3-bromo-2-methyl-2,1-borazaronaphthalene | 92765-54-3

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 3-bromo-2-methyl-2,1-borazaronaphthalene
• 英文别名: 3-bromo-2-methyl-1H-1,2-benzazaborinine
• CAS: 92765-54-3
• 化学式: C₉H₉BBrN
• 分子量: 221.892
• InChiKey: JXNITVWJQDYWNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  12
• 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：

  3-bromo-2-methyl-2,1-borazaronaphthalene 在 chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium (II) 、 溴 、 caesium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 6-bromo-3-(3-methoxyphenyl)-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-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

文献信息

• 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.
• 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
• Suzuki–Miyaura Cross-Coupling of Brominated 2,1-Borazaronaphthalenes with Potassium Alkenyltrifluoroborates
  作者：Gary A. Molander、Steven R. Wisniewski、Elham Etemadi-Davan

  DOI：10.1021/jo502260x

  日期：2014.11.21

  Conditions have been developed for the palladium-catalyzed cross-coupling of 3-bromo-2,1-borazaronaphthalenes with potassium alkenyltrifluoroborates. Twenty-seven alkenyl-substituted azaborines have been synthesized through this method, providing access to a family of 2,1-borazaronaphthalenes with alkenyl substitution at the C3 position.