(E)-1-[4-(5-hydroxy-1-pentenyl)phenyl]ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-[4-(5-hydroxy-1-pentenyl)phenyl]ethanone
• 英文别名: 1-[4-[(E)-5-hydroxypent-1-enyl]phenyl]ethanone
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: WRDIWBSUWPNDHT-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-戊炔-1-醇 、 4-碘代苯乙酮 在 t-Bu₃P-Pt(1,3-divinyl-1,1,3,3-tetramethyldisiloxane) 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 1,1,3,3-四甲基二硅氧烷 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以82%的产率得到(E)-1-[4-(5-hydroxy-1-pentenyl)phenyl]ethanone
  参考文献：
  名称：

  Highly Stereoselective Hydrocarbation of Terminal Alkynes via Pt-Catalyzed Hydrosilylation/Pd-Catalyzed Cross-Coupling Reactions

  摘要：

  [GRAPHICS]The formal addition of an aryl-H or alkenyl-H bond across a terminal alkyne has been accomplished by the combination of platinum-catalyzed hydrosilylation followed by palladium-catalyzed cross-coupling, The use of the t-Bu3P-Pt(DVDS) catalyst in combination with tetramethyldisiloxane gave excellent regio- and stereoselectivity with a number of alkyne substrates, Subsequent, fluoride-promoted cross-coupling proceeded in high yield and stereospecificity for a variety of aryl halides.

  DOI：

  10.1021/ol0156751

文献信息

• Regioselective Heck arylation of unsaturated alcohols by palladium catalysis in ionic liquid
  作者：Jun Mo、Lijin Xu、Jiwu Ruan、Shifang Liu、Jianliang Xiao

  DOI：10.1039/b608033b

  日期：——

  In contrast to almost all of the known examples of Heck arylation of unsaturated alcohols, which yield predominately β-arylated products, arylation under the Pd-DPPP catalysis in ionic liquid leads preferentially to aryl substitution at the α carbon, providing an easy pathway to this valuable class of olefins.

  与已知的不饱和醇的Heck芳基化反应几乎所有的例子（主要产生β-芳基化产物）不同，在离子液体中，Pd-DPPP催化下的芳基化反应优先导致α碳上的芳基取代，为这一类有价值的烯烃提供了便捷的合成途径。
• Highly Stereoselective Hydrocarbation of Terminal Alkynes via Pt-Catalyzed Hydrosilylation/Pd-Catalyzed Cross-Coupling Reactions
  作者：Scott E. Denmark、Zhigang Wang

  DOI：10.1021/ol0156751

  日期：2001.4.1

  [GRAPHICS]The formal addition of an aryl-H or alkenyl-H bond across a terminal alkyne has been accomplished by the combination of platinum-catalyzed hydrosilylation followed by palladium-catalyzed cross-coupling, The use of the t-Bu3P-Pt(DVDS) catalyst in combination with tetramethyldisiloxane gave excellent regio- and stereoselectivity with a number of alkyne substrates, Subsequent, fluoride-promoted cross-coupling proceeded in high yield and stereospecificity for a variety of aryl halides.