(E)-tert-butyl((4-(4-fluorophenyl)-1-phenylbut-3-en-1-yl)oxy)dimethylsilane | 1229597-21-0

• 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)-tert-butyl((4-(4-fluorophenyl)-1-phenylbut-3-en-1-yl)oxy)dimethylsilane
• 英文别名: tert-butyl-[(E)-4-(4-fluorophenyl)-1-phenylbut-3-enoxy]-dimethylsilane
• CAS: 1229597-21-0
• 化学式: C₂₂H₂₉FOSi
• 分子量: 356.556
• InChiKey: JIOAYVJJBJVUDY-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.99
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(4-fluorophenyl)-[1,3,2]-dioxaborolane 、 4-(tert-butyldimethylsilyloxy)-4-phenylbut-1-ene 在 Pd(IiPr)(OTs)2 、 氧气 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以87%的产率得到(E)-tert-butyl((4-(4-fluorophenyl)-1-phenylbut-3-en-1-yl)oxy)dimethylsilane
  参考文献：
  名称：

  A Highly Selective and General Palladium Catalyst for the Oxidative Heck Reaction of Electronically Nonbiased Olefins

  摘要：

  A general, highly selective oxidative Heck reaction is reported. The reaction is high-yielding under mild conditions without the need for base or high temperatures, and the selectivity is excellent, without the requirement for electronically biased olefins or other specific directing groups. A preliminary mechanistic investigation suggests that the unusually high selectivity may be due to the catalyst's sensitivity to C-H bond strength in the selectivity-determining beta-hydride elimination step.

  DOI：

  10.1021/ja1060998

文献信息

• Pd^II-Catalyzed Oxidative 1,1-Diarylation of Terminal Olefins
  作者：Erik W. Werner、Kaveri B. Urkalan、Matthew S. Sigman

  DOI：10.1021/ol1009575

  日期：2010.6.18

  Evaluation of the scope of a Pd-II-catalyzed oxidative 1,1-diarylation reaction of terminal olefins using aryl stannanes is reported. The reaction is shown to be tolerant of functionality commonly encountered in organic synthesis; however, the reaction outcome was found to be dependent on the nature of the aryl stannane used. A mechanistic rationale for the observation of this influence is provided.
• A Highly Selective and General Palladium Catalyst for the Oxidative Heck Reaction of Electronically Nonbiased Olefins
  作者：Erik W. Werner、Matthew S. Sigman

  DOI：10.1021/ja1060998

  日期：2010.10.13

  A general, highly selective oxidative Heck reaction is reported. The reaction is high-yielding under mild conditions without the need for base or high temperatures, and the selectivity is excellent, without the requirement for electronically biased olefins or other specific directing groups. A preliminary mechanistic investigation suggests that the unusually high selectivity may be due to the catalyst's sensitivity to C-H bond strength in the selectivity-determining beta-hydride elimination step.