(二氟)[(4-三氟甲基)苯基](苯基)硅烷 | 137364-37-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (二氟)[(4-三氟甲基)苯基](苯基)硅烷
• 英文名称: (difluoro)<(4-trifluoromethyl)phenyl>(phenyl)silane
• 英文别名: (difluoro)[(4-trifluoromethyl)phenyl](phenyl)silane；Difluoro-phenyl-[4-(trifluoromethyl)phenyl]silane
• CAS: 137364-37-5
• 化学式: C₁₃H₉F₅Si
• 分子量: 288.292
• InChiKey: JJRFGIKVDOUBHC-UHFFFAOYSA-N

物化性质

• 沸点：
  263.0±40.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (dichloro)<(4-trifluoromethyl)phenyl>(phenyl)silane 在 copper (II)-fluoride 作用下， 以 乙醚 为溶剂， 反应 8.0h， 以65%的产率得到(二氟)[(4-三氟甲基)苯基](苯基)硅烷
  参考文献：
  名称：

  Highly selective cross-coupling reactions of aryl(halo)silanes with aryl halides: A general and practical route to functionalized biaryls

  摘要：

  The palladium catalyzed cross-coupling reaction of aryl halides with aryl(halo)silanes (halogen= F, Cl) gives good yields of unsymmetrical biaryls and p-terphenyls. The reaction takes place smoothly in N,N-dimethylformamide in the presence of an appropriate palladium catalyst and potassium fluoride. Since this reaction is tolerant of a variety of reactive functional groups, highly functionalized 4,4'-, 3,4'-, 2,4'- and even sterically crowded 2,2'-disubstituted biaryls can be obtained in moderate to high yields. The synthetic utility of the method has been demonstrated by its application to a short synthesis of liquid crystals. Mechanistic aspects of transmetalation of an aryl(fluoro)silicate intermediate with a palladium complex are discussed on the basis of the substituent effects on the rate of the cross-coupling reactions.

  DOI：

  10.1016/s0040-4020(01)85554-x

文献信息

• Electronic effects and mechanistic features in the rearrangement-displacement reactions of aryl(chloromethyl)diphenylsilanes with fluoride ion
  作者：Steve L Aprahamian、Harold Shechter

  DOI：10.1016/s0040-4039(00)88733-x

  日期：1990.1

  At 25°C aryl migrations from negatively-charged pentacoordinate silicon correlate with the abilities of the rearranging groups to bear negative charge, but at lower temperatures the migrations become less dependent on electron-withdrawing stabilization.

  在25°C下，带负电荷的五配位硅的芳基迁移与重排基团带有负电荷的能力相关，但在较低的温度下，迁移对电子吸收稳定性的依赖性较小。
• APRAHAMIAN, STEVE L.;SHECHTER, HAROLD, TETRAHEDRON LETT., 31,(1990) N, C. 1089-1092
  作者：APRAHAMIAN, STEVE L.、SHECHTER, HAROLD

  DOI：——

  日期：——
• Hatanaka Yasuo, Goda Ken-ichi, Okahara Yoshinori, Hiyama Tamejiro, Tetrahedron, 50 (1994) N 28, S 8301-8316
  作者：Hatanaka Yasuo, Goda Ken-ichi, Okahara Yoshinori, Hiyama Tamejiro

  DOI：——

  日期：——