(E)-tetrahydro-2-<(10-hexadecen-12-ynyl)oxy>-2H-pyran | 72858-83-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (E)-tetrahydro-2-<(10-hexadecen-12-ynyl)oxy>-2H-pyran
• 英文别名: 2-hexadec-10t-en-12-ynyloxy-tetrahydro-pyran；2-(10E-Hexadecen-12-in-oxy)-tetrahydropyran
• CAS: 72858-83-4
• 化学式: C₂₁H₃₆O₂
• 分子量: 320.516
• InChiKey: XPDHRZOJWHKIIA-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  23.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-tetrahydro-2-<(10-hexadecen-12-ynyl)oxy>-2H-pyran 生成 (E,Z)-10,12-十六碳烯醇
  参考文献：
  名称：

  Samain,D.; Descoins,C., Bulletin de la Societe Chimique de France, 1979, vol. , p. 71 - 76

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-(11-hydroxy-1-undecenyl)boronic acid 在 sodium hydroxide 、 copper(l) iodide 、 bis(triphenylphosphine)palladium(II)-chloride 、 碘 、 对甲苯磺酸 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.5h， 生成 (E)-tetrahydro-2-<(10-hexadecen-12-ynyl)oxy>-2H-pyran
  参考文献：
  名称：

  摘要：

  The sex pheromone of Hemileuca eglanterina from the San Gabriel Mountains, California, was determined to be a combination of E10,Z12-hexadeca-10, 12-dien-1-yl acetate, E10,Z12-hexadeca-10, 12-dien-1-ol, and E10,Z12-hexadeca-10,12-dienal. Ratios of the compounds in extracts of female pheromone glands varied around a mean of 100:48: 1.1 of the acetate, alcohol, and aldehyde, respectively. Field trials with synthetic compounds indicated that the optimum ratio of alcohol to aldehyde was 10:1 and that this ratio was more critical than the ratio of either compound to the acetate. A synthetic blend of 100:10:1 acetate-alcohol-aldehyde was effective at attracting male moths in the field. Additional compounds found in both extract and aeration samples failed to significantly increase trap catches of male moths, although some of these minor components elicited responses from male moth antennae in coupled gas chromatography-electroantennography studies.

  DOI：

  10.1023/a:1020876229787

文献信息

• Stereospecific palladium-catalyzed coupling reactions of vinyl iodides with acetylenic tin reagents
  作者：J. K. Stille、James H. Simpson

  DOI：10.1021/ja00241a035

  日期：1987.4
• Syntheses of (<i>Z,E</i>)-5,7-Dodecadienol and (<i>E</i>,<i>Z</i>)-10,12-Hexadecadienol, Lepidoptera Pheromone Components, via Zinc Reduction of Enyne Precursors. Test of Pheromone Efficacy against the Siberian Moth
  作者：Ashot Khrimian、Jerome A. Klun、Yousef Hijji、Yuri N. Baranchikov、Vladimir M. Pet'ko、Victor C. Mastro、Matthew H. Kramer

  DOI：10.1021/jf020472s

  日期：2002.10.1

  Efficient syntheses of (ZE)-5,7-dodecadienol, a pheromone component of the Siberian moth, Dendrolimus superans sibiricus, and (E,Z)-10,12-hexadecadienol, a pheromone component of various Lepidoptera pheromones, were accomplished by cis reduction of the corresponding enynols with activated zinc. The most energetic reagent was zinc galvanized with copper and silver (Zn/Cu/Ag) that achieved rapid and high-yield reduction in methanol-water. The stereoselectivity of semihydrogenation was greater than or equal to98%. A process whereby zinc dust was continuously activated throughout the reduction with an acid was also satisfactory (95-98% cis). Field evaluation of the 1:1 mixture of (Z,E)-5,7-dodecadienol and (Z,E)-5,7-dodecadienal with the Siberian moth in Russia showed that the rubber septa pretreated with compound and stored at -80 degreesC were as effective as freshly treated septa. Moth responses to septa aged in open air indicated that lure effectiveness declined significantly after 2 weeks of aging. Thus, if rubber septa are used as pheromone dispensers in Siberian moth traps monitoring, they should be replaced biweekly with fresh septa for optimal trap effectiveness.