(Z)6,(Z)8-Heneicosadien-11-ol | 792915-87-8

• 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,(Z)8-Heneicosadien-11-ol
• 英文别名: 6Z,8Z-heneicosadien-11-ol；(6Z,8Z)-henicosa-6,8-dien-11-ol
• CAS: 792915-87-8
• 化学式: C₂₁H₄₀O
• 分子量: 308.548
• InChiKey: BJBRRXFULITXAA-CCLKJPSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 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,(Z)8-Heneicosadien-11-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到6Z,8Z-heneicosadien-11-one
  参考文献：
  名称：

  立体异构合成的所有四个异构体6,8-heneicosadien-11-ones：涂苹果蛾Teia anartoides的性信息素成分

  摘要：

  据报道，使用乙烯基硼酸和乙烯基碘化物中间体的Suzuki偶联，所有四个异构体6,8-heneicosadien-11-ones，涂苹果蛾Teia anartoides的性信息素成分都进行了立体定向合成。

  DOI：

  10.1016/j.tetlet.2004.08.095
• 作为产物：
  描述：

  十一醛 在 吡啶 、 4-二甲氨基吡啶 、 sodium periodate 、 四氧化锇 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 水 为溶剂， 反应 14.0h， 生成 (Z)6,(Z)8-Heneicosadien-11-ol
  参考文献：
  名称：

  (Z)6, (E)8-Heneicosadien-11-One: Synergistic Sex Pheromone Component of Douglas-Fir Tussock Moth, Orgyia pseudotsugata (McDunnough) (Lepidoptera: Lymantriidae)

  摘要：

  Three candidate sex pheromone components, (Z)6,(Z)9-, (Z)6,(E)8-, and (Z)6,(E)9-heneicosadien-11-one (Z6Z9, Z6E8, and Z6E9) were identified in pheromone gland extracts of female Douglas-fir tussock moths (DFTM), Orgyia pseudotsugata (McDunnough). Their occurrence in subnanogram quantities in extracts and structural conversion during analytical procedures and bioassays complicated chemical identifications. Complete identification required comparative analyses of stereoselectively synthesized and female-produced dienones by coupled gas chromatographic-electroantennographic detection (GC-EAD), high-performance liquid chromatography (HPLC) and coupled GC-mass spectrometry (MS). Determination of the pheromone component was contingent upon an experimental design that minimized structural rearrangement of dienones before and during the field test. In a 40-min field experiment, acetonitrile solutions of each of the above dienones were carried on Dry Ice to traps and were syringed onto cotton release devices below trap lids. In combination with the previously known sex pheromone component of DFTM, (Z)6-heneicosen-11-one (Z6), Z6E8 was the only synergistic dienone and the mixture was highly attractive. Because Z6 by itself attracts seven species of tussock moths (two sympatric with DFTM), a blend of Z6 and Z6E8 may impart specificity to DFTM pheromone communication. In commercial lures, this binary blend may facilitate species-specific, sensitive monitoring and efficacious control by mating disruption of this important forest defoliator.

  DOI：

  10.1023/b:joec.0000006343.38471.c7

文献信息

• Stereospecific synthesis of all four isomeric 6,8-heneicosadien-11-ones: sex pheromone components of the painted apple moth Teia anartoides
  作者：Daniel J. Comeskey、Barry J. Bunn、Simon Fielder

  DOI：10.1016/j.tetlet.2004.08.095

  日期：2004.10

  The stereospecific synthesis of all four isomeric 6,8-heneicosadien-11-ones, sex pheromone components of the painted apple moth, Teia anartoides, is reported using the Suzuki-coupling of vinyl boronic acid and vinyl iodide intermediates.

  据报道，使用乙烯基硼酸和乙烯基碘化物中间体的Suzuki偶联，所有四个异构体6,8-heneicosadien-11-ones，涂苹果蛾Teia anartoides的性信息素成分都进行了立体定向合成。
• (Z)6, (E)8-Heneicosadien-11-One: Synergistic Sex Pheromone Component of Douglas-Fir Tussock Moth, Orgyia pseudotsugata (McDunnough) (Lepidoptera: Lymantriidae)
  作者：Gerhard Gries、Keith N. Slessor、Regine Gries、Grigori Khaskin、Priyantha D. C. Wimalaratne、Tom G. Gray、Gary G. Grant、Alan S. Tracey、Mike Hulme

  DOI：10.1023/b:joec.0000006343.38471.c7

  日期：1997.1

  Three candidate sex pheromone components, (Z)6,(Z)9-, (Z)6,(E)8-, and (Z)6,(E)9-heneicosadien-11-one (Z6Z9, Z6E8, and Z6E9) were identified in pheromone gland extracts of female Douglas-fir tussock moths (DFTM), Orgyia pseudotsugata (McDunnough). Their occurrence in subnanogram quantities in extracts and structural conversion during analytical procedures and bioassays complicated chemical identifications. Complete identification required comparative analyses of stereoselectively synthesized and female-produced dienones by coupled gas chromatographic-electroantennographic detection (GC-EAD), high-performance liquid chromatography (HPLC) and coupled GC-mass spectrometry (MS). Determination of the pheromone component was contingent upon an experimental design that minimized structural rearrangement of dienones before and during the field test. In a 40-min field experiment, acetonitrile solutions of each of the above dienones were carried on Dry Ice to traps and were syringed onto cotton release devices below trap lids. In combination with the previously known sex pheromone component of DFTM, (Z)6-heneicosen-11-one (Z6), Z6E8 was the only synergistic dienone and the mixture was highly attractive. Because Z6 by itself attracts seven species of tussock moths (two sympatric with DFTM), a blend of Z6 and Z6E8 may impart specificity to DFTM pheromone communication. In commercial lures, this binary blend may facilitate species-specific, sensitive monitoring and efficacious control by mating disruption of this important forest defoliator.