perhydro-3a-methyl-5-oxo-4H-pyrrolo<1,2-a>quinoline | 143491-53-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: perhydro-3a-methyl-5-oxo-4H-pyrrolo<1,2-a>quinoline
• 英文别名: 3a-methyldecahydropyrrolo[1,2-a]quinolin-5(1H)-one；3a-methyl-1,2,3,4,5a,6,7,8,9,9a-decahydropyrrolo[1,2-a]quinolin-5-one
• CAS: 143491-53-6
• 化学式: C₁₃H₂₁NO
• 分子量: 207.316
• InChiKey: MVSPWSXIODTCPE-UHFFFAOYSA-N

物化性质

• 沸点：
  315.9±17.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  7-methylenebicyclo[4.1.0]heptane 以 甲苯 为溶剂， 反应 216.0h， 生成 perhydro-3a-methyl-5-oxo-4H-pyrrolo<1,2-a>quinoline
  参考文献：
  名称：

  Rearrangement of isoxazoline-5-spiro derivatives. 8. Selective formation of tetrahydropyridones from C,C-disubstituted nitrones

  摘要：

  The thermal rearrangement of isoxazolidines 3, 7, 9, 17, and 19 obtained by 1,3-dipolar cycloaddition of C,C-disubstituted nitrones and methylenecyclopropanes 1 and 6 has been studied. The lack of hydrogen at the C-3 position of the isoxazolidine ring leads selectively to azaheterocyclic ketones, structurally differentiated according to the stating dipoles and dipolarophiles. The process allows the "one-pot" synthesis of valuable perhydro pyridone, indolizinone, and pyrrolo[1,2-a]quinolinone ring systems with excellent overall yield and atom economy. A new entry to the functionalized 1-azaspiro[5.5]undecane 22 framework found in alkaloids of the histrionicotoxin family is also presented.

  DOI：

  10.1021/jo00047a019

文献信息

• Rearrangement of isoxazoline-5-spiro derivatives. 8. Selective formation of tetrahydropyridones from C,C-disubstituted nitrones
  作者：Alberto Brandi、Yasar Durust、Franca M. Cordero、Francesco De Sarlo

  DOI：10.1021/jo00047a019

  日期：1992.10

  The thermal rearrangement of isoxazolidines 3, 7, 9, 17, and 19 obtained by 1,3-dipolar cycloaddition of C,C-disubstituted nitrones and methylenecyclopropanes 1 and 6 has been studied. The lack of hydrogen at the C-3 position of the isoxazolidine ring leads selectively to azaheterocyclic ketones, structurally differentiated according to the stating dipoles and dipolarophiles. The process allows the "one-pot" synthesis of valuable perhydro pyridone, indolizinone, and pyrrolo[1,2-a]quinolinone ring systems with excellent overall yield and atom economy. A new entry to the functionalized 1-azaspiro[5.5]undecane 22 framework found in alkaloids of the histrionicotoxin family is also presented.