N-benzyl-N-tert-butyl-isonicotinamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-benzyl-N-tert-butyl-isonicotinamide
• 英文别名: N-benzyl-N-tert-butylpyridine-4-carboxamide
• 化学式: C₁₇H₂₀N₂O
• 分子量: 268.359
• InChiKey: XQWALAQTULPZQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-tert-butyl-isonicotinamide 在 lithium diisopropyl amide 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以46%的产率得到2-tert-butyl-3-phenyl-2,3-dihydro-pyrrolo[3,4-c]pyridin-1-one
  参考文献：
  名称：

  Cyclization of Lithiated Pyridine and Quinoline Carboxamides:  Synthesis of Partially Saturated Pyrrolopyridines and Spirocyclic β-Lactams

  摘要：

  [GRAPHICS]Lithiation of N-benzyl pyridine and quinoline carboxamides a to nitrogen gives anions that undergo intramolecular attack on the pyridine or quinoline ring, either directly or on activation of the ring by N-acylation. The resulting four-, five-, or six-membered-ring-containing compound may be oxidized, protonated, alkylated, or acylated to give a range of polycyclic heterocycles, including pyrrolopyridines, pyrroloquinolines, benzonaphthyridines, and azaspirocyclic beta-lactams.

  DOI：

  10.1021/ol051214u

文献信息

• Cyclization of Lithiated Pyridine and Quinoline Carboxamides:  Synthesis of Partially Saturated Pyrrolopyridines and Spirocyclic β-Lactams
  作者：Jonathan Clayden、Stuart D. Hamilton、Rukhsana T. Mohammed

  DOI：10.1021/ol051214u

  日期：2005.8.1

  [GRAPHICS]Lithiation of N-benzyl pyridine and quinoline carboxamides a to nitrogen gives anions that undergo intramolecular attack on the pyridine or quinoline ring, either directly or on activation of the ring by N-acylation. The resulting four-, five-, or six-membered-ring-containing compound may be oxidized, protonated, alkylated, or acylated to give a range of polycyclic heterocycles, including pyrrolopyridines, pyrroloquinolines, benzonaphthyridines, and azaspirocyclic beta-lactams.