Trimethyl-[1-(1-phenylprop-2-enoxy)prop-2-enyl]silane | 250234-74-3

• 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: Trimethyl-[1-(1-phenylprop-2-enoxy)prop-2-enyl]silane
• CAS: 250234-74-3
• 化学式: C₁₅H₂₂OSi
• 分子量: 246.425
• InChiKey: XRECWKFWYMTKMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Trimethyl-[1-(1-phenylprop-2-enoxy)prop-2-enyl]silane 在 cesium fluoride 、 盐酸 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 、 乙醚 为溶剂， 反应 16.0h， 以54%的产率得到(E)-6-phenylhexa-1,5-dien-3-ol
  参考文献：
  名称：

  Synthesis and Fluoride-Promoted Wittig Rearrangements of α-Alkoxysilanes

  摘要：

  [GRAPHICS]Lewis acid-catalyzed reaction of allyl and benzyl trichloroacetimidates with alpha-silyl alcohols was found to be a general method for the synthesis of alpha-alkoxysllanes. Upon exposure to CsF, these alpha-alkoxysilanes could be made to undergo [2,3]-Wittig rearrangement with an efficiency similar to that realized by the analogous but inherently more toxic alpha-alkoxystannanes.

  DOI：

  10.1021/ol9909132
• 作为产物：
  描述：

  cinnamyl 2,2,2-trichloroacetimidate 、 (1-羟基烯丙基)三甲基硅烷 在 三氟甲磺酸三甲基硅酯 作用下， 以 环己烷 为溶剂， 以1.25 g的产率得到Trimethyl-[1-(1-phenylprop-2-enoxy)prop-2-enyl]silane
  参考文献：
  名称：

  Synthesis and Fluoride-Promoted Wittig Rearrangements of α-Alkoxysilanes

  摘要：

  [GRAPHICS]Lewis acid-catalyzed reaction of allyl and benzyl trichloroacetimidates with alpha-silyl alcohols was found to be a general method for the synthesis of alpha-alkoxysllanes. Upon exposure to CsF, these alpha-alkoxysilanes could be made to undergo [2,3]-Wittig rearrangement with an efficiency similar to that realized by the analogous but inherently more toxic alpha-alkoxystannanes.

  DOI：

  10.1021/ol9909132

文献信息

• Studies on the deprotonation and subsequent [1,4]-Wittig rearrangement of α-benzyloxyallylsilanes
  作者：Edith N. Onyeozili、Robert E. Maleczka

  DOI：10.1016/j.tetlet.2006.07.018

  日期：2006.9

  Upon exposure to s-BuLi, benzyloxyallylsilane undergoes an unusually rapid and efficient [1,4]-Wittig rearrangement. Herein we describe efforts aimed at trapping the intermediate alpha-carbanion with an electrophile prior to rearrangement. The results of these experiments indicate that alpha-deprotonation and bond reorganization are separate events. Findings herein further indicate that the future success of benzyloxyallylsilanes in [1,4]-Wittig rearrangements will likely hinge on the acidity of the benzylic protons. (c) 2006 Elsevier Ltd. All rights reserved.