1,(Z)-5-Tetradecadien | 74076-53-2

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1,(Z)-5-Tetradecadien
• 英文别名: (5Z)-tetradeca-1,5-diene
• CAS: 74076-53-2
• 化学式: C₁₄H₂₆
• 分子量: 194.36
• InChiKey: KRJLSUCBCBOIOZ-LUAWRHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  14
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  1,(Z)-5-Tetradecadien 在 吡啶 、 9-Borabicyclononan 、 hydroxide 、 双氧水 作用下， 生成 (Z)-5-十四碳烯-1-醇乙酸酯
  参考文献：
  名称：

  Pheromone XXX. Identifizierung eines neuartigen Pheromonkomplexes aus der Graseule Scotia exclamationis (Lepidoptera).

  摘要：

  DOI：

  10.1016/s0040-4039(00)71462-6
• 作为产物：
  描述：

  1,5-环辛二烯 在 四甲基锡 、 五氯化钼 、 silica gel 9-borabicyclo[3.3.1]nonane dimer 作用下， 以 四氢呋喃 、 甲苯 为溶剂， -70.0~25.0 ℃ 、2.53 MPa 条件下， 反应 24.0h， 生成 1,(Z)-5-Tetradecadien
  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

文献信息

• Synthesis of Z-isomeric insect sex pheromone components via ethenolysis of 1,5-cyclooctadiene
  作者：Victor I Bykov、Tamara A Butenko、Elena B Petrova、Eugene Sh Finkelshtein

  DOI：10.1016/s0040-4020(99)00295-1

  日期：1999.7

  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.
• Pheromone XXX. Identifizierung eines neuartigen Pheromonkomplexes aus der Graseule Scotia exclamationis (Lepidoptera).
  作者：H.J. Bestmann、T. Brosche、K.H. Koschatzky、K. Michaelis、H. Platz、O. Vostrowsky、W. Knauf

  DOI：10.1016/s0040-4039(00)71462-6

  日期：1980.1