1-benzyl-2-(1-naphthyl)-2,1-borazaronaphthalene | 1510779-16-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-benzyl-2-(1-naphthyl)-2,1-borazaronaphthalene
• 英文别名: 1-Benzyl-2-naphthalen-1-yl-1,2-benzazaborinine；1-benzyl-2-naphthalen-1-yl-1,2-benzazaborinine
• CAS: 1510779-16-4
• 化学式: C₂₅H₂₀BN
• 分子量: 345.251
• InChiKey: BMULHXSIQJMWTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2-溴苯乙烯 在 四氯化硅 、 2-(二叔丁基膦)联苯 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 28.0h， 生成 1-benzyl-2-(1-naphthyl)-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

• A Convergent, Modular Approach to Functionalized 2,1-Borazaronaphthalenes from 2-Aminostyrenes and Potassium Organotrifluoroborates
  作者：Steven R. Wisniewski、Courtney L. Guenther、O. Andreea Argintaru、Gary A. Molander

  DOI：10.1021/jo402616w

  日期：2014.1.3

  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.