1-氯-6-十四碳炔 | 92329-07-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 中文名称: 1-氯-6-十四碳炔
• 英文名称: 1-chloro-6-tetradecyne
• 英文别名: 1-chloro-tetradec-6-yne；1-Chlor-tetradecin-(6)
• CAS: 92329-07-2
• 化学式: C₁₄H₂₅Cl
• 分子量: 228.805
• InChiKey: AKJVWOIMLVHFEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  15.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1-氯-6-十四碳炔 在 Pd-BaSO₄ 喹啉 、 三氟化硼乙醚 、 氢气 、 sodium hydride 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 甲基十六碳-8-烯酸酯
  参考文献：
  名称：

  摘要：

  Male-released semiochemicals of the stink bug Piezodorus hybneri (Heteroptera: Pentatomidae) elicit attraction of male and female bugs and homosexual behavior in males. Three active components were isolated from the airborne volatiles of males by flash chromatography, with the activity monitored by GC-EAD and behavioral bioassay. The pheromone system was characterized as a mixture of beta-sesquiphellandrene, (R)-15-hexadecanolide, and methyl 8-(Z)-hexadecenoate (ratio: 10:4:1), and the activity of the semiochemicals was assessed with authentic samples. Enantiomerically pure samples of the R and S macrolactones were obtained by Yamaguchi's and Mitsunobu's macrolactonization of a key intermediate, (R)-15-hydroxyhexadecanoic acid. The nonnatural S stereoisomer was neither a beneficial nor a behavioral antagonist. Individual constituents or binary mixtures were active, but the optimal male response was elicited only by the full mixture. Behavioral observation and the fact that the onset of pheromone production is coincident with ovarian development strongly suggest that these semiochemicals are, in fact, sex pheromones.

  DOI：

  10.1023/a:1022307600446
• 作为产物：
  描述：

  1-溴-5-氯戊烷 、 1-壬炔 生成 1-氯-6-十四碳炔
  参考文献：
  名称：

  摘要：

  Male-released semiochemicals of the stink bug Piezodorus hybneri (Heteroptera: Pentatomidae) elicit attraction of male and female bugs and homosexual behavior in males. Three active components were isolated from the airborne volatiles of males by flash chromatography, with the activity monitored by GC-EAD and behavioral bioassay. The pheromone system was characterized as a mixture of beta-sesquiphellandrene, (R)-15-hexadecanolide, and methyl 8-(Z)-hexadecenoate (ratio: 10:4:1), and the activity of the semiochemicals was assessed with authentic samples. Enantiomerically pure samples of the R and S macrolactones were obtained by Yamaguchi's and Mitsunobu's macrolactonization of a key intermediate, (R)-15-hydroxyhexadecanoic acid. The nonnatural S stereoisomer was neither a beneficial nor a behavioral antagonist. Individual constituents or binary mixtures were active, but the optimal male response was elicited only by the full mixture. Behavioral observation and the fact that the onset of pheromone production is coincident with ovarian development strongly suggest that these semiochemicals are, in fact, sex pheromones.

  DOI：

  10.1023/a:1022307600446

文献信息

• Grimmer,G.; Kracht,J., Chemische Berichte, 1963, vol. 96, p. 3370 - 3373
  作者：Grimmer,G.、Kracht,J.

  DOI：——

  日期：——