(R)-N-Methyl-2-(11'-hydroxyundecyl)piperidine | 68419-39-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (R)-N-Methyl-2-(11'-hydroxyundecyl)piperidine
• 英文别名: 11-[(2R)-1-methylpiperidin-2-yl]undecan-1-ol
• CAS: 68419-39-6
• 化学式: C₁₇H₃₅NO
• 分子量: 269.471
• InChiKey: RWRDCKSSQWOLAG-QGZVFWFLSA-N

物化性质

• 沸点：
  366.5±15.0 °C(Predicted)
• 密度：
  0.894±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  11-溴-1-十一醇 、 (R)-N-Methyl-2-(tributylstannyl)piperidine 在 正丁基锂 、 四甲基乙二胺 作用下， 生成 (R)-N-Methyl-2-(11'-hydroxyundecyl)piperidine 、 (S)-N-Methyl-2-(11'-hydroxyundecyl)piperidine
  参考文献：
  名称：

  Alkylation of 2-lithio-N-methylpiperidines and -pyrrolidines: scope, limitations, and stereochemistry

  摘要：

  The scope and limitations of the alkylation of racemic and nonracemic 2-lithiopiperidines and -pyrrolidines, obtained by transmetalation of the corresponding stannanes, is reported. These organolithiums react with a variety of electrophiles to afford 2-substituted pyrrolidines and piperidines in excellent yield. With primary alkyl halides the reaction proceeds with net inversion of configuration at the metal-bearing carbon in the piperidines; in the pyrrolidines there is a mixture of inversion and retention, with the former predominating. With most carbonyl electrophiles (carbon dioxide, dimethyl carbonate, methyl chloroformate, pivaloyl chloride, benzaldehyde, and dialkyl ketones), retention is observed in both cases. Electrophiles such as benzophenone, benzyl bromide, and tert-butyl bromoacetate afford racemic coupling products. A mechanistic interpretation is presented.

  DOI：

  10.1021/jo00123a008