1-Acetoxy-2,2,4,4-tetramethylpyrrolidine | 137256-19-0

• 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: 1-Acetoxy-2,2,4,4-tetramethylpyrrolidine
• 英文别名: (2,2,4,4-tetramethylpyrrolidin-1-yl) acetate
• CAS: 137256-19-0
• 化学式: C₁₀H₁₉NO₂
• 分子量: 185.266
• InChiKey: JNRJNMWMQIVDTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3,4-二氢-3,3,5-三甲基-2H-吡咯 1-氧化物 以 乙醚 为溶剂， 生成 1-Acetoxy-2,2,4,4-tetramethylpyrrolidine
  参考文献：
  名称：

  Origin of "hetero effect" on nitrogen inversion. Comparison of hydroxylamines and aminoxide anions

  摘要：

  Rate constants for nitrogen inversion in N-benzyl-N-methylhydroxylamine, NN-diethylhydroxylamine, 1-hydroxy-2,2,4,4-tetramethylpyrrolidine, their conjugate bases, and their O-acetyl derivatives in dimethylformamide-d7 were determined based on the H-1 NMR coalescence temperatures. Relative to -OH, the -O- substituent ought to either raise the barrier to inversion owing to stronger lone-pair repulsions or lower the barrier owing to weaker sigma-inductive effects. Yet nearly identical barriers to inversion, DELTA-G double dagger = 12.0-13.3 kcal/mol, are observed for both the hydroxylamine and its conjugate base. Since the observed barrier is little changed upon deprotonation, it is concluded that the pi-repulsive and sigma-inductive contributions must be nearly equal.

  DOI：

  10.1021/jo00025a016