(R)-N-Boc-2-(3,4-dimethoxy)phenylpiperidine | 1261081-79-1

• 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: (R)-N-Boc-2-(3,4-dimethoxy)phenylpiperidine
• 英文别名: tert-butyl (2R)-2-(3,4-dimethoxyphenyl)piperidine-1-carboxylate
• CAS: 1261081-79-1
• 化学式: C₁₈H₂₇NO₄
• 分子量: 321.417
• InChiKey: MXHHRPRVUMCTRO-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-N-Boc-2-(3,4-dimethoxy)phenylpiperidine 在 四甲基乙二胺 、 仲丁基锂 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Synthetic Applications and Inversion Dynamics of Configurationally Stable 2-Lithio-2-arylpyrrolidines and -piperidines

  摘要：

  In diethyl ether, N-Boc-2-lithio-2-arylpiperidines have been found to be configurationally stable at -80 degrees C, whereas N-Boc-2-lithio-2-arylpyrrolidines are configurationally stable at -60 degrees C. Several tertiary benzylic carbanions derived from enantioenriched 2-aryl heterocycles have been successfully alkylated or acylated with little to no loss of enantiopurity. The scope of the reactions has been explored. The enantiomerization dynamics of N-Boc-2-lithio-2-phenylpyrrolidine and N-Boc-2-lithio-2-phenylpiperidine have been studied in the presence of different solvents and achiral ligands.

  DOI：

  10.1021/ja306276w
• 作为产物：
  描述：

  1-Boc-哌啶 在 C₁₂H₂₄N₂O^(2-)*2Li⁽¹⁺⁾ 、 仲丁基锂 作用下， 以 乙醚 为溶剂， 反应 26.5h， 生成 (R)-N-Boc-2-(3,4-dimethoxy)phenylpiperidine
  参考文献：
  名称：

  Synthetic Applications and Inversion Dynamics of Configurationally Stable 2-Lithio-2-arylpyrrolidines and -piperidines

  摘要：

  In diethyl ether, N-Boc-2-lithio-2-arylpiperidines have been found to be configurationally stable at -80 degrees C, whereas N-Boc-2-lithio-2-arylpyrrolidines are configurationally stable at -60 degrees C. Several tertiary benzylic carbanions derived from enantioenriched 2-aryl heterocycles have been successfully alkylated or acylated with little to no loss of enantiopurity. The scope of the reactions has been explored. The enantiomerization dynamics of N-Boc-2-lithio-2-phenylpyrrolidine and N-Boc-2-lithio-2-phenylpiperidine have been studied in the presence of different solvents and achiral ligands.

  DOI：

  10.1021/ja306276w

文献信息

• Application of Catalytic Dynamic Resolution of <i>N</i>-Boc-2-lithiopiperidine to the Asymmetric Synthesis of 2-Aryl and 2-Vinyl Piperidines
  作者：Timothy K. Beng、Robert E. Gawley

  DOI：10.1021/ol102682r

  日期：2011.2.4

  The highly enantioselective synthesis of 2-aryl- and 2-vinyl-piperidines has been accomplished through a catalytic dynamic resolution (CDR) of N-Boc-2-lithiopiperidine. The method has been applied to the synthesis of both enantiomers of the tobacco alkaloid anabasine.
• Asymmetric Deprotonation of <i>N</i>-Boc Piperidine: React IR Monitoring and Mechanistic Aspects
  作者：Darren Stead、Giorgio Carbone、Peter O’Brien、Kevin R. Campos、Iain Coldham、Adam Sanderson

  DOI：10.1021/ja102043e

  日期：2010.6.2

  The high yielding asymmetric deprotonation trapping of N-Boc piperidine is successfully realized using s-BuLi and a (+)-sparteine surrogate. Monitoring of the lithiation by in situ React IR allowed the direct observation of a prelithiation complex.