3-bromo-2-(4-dibenzofuranyl)-2,1-borazaronaphthalene | 1616635-03-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-bromo-2-(4-dibenzofuranyl)-2,1-borazaronaphthalene
• 英文别名: 3-bromo-2-(dibenzo[b,d]furan-4-yl)-1,2-dihydrobenzo[e][1,2]azaborinine；3-bromo-2-dibenzofuran-4-yl-1H-1,2-benzazaborinine
• CAS: 1616635-03-0
• 化学式: C₂₀H₁₃BBrNO
• 分子量: 374.044
• InChiKey: VLWNAYCLPRYSDJ-UHFFFAOYSA-N

物化性质

• 熔点：
  132-134 °C
• 沸点：
  501.0±60.0 °C(predicted)
• 密度：
  1.50±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-bromo-2-(4-dibenzofuranyl)-2,1-borazaronaphthalene 、 N-Boc-4-碘哌啶 在 4-乙基吡啶 、 锰 、 氟硼酸钠 、 4,4'-二甲基-2,2'-联吡啶 、 氯化镍二甲氧基乙烷 作用下， 以 N,N-二甲基乙酰胺 、 环己烷 为溶剂， 反应 18.0h， 以89%的产率得到3-(4-(N-Boc)piperidenyl)-2-(4-dibenzofuranyl)-2,1-borazaronaphthalene
  参考文献：
  名称：

  Reductive Cross-Coupling of 3-Bromo-2,1-borazaronaphthalenes with Alkyl Iodides

  摘要：

  Conditions have been developed for the reductive cross-coupling of 3-bromo-2,1-borazaronaphthalenes with primary and secondary alkyl iodides. This method allows direct alkylation of azaborine cores, providing efficient access to functionalized isosteres of naphthalene derivatives.

  DOI：

  10.1021/ol501495d
• 作为产物：
  描述：

  2-(4-dibenzofuryl)-2,1-borazaronaphthalene 在 溴 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到3-bromo-2-(4-dibenzofuranyl)-2,1-borazaronaphthalene
  参考文献：
  名称：

  Accessing Molecularly Complex Azaborines: Palladium-Catalyzed Suzuki–Miyaura Cross-Couplings of Brominated 2,1-Borazaronaphthalenes and Potassium Organotrifluoroborates

  摘要：

  Despite their potential applications in both medicinal chemistry and materials science, there have been limited reports on the functionalization of 2,1-borazaronaphthalenes since their discovery in 1959. To access new chemical space and build molecular complexity, the Suzuki-Miyaura cross-coupling of brominated 2,1-borazaronaphthalenes been investigated. The palladium-catalyzed cross-coupling proceeds with an array of potassium (hetero)aryltrifluoroborates in high yield with low catalyst loadings under mild reaction conditions. By the use of a high-yielding bromination of various 2,1-borazaronaphthalenes to generate electrophilic azaborine species, a library of 3-(hetero)aryl and 3,6-diaryl-2,1-borazaronaphthalenes has been synthesized.

  DOI：

  10.1021/jo5011894

文献信息

• 3-Boryl-2,1-borazaronaphthalene: Umpolung Reagents for Diversifying Naphthalene Isosteres
  作者：Jordan S. Compton、Borna Saeednia、Christopher B. Kelly、Gary A. Molander

  DOI：10.1021/acs.joc.8b01197

  日期：2018.8.17

  A Pd-catalyzed Miyaura borylation of 3-bromo-2,1-borazaronaphthalenes is reported. This method allows the formation of umpolung reagents for subsequent Pd-mediated cross-coupling. Coupling of this nucleophilic partner with a variety of commercially available aryl- and heteroaryl halides allows facile and rapid diversification of these cores.