(5E)-undeca-1,5-diene | 106051-45-0

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (5E)-undeca-1,5-diene
• 英文别名: trans-1,5-undecadiene；(5E)-1,5-undecadiene；(E)-undeca-1,5-diene；(E)-1,5-undecadiene；1,5-Undecadiene
• CAS: 106051-45-0
• 化学式: C₁₁H₂₀
• 分子量: 152.28
• InChiKey: RVJZHJPKLYEVOX-PKNBQFBNSA-N

物化性质

• 沸点：
  188.4±10.0 °C(Predicted)
• 密度：
  0.765±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  (5E)-undeca-1,5-diene 在 copper(I) chloride 氧气 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以74%的产率得到undec-5(E)-en-2-one
  参考文献：
  名称：

  Diastereoselective synthesis of (E)-alkenes and (E)-1,ω-dienes starting from diastereoisomeric mixtures of 1-bromo-1-alkenes: New syntheses of monounsaturated or bridged ring-ketal naturally occurring substances.

  摘要：

  DOI：

  10.1016/s0040-4039(00)84576-1
• 作为产物：
  描述：

  3-Butenylmagnesium bromide 、 (E)-1-iodohept-1-ene 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 作用下， 以 乙醚 为溶剂， 反应 15.0h， 以87%的产率得到(5E)-undeca-1,5-diene
  参考文献：
  名称：

  Diastereoselective synthesis of (E)-alkenes and (E)-1,ω-dienes starting from diastereoisomeric mixtures of 1-bromo-1-alkenes: New syntheses of monounsaturated or bridged ring-ketal naturally occurring substances.

  摘要：

  DOI：

  10.1016/s0040-4039(00)84576-1

文献信息

• In Situ Generated Gold Nanoparticles on Active Carbon as Reusable Highly Efficient Catalysts for a C−C Stille Coupling
  作者：Julia Holz、Camilla Pfeffer、Hualiang Zuo、Dennis Beierlein、Gunther Richter、Elias Klemm、René Peters

  DOI：10.1002/anie.201902352

  日期：2019.7.22

  traditional C −C cross‐coupling reactions they have been rarely used and Pd catalysts usually give a superior performance. Herein we report that in situ formed gold metal nanoparticles are highly active catalysts for the cross coupling of allylstannanes and activated alkylbromides to form C −C bonds. Turnover numbers up to 29 000 could be achieved in the presence of active carbon as solid support, which allowed

  金纳米颗粒催化剂在许多工业生产过程中很重要。然而，对于传统的C -C交叉偶联反应，很少使用它们，并且Pd催化剂通常具有优异的性能。本文中，我们报道原位形成的金金属纳米颗粒是烯丙基锡烷与活化的烷基溴化物形成C -C键的交叉偶联的高活性催化剂。在活性炭作为固体载体的情况下，可实现高达29000的周转量，这有利于催化剂的回收和再利用。本研究是一种罕见的案例，其中在有机卤化物与有机金属试剂的交叉偶联反应中，金金属催化剂优于钯催化剂。
• Regioselective Hydrogenation Using Platinum-Support Zeolite Modified by CVD-Method
  作者：Hideyuki Kuno、Makoto Shibagaki、Kyoko Takahashi、Ichiro Honda、Hajime Matsushita

  DOI：10.1246/bcsj.64.2508

  日期：1991.8

  A platinum-support zeolite coupled with a silica layer was prepared by Chemical Vapor Deposition (CVD) of tetraethoxysilane, and was investigated in order to determine the catalytic characterization in an analysis of the surface. With this catalyst system, it was demonstrated that the terminal carbon–carbon double bond is preferentially hydrogenated in the case of several unsaturated hydrocarbons. Further, it was elucidated that a highly regioselective hydrogenation of compounds which possess plural double bonds was achieved over this catalyst system. As a result, a reaction model regarding this catalyst system has been put forward.

  通过四乙氧基硅烷的化学气相沉积（CVD）制备了一种铂支持的沸石并在其上覆盖了一层二氧化硅，并对其进行了表面催化特性分析。使用该催化剂系统，证明了在多种不饱和烃的情况下，末端碳-碳双键优先被氢化。此外，还阐明了在该催化剂系统下，对具有多个双键的化合物实现了高度区域选择性氢化。因此，提出了一个关于这一催化剂系统的反应模型。
• Catalytic Asymmetric Allylic and Homoallylic Diamination of Terminal Olefins via Formal C−H Activation
  作者：Haifeng Du、Baoguo Zhao、Yian Shi

  DOI：10.1021/ja8027394

  日期：2008.7.1

  This paper describes a catalytic asymmetric diamination process for terminal olefins at allylic and homoallylic carbons via formal C-H activation using di-tert-butyldiaziridinone as nitrogen source with a catalyst generated from Pd2(dba)3 and chiral phosphorus amidite ligand. A wide variety of readily available terminal olefins can be effectively diaminated in good yields with high regio-, diastereo-

  本文描述了使用二叔丁基二氮杂环丙烷酮作为氮源和由 Pd2(dba)3 和手性磷亚胺配体生成的催化剂，通过形式 CH 活化在烯丙基和均烯丙基碳上对末端烯烃进行催化不对称二胺化过程。多种易于获得的末端烯烃可以以良好的收率有效地二胺化，并具有高区域选择性、非对映选择性和对映选择性。
• Remarkable axial ligand effect on regioselectivity towards terminal alkenes in epoxidation of dienes by a robust manganese porphyrin
  作者：Tat-Shing Lai、Stephen K. S. Lee、Lam-Lung Yeung、Hai-Yang Liu、Ian D. Williams、Chi K. Chang

  DOI：10.1039/b210645k

  日期：2003.2.20

  With a highly encumbered manganese porphyrin as catalyst, significant improvements in regioselectivity towards less substituted C-C double bond in diene epoxidation were attained by simply adding organic bases as axial ligand.

  用高度阻碍的锰卟啉作为催化剂，通过简单地添加有机碱作为轴向配体，在向二烯环氧化中较少取代的CC双键的区域选择性上获得了显着的改善。
• Room-Temperature <i>Z</i>-Selective Homocoupling of α-Olefins by Tungsten Catalysts
  作者：Smaranda C. Marinescu、Richard R. Schrock、Peter Müller、Michael K. Takase、Amir H. Hoveyda

  DOI：10.1021/om200150c

  日期：2011.4.11

  3,5-Dimethylphenylimido complexes of tungsten can be prepared using procedures analogous to those employed for other tungsten catalysts, as can bispyrrolide species and MonoAryloxide-Pyrrolide (MAP) species. Homocouplings of 1-hexene, 1-octene, and methyl 10-undecenoate are achieved in 45-89% yield and a Z selectivity of > 99% with W(NAr '')-(C3H6)(pyr)(OHIPT) as a catalyst. Homocoupling of terminal olefins in the presence of (E)-olefins elsewhere in the molecule also was achieved with excellent selectivity.