1-(4-(5-methylhex-1-en-2-yl)phenyl)ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-(5-methylhex-1-en-2-yl)phenyl)ethanone
• 英文别名: 1-[4-(5-Methylhex-1-en-2-yl)phenyl]ethanone；1-[4-(5-methylhex-1-en-2-yl)phenyl]ethanone
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: XDAPJKBJXVGWNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-碘代苯乙酮 、 dimethyl(5-methylhex-1-en-2-yl)(perfluorophenyl)silane 在 四丁基氟化铵 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以87%的产率得到1-(4-(5-methylhex-1-en-2-yl)phenyl)ethanone
  参考文献：
  名称：

  Diversity-Oriented Synthesis of Disubstituted Alkenes Using Masked Silanols

  摘要：

  The regio- and stereoselective synthesis and subsequent Hiyama cross coupling of pentafluorophenyldimethylvinylsilanes has been developed, thus providing a convenient and robust method for the diversity-oriented synthesis of (E)-, (Z)- and alpha-disubstituted alkenes from terminal alkynes. Pentafluorophenyldimethylvinylsilanes undergo cross-coupling reactions with excellent selectivity and in good yields, offering an attractive alternative to existing masked silanols.

  DOI：

  10.1021/ol100895d

文献信息

• Vinyldisiloxanes: their synthesis, cross coupling and applications
  作者：Hannah F. Sore、Christine M. Boehner、Luca Laraia、Patrizia Logoteta、Cora Prestinari、Matthew Scott、Katharine Williams、Warren R. J. D. Galloway、David R. Spring

  DOI：10.1039/c0ob00338g

  日期：——

  During the studies towards the development of pentafluorophenyldimethylsilanes as a novel organosilicon cross coupling reagent it was revealed that the active silanolate and the corresponding disiloxane formed rapidly under basic conditions. The discovery that disiloxanes are in equilibrium with the silanolate led to the use of disiloxanes as cross coupling partners under fluoride free conditions. Our previous report focused on the synthesis and base induced cross coupling of aryl substituted vinyldisiloxanes with aryl halides; good yields and selectivities were achieved. As a continuation of our research, studies into the factors which influence the successful outcome of the cross coupling reaction with both alkyl and aryl substituted vinyldisiloxanes were examined and a proposed mechanism discussed. Further investigation into expanding the breadth and diversity of substituted vinyldisiloxanes in cross coupling was explored and applied to the synthesis of unsymmetrical trans-stilbenes and cyclic structures containing the trans-alkene architecture.

  在开发五氟苯基二甲基硅烷作为新型有机硅交叉耦合试剂的研究中，发现活性硅醇盐和相应的二硅氧烷在碱性条件下迅速形成。二硅氧烷与硅醇盐之间的平衡发现，促使在无氟条件下将二硅氧烷用作交叉耦合反应的反应伙伴。我们之前的报告集中于芳基取代的乙烯基二硅氧烷与芳基卤化物的合成以及碱诱导的交叉耦合反应，取得了良好的产率和选择性。作为研究的延续，我们考察了影响烷基和芳基取代的乙烯基二硅氧烷交叉耦合反应成功的因素，并讨论了提出的机制。进一步研究扩展取代乙烯基二硅氧烷在交叉耦合中的广度和多样性，并应用于合成不对称的反式-stilbene和含有反式烯烃结构的环状化合物。
• Palladium-Tetraphosphine Catalysed Heck Reaction with Simple Alkenes: Influence of Reaction Conditions on the Migration of the Double Bond
  作者：Henri Doucet、Maurice Santelli、Yacoub Fall、Florian Berthiol

  DOI：10.1055/s-2007-966063

  日期：2007.6

  The Heck reaction of aryl halides with simple alk-1-enes is a powerful method for the synthesis of ( E)-1-arylalk-1-ene derivatives. The major problem of this reaction is the palladium-catalysed migration of the carbon-carbon double bond along the alkyl chain. We observed that this migration could be partially controlled using appropriate reaction conditions. The ramification of the alkyl chain and

  芳基卤化物与简单的 alk-1-enes 的 Heck 反应是合成 (E)-1-arylalk-1-ene 衍生物的有效方法。该反应的主要问题是钯催化的碳-碳双键沿烷基链的迁移。我们观察到使用适当的反应条件可以部分控制这种迁移。烷基链的分支和芳基卤化物上的取代基对这种迁移也有重要影响。CIS, CIS, CIS-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane/[Pd(C 3 H 5 )Cl] 2 体系有效催化多种芳基卤化物与直链烯烃的 Heck 反应-1-烯和癸-1-烯或支链烯烃4-甲基己-1-烯、5-甲基己-1-烯、烯丙基环戊烷或烯丙基环己烷。大多数情况下，获得了 70-80% 的选择性。在某些情况下，可以观察到高达 97% 有利于 (E)-1-arylalk-1-enes。此外，可以使用非常低的催化剂负载量进行几个反应。
• Diversity-Oriented Synthesis of Disubstituted Alkenes Using Masked Silanols
  作者：Hannah F. Sore、David T. Blackwell、Simon J. F. MacDonald、David R. Spring

  DOI：10.1021/ol100895d

  日期：2010.6.18

  The regio- and stereoselective synthesis and subsequent Hiyama cross coupling of pentafluorophenyldimethylvinylsilanes has been developed, thus providing a convenient and robust method for the diversity-oriented synthesis of (E)-, (Z)- and alpha-disubstituted alkenes from terminal alkynes. Pentafluorophenyldimethylvinylsilanes undergo cross-coupling reactions with excellent selectivity and in good yields, offering an attractive alternative to existing masked silanols.