8-Dodecyn-1-ol | 41589-71-3

• 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: 8-Dodecyn-1-ol
• 英文别名: dodec-8-yn-1-ol
• CAS: 41589-71-3
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: WRCSSJVAMYNHDD-UHFFFAOYSA-N

物化性质

• 沸点：
  271.4±23.0 °C(Predicted)
• 密度：
  0.878±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  8-Dodecyn-1-ol 在 K-10 Montmorillonite clay 、 sodium hydride 、 1,3-丙二胺 作用下， 反应 12.0h， 生成 12-(四氢-2H-吡喃-2-基氧基)-1-十二碳炔
  参考文献：
  名称：

  Moth responses to selectively fluorinated sex pheromone analogs

  摘要：

  Partially fluorinated analogs of the European corn borer (Ostrinia nubilalis) female sex pheromone, 11-tetradecenyl acetate (97:3 Z: E), having mono- and trifluorosubstitutions at the terminal carbon of the pheromone chain, mimicked the biological activity of the pheromone, while analogs with fluorine at either side of the double bond and a pentafluoro analog were essentially inactive. Comparison of the pheromonal activity of these analogs with the previously reported activity of similarly fluorinated pheromones in five other species of moths revealed an unpredictable relationship between fluorine substitution pattern and pheromone-mimicking activity. Fluorine substitution pat terns that rendered pheromonal analogs biologically inactive in the European corn borer had no detrimental influence upon pheromonal activity in other species and the converse was also true. This is evidence that the relative importance of electronic qualities of sites within a pheromone molecule differ from species to species. Furthermore, it indicates that the biochemical components (pheromone receptor proteins, binding proteins, and enzymes) that make up moth olfactory chemosensory systems must also vary structurally from species to species, despite the fact that they are involved in olfactory sensing of compounds having very similar chemical structure.

  DOI：

  10.1007/bf02036202
• 作为产物：
  描述：

  7-溴-1-庚烯 在 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 、 sodium acetate 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 8-Dodecyn-1-ol
  参考文献：
  名称：

  Use of enyne compounds in the synthesis of insect pheromones

  摘要：

  DOI：

  10.1007/bf02273916

文献信息

• Insect pheromones and their analogs. XIII. Synthesis of dodec-8E-enyl and dodec-8Z-enyl acetates ? Components of the sex pheromones ofGrapholitha funebrana andGrapholitha molesta
  作者：V. N. Odinokov、G. Yu. Ishmuratov、G. G. Balezina、G. A. Tolstikov

  DOI：10.1007/bf00574216

  日期：——

  converted with the aid of sodium in liquid ammonia into the stereochemical individual dodec-8E-enol, while its reduction with the aid of 9-borabicyclo[3.3.1]nonane (BBN) gave the steroisomeric alcohol exclusively with the Z configuration, as followed from the results of capillary GLC and the IR spectra of the corresponding acetates. The PMR spectra of the compounds synthesized are also given.

  提出了一种合成 dodec-8E-enyl 和 dodec-8Z-enyl 乙酸酯的新路线，该路线基于格氏试剂从容易获得的 1-bromo-5-(1-ethoxyethoxy)pentane 与 1- bromohept-3-yne — 溴化物，得自 pent-1-yne 与 2-氯乙基乙烯基醚，hept-3-yn-1-ol 的 β-羟乙基化产物，通过其甲苯磺酸盐与溴化锂的复分解反应。关键合成子——dodec-8-yn-1-ol——在液氨中钠的帮助下被转化为立体化学个体dodec-8E-烯醇，而它在9-硼双环[3.3.1]壬烷的帮助下被还原(BBN) 根据毛细管 GLC 和相应乙酸酯的 IR 光谱结果得出完全具有 Z 构型的立体异构醇。还给出了合成化合物的 PMR 谱。
• Synthesis of aliphatic insect pheromones from alicyclic starting materials
  作者：K. Mori、M. Uchida、M. Matsui

  DOI：10.1016/0040-4020(77)80091-4

  日期：1977.1

  Both (Z)-6-heneicosen-11-one, the pheromone of Douglas fir tussock moth, and (Z)-8-dodecenyl acetate, the pheromone of oriental fruit moth, have been synthesized from cyclohexane-1,3-dione.

  花旗蛾的信息素（Z）-6-heneicosen-11-one和东方果蛾的信息素（Z）-8-十二碳烯基乙酸酯都是由环己烷-1,3-二酮合成的。
• Vinczer, Peter; Juvanecz, Zoltan; Novak, Lajos, Acta Chimica Hungarica, 1987, vol. 124, # 5, p. 737 - 748
  作者：Vinczer, Peter、Juvanecz, Zoltan、Novak, Lajos、Szantay, Csaba

  DOI：——

  日期：——
• Kovaleva,A.S. et al., Journal of Organic Chemistry USSR (English Translation), 1972, vol. 8, p. 2523 - 2527
  作者：Kovaleva,A.S. et al.

  DOI：——

  日期：——
• ODINOKOV, V. N.;ISHMURATOV, G. YU.;BALEZINA, G. G.;TOLSTIKOV, G. A., XIMIYA PRIROD. SOEDIN., 1985, N 3, 398-400
  作者：ODINOKOV, V. N.、ISHMURATOV, G. YU.、BALEZINA, G. G.、TOLSTIKOV, G. A.

  DOI：——

  日期：——