tert-butyl(2,2-difluoro-1-phenylbut-2-enyloxy)dimethylsilane | 1310740-26-1

• 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: tert-butyl(2,2-difluoro-1-phenylbut-2-enyloxy)dimethylsilane
• 英文别名: Tert-butyl-(2,2-difluoro-1-phenylbut-3-enoxy)-dimethylsilane；tert-butyl-(2,2-difluoro-1-phenylbut-3-enoxy)-dimethylsilane
• CAS: 1310740-26-1
• 化学式: C₁₆H₂₄F₂OSi
• 分子量: 298.448
• InChiKey: NNJXDYPRWZJJLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.57
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl(2,2-difluoro-1-phenylbut-2-enyloxy)dimethylsilane 在 二甲基氯化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.08h， 以83%的产率得到(Z)-tert-butyl((4-chloro-2-fluoro-1-phenylbut-2-en-1-yl)oxy)dimethylsilane
  参考文献：
  名称：

  Synthesis of (Z)-fluoroallyl azides through aluminium-mediated defluorinative functionalization reactions

  摘要：

  The reaction of difluorohomoallyl alcohols with Me2AlCl in CH2Cl2 selectively gave (Z)-fluoroallyl chlorides via S(N)2' type defluorinative chlorination. These chlorides were easily converted to the corresponding (Z)-fluoroallyl azides by the sequential nucleophilic azidation reaction using NaN3. Direct defluorinative azidation of the difluorohomoallyl alcohols was also achieved by treating with Me3SiN3 in the presence of Al(Oi-Pr)(3). Fluoroallyl azides thus obtained successfully applied to the Huisgen. 1,3-dipolar cycloaddition chemistry. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.12.128
• 作为产物：
  描述：

  2,2-二氟-1-苯基-3-丁烯-1-醇 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 以49%的产率得到tert-butyl(2,2-difluoro-1-phenylbut-2-enyloxy)dimethylsilane
  参考文献：
  名称：

  Copper-free defluorinative alkylation of allylic difluorides through Lewis acid-mediated C–F bond activation

  摘要：

  The reactions of difluorohomoallyl alcohols with trialkylaluminiums smoothly proceeded in CH2Cl2 at room temperature to give (Z)-fluoro-olefin products in excellent yields. On the basis of this chemistry, fluoro-olefinic dipeptide isostere of norvalinyl glycine was synthesized in stereoselective manner. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.148

文献信息

• Copper-free defluorinative alkylation of allylic difluorides through Lewis acid-mediated C–F bond activation
  作者：Hikaru Yanai、Haruna Okada、Azusa Sato、Midori Okada、Takeo Taguchi

  DOI：10.1016/j.tetlet.2011.03.148

  日期：2011.6

  The reactions of difluorohomoallyl alcohols with trialkylaluminiums smoothly proceeded in CH2Cl2 at room temperature to give (Z)-fluoro-olefin products in excellent yields. On the basis of this chemistry, fluoro-olefinic dipeptide isostere of norvalinyl glycine was synthesized in stereoselective manner. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of (Z)-fluoroallyl azides through aluminium-mediated defluorinative functionalization reactions
  作者：Azusa Sato、Hikaru Yanai、Daiki Suzuki、Midori Okada、Takeo Taguchi

  DOI：10.1016/j.tetlet.2014.12.128

  日期：2015.2

  The reaction of difluorohomoallyl alcohols with Me2AlCl in CH2Cl2 selectively gave (Z)-fluoroallyl chlorides via S(N)2' type defluorinative chlorination. These chlorides were easily converted to the corresponding (Z)-fluoroallyl azides by the sequential nucleophilic azidation reaction using NaN3. Direct defluorinative azidation of the difluorohomoallyl alcohols was also achieved by treating with Me3SiN3 in the presence of Al(Oi-Pr)(3). Fluoroallyl azides thus obtained successfully applied to the Huisgen. 1,3-dipolar cycloaddition chemistry. (C) 2014 Elsevier Ltd. All rights reserved.