11-chloro-1-iodo-1-undecyne | 219957-65-0

• 分子结构分类: 有机化合物 - 有机卤素化合物
• 英文名称: 11-chloro-1-iodo-1-undecyne
• 英文别名: 11-Chloro-1iodo-1-undecyne；11-chloro-1-iodoundec-1-yne
• CAS: 219957-65-0
• 化学式: C₁₁H₁₈ClI
• 分子量: 312.621
• InChiKey: OVHPWGOAMFMEQB-UHFFFAOYSA-N

物化性质

• 沸点：
  324.392±15.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.398±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  11-chloro-1-iodo-1-undecyne 在 二(3-甲基丁烷-2-基)硼烷 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 53.0h， 以78%的产率得到11-chloro-1-iodo-(Z)-1-undecene
  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：

  10-十一炔醇 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.75h， 生成 11-chloro-1-iodo-1-undecyne
  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