(1R*,5R*,6S*,7S*)-6,7-diphenyl-1-methoxy-8-azabicyclo<3.2.1>octane

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (1R*,5R*,6S*,7S*)-6,7-diphenyl-1-methoxy-8-azabicyclo<3.2.1>octane
• 英文别名: (1R,5R,6S,7S)-1-methoxy-6,7-diphenyl-8-azabicyclo[3.2.1]octane
• 化学式: C₂₀H₂₃NO
• 分子量: 293.409
• InChiKey: IVMLJTQBDWMMAA-IYWMVGAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  反式-1,2-二苯乙烯 、 6-Methoxy-2-tributylstannanyl-2,3,4,5-tetrahydro-pyridine 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以22%的产率得到(1R*,5R*,6S*,7S*)-6,7-diphenyl-1-methoxy-8-azabicyclo<3.2.1>octane
  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.