2-(1-butynyl)-2,1-borazaronaphthalene | 1510779-90-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2-(1-butynyl)-2,1-borazaronaphthalene
• 英文别名: 2-hex-1-ynyl-1H-1,2-benzazaborinine
• CAS: 1510779-90-4
• 化学式: C₁₄H₁₆BN
• 分子量: 209.099
• InChiKey: NBLBJYYSOXPQCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(1-butynyl)-2,1-borazaronaphthalene 在 溴 作用下， 以 二氯甲烷 为溶剂， 以29%的产率得到3-bromo-2-(hex-1-yn-1-yl)-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-(1-butynyl)-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