(3Z,6Z,9Z)-3,6,9-tricosatriene

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (3Z,6Z,9Z)-3,6,9-tricosatriene
• 英文别名: 3Z,6Z,9Z-Tricosatriene；(3Z,6Z,9Z)-tricosa-3,6,9-triene
• 化学式: C₂₃H₄₂
• 分子量: 318.586
• InChiKey: KUNIJGQAWCLQGU-JTBMWNAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  23
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  亚麻酸甲酯 在 吡啶 、 lithium aluminium tetrahydride 、 pyridinium chlorochromate 作用下， 以 乙醚 为溶剂， 生成 (3Z,6Z,9Z)-3,6,9-tricosatriene
  参考文献：
  名称：

  摘要：

  Five candidate pheromone components were identified by analyzing pheromone gland extracts by gas chromatography (GC, coupled GC-electro-antennographic detection (EAD), and coupled GC-mass spectrometry (MS): (E)-1 1-hexadecenol(E1 1-16: OH), (Z)-11-hexadecenol (ZI 1- 16: OH), (E)-11-hexadecenal, (E)-11-hexadecenyl acetate, and, (Z)-3,(Z)-6,(Z)-9-tricosatriene (Z3,Z6,Z9-23: Hy). In electroantennogram (EAG) recordings, synthetic El I 16: OH elicited stronger antennal responses at low doses than other candidate pheromone components. Field tests demonstrated that synthetic El 1-16: OH as a trap bait was effective in attracting males, whereas addition of ZI 1-16: OH inhibited the males' response. Z3,Z6,Z9-23: Hy strongly enhanced attractiveness of El 1-16: OH, but was not attractive by itself. A pheromone blend with synergistic behavioral activity of an alcohol (El 1- 16: OH) and hydrocarbon (Z3,Z6,Z9-23 : Hy) component is most unusual in the Lepidoptera. The synthetic two-component pheromone is approximately 60 times more attractive than the female-produced blend and might facilitate the control of this pest.

  DOI：

  10.1023/a:1012299021967

文献信息

• Facile and Efficient Syntheses of (3<i>Z</i>,6<i>Z</i>,9<i>Z</i>)-3,6,9-Nonadecatriene and Homologues:  Pheromone and Attractant Components of Lepidoptera
  作者：Shifa Wang、Aijun Zhang

  DOI：10.1021/jf070821o

  日期：2007.8.1

  Facile and efficient chemical syntheses of (3Z,6Z,9Z)-3,6,9-nonadecatriene and homologues from commercially available alpha-linolenic acid [(9Z,12Z,15Z)-9,12,15-octadecatrienoic acid] are reported. These straight-chain homoconjugated trienes are common sex pheromone and attractant components for many lepidopterous insect pests. The metal-catalyzed cross-coupling reactions between (9Z,12Z,15Z)-9,12

  报道了（3Z，6Z，9Z）-3,6,9-壬二烯三烯的简便有效的化学合成方法以及来自市售α-亚麻酸[（9Z，12Z，15Z）-9,12,15-十八碳三烯酸]的同系物。这些直链均轭三烯是许多鳞翅目害虫的常见性信息素和引诱剂成分。（9Z，12Z，15Z）-9,12,15-十八碳三烯基三氟甲磺酸盐与适当的格氏试剂之间的金属催化的交叉偶联反应在显着的温和条件下使用Li（2）CuCl（4）作为催化剂在二乙基中的反应非常快速地进行醚，得到的（3Z，6Z，9Z）-3,6,9-三烯具有几何构型保留，分离产率> 92％。
• 복숭아명나방 유인제 조성물, 이의 제조방법, 및 이의 용도
  申请人：Seoul National University R&DB Foundation 서울대학교산학협력단(120070509242) Corp. No ▼ 114371-0009224BRN ▼119-82-03684

  公开号：KR20220138754A

  公开（公告）日：2022-10-13

  복숭아명나방 복합 성페로몬을 포함하는 복숭아명나방 유인제 조성물, 상기 성페로몬을 제조하는 방법, 복숭아명나방 포획용 트랩, 복숭아명나방 방제 방법, 및 복숭아명나방 모니터링 방법을 제공한다. 상기 조성물은 복숭아명나방의 발생 모니터링이 가능할 뿐만 아니라, 대량포획 및 교미교란을 통해 해충의 밀도를 낮추는 환경친화적 해충 방제에 이용할 수 있다.

  提供含有桃小食心复合性信息素的桃小食心诱捕剂配方、制造上述信息素的方法、桃小食心捕捉陷阱、桃小食心防治方法和桃小食心监测方法。该配方不仅可以监测桃小食心的发生情况，而且还可以通过大规模捕捉和交配干扰来减少害虫密度，实现环保的害虫防治。
• ——
  作者：Aivlé Cabrera、Alvaro E. Eiras、Gerhard Gries、Regine Gries、Neudo Urdaneta、Beatriz Mirás、Cesar Badji、Klaus Jaffe

  DOI：10.1023/a:1012299021967

  日期：——

  Five candidate pheromone components were identified by analyzing pheromone gland extracts by gas chromatography (GC, coupled GC-electro-antennographic detection (EAD), and coupled GC-mass spectrometry (MS): (E)-1 1-hexadecenol(E1 1-16: OH), (Z)-11-hexadecenol (ZI 1- 16: OH), (E)-11-hexadecenal, (E)-11-hexadecenyl acetate, and, (Z)-3,(Z)-6,(Z)-9-tricosatriene (Z3,Z6,Z9-23: Hy). In electroantennogram (EAG) recordings, synthetic El I 16: OH elicited stronger antennal responses at low doses than other candidate pheromone components. Field tests demonstrated that synthetic El 1-16: OH as a trap bait was effective in attracting males, whereas addition of ZI 1-16: OH inhibited the males' response. Z3,Z6,Z9-23: Hy strongly enhanced attractiveness of El 1-16: OH, but was not attractive by itself. A pheromone blend with synergistic behavioral activity of an alcohol (El 1- 16: OH) and hydrocarbon (Z3,Z6,Z9-23 : Hy) component is most unusual in the Lepidoptera. The synthetic two-component pheromone is approximately 60 times more attractive than the female-produced blend and might facilitate the control of this pest.