1-phenyl-2-methyl-2,1-borazaronaphthalene | 1510780-04-7

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 1-phenyl-2-methyl-2,1-borazaronaphthalene
• 英文别名: 2-methyl-1-phenyl-1,2-dihydrobenz[e]-1,2-azaborin；2-Methyl-1-phenyl-1,2-benzazaborinine
• CAS: 1510780-04-7
• 化学式: C₁₅H₁₄BN
• 分子量: 219.094
• InChiKey: WRIGCUYKORJMEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  苯胺 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 42.0h， 生成 1-phenyl-2-methyl-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

• Aromatic Metamorphosis of Indoles into 1,2-Benzazaborins
  作者：Shun Tsuchiya、Hayate Saito、Keisuke Nogi、Hideki Yorimitsu

  DOI：10.1021/acs.orglett.9b01353

  日期：2019.5.17

  indoles represent a privileged class of substructures that is ubiquitous in natural products and pharmaceuticals. While numerous exocyclic functionalizations of indoles have provided access to a variety of useful derivatives, endocyclic transformations involving the cleavage of the C2–N bond remain challenging due to the high aromaticity and strength of this bond in indoles. Herein, we report the “aromatic

  在众多的芳香族化合物中，吲哚代表了在天然产物和药物中普遍存在的一类特殊的亚结构。尽管吲哚的许多外环官能化提供了各种有用衍生物的途径，但由于吲哚中该键的高芳香性和强度，涉及C2-N键断裂的环内转化仍然具有挑战性。在本文中，我们报告了通过将硼插入C2-N键将吲哚“芳族变态”为1,2-苯并氮杂硼烷。该环内插入包括使用锂金属的还原性开环和随后用有机硼酸酯捕获所得的双阴离子物质。考虑到1，2-天青素作为苯的BN异构体已引起了学术界和工业界的日益关注，