(E)-3-(trimethylsilyl)-3-(3-(trimethylsilyl)allyloxy)prop-1-ene

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (E)-3-(trimethylsilyl)-3-(3-(trimethylsilyl)allyloxy)prop-1-ene
• 英文别名: trimethyl-[1-[(E)-3-trimethylsilylprop-2-enoxy]prop-2-enyl]silane
• 化学式: C₁₂H₂₆OSi₂
• 分子量: 242.509
• InChiKey: AROBXBRVNKTPMC-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (E)-3-(trimethylsilyl)-3-(3-(trimethylsilyl)allyloxy)prop-1-ene 、 三甲基氯硅烷 在 TEA 、 仲丁基锂 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 3.0h， 生成 (E)-1-((E)-1,3-bis(trimethylsilyl)allyloxy)-1,3-bis(trimethylsilyl)prop-1-ene 、 (E)-1-((E)-3,3-bis(trimethylsilyl)prop-1-enyloxy)-1,3-bis(trimethylsilyl)prop-1-ene
  参考文献：
  名称：

  Studies on the deprotonation and subsequent [1,4]-Wittig rearrangement of α-benzyloxyallylsilanes

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2006.07.018
• 作为产物：
  描述：

  、 (1-羟基烯丙基)三甲基硅烷 在 三氟化硼乙醚 作用下， 以 环己烷 为溶剂， 以52%的产率得到(E)-3-(trimethylsilyl)-3-(3-(trimethylsilyl)allyloxy)prop-1-ene
  参考文献：
  名称：

  Studies on the deprotonation and subsequent [1,4]-Wittig rearrangement of α-benzyloxyallylsilanes

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2006.07.018

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.