((1-bromonaphthalen-2-yl)oxy)chlorodiisopropylsilane | 1240960-41-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ((1-bromonaphthalen-2-yl)oxy)chlorodiisopropylsilane
• CAS: 1240960-41-1
• 化学式: C₁₆H₂₀BrClOSi
• 分子量: 371.777
• InChiKey: SDOYAVNQLWURGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  ((1-bromonaphthalen-2-yl)oxy)chlorodiisopropylsilane 、 苯酚 在 咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以62%的产率得到((1-bromonaphthalen-2-yl)oxy)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
• 作为产物：
  描述：

  ((1-bromonaphthalen-2-yl)oxy)diisopropylsilane 在 三氯异氰尿酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到((1-bromonaphthalen-2-yl)oxy)chlorodiisopropylsilane
  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