2-(4-methylphenyl)-2,1-borazaronaphthalene | 1510779-93-7

• 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: 2-(4-methylphenyl)-2,1-borazaronaphthalene
• 英文别名: 2-(4-methylphenyl)-1H-1,2-benzazaborinine
• CAS: 1510779-93-7
• 化学式: C₁₅H₁₄BN
• 分子量: 219.094
• InChiKey: GGZDZHVIZCTCHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(4-methylphenyl)-2,1-borazaronaphthalene 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 XPhos Pd G2 、 potassium carbonate 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 水 、 甲基环己烷 、 叔丁醇 为溶剂， 反应 42.0h， 生成 8-(pyrimidin-5-yl)-2-(p-tolyl)-2,1-borazaronaphthalene
  参考文献：
  名称：

  Regioselective Diversification of 2,1-Borazaronaphthalenes: Unlocking Isosteric Space via C–H Activation

  摘要：

  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.

  DOI：

  10.1021/acs.joc.7b01331
• 作为产物：
  描述：

  2-氨基苯乙醇 在 四氯化硅 、 三乙胺 、 potassium hydroxide 作用下， 以 甲苯 为溶剂， 40.0~180.0 ℃ 、6.67 Pa 条件下， 反应 22.0h， 生成 2-(4-methylphenyl)-2,1-borazaronaphthalene
  参考文献：
  名称：

  A Convergent, Modular Approach to Functionalized 2,1-Borazaronaphthalenes from 2-Aminostyrenes and Potassium Organotrifluoroborates

  摘要：

  Azaborines are an important class of compounds with applications in both medicinal chemistry and materials science. The first borazaronaphthalene, 2-chloro-2,1-borazaronaphthalene, was reported in 1959; however, access to more highly functionalized substructures has been limited because of the harsh reaction conditions required to displace the chloride on boron. A convergent approach has been developed to synthesize disubstituted 2,1-borazaronaphthalenes from N-substituted 2-aminostyrenes and potassium organotrifluoroborates, where the potassium organotrifluoroborate is converted to the active R-BX2 species (X = Cl or F) in situ by addition of a fluorophile. Starting from aryl-, heteroaryl-, alkynyl-, alkenyl-, and alkyltrifluoroborates, a library of highly functionalized 2,1-borazaronaphthalenes were synthesized in one step under mild, transition-metal-free conditions.

  DOI：

  10.1021/jo402616w

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。