1-benzyl-2-phenyl-2,1-borazaronaphthalene | 1510778-89-8

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 1-benzyl-2-phenyl-2,1-borazaronaphthalene
• 英文别名: 1-Benzyl-2-phenyl-1,2-benzazaborinine
• CAS: 1510778-89-8
• 化学式: C₂₁H₁₈BN
• 分子量: 295.192
• InChiKey: KQMGTSGTTDLHNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-benzyl-2-phenyl-2,1-borazaronaphthalene 在 溴 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到1-benzyl-3-bromo-2-phenyl-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-溴苯乙烯 在 四氯化硅 、 2-(二叔丁基膦)联苯 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 28.0h， 生成 1-benzyl-2-phenyl-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

• Synthesis of bis-BN-Naphthalene-Fused Oxepins and Their Photoluminescence Including White-Light Emission
  作者：Dawei Tian、Qian Li、Yifan Zhao、Zijia Wang、Wenbin Li、Shuling Xia、Siyang Xing、Bolin Zhu、Jianying Zhang、Chunming Cui

  DOI：10.1021/acs.joc.9b02594

  日期：2020.1.17

  system. Interestingly, dual-fluorescent emissions were observed upon dissolving N-substituted derivatives 10-14 in dimethyl sulfoxide. Tunable emission colors especially for white-light emissions can be achieved by controlling the ratio of solvents, concentration, or temperature using only a single-molecule compound.

  通过溴化的2，1-硼硼烷萘和顺式双（硼基）烯烃的钯催化串联反应，合成了一系列新型的双-BN-萘稠合的环氧丙烷衍生物。X射线晶体学分析表明，双-BN-萘-融合的氧杂环丁烷具有平面框架。通过紫外可见光谱和荧光光谱以及密度泛函理论（DFT）计算研究了新型BN-萘基融合氧杂环丁烷的电子和光物理性质，该计算揭示了类似烃类系统的独特电子和光物理性质。有趣的是，将N-取代的衍生物10-14溶解在二甲基亚砜中观察到双荧光发射。通过控制溶剂的比例，浓度，