cis-7,8-epoxy-2-methyleicosane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: cis-7,8-epoxy-2-methyleicosane
• 英文别名: xylinalure；7,8-Epoxy-2-methyleicosane；2-dodecyl-3-(5-methylhexyl)oxirane
• 化学式: C₂₁H₄₂O
• 分子量: 310.564
• InChiKey: PJHDGXKZPWJTBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-十八碳炔-1-醇 在 copper(l) iodide 、 氢气 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 cis-7,8-epoxy-2-methyleicosane
  参考文献：
  名称：

  摘要：

  cis-7,8-Epoxy-2-methyleicosane is a sex pheromone component of the Casuarina moth, Lymantria xylina Swinhoe. The compound was extracted from pheromone glands of female moths and was identified by coupled gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometry. In field experiments in Taiwan, traps baited with either or both of (7R,8S)-cis-7,8-epoxy-2-methyleicosane (>99% eel [termed here (+)-xylinalure] and (7S,8R)-cis-7,8-epoxy-2-methyleicosane (>99% eel [termed here (-)-xylinalure] captured male L. xylina. Addition of further candidate pheromone components to xylinalure did not enhance its attractiveness. Demonstration of whether or not female L. xylina produce both optical isomers of xylinalure, and determination of the ratio, will require pheromone extract analyses on a chiral, enantiomer-separating column (as yet unavailable) or derivatization of epoxides in accumulated gland extracts. Attraction of male L. xylina to either enantiomer of xylinalure contrasts with enantiospecific production of, and/or response to, epoxy pheromones in congeners. With no other nocturnal lymantriid moth known in Taiwan to utilize xylinalure for pheromonal communication, enantiospecific "fine tuning" of xylinalure, or evolution of a more complex pheromone blend, may not have been necessary for L. xylina to maintain specificity of sexual communication. Racemic xylinalure will be appropriate for pheromone-based detection surveys of L, xylina in North America.

  DOI：

  10.1023/a:1020830309624

文献信息

• ——
  作者：Gerhard Gries、Paul W. Schaefer、Grigori Khaskin、Roger Hahn、Regine Gries、Jung-Tai Chao

  DOI：10.1023/a:1020830309624

  日期：——

  cis-7,8-Epoxy-2-methyleicosane is a sex pheromone component of the Casuarina moth, Lymantria xylina Swinhoe. The compound was extracted from pheromone glands of female moths and was identified by coupled gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometry. In field experiments in Taiwan, traps baited with either or both of (7R,8S)-cis-7,8-epoxy-2-methyleicosane (>99% eel [termed here (+)-xylinalure] and (7S,8R)-cis-7,8-epoxy-2-methyleicosane (>99% eel [termed here (-)-xylinalure] captured male L. xylina. Addition of further candidate pheromone components to xylinalure did not enhance its attractiveness. Demonstration of whether or not female L. xylina produce both optical isomers of xylinalure, and determination of the ratio, will require pheromone extract analyses on a chiral, enantiomer-separating column (as yet unavailable) or derivatization of epoxides in accumulated gland extracts. Attraction of male L. xylina to either enantiomer of xylinalure contrasts with enantiospecific production of, and/or response to, epoxy pheromones in congeners. With no other nocturnal lymantriid moth known in Taiwan to utilize xylinalure for pheromonal communication, enantiospecific "fine tuning" of xylinalure, or evolution of a more complex pheromone blend, may not have been necessary for L. xylina to maintain specificity of sexual communication. Racemic xylinalure will be appropriate for pheromone-based detection surveys of L, xylina in North America.