2-phenyl-2,1-borazaronaphthalene | 24341-84-2

• 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-phenyl-2,1-borazaronaphthalene
• 英文别名: 2-phenyl-1,2-dihydrobenzo[e][1,2]azaborinine；1,2-dihydro-2-phenyl-1,2-benzaborine；2-phenyl-1,2-dihydro-benz[e][1,2]azaborinine；2-Phenyl-1,2-dihydro-benz[e][1,2]azaborinin；2-phenyl-1H-1,2-benzazaborinine
• CAS: 24341-84-2
• 化学式: C₁₄H₁₂BN
• 分子量: 205.067
• InChiKey: CIBRLXAUYKEYLB-UHFFFAOYSA-N

物化性质

• 熔点：
  137.5-139.0 °C(Solv: ligroine (8032-32-4))
• 沸点：
  319.1±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  16
• 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：

  2-phenyl-2,1-borazaronaphthalene 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到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
• 作为产物：
  描述：

  氯化苯汞 在 amine 作用下， 生成 2-phenyl-2,1-borazaronaphthalene
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.9, 5.2.4, page 189 - 199

  摘要：

  DOI：

文献信息

• Photoredox Catalysis Enables Access to <i>N</i>-Functionalized 2,1-Borazaronaphthalenes
  作者：Xie Wang、Geraint H. M. Davies、Adriel Koschitzky、Steven R. Wisniewski、Christopher B. Kelly、Gary A. Molander

  DOI：10.1021/acs.orglett.9b00884

  日期：2019.4.19

  The synthesis and utilization of a class of 2,1-borazaronaphthyltrifluoroborate reagents that provide a general solution to the challenge of N-functionalization of the 2,1-borazaronaphthalene core is described. By adorning the nitrogen of this core with a trifluoroboratomethyl unit, a suite of odd-electron processes can be executed, installing motifs that would otherwise be inaccessible using a two-electron

  描述了一类2,1-硼硼烷基萘基三氟硼酸酯试剂的合成和利用，该试剂为应对2,1-硼硼烷基萘核的N-官能化提出了一般解决方案。通过用三氟硼氢化甲基单元修饰该核的氮，可以执行一套奇数电子过程，安装使用双电子方法无法获得的基序。另外，该方法使得能够快速成环，从而提供了迄今未知的多环BN物种。
• 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，
• Tricarbonylchromium Complexes of 1,2-Dihydro-1,2-benzazaborines
  作者：Jun Pan、Jeff W. Kampf、Arthur J. Ashe

  DOI：10.1021/om800383v

  日期：2009.1.26

  140 °C to form complex 18, in which the phenyl is η6-bound to chromium. 1,2-Dihydro-2-methyl-1,2-benzazaborine reacts with Cr(CO)3(CH3CN)3 in THF at 60 °C to form complex 23, in which the benzo ring is η6-bound to chromium. Treating 23 with potassium bis(trimethylsilyl)amide in THF forms the corresponding potassium salt 25, which on heating undergoes haptotropic isomerization to complex 26, in which

  含Cr（CO）1,2-二氢-2-苯基-1,2- benzazaborine发生反应3（CH 3 CN）3在THF中在140℃，以形成复合物18，其中所述苯基是η 6 -结合的铬。含Cr（CO）1,2-二氢-2-甲基-1,2- benzazaborine发生反应3（CH 3 CN）3在THF中在60℃，以形成复合物23，其中，所述苯并环是η 6 -结合到铬。在THF中用双（三甲基甲硅烷基）酰胺钾处理23形成相应的钾盐25，该钾盐在加热后经历触变异构化为配合物26，其中，所述阴离子性的杂环是η 6 -结合到铬。
• 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.