1-bromo-3E,5E-decadiene | 92080-85-8

• 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-decadiene
• 英文别名: (3e,5e)-3,5-Decadienyl bromide；(3E,5E)-1-bromodeca-3,5-diene
• CAS: 92080-85-8
• 化学式: C₁₀H₁₇Br
• 分子量: 217.149
• InChiKey: IHRNIHQXFZREKB-BSWSSELBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  11
• 可旋转键数：
  6
• 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：

  1-bromo-3E,5E-decadiene 在 sodium methylate 、 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 4.08h， 生成 (5E,7E)-5,7-dodecadienoic acid
  参考文献：
  名称：

  从被膜Pseudodistoma kanoko人工合成鞘氨醇相关的哌啶生物碱拟distominmin C

  摘要：

  从d-丝氨酸合成了从冲绳被膜Pseudodistoma kanoko分离出的哌啶生物碱Pseudodistomin C（1），它为d的整个结构提供了进一步的明确证据，1在C-4和C-上具有相反的绝对构型。从假瘤菌素A（2）和B（3）的5个手性中心得自同一被膜。

  DOI：

  10.1016/0040-4020(96)00137-8
• 作为产物：
  描述：

  1-环丙基-2E-庚烯-1-醇 在 三甲基溴硅烷 、 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以91%的产率得到1-bromo-3E,5E-decadiene
  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

• (−)-Pseudodistomin E: First Asymmetric Synthesis and Absolute Configuration Assignment
  作者：Stephen G. Davies、Ai M. Fletcher、Paul M. Roberts、James E. Thomson、David Zimmer

  DOI：10.1021/acs.orglett.7b00434

  日期：2017.4.7

  (−)-Pseudodistomin E has been prepared for the first time, allowing its structure and absolute configuration to be confirmed. The established conjugate addition of lithium (S)-N-allyl-N-(α-methyl-p-methoxybenzyl)amide to methyl (E,E)-hepta-2,5-dienoate generated the C(2)-stereocenter, and iodolactonisation of a derivative generated the remaining two stereogenic centers. Ensuing iodide displacement

  首次制备了（-）-假二甲毒素E，可以确认其结构和绝对构型。锂（S）-N-烯丙基-N-（α-甲基-对甲氧基苄基）酰胺与（E，E）-庚2,5-二烯酸甲酯的共轭加成生成C（2）-立体中心，衍生物的碘内酯化产生了剩下的两个立体生成中心。随后使用束缚策略实现了碘化物的置换，从而将氮原子引入C（5）。羧酸与二烷基锌试剂的脱羧偶联完成了十三碳二烯基链的构建。
• Synthesis of ?-silyloxyacylcyclopropanes catalyzed by zinc salts and the homoallylic rearrangement of cyclopropylcarbinols by the action of trimethylsilyl halides
  作者：N. M. Ivanova、B. A. Cheskis、A. M. Moiseenkov、O. M. Nefedov

  DOI：10.1007/bf00963040

  日期：1990.1
• IVANOVA, N. M.;CHEEKIS, B. A.;MOISEENKO, A. M.;NEFEDOV, O. M., IZV. AN CCCP. CEP. XIM.,(1990) N, S. 225-236
  作者：IVANOVA, N. M.、CHEEKIS, B. A.、MOISEENKO, A. M.、NEFEDOV, O. M.

  DOI：——

  日期：——
• 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.