1-Phenyl-2-[phenyl(trimethylsilyloxy)methyl]prop-2-en-1-one | 1094063-76-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-Phenyl-2-[phenyl(trimethylsilyloxy)methyl]prop-2-en-1-one
• 英文别名: 1-phenyl-2-[phenyl(trimethylsilyloxy)methyl]prop-2-en-1-one
• CAS: 1094063-76-9
• 化学式: C₁₉H₂₂O₂Si
• 分子量: 310.468
• InChiKey: ZEZAZDNPPUSYMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-trimethylsilyl-1-phenyl-2-propen-1-one 、 苯甲醛 在 三(2,4,6-三甲氧基苯基)磷 作用下， 以 丁腈 为溶剂， 反应 12.0h， 以81%的产率得到1-Phenyl-2-[phenyl(trimethylsilyloxy)methyl]prop-2-en-1-one
  参考文献：
  名称：

  Sila-Morita−Baylis−Hillman Reaction of Arylvinyl Ketones: Overcoming the Dimerization Problem

  摘要：

  Arylvinyl ketones, under Morita-Baylis-Hillman (MBH) reaction conditions, produce a mixture of dimerization products. We propose a solution to this problem: a sila-MBH reaction. This cascade reaction involves addition of phosphine catalyst to arylvinyl ketones, trapping of the forming beta-sllylenolate with aldehyde, followed by a 1,3-Brook rearrangement to give the Si-MBH adducts in good to excellent yields.

  DOI：

  10.1021/ol8026522

文献信息

• Sila-Morita−Baylis−Hillman Reaction of Arylvinyl Ketones: Overcoming the Dimerization Problem
  作者：Alexander Trofimov、Vladimir Gevorgyan

  DOI：10.1021/ol8026522

  日期：2009.1.1

  Arylvinyl ketones, under Morita-Baylis-Hillman (MBH) reaction conditions, produce a mixture of dimerization products. We propose a solution to this problem: a sila-MBH reaction. This cascade reaction involves addition of phosphine catalyst to arylvinyl ketones, trapping of the forming beta-sllylenolate with aldehyde, followed by a 1,3-Brook rearrangement to give the Si-MBH adducts in good to excellent yields.