2-isopropyl-2,1-borazaronaphthalene | 851668-40-1

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2-isopropyl-2,1-borazaronaphthalene
• 英文别名: 2-isopropyl-1,2-dihydrobenzo[e][1,2]azaborinine；2-propan-2-yl-1H-1,2-benzazaborinine
• CAS: 851668-40-1
• 化学式: C₁₁H₁₄BN
• 分子量: 171.05
• InChiKey: ZEDLYOAFRRSMSO-UHFFFAOYSA-N

物化性质

• 沸点：
  245.5±43.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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-isopropyl-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 3-(3-methoxyphenyl)-2-isopropyl-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：

  potassium isopropyltrifluoroborate 、 2-氨基苯乙烯 在 四氯化硅 、 三乙胺 作用下， 以 甲苯 为溶剂， 以82.9%的产率得到2-isopropyl-2,1-borazaronaphthalene
  参考文献：
  名称：

  氮杂硼酸苄基离子在离子聚合中的稳定性和反应性

  摘要：

  苄基阳离子和阴离子与关键有机转化的机制有关，例如苯乙烯聚合。我们研究了 BN 对 CC 键取代对苄基离子反应性的影响以及对 BN 2-乙烯基萘 (BN2VN) 离子聚合的影响。计算表明，N 供体与阳离子的接近会影响 BN 苄基阳离子的稳定性，从而合理化 BN2VN 的不成功质子化。有机锂试剂通过假设的缔合机制与 BN2VN 和相关的 BN 萘进行干净的亲核芳族取代。这些结果表明了主族芳烃取代的设计原则。

  DOI：

  10.1039/d1ob02467a

文献信息

• Accessing Molecularly Complex Azaborines: Palladium-Catalyzed Suzuki–Miyaura Cross-Couplings of Brominated 2,1-Borazaronaphthalenes and Potassium Organotrifluoroborates
  作者：Gary A. Molander、Steven R. Wisniewski

  DOI：10.1021/jo5011894

  日期：2014.7.18

  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.
• Azaborine benzylic ion stability and reactivity in ionic polymerization
  作者：Herbert Wakefield IV、Qifeng Jiang、Rebekka S. Klausen

  DOI：10.1039/d1ob02467a

  日期：——

  Benzylic cations and anions are implicated in the mechanism of critical organic transformations, such as styrene polymerization. We investigate the influence of BN for CC bond substitution on the reactivity of benzylic ions and the effect on BN 2-vinylnaphthalene (BN2VN) ionic polymerization. Calculations suggest that the proximity of a N donor to a cation influences the stability of a BN benzylic

  苄基阳离子和阴离子与关键有机转化的机制有关，例如苯乙烯聚合。我们研究了 BN 对 CC 键取代对苄基离子反应性的影响以及对 BN 2-乙烯基萘 (BN2VN) 离子聚合的影响。计算表明，N 供体与阳离子的接近会影响 BN 苄基阳离子的稳定性，从而合理化 BN2VN 的不成功质子化。有机锂试剂通过假设的缔合机制与 BN2VN 和相关的 BN 萘进行干净的亲核芳族取代。这些结果表明了主族芳烃取代的设计原则。