(2,2-difluoro-1-phenylvinyl)trimethylsilane | 107839-99-6

• 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: (2,2-difluoro-1-phenylvinyl)trimethylsilane
• 英文别名: (2,2-Difluoro-1-phenylethenyl)-trimethylsilane
• CAS: 107839-99-6
• 化学式: C₁₁H₁₄F₂Si
• 分子量: 212.314
• InChiKey: PVKWVRDXNXFAKD-UHFFFAOYSA-N

物化性质

• 沸点：
  175.3±40.0 °C(Predicted)
• 密度：
  0.995±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  14
• 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：
  2

反应信息

• 作为反应物：
  描述：

  (2,2-difluoro-1-phenylvinyl)trimethylsilane 在 potassium fluoride 、 18-冠醚-6 作用下， 以 四氢呋喃 为溶剂， 反应 60.0h， 生成 (2,2-二氟乙烯基)苯
  参考文献：
  名称：

  1-氟-2-苯基乙炔的生成和热聚合

  摘要：

  尝试了一些合成1-氟-2-苯基乙炔的途径。尽管不成功进行氯和溴代苯基乙炔的卤素交换以及二溴氟苯基乙炔的脱氢溴化，但是1,1-二氟-2-苯基-2-三甲基甲硅烷基乙烯的脱氟甲硅烷基化（通过溴化二氟氟乙烯基苯的锂化反应制得），然后用氟苯乙炔的烯烃基乙苯进行甲硅烷基化。苯基二氟乙烯基硅烷与CsF在DMF中在苯叠氮化物的存在下反应，得到1,3-偶极环加合物，氟代二苯基-1,2,3-三唑。苯基二氟乙烯基硅烷的气相真空热解产生了乙炔，其自发聚合。

  DOI：

  10.1016/s0022-1139(00)81946-6
• 作为产物：
  描述：

  2,2-difluoro-1-trimethylsilylethenyl p-toluenesulfonate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 copper(l) iodide 、 四(三苯基膦)钯 、 lithium bromide 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (2,2-difluoro-1-phenylvinyl)trimethylsilane
  参考文献：
  名称：

  Preparation of 2,2-difluoro-1-trialkylsilylethenylstannanes and their cross-coupling reactions

  摘要：

  Reaction of 2 with bis(tributyltin) in the presence of 3 mol % Pd-2(dba)(3), 6 mol % XPhos, and 30 equiv of LiBr in wet and air bubbled THF at reflux for 8 h afforded the desired products 3 in 73-74% yields. The cross-coupling reaction of 3a with aryl iodides in the presence of 10 mol % Pd(PPh3)(4) and 10 mol % CuI afforded the coupled products 4a-p in 47-90% yields. The coupling reaction of 3h with various alkynyl bromides having aryl-, alkyl, or trialkylsilyl group also afforded the corresponding 1,3-enynes 5a-g in 61-77% yields. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.071

文献信息

• Stereoselective Synthesis of Both Stereoisomers of β-Fluorostyrene Derivatives from a Common Intermediate
  作者：Grégory Landelle、Marc-Olivier Turcotte-Savard、Laetitia Angers、Jean-François Paquin

  DOI：10.1021/ol200302h

  日期：2011.3.18

  stereoselective synthesis of both cis- and trans-β-fluorostyrene derivatives from a common intermediate, (Z)-1-aryl-2-fluoro-1-(trimethylsilyl)ethenes, is described. The trans isomers are obtained by a stereospecific replacement of the silyl group in the presence of water and a fluoride source, whereas the preparation of the cis isomers is achieved by a bromination/desilicobromination sequence followed

  描述了从常见的中间体（Z）-1-芳基-2-氟-2-氟-1-（三甲基甲硅烷基）乙烯立体合成顺-和反-β-氟苯乙烯衍生物。的反式异构体是通过在水和氟化物源存在下的立体有择更换甲硅烷基得到的，而在制备顺式异构体是由溴化/ desilicobromination序列，随后通过还原新创建的C-Br键来实现。还提出了β-氟苯乙烯的两种立体异构体的立体选择性转化。
• Efficient synthesis of silylated 2,2-difluorostyrene derivatives through Suzuki–Miyaura cross-coupling of 2,2-difluoro-1-iodo-1-silylethenes
  作者：Marc-Olivier Turcotte-Savard、Jean-François Paquin

  DOI：10.1039/c2ob27221k

  日期：——

  We report a new synthetic sequence for the preparation of silylated 2,2-difluorostyrene derivatives. This new route has numerous advantages over the previous one including enhanced scope, higher yields, ease of purification, and significant reduction of the amount of desilylated side-products. An unexpected transformation of a silylated 2,2-difluorostyrene derivative is also presented.

  我们报告了一种制备硅烷化 2,2-二氟苯乙烯衍生物的新合成方法。与之前的方法相比，这种新方法具有许多优点，包括范围更广、产率更高、易于纯化以及显著减少脱硅副产物的数量。此外，还介绍了一种硅烷化 2,2-二氟苯乙烯衍生物的意外转化。
• Stereocontrolled Access to Unsymmetrical 1,1-Diaryl-2-fluoroethenes
  作者：Grégory Landelle、Marc-Olivier Turcotte-Savard、Judikaëlle Marterer、Pier Alexandre Champagne、Jean-François Paquin

  DOI：10.1021/ol9022672

  日期：2009.12.3

  A simple and effective method for stereocontrolled preparation of 1,1-diaryl-2-fluoroethenes is reported. First, 1-aryl-1-bromo-2-fluoroethenes are generated using an addition/elimination reaction of hydride to silylated beta,beta-difluorostyrene derivatives followed by a bromination/desilicobromination reaction. Subsequent Suzuki-Miyaura coupling with a variety of boronic acids gives access to the desired 1,1-diaryl-2-fluoroethenes.
• Stereocontrolled Approach to Bromofluoroalkenes and Their Use for the Synthesis of Tri- and Tetrasubstituted Fluoroalkenes
  作者：Grégory Landelle、Pier Alexandre Champagne、Xavier Barbeau、Jean-François Paquin

  DOI：10.1021/ol8027412

  日期：2009.2.5

  An addition/elimination reaction of organolithium reagents to silylated beta,beta-difluorostyrene derivatives followed by a bromination/desilicobromination reaction provides a simple and effective synthetic approach to a wide range of bromofluoroalkenes (up to >97/3). In addition, the bromofluoroalkenes can be used in Pd-catalyzed transformations giving access to both tri- and tetrasubstituted fluoroalkenes.