(6Z,10E)-4-methyl-6-propyl-quinolizidine

• 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: (6Z,10E)-4-methyl-6-propyl-quinolizidine
• 化学式: C₁₃H₂₅N
• 分子量: 195.348
• InChiKey: XWIGNCVWEVRDAL-LAGVYOHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  丙基氯化镁 、 cis-2-[3-(6-methyl-2-piperidyl)-propyl]-1,3-dioxolane 、 trans-2-[3-(6-methyl-2-piperidyl)-propyl]-1,3-dioxolane 在 potassium cyanide 作用下， 以 二氯甲烷 、 水 、 乙醚 为溶剂， 反应 2.0h， 生成 (6E,10Z)-4-methyl-6-propyl-quinolizidine 、 (6Z,10E)-4-methyl-6-propyl-quinolizidine 、 (6Z,10Z)-4-methyl-6-propyl-quinolizidine 、 (6E,10E)-4-methyl-6-propyl-quinolizidine
  参考文献：
  名称：

  摘要：

  Three alkaloids-two minor decahydroquinolines (DHQs) and a major quinolizidine-were detected in an extract of a Brazilian myrmicine ant (Solenopsis (Diplorhoptrum) sp. picea group). One DHQ (3) was identical to a known frog-skin alkaloid, cis-195A (cis-5-methyl-2-propyldecahydroquinoline), while the second DHQ, an isomer of 3, designated 195J, was assigned a tentative cis-2-methyl-5-propyldecahydroquinoline structure (2) based on mass and infrared spectra. The third alkaloid proved identical to the frog-skin alkaloid 195C, for which a structure had not been previously proposed. Mass and infrared spectral analysis, including chemical ionization tandem mass spectrometry, indicated a 4-methyl-6-propylquinolizidine structure (1) for 195C. The four possible diastereomers were synthesized and the (6Z,10E)-4-methyl-6-propylquinolizidine diastereomer (1b) was identical to the natural alkaloid. Skin extracts of a population of a Madagascan mantelline frog contained, among other alkaloids, minor amounts of the same alkaloid triad 1-3 with 1 again predominating. The common occurrence of alkaloids 1-3 in both ant and frog supports the hypothesis that ants are a likely dietary source for sequestered frog-skin alkaloids and brings to six, the alkaloid classes common to ant and frog.

  DOI：

  10.1023/a:1020898229304

文献信息

• ——
  作者：Tappey H. Jones、Jeffrey S. T. Gorman、Roy R. Snelling、Jacques H. C. Delabie、Murray S. Blum、H. Martin Garraffo、Poonam Jain、John W. Daly、Thomas F. Spande

  DOI：10.1023/a:1020898229304

  日期：——

  Three alkaloids-two minor decahydroquinolines (DHQs) and a major quinolizidine-were detected in an extract of a Brazilian myrmicine ant (Solenopsis (Diplorhoptrum) sp. picea group). One DHQ (3) was identical to a known frog-skin alkaloid, cis-195A (cis-5-methyl-2-propyldecahydroquinoline), while the second DHQ, an isomer of 3, designated 195J, was assigned a tentative cis-2-methyl-5-propyldecahydroquinoline structure (2) based on mass and infrared spectra. The third alkaloid proved identical to the frog-skin alkaloid 195C, for which a structure had not been previously proposed. Mass and infrared spectral analysis, including chemical ionization tandem mass spectrometry, indicated a 4-methyl-6-propylquinolizidine structure (1) for 195C. The four possible diastereomers were synthesized and the (6Z,10E)-4-methyl-6-propylquinolizidine diastereomer (1b) was identical to the natural alkaloid. Skin extracts of a population of a Madagascan mantelline frog contained, among other alkaloids, minor amounts of the same alkaloid triad 1-3 with 1 again predominating. The common occurrence of alkaloids 1-3 in both ant and frog supports the hypothesis that ants are a likely dietary source for sequestered frog-skin alkaloids and brings to six, the alkaloid classes common to ant and frog.