hexahydroquinolizine-1,4-dione | 26706-84-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: hexahydroquinolizine-1,4-dione
• 英文别名: 3,6,7,8,9,9a-hexahydro-2H-quinolizine-1,4-dione
• CAS: 26706-84-3
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: PJWOJYQKXUUBFP-UHFFFAOYSA-N

物化性质

• 熔点：
  68-69 °C
• 沸点：
  338.2±31.0 °C(Predicted)
• 密度：
  1.18±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：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  hexahydroquinolizine-1,4-dione 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium 10% on activated carbon 、 氢气 、 双(三甲基硅烷基)氨基钾 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， -78.0~80.0 ℃ 、303.99 kPa 条件下， 反应 28.25h， 生成 (1R,9aR)-1-ethyl-1,2,3,6,7,8,9,9a-octahydroquinolizin-4-one
  参考文献：
  名称：

  Synthesis of Highly Oxidized Quinolizidine via Reduction of Acylpyridinium Cations, and Total Syntheses of Quinolizidines 207I and 1-epi-207I

  摘要：

  A new strategy for synthesizing quinolizidine skeletons by reductive cyclization via acylpyridinium cations was developed. Several functional groups, including carbonyl, silyl, and acetal, were tolerated under mild reaction conditions. The reaction was successfully extended to a one-pot synthesis of a bicyclic compound, and the synthetic strategy was applied to concise total syntheses of quinolizidines 207I and 1-epi-207I, without protecting groups.

  DOI：

  10.1021/ol300541u
• 作为产物：
  描述：

  4-羰基-4-(2-吡啶基)丁酸 在 1-氯-N,N,2-三甲基丙烯胺 、 palladium on activated charcoal 、 氢气 作用下， 以 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 50.25h， 生成 hexahydroquinolizine-1,4-dione
  参考文献：
  名称：

  Synthesis of Highly Oxidized Quinolizidine via Reduction of Acylpyridinium Cations, and Total Syntheses of Quinolizidines 207I and 1-epi-207I

  摘要：

  A new strategy for synthesizing quinolizidine skeletons by reductive cyclization via acylpyridinium cations was developed. Several functional groups, including carbonyl, silyl, and acetal, were tolerated under mild reaction conditions. The reaction was successfully extended to a one-pot synthesis of a bicyclic compound, and the synthetic strategy was applied to concise total syntheses of quinolizidines 207I and 1-epi-207I, without protecting groups.

  DOI：

  10.1021/ol300541u

文献信息

• A versatile approach to 6-substituted-5-methoxy-δ-lactam framework and application to the formal synthesis of (±)-homopumiliotoxin 223G
  作者：Bo-Fong Chen、Min-Ruei Tasi、Cheng-Yu Yang、Jung-Kai Chang、Nein-Chen Chang

  DOI：10.1016/j.tet.2004.09.001

  日期：2004.11

  Of the various 6-substituted-5-methoxy-delta-lactams 6 were synthesized from alpha-sulfonyl acetamide 9 in 4 steps in good yield. The key glutarimides 7 were obtained via facile [3+3] annulation. The method featured regioselective introduction of C-6 substituents in glutarimides 7. Synthesis of tribenzyl lactam 8 and the formal synthesis of (+/-)-homopumiliotoxin 223G were also reported. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of Highly Oxidized Quinolizidine via Reduction of Acylpyridinium Cations, and Total Syntheses of Quinolizidines <b>207I</b> and 1-<i>epi</i>-<b>207I</b>
  作者：Chihiro Tsukano、Atsuko Oimura、Iderbat Enkhtaivan、Yoshiji Takemoto

  DOI：10.1021/ol300541u

  日期：2012.4.6

  A new strategy for synthesizing quinolizidine skeletons by reductive cyclization via acylpyridinium cations was developed. Several functional groups, including carbonyl, silyl, and acetal, were tolerated under mild reaction conditions. The reaction was successfully extended to a one-pot synthesis of a bicyclic compound, and the synthetic strategy was applied to concise total syntheses of quinolizidines 207I and 1-epi-207I, without protecting groups.