tert-butyl 2-benzyl-2-cyanopiperidine-1-carboxylate | 1510798-88-5

• 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 2-benzyl-2-cyanopiperidine-1-carboxylate
• 英文别名: Tert-butyl 2-benzyl-2-cyanopiperidine-1-carboxylate
• CAS: 1510798-88-5
• 化学式: C₁₈H₂₄N₂O₂
• 分子量: 300.401
• InChiKey: UIWQNNGKZSTIHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 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：
  53.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-Boc-2-氰基哌啶 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.17h， 生成 tert-butyl 2-benzyl-2-cyanopiperidine-1-carboxylate
  参考文献：
  名称：

  Arylthio-Metal Exchange of α-Arylthioalkanenitriles

  摘要：

  The addition of BuLi, Bu3MgLi, Et2ZnBuLi, or Me2CuLi to alpha-arylthioalkanenitriles triggers an arylthio-metal exchange. NMR spectroscopic analyses implicate organometallic attack on sulfur forming a three-coordinate sulfidate as the key intermediate. Electrophilic trapping affords tertiary and quaternary nitriles in high yield. The method addresses the challenge of improving the functional group tolerance and preventing polyalkylations.

  DOI：

  10.1021/ol403020s

文献信息

• Arylthio-Metal Exchange of α-Arylthioalkanenitriles
  作者：Dinesh Nath、Melanie C. Skilbeck、Iain Coldham、Fraser F. Fleming

  DOI：10.1021/ol403020s

  日期：2014.1.3

  The addition of BuLi, Bu3MgLi, Et2ZnBuLi, or Me2CuLi to alpha-arylthioalkanenitriles triggers an arylthio-metal exchange. NMR spectroscopic analyses implicate organometallic attack on sulfur forming a three-coordinate sulfidate as the key intermediate. Electrophilic trapping affords tertiary and quaternary nitriles in high yield. The method addresses the challenge of improving the functional group tolerance and preventing polyalkylations.