1,5-hexadiene | 144368-14-9

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1,5-hexadiene
• 英文别名: Hexadeca-1,5-diene
• CAS: 144368-14-9
• 化学式: C₁₆H₃₀
• 分子量: 222.414
• InChiKey: FJHFYWSKGPONQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  16
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  1,5-hexadiene 在 potassium permanganate 作用下， 生成 (R)-1-[(2R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-undecan-1-ol
  参考文献：
  名称：

  Approach to the synthesis of annonaceous acetogenins from D-glucose

  摘要：

  The preparation from D-glucose of threo-trans-threo and threo-cis-threo synthons 12 and 13 of the monochiral synthesis of mono (or eventually bis) tetrahydrofuran acetogenins is described. Their structure have been proven by degradation and comparison with a racemic sample of a threo-cis-threo aldehyde prepared by permanganate oxidation of the corresponding diene.

  DOI：

  10.1016/s0040-4039(00)79126-x
• 作为产物：
  描述：

  isopropyl tridec-1-en-3-yl carbonate 、 烯丙基硼酸频哪醇酯 在 四(三苯基膦)镍 作用下， 以 四氢呋喃 为溶剂， 生成 1,5-hexadiene 、 3-decylhexa-1,5-diene
  参考文献：
  名称：

  选择性官能团耐受的sp3-sp3碳-碳键形成中的钯（0）与镍（0）催化

  摘要：

  我们发现了Pd 0催化的分子间非对称Suzuki–Miyaura型sp 3 –sp 3碳酸烯丙酯与无毒烯丙基，烯丙基或炔丙基硼酸酯之间的C–C键形成。该报告代表了在这种特定情况下首次使用这些类型的硼酸酯。本发明的转化在非常温和的条件下以高选择性进行，并且证明包括醛官能团在内的各种官能团是相容的。另外，发现一些硼酸盐显示出非常不寻常的反应模式。还清楚地证明了硼与硅的反应性更高。最后，通过使用市售的Ni 0催化剂解决了与中间烯丙基-Pd物种相关的β-氢化物消除的固有问题。

  DOI：

  10.1002/chem.200902221

文献信息

• Mechanism of the cyclization of normal penta- and hexadienes over iron-magnesium oxide catalyst
  作者：G. V. Isagulyants、K. M. Gitis、M. I. Rozengart、K. Ya. Burshtein、V. F. Il'in

  DOI：10.1007/bf01094635

  日期：1981.11
• 10.1002/chem.202400860
  作者：Mingueza-Verdejo, Paloma、Rodríguez-Nuévalos, Silvia、Oliver-Meseguer, Judit、Leyva-Pérez, Antonio

  DOI：10.1002/chem.202400860

  日期：——

  Abstract2,5‐Dimethyl‐2,4‐hexadiene is a readily available and easily managable compound, whose symmetric and polymethylated dienic structure should be prone to engage in cross‐metathesis reactions with other alkenes, but this has not been apparently exploited so far. Here we show that this reactant enables the easy synthesis of tri‐ and tetra‐susbtituted alkenes (i. e. isobutylenyl and prenyl groups) from simple alkenes under mild reaction conditions, not only with the conventional 2nd generation Grubbs catalyst but also with other Grela‐type catalyts such as StickyCat,TM AquaMetTM and GreenCatTM. The use of liquid and low volatile 2,5‐dimethyl‐2,4‐hexadiene avoids the use of gaseous alkene reactants and, besides, showcases the reactivity of polyisoprene (rubber), thus allowing to optimize the reaction conditions for rubber upcycling, after metathesis reaction of the pristine or used polymer with simple alkenes. These results bring low volatile isoprene‐type compounds as privileged poly‐substituted reactants for alkene cross‐metathesis reactions.
• Palladium(0) versus Nickel(0) Catalysis in Selective Functional-Group-Tolerant sp³-sp³Carbon-Carbon Bond Formations
  作者：Emmanuel Ferrer Flegeau、Uwe Schneider、Shū Kobayashi

  DOI：10.1002/chem.200902221

  日期：2009.11.16

  formations between allyl carbonates and nontoxic allyl, allenyl, or propargyl boronates. This report represents the first use of these types of boronic esters in this particular context. The present transformations proceeded with high selectivity under remarkably mild conditions, and various functional groups including an aldehyde function proved to be compatible. In addition, several boronates were found

  我们发现了Pd 0催化的分子间非对称Suzuki–Miyaura型sp 3 –sp 3碳酸烯丙酯与无毒烯丙基，烯丙基或炔丙基硼酸酯之间的C–C键形成。该报告代表了在这种特定情况下首次使用这些类型的硼酸酯。本发明的转化在非常温和的条件下以高选择性进行，并且证明包括醛官能团在内的各种官能团是相容的。另外，发现一些硼酸盐显示出非常不寻常的反应模式。还清楚地证明了硼与硅的反应性更高。最后，通过使用市售的Ni 0催化剂解决了与中间烯丙基-Pd物种相关的β-氢化物消除的固有问题。
• Approach to the synthesis of annonaceous acetogenins from D-glucose
  作者：Philippe Bertrand、Jean-Pierre Gesson

  DOI：10.1016/s0040-4039(00)79126-x

  日期：1992.9

  The preparation from D-glucose of threo-trans-threo and threo-cis-threo synthons 12 and 13 of the monochiral synthesis of mono (or eventually bis) tetrahydrofuran acetogenins is described. Their structure have been proven by degradation and comparison with a racemic sample of a threo-cis-threo aldehyde prepared by permanganate oxidation of the corresponding diene.