angustifoline N-carboxyethyl ester | 145889-88-9

• 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: angustifoline N-carboxyethyl ester
• 英文别名: ethyl (1S,2R,9S,10S)-6-oxo-10-prop-2-enyl-7,11-diazatricyclo[7.3.1.02,7]tridecane-11-carboxylate
• CAS: 145889-88-9
• 化学式: C₁₇H₂₆N₂O₃
• 分子量: 306.405
• InChiKey: XPLHFSXEZDJFCO-ZQDZILKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (-)-Angustifoline 、 氯甲酸乙酯 以 甲苯 为溶剂， 反应 2.0h， 以90%的产率得到angustifoline N-carboxyethyl ester
  参考文献：
  名称：

  Lupin alkaloids from Lupinus polyphyllus

  摘要：

  Twenty-nine quinolizidine alkaloids have been found and characterized from the combined leaf/hypocotyl extracts of Lupinus polyphyllus. Twelve have not been found previously in this plant and the structure of 10 has been unambiguously assigned from a combination of mass spectroscopy and NMR data, and by direct comparison with synthetic material for the N-carboxymethyl ester, N-carboxyethyl ester and N-formyl derivatives of angustifoline. The co-occurrence of 13alpha-hydroxylupanine and its 13beta-isomer is reported for the first time in a quinolizidine alkaloid-accumulating species.

  DOI：

  10.1016/0031-9422(92)80471-p

文献信息

• Lupin alkaloids from Lupinus polyphyllus
  作者：Gerhard Veen、Claudia Schmidt、Ludger Witte、Victor Wray、Franz-Christian Czygan

  DOI：10.1016/0031-9422(92)80471-p

  日期：1992.12

  Twenty-nine quinolizidine alkaloids have been found and characterized from the combined leaf/hypocotyl extracts of Lupinus polyphyllus. Twelve have not been found previously in this plant and the structure of 10 has been unambiguously assigned from a combination of mass spectroscopy and NMR data, and by direct comparison with synthetic material for the N-carboxymethyl ester, N-carboxyethyl ester and N-formyl derivatives of angustifoline. The co-occurrence of 13alpha-hydroxylupanine and its 13beta-isomer is reported for the first time in a quinolizidine alkaloid-accumulating species.