1-Methyl-2-phenyl-1,2,3,4-tetrahydro-1,3,2-benzodiazaborin-4-on | 28257-00-3

• 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: 1-Methyl-2-phenyl-1,2,3,4-tetrahydro-1,3,2-benzodiazaborin-4-on
• 英文别名: 2,3-Dihydro-1-methyl-2-phenyl-1,3,2-benzodiazaborin-4(1H)on；2,3-dihydro-1-methyl-2-phenylbenzo[d][1,3,2]diazaborinin-4(1H)-one；1-methyl-2-phenyl-2,3-dihydro-1H-benzo[1,3,2]diazaborinin-4-one；1-methyl-2-phenyl-3H-1,3,2-benzodiazaborinin-4-one
• CAS: 28257-00-3
• 化学式: C₁₄H₁₃BN₂O
• 分子量: 236.081
• InChiKey: IEVNVSHSPZFAST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二甲基苯基硅烷 、 1-Methyl-2-phenyl-1,2,3,4-tetrahydro-1,3,2-benzodiazaborin-4-on 在 RuH₂(CO)(PPh₃)₃ 、 norbornene 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以86%的产率得到2-[2-(dimethylphenylsilyl)phenyl]-2,3-dihydro-1-methylbenzo[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
• 作为产物：
  描述：

  2-甲氨基苯甲酰胺 、 苯硼酸 以 xylene 为溶剂， 生成 1-Methyl-2-phenyl-1,2,3,4-tetrahydro-1,3,2-benzodiazaborin-4-on
  参考文献：
  名称：

  Yale,H.L., Journal of Heterocyclic Chemistry, 1971, vol. 8, p. 193 - 204

  摘要：

  DOI：

文献信息

• Yale,H.L., Journal of Heterocyclic Chemistry, 1971, vol. 8, p. 193 - 204
  作者：Yale,H.L.

  DOI：——

  日期：——
• Insect chemosterilants. VIII. Boron compounds
  作者：Joseph A. Settepani、Jerry B. Stokes、Alexej B. Borkovec

  DOI：10.1021/jm00295a032

  日期：1970.1
• 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.