o-(hydroxydimethylsilyl)(dimesitylboryl)benzene | 1058708-16-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: o-(hydroxydimethylsilyl)(dimesitylboryl)benzene
• 英文别名: [2-Bis(2,4,6-trimethylphenyl)boranylphenyl]-hydroxy-dimethylsilane；[2-bis(2,4,6-trimethylphenyl)boranylphenyl]-hydroxy-dimethylsilane
• CAS: 1058708-16-9
• 化学式: C₂₆H₃₃BOSi
• 分子量: 400.444
• InChiKey: ARGCMHLJWZMRHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  o-(hydroxydimethylsilyl)(dimesitylboryl)benzene 以 氘代四氢呋喃 为溶剂， 以64%的产率得到5,5-dimesityl-2,2-dimethyl-3,4-benzo-1,2,5-oxasilaboracyclopentene
  参考文献：
  名称：

  Intramolecular Reaction of Silanol and Triarylborane: Boron−Aryl Bond Cleavage and Formation of a Si−O−B Heterocyle

  摘要：

  o-(Hydroxydimethylsilyl)(dimesitylboryl)benzene (1) underwent intrarnolecular cyclization to give 5,5-dimesityl-2,2-dimethyl-3,4-benzo-1,2,5-oxasilaboracyclopentene (4) and mesitylene by boron-aryl bond cleavage. Whereas triethylamine as an additive accelerated the cyclization, DBU stabilized a silyloxyborate complex, 1,8-diazabicyclo[5.4.0]-7-undecenium 5,5-dimesityl-2,2-dimethyl-3,4-benzo-1,2,5-oxasilaboratacyclopentene, which was characterized by X-ray crystallographic analysis and HF calculations. The deuterium-labeling experiments revealed that the hydrogen migrated from the hydroxyl group in 1 to the leaving mesitylene.

  DOI：

  10.1021/om8004405
• 作为产物：
  描述：

  o-(dimesitylboryl)(dimethylsilyl)benzene 、 水 以 四氢呋喃 为溶剂， 以90%的产率得到o-(hydroxydimethylsilyl)(dimesitylboryl)benzene
  参考文献：
  名称：

  Intramolecular Reaction of Silanol and Triarylborane: Boron−Aryl Bond Cleavage and Formation of a Si−O−B Heterocyle

  摘要：

  o-(Hydroxydimethylsilyl)(dimesitylboryl)benzene (1) underwent intrarnolecular cyclization to give 5,5-dimesityl-2,2-dimethyl-3,4-benzo-1,2,5-oxasilaboracyclopentene (4) and mesitylene by boron-aryl bond cleavage. Whereas triethylamine as an additive accelerated the cyclization, DBU stabilized a silyloxyborate complex, 1,8-diazabicyclo[5.4.0]-7-undecenium 5,5-dimesityl-2,2-dimethyl-3,4-benzo-1,2,5-oxasilaboratacyclopentene, which was characterized by X-ray crystallographic analysis and HF calculations. The deuterium-labeling experiments revealed that the hydrogen migrated from the hydroxyl group in 1 to the leaving mesitylene.

  DOI：

  10.1021/om8004405