14-chloro-(Z)-2,(E)-4-tetradecadiene | 219957-69-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: 14-chloro-(Z)-2,(E)-4-tetradecadiene
• CAS: 219957-69-4
• 化学式: C₁₄H₂₅Cl
• 分子量: 228.805
• InChiKey: ZSJVASBALWJYSO-AWYLAFAOSA-N

物化性质

• 沸点：
  302.812±11.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.886±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  15.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  potassium acetate 、 14-chloro-(Z)-2,(E)-4-tetradecadiene 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以89%的产率得到(10E,12Z)-tetradeca-10,12-dien-1-yl acetate
  参考文献：
  名称：

  摘要：

  (Z)-10,(Z)-12-Tetradecadienyl acetate (Z10,Z12-14:OAc) and (E)-10,(E)-12-tetradecadienyl acetate (E10,E12-14:OAc) are sex pheromone components of the apple blotch leafminer (ABLM), Phyllonorycter crataegella. Compounds extracted from female pheromone glands were identified by coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses, retention index calculations of BAD-active compounds, and by comparative CC-BAD analyses of female ABLM-produced and authentic (synthetic) compounds. In field experiments in apple Malus domestica orchards in Connecticut, Z10,Z12-14:OAc done attracted ABLM males. Addition of E10,E12-14:OAc to 210,Z12-14:OAc at 0.1:10 or 1:10 ratios enhanced attractiveness of the lure. Geometrical isomers Z10,E12- or E10,Z12-14:OAc at equivalent ratios were behaviorally benign and slightly inhibitory, respectively. In field experiments in British Columbia, Z10,Z12-14:OAc plus E10,E12-14:OAc did not attract Phyllonorycter moths, supporting the contention that ABLM is not present in the fruit growing regions of British Columbia. Z10,Z12-14:OAc added to P. mespilella pheromone, (E)-4,(E)10-dodecadienyl acetate, strongly inhibited response by P. mespilella males. Recognition of the ABLM pheromone blend by allopatric P. mespilella males suggests a phylogenetic relationship and previous sympatry of these two Phyllonorycter spp. If pheromonal attraction of ABLM males were reciprocally inhibited by P. mespilella pheromone, a generic Phyllonorycter pheromone blend could be tested for pheromone-based mating disruption of the apple leaf-mining Phyllonorycter guild in North America.

  DOI：

  10.1023/a:1020785609797
• 作为产物：
  描述：

  11-氯-1-十一碳炔 在 正丁基锂 、 (Sia)2BH 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 30.33h， 生成 14-chloro-(Z)-2,(E)-4-tetradecadiene
  参考文献：
  名称：

  摘要：

  (Z)-10,(Z)-12-Tetradecadienyl acetate (Z10,Z12-14:OAc) and (E)-10,(E)-12-tetradecadienyl acetate (E10,E12-14:OAc) are sex pheromone components of the apple blotch leafminer (ABLM), Phyllonorycter crataegella. Compounds extracted from female pheromone glands were identified by coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses, retention index calculations of BAD-active compounds, and by comparative CC-BAD analyses of female ABLM-produced and authentic (synthetic) compounds. In field experiments in apple Malus domestica orchards in Connecticut, Z10,Z12-14:OAc done attracted ABLM males. Addition of E10,E12-14:OAc to 210,Z12-14:OAc at 0.1:10 or 1:10 ratios enhanced attractiveness of the lure. Geometrical isomers Z10,E12- or E10,Z12-14:OAc at equivalent ratios were behaviorally benign and slightly inhibitory, respectively. In field experiments in British Columbia, Z10,Z12-14:OAc plus E10,E12-14:OAc did not attract Phyllonorycter moths, supporting the contention that ABLM is not present in the fruit growing regions of British Columbia. Z10,Z12-14:OAc added to P. mespilella pheromone, (E)-4,(E)10-dodecadienyl acetate, strongly inhibited response by P. mespilella males. Recognition of the ABLM pheromone blend by allopatric P. mespilella males suggests a phylogenetic relationship and previous sympatry of these two Phyllonorycter spp. If pheromonal attraction of ABLM males were reciprocally inhibited by P. mespilella pheromone, a generic Phyllonorycter pheromone blend could be tested for pheromone-based mating disruption of the apple leaf-mining Phyllonorycter guild in North America.

  DOI：

  10.1023/a:1020785609797