(E)-5-phenyl-5-decene | 66619-22-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-5-phenyl-5-decene
• 英文别名: (E)-5-phenyldec-5-ene；[(1E)-1-butyl-1-hexenyl]benzene；[(E)-dec-5-en-5-yl]benzene
• CAS: 66619-22-5
• 化学式: C₁₆H₂₄
• 分子量: 216.367
• InChiKey: OKQXJTHODYIKCT-NTCAYCPXSA-N

物化性质

• 沸点：
  298.6±7.0 °C(Predicted)
• 密度：
  0.867±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  溴苯 在 CoBr₂(bpy) 、 3-氯丙烯 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 0.58h， 生成 (E)-5-phenyl-5-decene
  参考文献：
  名称：

  Cobalt-catalysed synthesis of highly substituted styrene derivatives via arylzincation of alkynes

  摘要：

  一种新的两步法被开发出来，通过对内烯和末端炔的碳锌化反应合成高功能化的乙烯基锌溴化物。在温和的反应条件下，以立体选择性的方式制备了多种三取代和四取代烯烃，产率中等到好。这种方法代表了一种有趣的替代方案，优于已知的其他方法。

  DOI：

  10.1039/c2cc36676b

文献信息

• Palladium-catalyzed cross-coupling reaction of alkenylalkoxysilanes with aryl and alkenyl halides in the presence of a fluoride ion
  作者：Kohei Tamao、Kenji Kobayashi、Yoshihiko Ito

  DOI：10.1016/s0040-4039(01)93852-3

  日期：1989.1

  trialkoxysilanes undergo palladium-catalyzed cross-coupling reaction with alkenyl and aryl halides in the presence of tetra-n-butylammonium fluoride. A one-pot transformation of a homopropargyl alcohol to regio- and stereo-defined trisubstituted homoallyl alcohols has been achieved by a sequence of intramolecular hydrosilation and the palladium-catalyzed coupling reaction.

  在氟化四正丁基铵存在下，烯基单烷氧基二甲基硅烷，二烷氧基甲基硅烷和三烷氧基硅烷与烯基卤化物和芳基卤化物进行钯催化的交叉偶联反应。通过一系列的分子内硅氢化反应和钯催化的偶联反应，已经实现了高炔丙醇向区域和立体定义的三取代均烯丙基醇的一锅转化。
• Recyclable and reusable PdCl₂(PPh₃)₂/PEG-400/H₂O system for the hydrophenylation of alkynes with sodium tetraphenylborate
  作者：Rong Liu、Tingli Zhang、Bin Huang、Mingzhong Cai

  DOI：10.1177/1747519820934379

  日期：2021.1

  A stable and efficient PdCl₂(PPh₃)₂/PEG-400/H₂O catalytic system for the hydrophenylation reaction of alkynes has been developed. In the presence of 3 mol% PdCl₂(PPh₃)₂ and 2 equiv. of HOAc, the hydrophenylation of both terminal and internal alkynes with sodium tetraphenylborate proceeded smoothly in a mixture of PEG-400 and water at room temperature or 50 °C to afford a variety of phenyl-substituted alkenes in moderate to high yields. The isolation of the products was easily performed by extraction with petroleum ether, and the PdCl₂(PPh₃)₂/PEG-400/H₂O system could be readily recycled and reused six times without apparent loss of catalytic activity.

  已开发出一种稳定高效的PdCl₂(PPh₃)₂/PEG-400/H₂O催化体系，用于炔烃的加氢苯基化反应。在存在3 mol% PdCl₂(PPh₃)₂和2当量的HOAc的情况下，终末和内部炔烃与四苯硼酸钠在PEG-400和水的混合物中在室温或50 °C下顺利进行了苯基化反应，产率中等到较高。 产品的分离可通过石油醚萃取轻松进行，PdCl₂(PPh₃)₂/PEG-400/H₂O体系可轻松回收和重复使用六次而无明显失活。
• Palladium‐Catalyzed C−H Alkenylation of Arenes with Alkynes: Stereoselective Synthesis of Vinyl Chlorides via a 1,4‐Chlorine Migration
  作者：Zhen Li、Wei‐Liang Duan

  DOI：10.1002/anie.201808866

  日期：2018.12.3

  A directing group‐free, ligand‐promoted palladium‐catalyzed C−H arylation of internal alkynes with simple arenes was developed. Alkenyl chlorides resulting from a 1,4‐chlorine migration or trisubstituted alkenes were produced in moderate to good yields depending on the type of alkyne.

  开发了一种无配位基团，配体促进钯催化的内部炔烃与简单芳烃的CH芳基化反应。由1,4-氯迁移或三取代烯烃制得的链烯基氯化物，根据炔烃的类型，以中等至良好的收率生产。
• Chalcogen electrophile induced rearrangement of 1-alkynyltrialkyl borates: controlled syntheses of trisubstituted olefins from 1-alkynes
  作者：Julien Gerard、László Hevesi

  DOI：10.1016/s0040-4020(01)00904-8

  日期：2001.10

  The reaction of 1-alkynyltrialkyl borates with sulfenyl, selenenyl and tellurenyl halides produces β-chalcogeno alkenylboranes in good yields, with a cis relationship between the boron and the chalcogen moities. Protodeborylation of these compounds by acetic acid, or by a transmetalation–protonolysis sequence, leads to vinyl chalcogenides, which can be converted to alkenes by means of a nickel catalyzed

  1-炔基三烷基硼酸酯与亚硫基，亚硒基和碲基卤化物的反应以良好的产率产生β-硫属元素烯基硼烷，其中硼与硫属元素之间具有顺式关系。这些化合物通过乙酸或通过金属转移-质子分解序列进行原脱硼化反应，生成乙烯基硫属元素化物，可以通过镍与格利雅试剂的偶联将其转化为烯烃。由于最后两个步骤是在保留立体化学的情况下发生的，因此整个序列代表了高度区域和立体选择性的烯烃合成。
• Stereoselective <i>cis</i>-Addition of Aromatic C−H Bonds to Alkynes Catalyzed by Dinuclear Palladium Complexes
  作者：Naofumi Tsukada、Tomohiro Mitsuboshi、Hiroyuki Setoguchi、Yoshio Inoue

  DOI：10.1021/ja0375075

  日期：2003.10.1

  Reactions of alkynes with arenes proceeded in the presence of dinuclear palladium complexes and trialkylboranes to yield alkyne hydroarylation products with high stereoselectivity. In the reactions of monosubstituted benzenes, meta and para products were formed in statistical ratios, while no ortho isomers were detected.

  炔烃与芳烃的反应在双核钯配合物和三烷基硼烷的存在下进行，以产生具有高立体选择性的炔烃加氢芳基化产物。在单取代苯的反应中，间位和对位产物以统计比例形成，而没有检测到邻位异构体。