6-(benzotriazol-1-yl)-2-piperidinone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 6-(benzotriazol-1-yl)-2-piperidinone
• 英文别名: 6-(Benzotriazol-1-yl)piperidin-2-one
• 化学式: C₁₁H₁₂N₄O
• 分子量: 216.242
• InChiKey: GIWWYMCJRJZZLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  59.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  T406石油添加剂 、 6-乙氧基哌啶-2-酮 在 溶剂黄146 作用下， 反应 36.0h， 以79%的产率得到6-(benzotriazol-1-yl)-2-piperidinone
  参考文献：
  名称：

  Cycloaddition of Heteroatom-Substituted 2-Azaallyl Anions with Alkenes. Synthesis of 1-Pyrrolines and Bridged Azabicyclic Compounds

  摘要：

  Nonstabilized 2-azaallyl anions bearing heteroatom substituents [(RCHNC)-C-1(X)R-2(-)Li(+), where R-1 and R-2 are hydrogen or alkyl groups and X = OMe, SPh, or NR2] were generated and found to undergo efficient [3 + 2] cycloadditions with alkenes to provide 1-pyrrolines after loss of LiX. The 2-azaallyl anions were generated by tin-lithium exchange on stannyl imidates, thioimidates, or amidines (RCH)-C-1(SnBu3)N=C(X)R-2 with n-butyllithium. The initially formed 1-pyrrolines were found to be deprotonated under the reaction conditions to afford 1-metalloenamines, which could be quenched with alkyl halides, carbonyl compounds, or MeSSMe to provide further functionalized 1-pyrrolines. Cyclic methoxy-substituted 2-azaallyl anions were generated and were found to undergo cycloadditions with alkenes to afford bridged azabicyclic compounds (1-methoxy-7-azabicyclo[2.2.1]heptanes and 1-methoxy-8-azabicyclo[3.2.1]octanes). These are the first examples of cyclic nonstabilized 2-azaallyl anions.

  DOI：

  10.1021/jo981457i

文献信息

• Cycloaddition of Heteroatom-Substituted 2-Azaallyl Anions with Alkenes. Synthesis of 1-Pyrrolines and Bridged Azabicyclic Compounds
  作者：William H. Pearson、Erland P. Stevens

  DOI：10.1021/jo981457i

  日期：1998.12.1

  Nonstabilized 2-azaallyl anions bearing heteroatom substituents [(RCHNC)-C-1(X)R-2(-)Li(+), where R-1 and R-2 are hydrogen or alkyl groups and X = OMe, SPh, or NR2] were generated and found to undergo efficient [3 + 2] cycloadditions with alkenes to provide 1-pyrrolines after loss of LiX. The 2-azaallyl anions were generated by tin-lithium exchange on stannyl imidates, thioimidates, or amidines (RCH)-C-1(SnBu3)N=C(X)R-2 with n-butyllithium. The initially formed 1-pyrrolines were found to be deprotonated under the reaction conditions to afford 1-metalloenamines, which could be quenched with alkyl halides, carbonyl compounds, or MeSSMe to provide further functionalized 1-pyrrolines. Cyclic methoxy-substituted 2-azaallyl anions were generated and were found to undergo cycloadditions with alkenes to afford bridged azabicyclic compounds (1-methoxy-7-azabicyclo[2.2.1]heptanes and 1-methoxy-8-azabicyclo[3.2.1]octanes). These are the first examples of cyclic nonstabilized 2-azaallyl anions.