2-[2-(dimethylphenylsilyl)thiophen-3-yl]-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one | 1296939-38-2

• 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: 2-[2-(dimethylphenylsilyl)thiophen-3-yl]-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one
• 英文别名: 2-[2-[Dimethyl(phenyl)silyl]thiophen-3-yl]-1,3-dihydro-1,3,2-benzodiazaborinin-4-one；2-[2-[dimethyl(phenyl)silyl]thiophen-3-yl]-1,3-dihydro-1,3,2-benzodiazaborinin-4-one
• CAS: 1296939-38-2
• 化学式: C₁₉H₁₉BN₂OSSi
• 分子量: 362.335
• InChiKey: IXUAZEMUKFVHNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  69.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基苯甲酰胺 在 RuH₂(CO)(PPh₃)₃ 、 norbornene 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 2-[2-(dimethylphenylsilyl)thiophen-3-yl]-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one
  参考文献：
  名称：

  Anthranilamide: A Simple, Removable ortho-Directing Modifier for Arylboronic Acids Serving also as a Protecting Group in Cross-Coupling Reactions

  摘要：

  Anthranilamide (AAM) serves as a bifunctional modifier on the boron atom in catalytic transformations of arylboronic acids. It makes boronyl groups unreactive in Suzuki-Miyaura coupling and promotes Ru-catalyzed ortho-silylation. Suzuki-Miyaura coupling of AAM-modified bromophenylboronic acids with tolylboronic acid gave 1,1'-biaryl-4-boronic acid bearing AAM on the boron atom, which subsequently underwent Ru-catalyzed ortho-silylation at the 3-position by virtue of the ortho-directing effect of the AAM group.

  DOI：

  10.1021/ol200764g

文献信息

• Anthranilamide: A Simple, Removable <i>ortho</i>-Directing Modifier for Arylboronic Acids Serving also as a Protecting Group in Cross-Coupling Reactions
  作者：Hideki Ihara、Masashi Koyanagi、Michinori Suginome

  DOI：10.1021/ol200764g

  日期：2011.5.20

  Anthranilamide (AAM) serves as a bifunctional modifier on the boron atom in catalytic transformations of arylboronic acids. It makes boronyl groups unreactive in Suzuki-Miyaura coupling and promotes Ru-catalyzed ortho-silylation. Suzuki-Miyaura coupling of AAM-modified bromophenylboronic acids with tolylboronic acid gave 1,1'-biaryl-4-boronic acid bearing AAM on the boron atom, which subsequently underwent Ru-catalyzed ortho-silylation at the 3-position by virtue of the ortho-directing effect of the AAM group.