(E,E)-1-(Triethylsilyl)-5-phenyl-1,4-pentadien-3-ol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E,E)-1-(Triethylsilyl)-5-phenyl-1,4-pentadien-3-ol
• 英文别名: (1E,4E)-1-phenyl-5-triethylsilylpenta-1,4-dien-3-ol
• 化学式: C₁₇H₂₆OSi
• 分子量: 274.478
• InChiKey: VVHSUBAFFFRWBI-SQIWNDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  三乙基硅烷 、 (E)-1-phenylpent-1-en-4-yn-3-ol 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 三苯基膦 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以90%的产率得到(E,E)-1-(Triethylsilyl)-5-phenyl-1,4-pentadien-3-ol
  参考文献：
  名称：

  Cationic rhodium complex-catalysed highly selective hydrosilylation of propynylic alcohols: a convenient synthesis of (E)-γ-silyl allylic alcohols

  摘要：

  阳离子铑络合物催化的烷-1-炔醇（包括丙炔醇）与三乙基硅烷的硅氢化反应具有高度的选择性，能够以极佳的产率生成产物（E）-1-三乙基硅基烷-1-醇。

  DOI：

  10.1039/c39940001777

文献信息

• Cationic rhodium complex-catalysed highly selective hydrosilylation of propynylic alcohols: a convenient synthesis of (E)-γ-silyl allylic alcohols
  作者：Ryo Takeuchi、Shuichi Nitta、Dai Watanabe

  DOI：10.1039/c39940001777

  日期：——

  Cationic rhodium compex-catalysed hydrosilylation of alk-1-ynols including propynylic alcohols with triethylsilane is highly selective to give (E)-1-triethylsilyl alk-1-enols as products in excellent yields.

  阳离子铑络合物催化的烷-1-炔醇（包括丙炔醇）与三乙基硅烷的硅氢化反应具有高度的选择性，能够以极佳的产率生成产物（E）-1-三乙基硅基烷-1-醇。
• Takeuchi Ryo, Nitta Shuichi, Watanabe Dai, J. Chem. Soc. Chem. Commun, (1994) N 15, S 1777-1778
  作者：Takeuchi Ryo, Nitta Shuichi, Watanabe Dai

  DOI：——

  日期：——
• A Selective Synthesis of (E)-Vinylsilanes by Cationic Rhodium Complex-Catalyzed Hydrosilylation of 1-Alkynes and Tandem Hydrosilylation/Isomerization Reaction of Propargylic Alcohols to .beta.-Silyl Ketones
  作者：Ryo Takeuchi、Shuichi Nitta、Dai Watanabe

  DOI：10.1021/jo00115a020

  日期：1995.5

  (E)-Vinylsilanes were obtained with high selectivities by [Rh(COD)(2)]BF4/2PPh(3)-catalyzed hydrosilylation of 1-alkynes with triethylsilane. A wide range of 1-alkynes were used. The hydrosilylation of propargylic alcohols with triethylsilane gave (E)-gamma-silyl allylic alcohols 2h-r, a useful source of a chiral alcohol, with high selectivities in excellent yields. The reaction can be carried out without protecting the alcohol functionality. The resulting (E)-gamma-silyl allylic alcohols could be transformed into beta-silyl ketones. The isomerization was also catalyzed by [Rh(COD)(2)]BF4/2PPh(3). Furthermore, the tandem hydrosilylation-isomerization of secondary propargylic alcohols could be carried out in a one-pot procedure.

  （E）-丙二烯二硅烷通过使用[Rh(COD)(2)]BF4/2PPh(3)协同催化的水硅化反应获得了高选择性，适用于多种一元炔烃底物。丙炔醇的水硅化反应产生γ-硅基 allylic 醇2h-R，并提供了一种高效产率的构象选择性高的旋多糖醇。该反应无需保护醇的功能性即可进行。由此产生的（E）-γ-硅基 allylic 醇可以通过转化得到β-硅基酮。此外，该[Rh(COD)(2)]BF4/2PPh(3)催化还可以催化丙炔醇的同分异构化反应。Furthermore, a one-pot tandem hydrosilylation-isomerization of secondary propargylic alcohols can be achieved using this approach.