2-[3-(6-methyl-2-pyridyl)-propyl]-1,3-dioxolane | 181221-90-9

• 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: 2-[3-(6-methyl-2-pyridyl)-propyl]-1,3-dioxolane
• 英文别名: 2-[3-(6-Methyl-2-pyridyl)propyl]-1,3-dioxolane
• CAS: 181221-90-9
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: YVBVVUVQRQZNJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  31.35
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-[3-(6-methyl-2-pyridyl)-propyl]-1,3-dioxolane 在 盐酸 、 正丁基锂 、 乙醇 、 水 、 sodium 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 26.5h， 生成 cis-2-Methyl-6-(Z,4-nonenyl)piperidine
  参考文献：
  名称：

  Chemistry of venom alkaloids in someSolenopsis (Diplorhoptrum) species from Puerto Rico

  摘要：

  A number of 15-carbon alkaloids have been identified in venom extracts of four Puerto Rican species of ants in the genus Solenopsis (Diplorhoptrum). Workers of a species from El Verde produced the cis and trans isomers of 2-methyl-6-nonylpiperidine with the latter isomer predominating. The same compounds were identified in queens of a species from Rio Grande, but in this species no alkaloids were detected in worker extracts. Workers of a Diplorhoptrum species collected on Mona Island produced primarily a trans-2-methyl-6-(Z-4-nonenyl)piperidine, 3, with smaller amounts of the cis isomer, whereas the major compound found in the queens of the same species on Mona Island was (5Z,9Z)-3-hexyl-5-methylindolizidine, identical with the alkaloid produced by queens of a species collected on Cabo Rojo. Surprisingly, workers of the Cabo Rojo species produced (5Z,9Z)- and (5E,9E)-3-butyl-5-propylindolizidine (4 and 5, respectively) reported earlier as the 223AB indolizidines from skins of dendrobatid frogs. The possible significance of the qualitative and quantitative differences in the venom alkaloids synthesized by queens and workers is discussed as is the possibility that ants containing such alkaloids may serve as a dietary source for the skin alkaloids used by certain frogs in chemical defense.

  DOI：

  10.1007/bf02266962
• 作为产物：
  描述：

  2-(2-溴乙基)-1,3-二恶烷 、 2,6-二甲基吡啶 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 0.5h， 生成 2-[3-(6-methyl-2-pyridyl)-propyl]-1,3-dioxolane 、
  参考文献：
  名称：

  Chemistry of venom alkaloids in someSolenopsis (Diplorhoptrum) species from Puerto Rico

  摘要：

  A number of 15-carbon alkaloids have been identified in venom extracts of four Puerto Rican species of ants in the genus Solenopsis (Diplorhoptrum). Workers of a species from El Verde produced the cis and trans isomers of 2-methyl-6-nonylpiperidine with the latter isomer predominating. The same compounds were identified in queens of a species from Rio Grande, but in this species no alkaloids were detected in worker extracts. Workers of a Diplorhoptrum species collected on Mona Island produced primarily a trans-2-methyl-6-(Z-4-nonenyl)piperidine, 3, with smaller amounts of the cis isomer, whereas the major compound found in the queens of the same species on Mona Island was (5Z,9Z)-3-hexyl-5-methylindolizidine, identical with the alkaloid produced by queens of a species collected on Cabo Rojo. Surprisingly, workers of the Cabo Rojo species produced (5Z,9Z)- and (5E,9E)-3-butyl-5-propylindolizidine (4 and 5, respectively) reported earlier as the 223AB indolizidines from skins of dendrobatid frogs. The possible significance of the qualitative and quantitative differences in the venom alkaloids synthesized by queens and workers is discussed as is the possibility that ants containing such alkaloids may serve as a dietary source for the skin alkaloids used by certain frogs in chemical defense.

  DOI：

  10.1007/bf02266962

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.