10-iodo-1,Z-5-decadiene | 244771-28-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 10-iodo-1,Z-5-decadiene
• 英文别名: (5Z)-10-iododeca-1,5-diene
• CAS: 244771-28-6
• 化学式: C₁₀H₁₇I
• 分子量: 264.149
• InChiKey: WACQNZJEVQAOTP-WAYWQWQTSA-N

物化性质

• 沸点：
  251.5±29.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  10-iodo-1,Z-5-decadiene 在 9-borabicyclo[3.3.1]nonane dimer 作用下， 以 四氢呋喃 为溶剂， 生成 (Z)-2-Methyl-7-octadecen
  参考文献：
  名称：

  Synthesis of Z-isomeric insect sex pheromone components via ethenolysis of 1,5-cyclooctadiene

  摘要：

  A novel syntheses of Z-5-decenol, Z-5-decenyl acetate, Z-7-dodecenol, Z-7-dodecenyl acetate, Z-9-tricosene, Z-7,8-epoxy-2-methyloctadecane which are sex pheromone components of Lepidoptera and Diptera orders, have been realized via stereoselective cometathesis of 1,5-cyclooctadiene with ethylene in the presence of MoCl5/SiO2-SnMe4 as a key reaction. The main cometathesis product, 1,Z-5,9-decatriene, has been converted into pheromone components mentioned above by regioselective partial hydroboration or hydrozirconation with help of 9-BBN and Cp2ZrHCl, correspondingly. The protonolysis of the obtained zirconosene derivative gave 1,Z-5-decadiene. Hydroboration-oxidation or hydroboration-Cz-homologation of the latter led to Z-5- or Z-7 monoene pheromone components. Hydroboration-iodination of terminal double bond in 1,Z-5,9-decatriene, and further cross-coupling of the obtained iodine derivative with convenient lithium cuprates resulted in Z-9-tricosene, the main sex pheromone component of House Fly ( Musca Domestica), or in 2-methyl-Z-7-octadecene, the precursor of Gypsy Moth (Lymantria Dispar) sex attractant. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00295-1
• 作为产物：
  描述：

  (Z)-deca-1,5,9-triene 在 9-borabicyclo[3.3.1]nonane dimer 、 碘 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以35%的产率得到10-iodo-1,Z-5-decadiene
  参考文献：
  名称：

  Synthesis of Z-isomeric insect sex pheromone components via ethenolysis of 1,5-cyclooctadiene

  摘要：

  A novel syntheses of Z-5-decenol, Z-5-decenyl acetate, Z-7-dodecenol, Z-7-dodecenyl acetate, Z-9-tricosene, Z-7,8-epoxy-2-methyloctadecane which are sex pheromone components of Lepidoptera and Diptera orders, have been realized via stereoselective cometathesis of 1,5-cyclooctadiene with ethylene in the presence of MoCl5/SiO2-SnMe4 as a key reaction. The main cometathesis product, 1,Z-5,9-decatriene, has been converted into pheromone components mentioned above by regioselective partial hydroboration or hydrozirconation with help of 9-BBN and Cp2ZrHCl, correspondingly. The protonolysis of the obtained zirconosene derivative gave 1,Z-5-decadiene. Hydroboration-oxidation or hydroboration-Cz-homologation of the latter led to Z-5- or Z-7 monoene pheromone components. Hydroboration-iodination of terminal double bond in 1,Z-5,9-decatriene, and further cross-coupling of the obtained iodine derivative with convenient lithium cuprates resulted in Z-9-tricosene, the main sex pheromone component of House Fly ( Musca Domestica), or in 2-methyl-Z-7-octadecene, the precursor of Gypsy Moth (Lymantria Dispar) sex attractant. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00295-1