3-acetamido-1-azabicyclo<2.2.2>octane-3H | 173031-35-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 英文名称: 3-acetamido-1-azabicyclo<2.2.2>octane-3H
• 英文别名: N-(2,3-ditritio-1-azabicyclo[2.2.2]octan-3-yl)acetamide
• CAS: 173031-35-1
• 化学式: C₉H₁₆N₂O
• 分子量: 172.223
• InChiKey: USNCYWOZRFYMOR-YYZDYREPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-acetamido-1-azabicyclo<2.2.2>octane-3H 在 盐酸 、 ammonium hydroxide 、 TEA 、 sodium butanolate 作用下， 以 氯仿 、 正丁醇 为溶剂， 反应 151.0h， 生成 (S)-6-amino-2-(1-azabicyclo[2.2.2]-octyl)-5-chloro-2,3-dihydro-1,3-dioxo-1H-benzo(de)isoquinoline hydrochloride-3H
  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
• 作为产物：
  描述：

  quinuclidin-3-spiro-2'-(4'-thiazolidinone) 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 超重氢 、 镍 、 硫酰氯 作用下， 以 乙醇 、 苯 为溶剂， 反应 86.0h， 生成 3-acetamido-1-azabicyclo<2.2.2>octane-3H
  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%.