(Z)-6-heneicosen-9-ol | 234762-15-3

• 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)-6-heneicosen-9-ol
• 英文别名: (Z)-henicos-6-en-9-ol
• CAS: 234762-15-3
• 化学式: C₂₁H₄₂O
• 分子量: 310.564
• InChiKey: USJYEEBDGAHQPJ-ICFOKQHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  22
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 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)-6-heneicosen-9-ol 在 pyridium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以85.5%的产率得到(Z)-6-heneicosen-9-one
  参考文献：
  名称：

  摘要：

  In 1996, the exotic white-spotted tussock moth (WSTM), Orgyia thyellina (Lepidoptera: Lymantriidae), was discovered in Auckland, New Zealand. Because establishment of WSTM would threaten New Zealand's orchard industry and international trade, eradication of WSTM with microbial insecticide was initiated To monitor and complement eradication of WSTM by capture of male moths in pheromone-baited traps, pheromone components of female WSTM needed to be identified. Coupled gas chromatographic-electroantennographic detection analysis of pheromone gland extract revealed several compounds that elicited responses from male moth antennae. Mass spectra of the two most EAD-active compounds suggested, and comparative GC-MS of authentic standards confirmed, that they were (Z)-6-heneicosen-11-one (Z6-11-one) and (Z)-6-heneicosen-9-one, the latter termed here "thyellinone." In field experiments in Japan, Z6-11-one plus thyellinone at a 100:5 ratio attracted WSTM males, whereas either ketone alone failed to attract a single male moth. Addition of further candidate pheromone components did not enhance attractiveness of the binary blend. Through the 1997-1998 summer, 45,000 commercial trap lures baited with 2000 mu g of Z6-11-one and 100 mu g of thyellinone were deployed in Auckland towards eradication of the residual WSTM population.

  DOI：

  10.1023/a:1020833909739
• 作为产物：
  描述：

  1-十四烯 在 正丁基锂 、 氢气 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 4.0h， 生成 (Z)-6-heneicosen-9-ol
  参考文献：
  名称：

  摘要：

  In 1996, the exotic white-spotted tussock moth (WSTM), Orgyia thyellina (Lepidoptera: Lymantriidae), was discovered in Auckland, New Zealand. Because establishment of WSTM would threaten New Zealand's orchard industry and international trade, eradication of WSTM with microbial insecticide was initiated To monitor and complement eradication of WSTM by capture of male moths in pheromone-baited traps, pheromone components of female WSTM needed to be identified. Coupled gas chromatographic-electroantennographic detection analysis of pheromone gland extract revealed several compounds that elicited responses from male moth antennae. Mass spectra of the two most EAD-active compounds suggested, and comparative GC-MS of authentic standards confirmed, that they were (Z)-6-heneicosen-11-one (Z6-11-one) and (Z)-6-heneicosen-9-one, the latter termed here "thyellinone." In field experiments in Japan, Z6-11-one plus thyellinone at a 100:5 ratio attracted WSTM males, whereas either ketone alone failed to attract a single male moth. Addition of further candidate pheromone components did not enhance attractiveness of the binary blend. Through the 1997-1998 summer, 45,000 commercial trap lures baited with 2000 mu g of Z6-11-one and 100 mu g of thyellinone were deployed in Auckland towards eradication of the residual WSTM population.

  DOI：

  10.1023/a:1020833909739