6-bromo-3-(3-methoxyphenyl)-2-methyl-2,1-borazaronaphthalene | 1616634-77-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-bromo-3-(3-methoxyphenyl)-2-methyl-2,1-borazaronaphthalene
• 英文别名: 6-bromo-3-(3-methoxyphenyl)-2-methyl-1H-1,2-benzazaborinine
• CAS: 1616634-77-5
• 化学式: C₁₆H₁₅BBrNO
• 分子量: 328.016
• InChiKey: LLNNKPABRJDMKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  21.26
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3.5-二甲氧基苯基三氟硼酸钾 、 6-bromo-3-(3-methoxyphenyl)-2-methyl-2,1-borazaronaphthalene 在 chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium (II) 、 caesium carbonate 作用下， 以 水 为溶剂， 反应 18.0h， 以86%的产率得到6-(3-methoxy-5-methylphenyl)-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：

  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