2-[6-(1,1-Dioxo-2,5-dihydro-1H-1λ6-thiophen-2-yl)-hexyloxy]-tetrahydro-pyran | 302921-07-9

• 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: 2-[6-(1,1-Dioxo-2,5-dihydro-1H-1λ6-thiophen-2-yl)-hexyloxy]-tetrahydro-pyran
• CAS: 302921-07-9
• 化学式: C₁₅H₂₆O₄S
• 分子量: 302.435
• InChiKey: OIRRSOSVFHHNTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-[6-(1,1-Dioxo-2,5-dihydro-1H-1λ6-thiophen-2-yl)-hexyloxy]-tetrahydro-pyran 在 重铬酸吡啶 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 丙醇 、 二氯甲烷 为溶剂， 生成 (E)-2-hexenyl (E)-7,9-decadienoate
  参考文献：
  名称：

  摘要：

  This study was undertaken to identify sex pheromone components of nettle caterpillars Darna trima and Darna bradleyi (Lepidoptera: Limacodidae) whose larvae defoliate oil palm, Elaeis guineensis, in southeast Asia. Coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone gland extracts revealed two antennally active compounds produced by female D. trima and two by female D. bradleyi. Molecular structures of these candidate pheromone components were identified by electron-impact and chemical-ionization mass spectrometry; retention-index calculations on DB-5, DB-23, and DB-210 columns; microanalytical treatments, as well as syntheses of "auxilliary" compounds that facilitated identification of the compounds. The compounds from D. trima were 2-methylbutyl (E)-7,9-decadienoate (A) and (E)-2-hexenyl (E)-7,9-decadienoate (B); from D. bradleyi we identified methyl (E)-7,9-decadienoate (C), and isobutyl (E)-7,9-decadienoate (D). In field experiments in Malaysia, (S)-2-methylbutyl (E)-7,9-decadienoate (SA) in combination with B proved to be essential and synergistic pheromone components for attraction of male D. trima. (R)-2-Methylbutyl (E)-7,9-decadienoate (RA) had no behavioral activity. Compound D singly attracted male D. bradleyi, but addition of C to D at a 1:10 ratio significantly enhanced attractiveness of the bait. Synthetic pheromone blends were more effective trap baits than unmated female moths and could be developed for monitoring populations of D. trima and D. bradleyi in Asian oil palm plantations.

  DOI：

  10.1023/a:1005561127155
• 作为产物：
  描述：

  3-环丁烯砜 、 6-iodohexanol, tetrahydropyranyl ether 在 lithium hexamethyldisilazane 作用下， 以 六甲基磷酰三胺 为溶剂， 生成 2-[6-(1,1-Dioxo-2,5-dihydro-1H-1λ6-thiophen-2-yl)-hexyloxy]-tetrahydro-pyran
  参考文献：
  名称：

  摘要：

  This study was undertaken to identify sex pheromone components of nettle caterpillars Darna trima and Darna bradleyi (Lepidoptera: Limacodidae) whose larvae defoliate oil palm, Elaeis guineensis, in southeast Asia. Coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone gland extracts revealed two antennally active compounds produced by female D. trima and two by female D. bradleyi. Molecular structures of these candidate pheromone components were identified by electron-impact and chemical-ionization mass spectrometry; retention-index calculations on DB-5, DB-23, and DB-210 columns; microanalytical treatments, as well as syntheses of "auxilliary" compounds that facilitated identification of the compounds. The compounds from D. trima were 2-methylbutyl (E)-7,9-decadienoate (A) and (E)-2-hexenyl (E)-7,9-decadienoate (B); from D. bradleyi we identified methyl (E)-7,9-decadienoate (C), and isobutyl (E)-7,9-decadienoate (D). In field experiments in Malaysia, (S)-2-methylbutyl (E)-7,9-decadienoate (SA) in combination with B proved to be essential and synergistic pheromone components for attraction of male D. trima. (R)-2-Methylbutyl (E)-7,9-decadienoate (RA) had no behavioral activity. Compound D singly attracted male D. bradleyi, but addition of C to D at a 1:10 ratio significantly enhanced attractiveness of the bait. Synthetic pheromone blends were more effective trap baits than unmated female moths and could be developed for monitoring populations of D. trima and D. bradleyi in Asian oil palm plantations.

  DOI：

  10.1023/a:1005561127155