4-[tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silyl]benzyl bromide

• 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: 4-[tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silyl]benzyl bromide
• 英文别名: [4-(bromomethyl)phenyl]{tris[2-(perfluorohexyl)ethyl]}silane；[4-(Bromomethyl)phenyl]-tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane
• 化学式: C₃₁H₁₈BrF₃₉Si
• 分子量: 1239.41
• InChiKey: QKIXMWSLHSTPRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.62
• 重原子数：
  72
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  39

反应信息

• 作为反应物：
  描述：

  4-[tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silyl]benzyl bromide 在 Amberlite 900 [CO₃^(2-) form] 作用下， 以 苯 为溶剂， 反应 4.0h， 以31%的产率得到4-[tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silyl]benzyl alcohol
  参考文献：
  名称：

  Perfluoro-Tagged Benzyloxycarbonyl Protecting Group and Its Application in Fluorous Biphasic Systems

  摘要：

  The synthesis of a new perfluoro-tagged benzyloxycarbonyl protecting group is reported, as well as its application in the parallel protection of amines. Isolation of the protected amines was performed by simple liquid-liquid extraction between perfluorinated and organic solvents, Deprotection was achieved by standard hydrogenolysis. The novel protecting group was also applied to cyclization protocols leading to quinazoline-2,4-diones. These products were isolated by simple extraction procedures.

  DOI：

  10.1002/1522-2675(200201)85:1<255::aid-hlca255>3.0.co;2-5
• 作为产物：
  描述：

  1-碘-1H,1H,2H,2H-全氟辛烷 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 溴 、 magnesium 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 为溶剂， 反应 242.5h， 生成 4-[tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silyl]benzyl bromide
  参考文献：
  名称：

  Perfluoro-Tagged Benzyloxycarbonyl Protecting Group and Its Application in Fluorous Biphasic Systems

  摘要：

  The synthesis of a new perfluoro-tagged benzyloxycarbonyl protecting group is reported, as well as its application in the parallel protection of amines. Isolation of the protected amines was performed by simple liquid-liquid extraction between perfluorinated and organic solvents, Deprotection was achieved by standard hydrogenolysis. The novel protecting group was also applied to cyclization protocols leading to quinazoline-2,4-diones. These products were isolated by simple extraction procedures.

  DOI：

  10.1002/1522-2675(200201)85:1<255::aid-hlca255>3.0.co;2-5

文献信息

• Preparation of a fluorous benzyl protecting group and its use in fluorous synthesis approach to a disaccharide
  作者：Dennis P. Curran、Rafael Ferritto、Ye Hua

  DOI：10.1016/s0040-4039(98)00961-7

  日期：1998.7

  Benzylation of glucal with a fluorous benzyl group provided a fluorous tribenzyl glucal derivative which was coupled with excess diacetone galactose to make a fluorous disaccharide. These experiments break ground for a fluorous approach to oligosaccharide synthesis.

  葡萄糖与氟苄基的苄基化提供了氟三苄基葡糖衍生物，其与过量的双丙酮半乳糖偶联以制备氟二糖。这些实验为寡糖合成的氟方法开辟了道路。
• Enantioselective addition of diethylzinc to aldehydes catalyzed by fluorous β-aminoalcohols
  作者：Yutaka Nakamura、Seiji Takeuchi、Kazuo Okumura、Yoshiaki Ohgo

  DOI：10.1016/s0040-4020(01)00483-5

  日期：2001.6

  A fluorous aminoalcohol prepared from ephedrine has been used as a catalyst for the enantioselective addition of diethylzinc to aldehydes to afford the corresponding alcohols in up to 84% ee. The fluorous amino alcohol was easily recovered by a simple filtration through a fluorous reverse phase silica gel and was reusable without purification. (C) 2001 Elsevier Science Ltd. AU rights reserved.
• Perfluoro-Tagged Benzyloxycarbonyl Protecting Group and Its Application in Fluorous Biphasic Systems
  作者：Dominik Schwinn、Willi Bannwarth

  DOI：10.1002/1522-2675(200201)85:1<255::aid-hlca255>3.0.co;2-5

  日期：2002.1

  The synthesis of a new perfluoro-tagged benzyloxycarbonyl protecting group is reported, as well as its application in the parallel protection of amines. Isolation of the protected amines was performed by simple liquid-liquid extraction between perfluorinated and organic solvents, Deprotection was achieved by standard hydrogenolysis. The novel protecting group was also applied to cyclization protocols leading to quinazoline-2,4-diones. These products were isolated by simple extraction procedures.