tert-butyl (2S,3S)-2-phenylpiperidine-3-carboxylate | 1026773-70-5

• 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: tert-butyl (2S,3S)-2-phenylpiperidine-3-carboxylate
• CAS: 1026773-70-5
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: OBHIEODEKHCIHH-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (5S,6S)-5-tert-butoxycarbonyl-6-phenyl-piperidin-2-one 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到tert-butyl (2S,3S)-2-phenylpiperidine-3-carboxylate
  参考文献：
  名称：

  Diastereoselective Synthesis of δ-Aminoacids through Domino Ireland−Claisen Rearrangement and Michael Addition

  摘要：

  domino reaction-stereoselective Ireland-Claisen rearrangement and asymmetric Michael addition-is described. A protocol starting from Baylis-Hillman adducts 3a-f using chiral lithium amide affords optically active gamma-substituted delta-aminoacids 4a-f with high diastereoselectivities and enantioselectivities. The acid can be isolated easily from large-scale reactions and transformed to 2,3-disubstituted piperidines 11 or 2-substituted nipecotic acid derivates 12.

  DOI：

  10.1021/ol8001464

文献信息

• A Direct Stereoselective Approach to <i>trans</i>-2,3-Disubstituted Piperidines: Application in the Synthesis of 2-Epi-CP-99,994 and (+)-Epilupinine
  作者：M’hamed Ahari、Amandine Perez、Christine Menant、Jean-Luc Vasse、Jan Szymoniak

  DOI：10.1021/ol800722a

  日期：2008.6.1

  A simple synthesis of enantiomerically pure piperidine esters is described, offering a straightforward access to the trans-2,3-disubstituted piperidine skeleton which is present in a broad range of biologically active compounds.
• Diastereoselective Synthesis of δ-Aminoacids through Domino Ireland−Claisen Rearrangement and Michael Addition
  作者：Narciso M. Garrido、Mercedes García、David Díez、M. Rosa Sánchez、F. Sanz、Julio G. Urones

  DOI：10.1021/ol8001464

  日期：2008.5.1

  domino reaction-stereoselective Ireland-Claisen rearrangement and asymmetric Michael addition-is described. A protocol starting from Baylis-Hillman adducts 3a-f using chiral lithium amide affords optically active gamma-substituted delta-aminoacids 4a-f with high diastereoselectivities and enantioselectivities. The acid can be isolated easily from large-scale reactions and transformed to 2,3-disubstituted piperidines 11 or 2-substituted nipecotic acid derivates 12.