3-bromo-2-phenyl-2,1-borazaronaphthalene | 1616634-99-1

• 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: 3-bromo-2-phenyl-2,1-borazaronaphthalene
• 英文别名: 3-bromo-2-phenyl-1H-1,2-benzazaborinine
• CAS: 1616634-99-1
• 化学式: C₁₄H₁₁BBrN
• 分子量: 283.963
• InChiKey: CYPRHPBMRWDPGA-UHFFFAOYSA-N

物化性质

• 沸点：
  364.1±52.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-bromo-2-phenyl-2,1-borazaronaphthalene 在 palladium diacetate 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 15.0h， 生成 2,10-bis(4-methoxyphenyl)-13,14-diphenyl-di-2,1-borazaronaphtho[2,3-b:2′,3′-f]oxepine
  参考文献：
  名称：

  双BN萘基环氧丙烷的合成及其光致发光，包括白光发射。

  摘要：

  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，

  DOI：

  10.1021/acs.joc.9b02594
• 作为产物：
  描述：

  2-氨基苯乙烯 在 四氯化硅 、 溴 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 18.0h， 生成 3-bromo-2-phenyl-2,1-borazaronaphthalene
  参考文献：
  名称：

  Accessing Elaborated 2,1-Borazaronaphthalene Cores Using Photoredox/Nickel Dual-Catalytic Functionalization

  摘要：

  A highly effective method for derivatizing 2,1-borazaronaphthalene cores using ammonium alkylbis-(catecholato)silicates via photoredox/nickel dual catalysis is reported. By forging C-sp(3)-C-sp(2) bonds via this approach, alkyl fragments with various functional groups can be introduced to the azaborine core, affording previously inaccessible heterocyclic isosteres in good to excellent yields. The base-free, room-temperature conditions outlined allow sensitive functional group tolerance, even permitting the cross-coupling of unprotected primary and secondary amines.

  DOI：

  10.1021/acs.orglett.6b00466

文献信息

• The synthesis of BN-embedded tetraphenes and their photophysical properties
  作者：Huanan Huang、Zexiong Pan、Chunming Cui

  DOI：10.1039/c6cc00161k

  日期：——

  A series of intensely blue fluorescent BN-embedded tetraphene derivatives have been synthesized by the catalytic cyclization of BN-naphthalenes with alkynes.

  一系列强烈蓝色荧光的嵌入硼氮的四苯衍生物已通过催化氮-萘烯与炔烃的环化合成。
• 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.
• Reductive Cross-Coupling of 3-Bromo-2,1-borazaronaphthalenes with Alkyl Iodides
  作者：Gary A. Molander、Steven R. Wisniewski、Kaitlin M. Traister

  DOI：10.1021/ol501495d

  日期：2014.7.18

  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.
• 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.
• Accessing Molecularly Complex Azaborines: Palladium-Catalyzed Suzuki–Miyaura Cross-Couplings of Brominated 2,1-Borazaronaphthalenes and Potassium Organotrifluoroborates
  作者：Gary A. Molander、Steven R. Wisniewski

  DOI：10.1021/jo5011894

  日期：2014.7.18

  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.