(2R)-tert-butyl 2-methyl-2-phenylpiperidine-1-carboxylate | 1395055-66-9

• 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)-tert-butyl 2-methyl-2-phenylpiperidine-1-carboxylate
• 英文别名: tert-butyl (2R)-2-methyl-2-phenylpiperidine-1-carboxylate
• CAS: 1395055-66-9
• 化学式: C₁₇H₂₅NO₂
• 分子量: 275.391
• InChiKey: WAVNRUNVRWHPKF-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：

  (2R)-tert-butyl 2-methyl-2-phenylpiperidine-1-carboxylate 在 氯化亚砜 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成 (R)-2-methyl-2-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
• 作为产物：
  描述：

  1-Boc-哌啶 在 四甲基乙二胺 、 C₁₂H₂₄N₂O^(2-)*2Li⁽¹⁺⁾ 、 仲丁基锂 作用下， 以 乙醚 为溶剂， 反应 27.0h， 生成 (2R)-tert-butyl 2-methyl-2-phenylpiperidine-1-carboxylate
  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

• Synthesis and kinetic resolution of <i>N</i>-Boc-2-arylpiperidines
  作者：Edward J. Cochrane、Daniele Leonori、Lorraine A. Hassall、Iain Coldham

  DOI：10.1039/c4cc04576a

  日期：——

  An efficient kinetic resolution of 2-arylpiperidines was developed using a chiral base.

  开发了一种使用手性碱的高效动力学拆分2-芳基哌啶的方法。
• Synthetic Applications and Inversion Dynamics of Configurationally Stable 2-Lithio-2-arylpyrrolidines and -piperidines
  作者：Timothy K. Beng、Jin Sun Woo、Robert E. Gawley

  DOI：10.1021/ja306276w

  日期：2012.9.12

  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.