(S)-(+)-1-(1,2-diphenylethyl)piperidine | 127529-18-4

• 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: (S)-(+)-1-(1,2-diphenylethyl)piperidine
• 英文别名: Tocris-0360；1-[(1S)-1,2-diphenylethyl]piperidine
• CAS: 127529-18-4
• 化学式: C₁₉H₂₃N
• 分子量: 265.398
• InChiKey: JQWJJJYHVHNXJH-IBGZPJMESA-N

物化性质

• 沸点：
  351.3±11.0 °C(Predicted)
• 密度：
  1.045±0.06 g/cm3(Predicted)

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：

  (S)-(+)-1-(1,2-diphenylethyl)piperidine 在 盐酸 、 水 作用下， 以83%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：

  二苯基乙酮 在 (R,R)-QuinoxP 、 titanium(IV) isopropylate 、 ammonium cerium (IV) nitrate 、 nickel(II) bis[bis((trifluoromethyl)sulfonyl)amide] 、 potassium carbonate 作用下， 以 水 、 异丙醇 、 乙腈 为溶剂， 反应 58.0h， 生成 (S)-(+)-1-(1,2-diphenylethyl)piperidine
  参考文献：
  名称：

  镍催化醇中苄酮的对映选择性还原胺化

  摘要：

  不对称还原胺化直接将酮和胺转化为烷基胺，这是药物中的重要基序。我们报道了手性二膦的阳离子镍配合物促进了苯甲基酮与芳基胺和苯甲酰肼的对映选择性还原胺化。使用异丙醇代替甲酸作为安全且廉价的氢源。该反应可以很容易地应用于二芳基乙胺（一类神经活性物质）的简明合成。

  DOI：

  10.1007/s11426-024-2019-1

文献信息

• 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.
• 10.1007/s11426-024-2019-1
  作者：Wang, Xiuhua、Zhou, Jianrong Steve

  DOI：10.1007/s11426-024-2019-1

  日期：——

  Asymmetric reductive amination directly converts ketones and amines to alkylamines, which are important motifs in medicines. We report that cationic nickel complexes of chiral diphosphines promote enantioselective reductive amination of benzylic ketones with both arylamines and benzhydrazide. Isopropanol was used as a safe and cheap source of hydrogen instead of formic acid. The reaction can be readily

  不对称还原胺化直接将酮和胺转化为烷基胺，这是药物中的重要基序。我们报道了手性二膦的阳离子镍配合物促进了苯甲基酮与芳基胺和苯甲酰肼的对映选择性还原胺化。使用异丙醇代替甲酸作为安全且廉价的氢源。该反应可以很容易地应用于二芳基乙胺（一类神经活性物质）的简明合成。