(R)-2-methyl-2-phenylpiperidine | 1272031-55-6

• 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)-2-methyl-2-phenylpiperidine
• 英文别名: (2R)-2-methyl-2-phenylpiperidine
• CAS: 1272031-55-6
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: FLNODMVWOCAIEF-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-2-methyl-2-phenylpiperidine 、 三氟乙酸酐 在 吡啶 作用下， 生成
  参考文献：
  名称：

  硼酸酯合成高对映体富集的C-叔胺：在合成亚胺的应用

  摘要：

  优于所有其他化合物：叔硼酸酯（使用锂化-硼化反应可轻松获得）已在非常高的ee中转化为叔烷基胺。这项工作已被应用于药物艾美辛和手性2,2-二取代哌啶的简短，模块化和完全立体控制的合成。

  DOI：

  10.1002/anie.201006037
• 作为产物：
  描述：

  1-Boc-哌啶 在 氯化亚砜 、 四甲基乙二胺 、 C₁₂H₂₄N₂O^(2-)*2Li⁽¹⁺⁾ 、 仲丁基锂 、 sodium hydroxide 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 33.0h， 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

文献信息

• Synthesis of Highly Enantioenriched C-Tertiary Amines From Boronic Esters: Application to the Synthesis of Igmesine
  作者：Viktor Bagutski、Tim G. Elford、Varinder K. Aggarwal

  DOI：10.1002/anie.201006037

  日期：2011.2.1

  Better than all the rest: Tertiary boronic esters, readily available using the lithiation–borylation reaction, have been converted into tertiary alkylamines in very high ee. The work has been applied to a short, modular, and fully stereocontrolled synthesis of the pharmaceutical igmesine and chiral 2,2‐disubstituted piperidines.

  优于所有其他化合物：叔硼酸酯（使用锂化-硼化反应可轻松获得）已在非常高的ee中转化为叔烷基胺。这项工作已被应用于药物艾美辛和手性2,2-二取代哌啶的简短，模块化和完全立体控制的合成。
• 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.