3--3-acetamido-1-azabicyclo<2.2.2>oct-2-ene

• 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: 3--3-acetamido-1-azabicyclo<2.2.2>oct-2-ene
• 英文别名: N-(1-azabicyclo[2.2.2]oct-2-en-3-yl)-N-[(1R)-1-phenylethyl]acetamide
• 化学式: C₁₇H₂₂N₂O
• 分子量: 270.374
• InChiKey: CDJLTPITBOHGGC-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-奎宁环酮 在 吡啶 、 4 A molecular sieve 作用下， 以 苯 为溶剂， 反应 49.0h， 生成 3--3-acetamido-1-azabicyclo<2.2.2>oct-2-ene
  参考文献：
  名称：

  Synthesis of tritium labelled (R) and (S)-3-aminoquinuclidine: A ubiquitous component of serotonin receptor ligands, part I

  摘要：

  (R) and (S)-3-aminoquinuclidines-H-3 with the specific activity of 35 Ci/mmol were prepared. Reduction of enamide 2 with carrier free tritium gas over RhCODCl dimer, (2S, 3S) Chiraphos in methanol gave racemic amide 9c. Hydrolysis followed by resolution of the enantiomers with (R)-methyl benzyl isocyanate gave (R) and (S)-3-aminoquinuclidine-H-3 10c-S and 10c-R. The enantiopurity purity of both isomers was >99.5%.

  DOI：

  10.1002/(sici)1099-1344(199601)38:1<41::aid-jlcr811>3.0.co;2-n

文献信息

• Synthesis of tritium labelled (R) and (S)-3-aminoquinuclidine: A ubiquitous component of serotonin receptor ligands, part I
  作者：Mohammad R. Masjedizadeh、Howard Parnes

  DOI：10.1002/(sici)1099-1344(199601)38:1<41::aid-jlcr811>3.0.co;2-n

  日期：1996.1

  (R) and (S)-3-aminoquinuclidines-H-3 with the specific activity of 35 Ci/mmol were prepared. Reduction of enamide 2 with carrier free tritium gas over RhCODCl dimer, (2S, 3S) Chiraphos in methanol gave racemic amide 9c. Hydrolysis followed by resolution of the enantiomers with (R)-methyl benzyl isocyanate gave (R) and (S)-3-aminoquinuclidine-H-3 10c-S and 10c-R. The enantiopurity purity of both isomers was >99.5%.