2-methyl-2,1-borazaronaphthalene | 2622-56-2

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2-methyl-2,1-borazaronaphthalene
• 英文别名: 2-Methyl-1,2-dihydro-1,2-benzazaborinine；2-methyl-1H-1,2-benzazaborinine
• CAS: 2622-56-2
• 化学式: C₉H₁₀BN
• 分子量: 142.996
• InChiKey: DIHWSTCCUNONKQ-UHFFFAOYSA-N

物化性质

• 熔点：
  73-74 °C(Solv: ligroine (8032-32-4))
• 沸点：
  213.7±43.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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-methyl-2,1-borazaronaphthalene 在 溴 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到3-bromo-2-methyl-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-methyl-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

• 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。
• 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。
• 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.
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.1, 2.9.6.2.1.1, page 207 - 212
  作者：

  DOI：——

  日期：——
• New Heteroaromatic Compounds. XV.¹ Halogenation of 2-Methyl-2,1-borazaronaphthalene
  作者：MICHAEL J. S. DEWAR、ROY DIETZ

  DOI：10.1021/jo01067a053

  日期：1961.9