2-(3-methoxyphenyl)-2,1-borazaronaphthalene | 1616634-85-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3-methoxyphenyl)-2,1-borazaronaphthalene
• 英文别名: 2-(3-methoxyphenyl)-1H-1,2-benzazaborinine
• CAS: 1616634-85-5
• 化学式: C₁₅H₁₄BNO
• 分子量: 235.093
• InChiKey: CRBWFAXIWGUOPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  21.26
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(3-methoxyphenyl)-2,1-borazaronaphthalene 在 溴 作用下， 以 二氯甲烷 为溶剂， 以52%的产率得到3-bromo-2-(3-methoxyphenyl)-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
• 作为产物：
  描述：

  2-氨基苯乙烯 、 (3-甲氧基苯基)三氟硼酸钾 在 四氯化硅 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以71%的产率得到2-(3-methoxyphenyl)-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

• Stepwise Asymmetric Allylic Substitution‐Isomerization Enabled Mimetic Synthesis of Axially Chiral B,N‐Heterocycles
  作者：Xiu‐Lian Zhang、Jun Gu、Wen‐Hao Cui、Zhiwen Ye、Wenbin Yi、Qiang Zhang、Ying He

  DOI：10.1002/anie.202210456

  日期：2022.12.19

  By means of stepwise asymmetric allylic substitution-isomerization (AASI) strategy, diaxially chiral B,N-heterocycles bearing B−C and C−N axes that are related to the moieties of axially chiral enamines and arylborons were obtained. Density functional theory (DFT) studies demonstrated that the NH⋅⋅⋅π interactions played a unique effect on the promotion of stereospecific isomerization.

  通过逐步不对称烯丙基取代异构化（ AASI ）策略，获得了带有 B−C 和 C−N 轴的双轴手性 B,N 杂环，这些轴与轴向手性烯胺和芳基硼部分相关。密度泛函理论（DFT）研究表明，NH····π相互作用对促进立体异构化具有独特的作用。
• Regioselective Diversification of 2,1-Borazaronaphthalenes: Unlocking Isosteric Space via C–H Activation
  作者：Geraint H. M. Davies、Matthieu Jouffroy、Fatemeh Sherafat、Borna Saeednia、Casey Howshall、Gary A. Molander

  DOI：10.1021/acs.joc.7b01331

  日期：2017.8.4

  Methods for the regioselective C-H borylation and subsequent cross-coupling of the 2,1-borazaronaphthalene core are reported. Azaborines are dependent on B-N/C=C isosterism when employed in strategies for developing diverse heterocyclic scaffolds. Although 2,1-borazaronaphthalene is closely related to naphthalene in terms of structure, the argument is made that the former has electronic similarities to indole. Based on that premise, iridium-mediated C-H activation has enabled facile installation of a versatile, nucleophilic coupling handle at a previously inaccessible site of 2,1-borazaronaphthalenes. A variety of substituted 2,1-borazaronaphthalene cores can be successfully borylated and further cross coupled in a facile manner to yield diverse C(8)-substituted 2,1-borazaronaphthalenes.