(2R,4R)-1-(tert-butoxycarbonyl)-2-methyl-4-phenylpiperidine | 1049705-20-5

• 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: (2R,4R)-1-(tert-butoxycarbonyl)-2-methyl-4-phenylpiperidine
• 英文别名: tert-butyl (2R,4R)-2-methyl-4-phenylpiperidine-1-carboxylate
• CAS: 1049705-20-5
• 化学式: C₁₇H₂₅NO₂
• 分子量: 275.391
• InChiKey: GNAOAYRTCWQFOB-UKRRQHHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  碘甲烷 、 (2R,4R)-1-(tert-butoxycarbonyl)-2-methyl-4-phenylpiperidine 在 四甲基乙二胺 、 仲丁基锂 作用下， 生成 (2R,6R)-2,6-Dimethyl-4-phenyl-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  .alpha.-Lithioamine synthetic equivalents: syntheses of diastereoisomers from the Boc-piperidines

  摘要：

  DOI：

  10.1021/jo00296a008
• 作为产物：
  描述：

  碘甲烷 、 4-苯基-1-哌啶羧酸叔丁酯 在 四甲基乙二胺 、 仲丁基锂 作用下， 生成 (2R,4R)-1-(tert-butoxycarbonyl)-2-methyl-4-phenylpiperidine
  参考文献：
  名称：

  .alpha.-Lithioamine synthetic equivalents: syntheses of diastereoisomers from the Boc-piperidines

  摘要：

  DOI：

  10.1021/jo00296a008

文献信息

• A Synthetic and Spectroscopic Investigation of the Asymmetric α-Lithiation-trapping of Six-Membered N-Boc Heterocycles Using Alexakis Diamines
  作者：Peter O'Brien、James D. Firth、Giacomo Gelardi、Peter J. Rayner、Darren Stead

  DOI：10.3987/com-18-s(t)87

  日期：——

  The asymmetric lithiation-trapping of six-membered N-Boc heterocycles using s-BuLi and two different Alexakis diamines is reported. These readily available ligands outperform the current 'best-in-class' sparteine-type diamines in the lithiation and benzophenone trapping of N-Boc piperazines and the lithiation-cyclisation-trapping of N-Boc-4-chloropiperidine. In situ IR spectroscopy has been used to optimise lithiation times and to discover previously unknown subtleties regarding the lithiation step.
• An Enantioselective Synthetic Route to <i>cis</i>-2,4-Disubstituted and 2,4-Bridged Piperidines
  作者：Mercedes Amat、Maria Pérez、Annamaria T. Minaglia、Joan Bosch

  DOI：10.1021/jo801172b

  日期：2008.9.1

  A synthetic route to enantiopure cis-2,4-disubstituted and 2,4-bridged piperidines is reported, the key step being a stereoselective conjugate addition of an organocuprate to a phenylglycinol-derived unsaturated lactam bearing a substituent at the 8a-position.