(E)-1-phenyl-1-trimethylsilylbut-2-ene | 146566-29-2

• 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)-1-phenyl-1-trimethylsilylbut-2-ene
• 英文别名: trimethyl-[(E)-1-phenylbut-2-enyl]silane
• CAS: 146566-29-2
• 化学式: C₁₃H₂₀Si
• 分子量: 204.387
• InChiKey: ZSLFISUVTSGYRT-WEVVVXLNSA-N

物化性质

• 沸点：
  240.9±9.0 °C(predicted)
• 密度：
  0.870±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (E)-1-phenyl-1-trimethylsilylbut-2-ene 在 碳酸氢钠 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成 rac-(Z)-4-phenylbut-3-en-2-ol
  参考文献：
  名称：

  Optically active allylsilanes. 8. Stereochemistry in the reaction of optically active allylsilanes with m-chloroperoxybenzoic acid

  摘要：

  DOI：

  10.1021/jo00196a023
• 作为产物：
  描述：

  (E)-cinnamic acid benzyl ester 在 palladium on activated charcoal 氢气 、 N,N-二甲基甲酰胺二甲基缩醛 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 12.33h， 生成 (E)-1-phenyl-1-trimethylsilylbut-2-ene
  参考文献：
  名称：

  Fleming, Ian; Gil, Salvador; Sarkar, Achintya K., Journal of the Chemical Society. Perkin transactions I, 1992, # 24, p. 3351 - 3362

  摘要：

  DOI：

文献信息

• Regioselective Silylations of Propargyl and Allyl Pivalates through Ca-Promoted Reductive C(sp³)–O Bond Cleavage
  作者：Tianyuan Zhang、Suhua Zheng、Taro Kobayashi、Hirofumi Maekawa

  DOI：10.1021/acs.orglett.1c02532

  日期：2021.9.17

  1-phenylallyl pivalates was developed through reductive C(sp3)–O bond cleavage. This method represents the first example of the direct application of vastly abundant calcium granules to a reductive coupling reaction. A broad range of propargylsilanes and allylsilanes are simply prepared using easy-to-handle pivalates and chlorotrimethylsilane under mild catalyst-free and additive-free conditions.

  通过还原 C(sp 3 )–开发了一种从易于获得的 3-苯基炔丙基和 1-苯基烯丙基新戊酸酯区域选择性制备 3-苯基炔丙基硅烷和 3-苯基烯丙基硅烷的实用方案，产率分别为 36-77% 和 48-86%。O 键断裂。这种方法代表了将大量钙颗粒直接应用于还原偶联反应的第一个例子。在温和的无催化剂和无添加剂的条件下，使用易于处理的新戊酸酯和氯三甲基硅烷可以简单地制备各种炔丙基硅烷和烯丙基硅烷。
• Diastereoselective aldol reactions of β-silylenolates: a new regiocontrolled synthesis of allylsilanes
  作者：Lan Fleming、Achintya K. Sarkar

  DOI：10.1039/c39860001199

  日期：——

  Allylsilanes are prepared stereospecifically trans(10) or cis(12) and with complete regiocontrol by decarboxylative elimination of the β-hydroxy acids (9).

  通过立体定向反式（10）或顺式（12）制备烯丙基硅烷，并通过β-羟基酸的脱羧消除来完全控制区域（9）。
• Silylation of Allylic Trifluoroacetates and Acetates Using Organodisilanes Catalyzed by Palladium Complex
  作者：Yasushi Tsuji、Masahiro Funato、Masakatsu Ozawa、Hiroaki Ogiyama、Satoshi Kajita、Takashi Kawamura

  DOI：10.1021/jo960345t

  日期：1996.1.1

  Silylation of allylic acetates (1) using organodisilanes (2) was carried out in the presence of a catalytic amount of Pd(DBA)2-LiCl at 100 degrees C. The silylation proceeded smoothly without beta-hydrogen elimination of. resulting (pi-allyl)palladium intermediate. The added chloride salt such as LiCl or NaCl was indispensable for the catalytic activity. On the other hand, remarkable improvement of the silylation was realized by employing allylic trifluoroacetates (4) in place of the acetates (1) as the substrates. The silylation proceeded even at room temperature, and the added chloride salts was not necessary as the catalyst component. In the silylation, transmetalation of the disilanes (2) with (eta(3)-allyl)palladium intermediate (7) might be a critical step in the catalytic cycle. Model reactions for the transmetalation were carried out.
• Fleming, Ian; Higgins, Dick; Lawrence, Nicholas J., Journal of the Chemical Society. Perkin transactions I, 1992, # 24, p. 3331 - 3350
  作者：Fleming, Ian、Higgins, Dick、Lawrence, Nicholas J.、Thomas, Andrew P.

  DOI：——

  日期：——
• Synthesis of Allylsilanes by Reductive Lithiation of Thioethers
  作者：Stéphane Streiff、Nigel Ribeiro、Laurent Désaubry

  DOI：10.1021/jo049237u

  日期：2004.10.1

  Although much work in reductive lithiation has been done, the utilization of allylthioethers bearing various substituents to prepare allylsilanes has not been explored. The main reason clearly stems from the anticipated lack of regioselectivity. We describe herein the first study on the regioselectivity of the reductive silylation involving dissymmetric allylthioethers. We surveyed a broad spectrum of parameters and showed that this process displays a great dependence of the reaction conditions. We also discovered that an electron transporter, DBB or naphthalene, can cleave THF at room temperature by sonication, to generate a strong base, 4-lithiobutoxide. This feature was successfully exploited to the straightforward synthesis of bis-silanes in one pot. Examples are provided for maximizing both the chemical yield and the regioselectivity of the reductive silylation through the tuning of the reaction conditions. By changing these conditions, several allylsilanes can be selectively synthesized from one thioether.