3-acetamidoquinuclidin-2-ene | 161153-84-0

• 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-acetamidoquinuclidin-2-ene
• 英文别名: 3-acetamido-1-azabicyclo<2.2.2>oct-2-ene；3-Acetamido-1-azabicyclo[2.2.2.]oct-2-ene；N-(1-azabicyclo[2.2.2]oct-2-en-3-yl)acetamide
• CAS: 161153-84-0
• 化学式: C₉H₁₄N₂O
• 分子量: 166.223
• InChiKey: XHEIULMLQXIGIV-UHFFFAOYSA-N

物化性质

• 沸点：
  346.8±25.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 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-acetamidoquinuclidin-2-ene 在 盐酸 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 超重氢 、 硫酰氯 作用下， 以 乙醇 为溶剂， 反应 47.5h， 生成 3-amino-1-azabicyclo[2.2.2]octane-3H dihydrochloride
  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 镍 作用下， 以 苯 为溶剂， 反应 42.0h， 以70%的产率得到3-acetamidoquinuclidin-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

• Novel heterocycles derived from 3-acyloxy- and 3-acetamidoquinuclidines
  作者：Yevgeny Besidsky、Kristina Luthman、Uli Hacksell

  DOI：10.1002/jhet.5570310636

  日期：1994.11

  3-mesyloxy-, 3-acetoxy-, and 3-acetamidoquinuclidine-3-carbonitrile, respectively, by treatment with base. Treatment of 3-acetamidoquinuclidine-3-carbonitrile (3) with potassium hydride resulted in decyanation whereas alkyllithium reagents attacked the cyano group in 3 to produce the corresponding imines. Oxidative cyclization of the N-benzylated derivative of 3 with palladium acetate gave the tetracyclic

  通过用碱处理，分别由3-甲酰氧基-，3-乙酰氧基-和3-乙酰酰胺基喹核苷-3-甲腈合成了具有3-螺氧基化的氧杂噻吩啉，呋喃酮和吡咯烷酮杂环的新的奎尼丁衍生物。用氢化钾处理3-乙酰氨基喹啉环-3-甲腈（3）导致脱氰，而烷基锂试剂攻击3中的氰基以产生相应的亚胺。用乙酸钯将3的N-苄基化衍生物氧化环化，得到四环化合物5-乙酰基-1,4-乙醇-1,2,3,4,5,6-六氢苯并[ c ] -1,5-萘啶。
• 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%.