2-(噻吩-3-基)-2,3-二氢苯并[D][1,3,2]二氮杂硼硼烷-4(1H)-酮 | 1296939-24-6

• 物质功能分类: 化学试剂 - 有机试剂 - 硼烷
• 分子结构分类: 有机化合物 - 苯类化合物
• 中文名称: 2-(噻吩-3-基)-2,3-二氢苯并[D][1,3,2]二氮杂硼硼烷-4(1H)-酮
• 英文名称: 2-(thiophen-3-yl)-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one
• 英文别名: 2-(Thiophen-3-yl)-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one；2-thiophen-3-yl-1,3-dihydro-1,3,2-benzodiazaborinin-4-one
• CAS: 1296939-24-6
• 化学式: C₁₁H₉BN₂OS
• 分子量: 228.082
• InChiKey: YVRQGWCMYNHZBJ-UHFFFAOYSA-N

物化性质

• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(噻吩-3-基)-2,3-二氢苯并[D][1,3,2]二氮杂硼硼烷-4(1H)-酮 、 二甲基苯基硅烷 在 RuH₂(CO)(PPh₃)₃ 、 norbornene 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以85%的产率得到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
• 作为产物：
  描述：

  2-氨基苯甲酰胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium acetate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 、 氯苯 为溶剂， 反应 19.5h， 生成 2-(噻吩-3-基)-2,3-二氢苯并[D][1,3,2]二氮杂硼硼烷-4(1H)-酮
  参考文献：
  名称：

  Anthranilamide (aam)-substituted diboron: palladium-catalyzed selective B(aam) transfer

  摘要：

  一种含有蒽酰胺（aam）取代基的非对称二硼烷被合成，并通过Pd催化选择性B(aam)转移转化为芳基硼烷。

  DOI：

  10.1039/c8cc05645e

文献信息

• An Efficient Ni/Pd Catalyzed Chemoselective Synthesis of 1,3,2‐Benzodiazaborininones from Boronic Acids and Anthranilamides
  作者：Hao‐Jie Wang、Mo Zhang、Wen‐Jing Li、Yu Ni、Jin Lin、Zhan‐Hui Zhang

  DOI：10.1002/adsc.201900827

  日期：2019.11.5

  An efficient Ni/Pd catalyzed chemoselective synthesis of 1,3,2‐benzodiazaborininones from boronic acids and anthranilamide has been developed. This protocol allows for the rapid and straightforward access to a wide range of 1,3,2‐benzodiazaborininones at roomtemperature with excellent functional group tolerance.

  已经开发了一种高效的Ni / Pd催化从硼酸和邻氨基苯甲酰胺化学合成1,3,2-苯并二氮杂硼杂环丁烷酮的方法。该协议允许在室温下快速，直接地获得具有出色的官能团耐受性的各种1,3,2-苯并二氮杂硼硼烷酮。
• Electrochemical Synthesis of Azaborininones under Metal‐Catalyst‐Free Mild Conditions
  作者：Dongwen Zeng、Lizhu Zhang、Wei Wang、Ganpeng Li、Xiao‐Jing Zhao、Yonghui He

  DOI：10.1002/ejoc.202200679

  日期：2022.7.27

  efficient electrochemical reaction. Various 1,3,2-benzodiazaborininones were obtained in moderate to excellent yields. Notably, this method features free-oxidants, open-air and eco-friendly reaction conditions.

  在这里，我们描述了一种有效的电化学反应。各种 1,3,2-苯并二氮杂硼杂环酮以中等至优异的产率获得。值得注意的是，该方法具有无氧化剂、露天和环保的反应条件。
• Anthranilamide (aam)-substituted diboron: palladium-catalyzed selective B(aam) transfer
  作者：Shintaro Kamio、Ikuo Kageyuki、Itaru Osaka、Sayaka Hatano、Manabu Abe、Hiroto Yoshida

  DOI：10.1039/c8cc05645e

  日期：——

  An unsymmetrical diboron bearing an anthranilamide (aam) substituent was synthesized and was converted into arylboranes via Pd-catalyzed selective B(aam) transfer.

  一种含有蒽酰胺（aam）取代基的非对称二硼烷被合成，并通过Pd催化选择性B(aam)转移转化为芳基硼烷。
• 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.