(Z)-5-Octadecen-1-ol | 41207-39-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-5-Octadecen-1-ol
• 英文别名: (Z)-octadec-5-en-1-ol
• CAS: 41207-39-0
• 化学式: C₁₈H₃₆O
• 分子量: 268.483
• InChiKey: SUZHDNXQMDDDOJ-YPKPFQOOSA-N

物化性质

• 沸点：
  369.5±21.0 °C(Predicted)
• 密度：
  0.847±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  19
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-5-Octadecen-1-ol 在 copper(l) iodide 、 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
• 作为产物：
  描述：

  溴代十二烷 在 六甲基磷酰三胺 、 正丁基锂 、 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 (Z)-5-Octadecen-1-ol
  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

• Selective reduction of alkynes to (Z)-alkenes via niobium- or tantalum-alkyne complexes
  作者：Yasutaka Kataoka、Kazuhiko Takai、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1021/jo00031a057

  日期：1992.2