(E)-(1,2-diphenylvinyl)trimethylsilane | 57266-93-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-(1,2-diphenylvinyl)trimethylsilane
• 英文别名: [(E)-1,2-diphenylethenyl]-trimethylsilane
• CAS: 57266-93-0
• 化学式: C₁₇H₂₀Si
• 分子量: 252.431
• InChiKey: VGTMRFDPRSLOHW-SAPNQHFASA-N

物化性质

• 沸点：
  318.6±31.0 °C(Predicted)
• 密度：
  0.966±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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)-(1,2-diphenylvinyl)trimethylsilane 在 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 (E)-(1-fluoroethene-1,2-diyl)dibenzene 、 (Z)-(1-fluoro-2-phenylethenyl)benzene
  参考文献：
  名称：

  Acceleration of alkenyltrimethylsilane fluorination under mild conditions using ultrasound

  摘要：

  Alkenyltrimethylsilanes are selectively fluorodesilated to alkenyl fluoride very readily by reaction with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2,2,2]octane bis-tetrafluoroborate (Selectfluor) and N-fluorobenzensulfonimids at room temperature under ultrasound. In the presence of ultrasound irradiation in the case atone of the reactions, the yield was 85% after 25 min, but using the previously established thermal method the yield was only 32% after 20 h. Crown Copyright (C) 2010 Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2010.02.007
• 作为产物：
  描述：

  乙烯基三甲基硅烷 在 palladium diacetate 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 生成 (E)-(1,2-diphenylvinyl)trimethylsilane
  参考文献：
  名称：

  Ikenaga, Kazutoshi; Kikukawa, Kiyoshi; Matsuda, Tsutomu, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1959 - 1964

  摘要：

  DOI：

文献信息

• An Electroreductive Approach to Radical Silylation via the Activation of Strong Si–Cl Bond
  作者：Lingxiang Lu、Juno C. Siu、Yihuan Lai、Song Lin

  DOI：10.1021/jacs.0c10899

  日期：2020.12.23

  In this context, reactions mediated by silyl radicals have become increasingly attractive but methods for accessing these intermediates remain limited. We present a new strategy for silyl radical generation via electroreduction of readily available chlorosilanes. At highly biased potentials, electrochemistry grants access to silyl radicals through energetically uphill reductive cleavage of strong

  C(sp3)-Si 键的构建在合成、医药和材料化学中很重要。在这种情况下，由甲硅烷基介导的反应变得越来越有吸引力，但获得这些中间体的方法仍然有限。我们提出了一种通过电还原容易获得的氯硅烷来生成甲硅烷基自由基的新策略。在高度偏置的电位下，电化学通过强 Si-Cl 键的能量上坡还原裂解获得甲硅烷基自由基。事实证明，该策略在简单且无过渡金属条件下的各种烯烃甲硅烷化反应中是通用的，包括二甲硅烷基化、氢化甲硅烷基化和烯丙基甲硅烷基化。
• Regioselective Synthesis of α-Functional Stilbenes via Precise Control of Rapid <i>cis</i>–<i>trans</i> Isomerization in Flow
  作者：Hyune-Jea Lee、Yuya Yonekura、Nayoung Kim、Jun-ichi Yoshida、Heejin Kim

  DOI：10.1021/acs.orglett.1c00538

  日期：2021.4.16

  The rapid cis–trans isomerization of α-anionic stilbene was regioselectively controlled by using flow microreactors, and its reaction with various electrophiles was conducted. The reaction time was precisely controlled within milliseconds to seconds at −50 °C to selectively give the cis- or trans-isomer in high yields. This synthetic method in flow was well-applied to synthesize precursors of commercial

  通过使用流动微反应器可选择性地控制α-阴离子的快速顺式-反式异构化，并使其与各种亲电试剂进行反应。将反应时间精确控制在-50°C的毫秒至秒之间，以高收率选择性地产生顺式或反式异构体。这种流动的合成方法被很好地用于合成具有高区域选择性和生产率的商品药物化合物（E）-和（Z）-他莫昔芬的前体。
• Stereospecific phenylation of alkenylsilanes with phenylpalladium acetate
  作者：Kiyoshi Kikukawa、Kazutoshi Ikenaga、Fumio Wada、Tsutomu Matsuda

  DOI：10.1016/s0040-4039(01)81687-7

  日期：1984.1

  (E)- and (Z)-RCH=CHSiMe3(R=Ph, n-C6H13, CH3OCH2) reacted stereospecifically with Ph-Pd-OAc to give RCH=C(Ph)SiMe3 and R(Ph)C=CHSiMe3 with inversion of the starting geometry with respect to R and Me3Si groups.

  （E）-和（Z）-RCH ＝ CHSiMe 3（R ＝ Ph，nC 6 H 13，CH 3 OCH 2）与Ph-Pd-OAc立体反应，得到RCH ＝ C（Ph）SiMe 3和R（Ph C ＝ CHSiMe 3，相对于R和Me 3 Si基团，起始几何形状反转。
• Stereoselective Synthesis of Silylated Vinylboronates by a Boron‐Wittig Reaction and Their Application to Tetrasubstituted Olefins
  作者：Subrata Hazra、Santanu Panda

  DOI：10.1002/chem.202303056

  日期：2024.2.12

  series of tetrasubstituted silylated pinacol vinylboronates and trisubstituted silylated vinyl MIDA-boronates was synthesized by using the boron-Wittig approach. By using this protocol, the boryl and the silyl groups can be directly and highly stereoselectively incorporated into the olefin‘s anti-position. Further, sequential Suzuki coupling of the silylated vinyl boronates allows access to several

  采用硼-维蒂希法合成了一系列四取代甲硅烷基化频哪醇乙烯基硼酸酯和三取代甲硅烷基化乙烯基MIDA-硼酸酯。通过使用该方案，硼基和甲硅烷基可以直接且高度立体选择性地结合到烯烃的反位中。此外，硅烷化乙烯基硼酸酯的连续 Suzuki 偶联可以得到几种全碳四取代烯烃、抗癌药物他莫昔芬和 AIEgen 试剂 TPE-TF17。
• Stereospecific arylation of alkenylsilanes with arylpalladium acetates
  作者：Kazutoshi Ikenaga、Kiyoshi Kikukawa、Tsutomu Matsuda

  DOI：10.1021/jo00383a019

  日期：1987.4