(2-bromophenoxy)diisopropyl(phenoxy)silane | 1227735-25-2

• 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: (2-bromophenoxy)diisopropyl(phenoxy)silane
• 英文别名: (2-Bromophenoxy)-phenoxy-di(propan-2-yl)silane；(2-bromophenoxy)-phenoxy-di(propan-2-yl)silane
• CAS: 1227735-25-2
• 化学式: C₁₈H₂₃BrO₂Si
• 分子量: 379.369
• InChiKey: ZPGFSWXGNVJTAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-bromophenoxy)diisopropyl(phenoxy)silane 在 potassium phosphate 、 palladium diacetate 、 silver carbonate 、 三(五氟苯基)膦 作用下， 以 均三甲苯 为溶剂， 反应 5.0h， 以73%的产率得到6,6-diisopropyldibenzo[d,f][1,3,2]dioxasilepine
  参考文献：
  名称：

  Synthesis of Unsymmetrical o-Biphenols and o-Binaphthols via Silicon-Tethered Pd-Catalyzed C−H Arylation

  摘要：

  A mild, practical, and efficient method for the synthesis of unsymmetrical o-biphenols (including o-phenol-naphthols and o-binaphthols) has been developed. Unsymmetrical bis-aryloxy silanes, which were readily prepared in a semi-one-pot fashion, underwent the Pd-catalyzed intramolecular arylation followed by a routine TBAF desilylation step to furnish valuable unsymmetrical biphenols without necessity of isolation of seven-membered intermediates. The excellent functional group tolerance allows for synthesis of a variety of functionalized o-biphenols and o-binaphthols from easily available staring materials.

  DOI：

  10.1021/ol100924n
• 作为产物：
  描述：

  (2-bromophenoxy)chlorodiisopropylsilane 、 苯酚 在 咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以81%的产率得到(2-bromophenoxy)diisopropyl(phenoxy)silane
  参考文献：
  名称：

  Synthesis of Unsymmetrical o-Biphenols and o-Binaphthols via Silicon-Tethered Pd-Catalyzed C−H Arylation

  摘要：

  A mild, practical, and efficient method for the synthesis of unsymmetrical o-biphenols (including o-phenol-naphthols and o-binaphthols) has been developed. Unsymmetrical bis-aryloxy silanes, which were readily prepared in a semi-one-pot fashion, underwent the Pd-catalyzed intramolecular arylation followed by a routine TBAF desilylation step to furnish valuable unsymmetrical biphenols without necessity of isolation of seven-membered intermediates. The excellent functional group tolerance allows for synthesis of a variety of functionalized o-biphenols and o-binaphthols from easily available staring materials.

  DOI：

  10.1021/ol100924n

文献信息

• Synthesis of Unsymmetrical <i>o</i>-Biphenols and <i>o</i>-Binaphthols via Silicon-Tethered Pd-Catalyzed C−H Arylation
  作者：Chunhui Huang、Vladimir Gevorgyan

  DOI：10.1021/ol100924n

  日期：2010.5.21

  A mild, practical, and efficient method for the synthesis of unsymmetrical o-biphenols (including o-phenol-naphthols and o-binaphthols) has been developed. Unsymmetrical bis-aryloxy silanes, which were readily prepared in a semi-one-pot fashion, underwent the Pd-catalyzed intramolecular arylation followed by a routine TBAF desilylation step to furnish valuable unsymmetrical biphenols without necessity of isolation of seven-membered intermediates. The excellent functional group tolerance allows for synthesis of a variety of functionalized o-biphenols and o-binaphthols from easily available staring materials.