(3-Carbazol-9-ylphenoxy)-methyl-bis(trimethylsilyloxy)silane | 1357930-03-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (3-Carbazol-9-ylphenoxy)-methyl-bis(trimethylsilyloxy)silane
• CAS: 1357930-03-0
• 化学式: C₂₅H₃₃NO₃Si₃
• 分子量: 479.798
• InChiKey: AUDPWGDIFJSQAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.43
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  32.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  双三甲基硅氧基甲基硅烷 、 9-(3-methoxyphenyl)-9H-carbazole 在 三(五氟苯基)硼烷 作用下， 以 甲苯 为溶剂， 以86%的产率得到(3-Carbazol-9-ylphenoxy)-methyl-bis(trimethylsilyloxy)silane
  参考文献：
  名称：

  Liquid Triarylamines: The Scope and Limitations of Piers–Rubinsztajn Conditions for Obtaining Triarylamine–Siloxane Hybrid Materials

  摘要：

  New liquid triarylamine-siloxane hybrid materials are produced using the Piers-Rubinsztajn reaction. Under mild conditions, liquid analogues of conventional and commonly crystalline triarylamines are easily synthesized from readily available or accessible intermediates. Using a diverse selection of triarylamines, we explored the effects of siloxane group and substitution pattern on the physical properties of these materials, and we have demonstrated that relatively large molecular liquids with desirable electrochemical properties can be produced. The interactions between the strongly Lewis acidic catalyst used for this transformation, tris(pentafluorophenyl)borane (BCF), and the Lewis basic triarylamine substrates were studied. Through UV-vis-NIR and F-19 NMR spectroscopy, we have proposed that the catalyst undergoes a reversible redox reaction with the substrates to produce a charge transfer complex. The formation of this charge transfer complex is sensitive to the oxidation potential of the triarylamine and can greatly affect the kinetics of the Piers-Rubinsztajn reaction.

  DOI：

  10.1021/jo2020906

文献信息

• Liquid Triarylamines: The Scope and Limitations of Piers–Rubinsztajn Conditions for Obtaining Triarylamine–Siloxane Hybrid Materials
  作者：Brett A. Kamino、Bridget Mills、Christopher Reali、Michael J. Gretton、Michael A. Brook、Timothy P. Bender

  DOI：10.1021/jo2020906

  日期：2012.2.17

  New liquid triarylamine-siloxane hybrid materials are produced using the Piers-Rubinsztajn reaction. Under mild conditions, liquid analogues of conventional and commonly crystalline triarylamines are easily synthesized from readily available or accessible intermediates. Using a diverse selection of triarylamines, we explored the effects of siloxane group and substitution pattern on the physical properties of these materials, and we have demonstrated that relatively large molecular liquids with desirable electrochemical properties can be produced. The interactions between the strongly Lewis acidic catalyst used for this transformation, tris(pentafluorophenyl)borane (BCF), and the Lewis basic triarylamine substrates were studied. Through UV-vis-NIR and F-19 NMR spectroscopy, we have proposed that the catalyst undergoes a reversible redox reaction with the substrates to produce a charge transfer complex. The formation of this charge transfer complex is sensitive to the oxidation potential of the triarylamine and can greatly affect the kinetics of the Piers-Rubinsztajn reaction.