiomer and used them as precursors for synthesis of (S)- and (R)-1-(1,2-diphenylethyl)piperidine,flexible homeomorphs of the NMDA channel blocker MK-801. We also describe the synthesis of the dicyclohexyl analogues of DPEA. These and related compounds were tested as inhibitors of [(3)H]MK-801 binding to rat brain membranes. Stereospecificity ranged between factors of 0.5 and 50. Some blockers exhibited stereospecific sensitivity to the modulator spermine. Our results may help to elucidate in more detail the NMDA channel pharmacophore. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.025

文献信息

• Determination of the chiral status of different novel psychoactive substance classes by capillary electrophoresis and β‐cyclodextrin derivatives
  作者：Johannes S. Hägele、Eva‐Maria Hubner、Martin G. Schmid

  DOI：10.1002/chir.23268

  日期：2020.9

  aforementioned compound classes. Enantioresolution was achieved by simply adding native β‐cyclodextrin, acetyl‐β‐cyclodextrin, 2‐hydroxypropyl‐β‐cyclodextrin, or carboxymethyl‐β‐cyclodextrin as chiral selector additives to the background electrolyte. Fifty‐one chiral NPS served as analytes mainly purchased from online vendors via the Internet. Using 10 mM of the aforementioned β‐cyclodextrins in a 10 mM

  除了滥用众所周知的非法药物外，消费者还发现了新的合成化合物，它们具有相似的作用，但化学结构发生了微小变化。最初，创建这些所谓的新型精神活性物质（NPS）是为了规避因滥用毒品而引起的起诉法。在过去的十年中，此类化合物世代相传，最流行的化合物是合成的甲基吡啶酮衍生物，称为甲氧麻黄酮。卡西酮在结构上与苯丙胺有关；迄今为止，已经合成了120多种全新的衍生物，并通过Internet进行了交易。卡西酮具有手性中心。然而，关于其对映体的药理学知之甚少。但是，NPS还包含其他手性化合物，例如苯丙胺衍生物，氯胺酮，2-（氨基丙基）苯并呋喃，和吩啶。在我们的项目继续中，以前介绍的一种廉价，易于执行的手性毛细管电泳区分离卡西酮的方法已扩展到上述化合物类别。通过将天然β-环糊精，乙酰基-β-环糊精，2-羟丙基-β-环糊精或羧甲基-β-环糊精作为手性选择剂添加到背景电解质中，即可实现对映体拆分。51个手性NPS用作
• NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds
  作者：Michael L. Berger、Anna Schweifer、Patrick Rebernik、Friedrich Hammerschmidt

  DOI：10.1016/j.bmc.2009.03.025

  日期：2009.5

  We resolved 1,2-diphenylethylamine (DPEA) into its (S)- and (R)- enantiomer and used them as precursors for synthesis of (S)- and (R)-1-(1,2-diphenylethyl)piperidine,flexible homeomorphs of the NMDA channel blocker MK-801. We also describe the synthesis of the dicyclohexyl analogues of DPEA. These and related compounds were tested as inhibitors of [(3)H]MK-801 binding to rat brain membranes. Stereospecificity ranged between factors of 0.5 and 50. Some blockers exhibited stereospecific sensitivity to the modulator spermine. Our results may help to elucidate in more detail the NMDA channel pharmacophore. (C) 2009 Elsevier Ltd. All rights reserved.