(E)-1-phenyl-3(R)-(trimethylsilyl)-1-butene | 144789-20-8

• 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-3(R)-(trimethylsilyl)-1-butene
• 英文别名: (E)-1-phenyl-3(S)-(trimethylsilyl)-1-butene；(E)-trimethyl(4-phenylbut-3-en-2-yl)silane；trimethyl-[(E)-4-phenylbut-3-en-2-yl]silane
• CAS: 144789-20-8
• 化学式: C₁₃H₂₀Si
• 分子量: 204.387
• InChiKey: HZIQEHHHYNFRDI-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 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-3(R)-(trimethylsilyl)-1-butene 在 palladium on activated charcoal 氢气 作用下， 以 苯 为溶剂， 以96%的产率得到1-phenyl-3-(trimethylsilyl)butane
  参考文献：
  名称：

  Asymmetric synthesis catalyzed by chiral ferrocenylphosphine-transition metal complexes. 3. Preparation of optically active allylsilanes by palladium-catalyzed asymmetric Grignard cross-coupling

  摘要：

  DOI：

  10.1021/jo00370a006
• 作为产物：
  描述：

  烯丙苯 、 alkaline earth salt of/the/ methylsulfuric acid 在 仲丁基锂 作用下， 反应 2.75h， 生成 (E)-1-phenyl-3(R)-(trimethylsilyl)-1-butene
  参考文献：
  名称：

  Lamothe, S.; Cook, K. L.; Chan, T. H., Canadian Journal of Chemistry, 1992, vol. 70, # 6, p. 1733 - 1742

  摘要：

  DOI：

文献信息

• Attenuation of Ni(0) Decomposition: Mechanistic Insights into AgF-Assisted Nickel-Mediated Silylation
  作者：Venkadesh Balakrishnan、Vetrivelan Murugesan、Bincy Chindan、Ramesh Rasappan

  DOI：10.1021/acs.inorgchem.1c03108

  日期：2022.1.24

  species remains elusive. Recently, both Ni(0) and Ni(I) intermediate complexes are identified as active species in Kumada cross-coupling reactions. Control experiments in combination with 31P nuclear magnetic resonance (NMR) suggest that AgF attenuates the decomposition of in situ generated Ni(0) species. The plausible Ni(0) and Ni(I) intermediate complexes were synthesized, and experimental findings

  在镍介导的 Kumada 交叉偶联反应中，通常会原位生成低价活性镍络合物，而配体通常控制这些络合物的反应性或稳定性。但是，如果后续反应缓慢，活性镍络合物的分解是不可避免的。虽然我们最近开发了 AgF 辅助镍催化来交叉偶联甲基醚和甲硅烷基镁试剂，但 AgF 和实际活性镍物种的有趣催化作用仍然难以捉摸。最近，Ni(0) 和 Ni(I) 中间配合物被确定为 Kumada 交叉偶联反应中的活性物质。结合31个对照实验P 核磁共振 (NMR) 表明 AgF 减弱了原位生成的 Ni(0) 物种的分解。合成了似是而非的 Ni(0) 和 Ni(I) 中间配合物，实验结果与 Ni(0)/Ni(II) 而不是 Ni(I)/Ni(III) 的实际催化循环一致。
• 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.
• Nickel-Mediated Enantiospecific Silylation via Benzylic C–OMe Bond Cleavage
  作者：Venkadesh Balakrishnan、Vetrivelan Murugesan、Bincy Chindan、Ramesh Rasappan

  DOI：10.1021/acs.orglett.0c04316

  日期：2021.2.19
• Regio- and stereoselective synthesis of allylsilanes using (methylphenylamino) tributylphosphonium iodine
  作者：Yoshio Tanigawa、Yoshihide Fuse、Shun-Ichi Murahashi

  DOI：10.1016/s0040-4039(00)86888-4

  日期：1982.1
• TANIGAWA, YOSHIO;FUSE, YOSHIHIDE;MURAHASHI, SHUN-ICHI, TETRAHEDRON LETT., 1982, 23, N 5, 557-560
  作者：TANIGAWA, YOSHIO、FUSE, YOSHIHIDE、MURAHASHI, SHUN-ICHI

  DOI：——

  日期：——