trans-1-(triethylsilyl)-1-buten-4-ol | 157986-05-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: trans-1-(triethylsilyl)-1-buten-4-ol
• 英文别名: (E)-1-(Triethylsilyl)-1-buten-4-ol；(E)-4-(triethylsilyl)but-3-en-1-ol；(E)-1-triethylsilyl-1-buten-4-ol；(E)-1-triethylsilylbut-1-en-4-ol；E-1-triethylsilyl-1-buten-4-ol；4-(triethylsilyl)-1-but-3-enol；(E)-4-triethylsilylbut-3-en-1-ol
• CAS: 157986-05-5
• 化学式: C₁₀H₂₂OSi
• 分子量: 186.37
• InChiKey: ADNFSAYBXCQLFL-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-氯苯磺酰氯 、 trans-1-(triethylsilyl)-1-buten-4-ol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以76%的产率得到(E)-4-triethylsilylbut-3-enyl 4-chlorobenzenesulfonate
  参考文献：
  名称：

  氮杂环丁烷-2-酮生成的涉及π-亲核试剂和N-酰基亚胺阳离子的分子内取代反应

  摘要：

  报道了路易斯酸催化的4-乙烯基氧基-或4-酰氧基-氮杂环丁烷-2-酮与氮键合的烯丙基，炔丙基和乙烯基硅烷的分子内取代反应，从而导致咔唑或萘草。没有观察到碳青霉烯的形成。为了说明这些反应在固相条件下进行的潜力，通过环化/裂解方法进行了非对映异构的5-乙烯基碳烯化合物的合成。

  DOI：

  10.1016/j.tet.2010.03.108
• 作为产物：
  描述：

  三乙基硅烷 、 3-丁炔-1-醇 以97%的产率得到trans-1-(triethylsilyl)-1-buten-4-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

• 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.
• A palladium-mediated tandem carbon-carbon bond forming method featuring nucleophilic substitution of intermediate π-allylpalladium complexes produced via the heck reaction
  作者：Christine S. Nylund、Daniel T. Smith、John M. Klopp、Steven M. Weinreb

  DOI：10.1016/0040-4020(95)00518-d

  日期：1995.8

  Carbon nucleophiles are alkylated with π-allylpalladium complexes formed by the palladium-catalyzed Heck reaction of a vinyl bromide and an olefin. This methodology achieves the consecutive formation of two carbon-carbon bonds in one simple operation and can be applied both inter- and intramolecularly. The rapid construction of functionalized carbobicyclic compounds is effected by the intramolecular

  碳亲核体被通过钯催化的乙烯基溴和烯烃的Heck反应形成的π-烯丙基铝络合物烷基化。该方法通过一次简单的操作即可连续形成两个碳-碳键，并且可以在分子内和分子内应用。官能化碳双环化合物的快速构建受此缩合的分子内形式影响。
• A recyclable and reusable K₂PtCl₄/Xphos-SO₃Na/PEG-400/H₂O system for highly regio- and stereoselective hydrosilylation of terminal alkynes
  作者：Caifeng Xu、Bin Huang、Tao Yan、Mingzhong Cai

  DOI：10.1039/c7gc02823g

  日期：——

  K2PtCl4/Xphos-SO3Na in a mixture of poly(ethylene glycol) (PEG-400) and water is shown to be a highly regio- and stereoselective catalyst for the hydrosilylation of terminal alkynes with hydrosilanes. The reaction could be conducted under mild conditions, yielding a variety of functionalized β-(E)-vinylsilanes in good to excellent yields with a total β-(E)-selectivity. The isolation of the products

  在聚（乙二醇）（PEG-400）和水的混合物中，K 2 PtCl 4 / Xphos-SO 3 Na被证明是高度炔和立体选择性的催化剂，用于末端炔烃与氢硅烷的硅氢化反应。该反应可以在温和的条件下进行，以良好的至优异的产率产生各种官能化的β-（E）-乙烯基硅烷，并具有总的β-（E）-选择性。产物的分离很容易通过环己烷萃取，更重要的是，在PEG-400 / H 2中用昂贵的K 2 PtCl 4和Xphos-SO 3 Na萃取。O系统可以轻松回收再利用至少八次，而不会损失任何催化活性。
• Gold-Film-Catalysed Hydrosilylation of Alkynes by Microwave-Assisted, Continuous-Flow Organic Synthesis (MACOS)
  作者：Gjergji Shore、Michael G. Organ

  DOI：10.1002/chem.200801610

  日期：2008.10.29

  Thin gold films on the surface of glass capillaries have proven to be highly active catalysts for the rapid hydrosilylation of alkynes that are flowed through the reactor while being heated by microwave irradiation. The films are able to be reused at least five times with no loss of activity and with no detectable levels of gold showing up in the hydrosilylated products.

  事实证明，玻璃毛细管表面的金薄膜是用于炔烃快速氢化硅烷化的高活性催化剂，这些炔烃在通过微波辐射加热的同时流经反应器。该膜能够重复使用至少五次，而不会丧失活性，并且在氢化硅烷化产物中不会出现可检测的金含量。
• A highly regio- and stereoselective transition metal-catalyzed hydrosilylation of terminal alkynes under ambient conditions of air, water, and room temperature
  作者：Wei Wu、Chao-Jun Li

  DOI：10.1039/b302259e

  日期：——

  A highly efficient and stereoselective hydrosilylation of terminal alkynes was developed at room temperature in air and water.

  在室温下在空气和水中开发了末端炔烃的高效和立体选择性氢化硅烷化。