1-bromo-3E,5E-tetradecadiene | 132119-99-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 1-bromo-3E,5E-tetradecadiene
• 英文别名: (3E,5E)-1-bromotetradeca-3,5-diene
• CAS: 132119-99-4
• 化学式: C₁₄H₂₅Br
• 分子量: 273.256
• InChiKey: VWRUGAJNQZYYCP-HULFFUFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 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 、 1-bromo-3E,5E-tetradecadiene 在 二苯并-18-冠醚-6 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以84%的产率得到3E,5E-tetradecadienyl acetate
  参考文献：
  名称：

  Stereospecific synthesis of transoid mono- and 1,3-diene pheromones ofLepidoptera from secondary cyclopropylcarbinols

  摘要：

  The zinc halide-initiated homoallylic rearrangement of saturated or allylic cyclopropylcarbinols in the presence of trimethylsilyl halides has been employed as the key step in the total synthesis of seven behavioral regulators in twenty insects of the Lepidoptera family, namely 9E-tetradecenol and its acetate, 11E-hexadecenol and its acetate, 11E-hexadecenal, 5E, 7E-dodecadienol, and 3E,5E-tetradecadienyl acetate.

  DOI：

  10.1007/bf00958841
• 作为产物：
  描述：

  (E)-1-cyclopropylundec-2-en-1-one 在 sodium tetrahydroborate 、 cerium(III) chloride 、 三甲基溴硅烷 、 zinc dibromide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 1-bromo-3E,5E-tetradecadiene
  参考文献：
  名称：

  Simple synthesis of?-silyloxyacylcyclopropanes and the homoallyl rearrangement of cyclopropylcarbinols by the action of trimethylsilyl halides in the presence of zinc halides

  摘要：

  The ZnCl2 catalyzed condensation of 1-trimethylsilyloxyvinylcyclopropane with aldehydes and ketones gave beta-silyloxyacylcyclopropanes, which were converted by the action of TsOH in boiling benzene into 1-cyclopropyl-2E-alken-1-ones. Reduction of the latter gave saturated and allyl cyclopropylcarbinols, which by means of Me3SiX and catalytic amounts of ZnX2 (X = Cl, Br) were highly selectively converted into the corresponding linear mono- and dienic E-homoallyl halides. The sequence of reactions that was worked out provided an effective synthesis of 3E-dodecenyl acetate, a sex pheromone of the sugar beet moth.

  DOI：

  10.1007/bf00958248

文献信息

• CHESKIS, B. A.;IVANOVA, N. M.;MOISEENKOV, A. M.;NEFEDOV, O. M., IZV. AN CCCP. CEP. XIM.,(1990) N, S. 2025-2036
  作者：CHESKIS, B. A.、IVANOVA, N. M.、MOISEENKOV, A. M.、NEFEDOV, O. M.

  DOI：——

  日期：——
• Simple synthesis of?-silyloxyacylcyclopropanes and the homoallyl rearrangement of cyclopropylcarbinols by the action of trimethylsilyl halides in the presence of zinc halides
  作者：B. A. Cheskis、N. M. Ivanova、A. M. Moiseenkov、O. M. Nefedov

  DOI：10.1007/bf00958248

  日期：1990.9

  The ZnCl2 catalyzed condensation of 1-trimethylsilyloxyvinylcyclopropane with aldehydes and ketones gave beta-silyloxyacylcyclopropanes, which were converted by the action of TsOH in boiling benzene into 1-cyclopropyl-2E-alken-1-ones. Reduction of the latter gave saturated and allyl cyclopropylcarbinols, which by means of Me3SiX and catalytic amounts of ZnX2 (X = Cl, Br) were highly selectively converted into the corresponding linear mono- and dienic E-homoallyl halides. The sequence of reactions that was worked out provided an effective synthesis of 3E-dodecenyl acetate, a sex pheromone of the sugar beet moth.
• Stereospecific synthesis of transoid mono- and 1,3-diene pheromones ofLepidoptera from secondary cyclopropylcarbinols
  作者：B. A. Cheskis、N. M. Ivanova、A. M. Moiseenkov、O. M. Nefedov

  DOI：10.1007/bf00958841

  日期：1990.11

  The zinc halide-initiated homoallylic rearrangement of saturated or allylic cyclopropylcarbinols in the presence of trimethylsilyl halides has been employed as the key step in the total synthesis of seven behavioral regulators in twenty insects of the Lepidoptera family, namely 9E-tetradecenol and its acetate, 11E-hexadecenol and its acetate, 11E-hexadecenal, 5E, 7E-dodecadienol, and 3E,5E-tetradecadienyl acetate.