(Z)-dimethyl(phenyl)(3,3,3-trifluoroprop-1-en-1-yl)silane | 1187552-61-9

• 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: (Z)-dimethyl(phenyl)(3,3,3-trifluoroprop-1-en-1-yl)silane
• 英文别名: (Z)-3,3,3-trifluoro-1-(dimethylphenylsilyl)propene；dimethyl-phenyl-[(Z)-3,3,3-trifluoroprop-1-enyl]silane
• CAS: 1187552-61-9
• 化学式: C₁₁H₁₃F₃Si
• 分子量: 230.305
• InChiKey: BMYBOMDXHJFZRJ-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,3,3-Trifluoro-1-(phenyldimethylsilyl)propyne 在 titanium(IV) isopropylate 、 异丙基氯化镁 、 水 作用下， 以 乙醚 为溶剂， 反应 3.5h， 以89%的产率得到(Z)-dimethyl(phenyl)(3,3,3-trifluoroprop-1-en-1-yl)silane
  参考文献：
  名称：

  Generation and Reactions of Trifluoromethylethenyl Titanium(II) Species

  摘要：

  The reaction of (trifluoromethyl)dimethylphenylsilyacetylene and (eta(2)-propene)Ti((OPr)-Pr-i)(2) generated in situ smoothly proceeded giving the corresponding (eta(2)-1-dimethylphenyl-silyl-2-trifluoromethylalkyne)Ti((OPr)-Pr-i)(2), which reacted with aldehydes and ketones to afford the corresponding addition products in good yields with good to excellent regioselectivity.

  DOI：

  10.1021/jo901392n

文献信息

• Fluorinated Vinylsilanes from the Copper-Catalyzed Defluorosilylation of Fluoroalkene Feedstocks
  作者：Hironobu Sakaguchi、Masato Ohashi、Sensuke Ogoshi

  DOI：10.1002/anie.201710866

  日期：2018.1.2

  Herein, a copper‐catalyzed C−F bond defluorosilylation reaction of tetrafluoroethylene and other polyfluoroalkenes is described. Mechanistic studies, based on a series of stoichiometric reactions with copper complexes, revealed that the key steps of this defluorosilylation reaction are 1) the 1,2‐addition of a silylcopper intermediate to the polyfluoroalkene and 2) a subsequent selective β‐fluorine

  在此，描述了四氟乙烯和其他多氟烯烃的铜催化的CF键脱氟甲硅烷基化反应。基于一系列与铜配合物的化学计量反应的机理研究表明，该脱氟甲硅烷基化反应的关键步骤是：1）将1,2-甲硅烷基铜中间体添加到多氟烯烃中，以及2）随后的选择性β-氟消除，生成Cu-F物种。Lewis酸性F-Bpin促进了β-氟的消除，这是在脱氟甲硅烷基化过程中原位产生的。
• Selective nickel-catalyzed fluoroalkylations of olefins
  作者：Shaoke Zhang、Florian Weniger、Fei Ye、Jabor Rabeah、Stefan Ellinger、Florencio Zaragoza、Christoph Taeschler、Helfried Neumann、Angelika Brückner、Matthias Beller

  DOI：10.1039/d0cc06652d

  日期：——

  Mild and selective nickel-catalyzed trifluoromethylation and perfluoroalkylation reactions of alkenes were developed to provide fluorinated olefins, including natural products, pharmaceuticals, and variety of synthetic building blocks in good to excellent yields (38 examples). Control experiments, kinetic measurements and in situ EPR studies reveal the importance of radical species and the formation

  开发了轻度和选择性的镍催化的烯烃的三氟甲基化和全氟烷基化反应，以良好的产率提供了氟化烯烃，包括天然产物，药物和各种合成结构单元（38个实例）。对照实验，动力学测量和原位EPR研究表明，自由基种类和作为中间体的1,2-加合物形成的重要性。
• Generation and Reactions of Trifluoromethylethenyl Titanium(II) Species
  作者：Takeshi Hanamoto、Kenji Yamada

  DOI：10.1021/jo901392n

  日期：2009.10.2

  The reaction of (trifluoromethyl)dimethylphenylsilyacetylene and (eta(2)-propene)Ti((OPr)-Pr-i)(2) generated in situ smoothly proceeded giving the corresponding (eta(2)-1-dimethylphenyl-silyl-2-trifluoromethylalkyne)Ti((OPr)-Pr-i)(2), which reacted with aldehydes and ketones to afford the corresponding addition products in good yields with good to excellent regioselectivity.