2-[2-(dimethylphenylsilyl)phenyl]-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one | 1296939-27-9

• 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: 2-[2-(dimethylphenylsilyl)phenyl]-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one
• 英文别名: 2-[2-[Dimethyl(phenyl)silyl]phenyl]-1,3-dihydro-1,3,2-benzodiazaborinin-4-one；2-[2-[dimethyl(phenyl)silyl]phenyl]-1,3-dihydro-1,3,2-benzodiazaborinin-4-one
• CAS: 1296939-27-9
• 化学式: C₂₁H₂₁BN₂OSi
• 分子量: 356.307
• InChiKey: YCSMQJPQYOJQCO-UHFFFAOYSA-N

物化性质

• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[2-(dimethylphenylsilyl)phenyl]-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以96%的产率得到2,4,6-tris[2-(dimethylphenylsilyl)phenyl]boroxine
  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：

  苯硼酸 在 降冰片烯 、 carbonyldihydridotris(triphenylphosphine)ruthenium 作用下， 以 甲苯 为溶剂， 反应 20.0h， 生成 2-[2-(dimethylphenylsilyl)phenyl]-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one
  参考文献：
  名称：

  芳烃及其芳烃的前体通过催化C–H甲硅烷基化反应

  摘要：

  提出了一种新的，操作简单的方法，该方法基于Ru催化的芳基硼酸酯的C–H甲硅烷基化来获得芳烃及其氟化物活化的前体。色谱纯化可推迟至芳烃捕获后进行，使芳基硼酸酯成为事实上的前体。展示了使用各种新的芳烃及其衍生物的方法，包括首次使用基于2,3-咔唑基和2,3-芴炔核的芳烃，这些化合物为与材料化学相关的图案的新颖衍生化铺平了道路。

  DOI：

  10.1021/acs.joc.9b00221

文献信息

• Anthranilamide-masked <i>o</i>-Iodoarylboronic Acids as Coupling Modules for Iterative Synthesis of <i>ortho</i>-Linked Oligoarenes
  作者：Masashi Koyanagi、Nils Eichenauer、Hideki Ihara、Takeshi Yamamoto、Michinori Suginome

  DOI：10.1246/cl.130136

  日期：2013.5.5

  Anthranilamide (AAM)-masked o-iodoarylboronic acids were prepared from AAM-masked arylboronic acids via Ru-catalyzed o-C–H silylation, followed by iododesilylation with ICl. The Suzuki–Miyaura coupling of AAM-masked o-haloarylboronic acids with arylboronic acids proceeded under ligand-free conditions. Oligo(o-phenylene)s and oligo(naphthalene-2,3-diyl)s were synthesized via iterative Suzuki–Miyaura coupling sequences.

  采用Ru催化的o-C–H硅烷化反应，从AAM掩蔽的芳基硼酸制备了AAM掩蔽的o-碘芳基硼酸，随后通过ICl进行碘去硅化。在无配体条件下，AAM掩蔽的o-卤芳基硼酸与芳基硼酸的铃木-宫浦偶联反应得以进行。通过迭代的铃木-宫浦偶联序列合成了寡(o-苯基)和寡(萘-2,3-二基)。
• 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.
• Arynes and Their Precursors from Arylboronic Acids via Catalytic C–H Silylation
  作者：Karthik Devaraj、Fredric J. L. Ingner、Carina Sollert、Paul J. Gates、Andreas Orthaber、Lukasz T. Pilarski

  DOI：10.1021/acs.joc.9b00221

  日期：2019.5.3

  A new, operationally simple approach is presented to access arynes and their fluoride-activated precursors based on Ru-catalyzed C–H silylation of arylboronates. Chromatographic purification may be deferred until after aryne capture, rendering the arylboronates de facto precursors. Access to various new arynes and their derivatives is demonstrated, including, for the first time, those based on a 2

  提出了一种新的，操作简单的方法，该方法基于Ru催化的芳基硼酸酯的C–H甲硅烷基化来获得芳烃及其氟化物活化的前体。色谱纯化可推迟至芳烃捕获后进行，使芳基硼酸酯成为事实上的前体。展示了使用各种新的芳烃及其衍生物的方法，包括首次使用基于2,3-咔唑基和2,3-芴炔核的芳烃，这些化合物为与材料化学相关的图案的新颖衍生化铺平了道路。