[4-(13)C,2,3-(15)N2]-1,2-dihydro-1-hydroxy-2,3,1-benzodiazaborine | 194552-63-1

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: [4-(13)C,2,3-(15)N2]-1,2-dihydro-1-hydroxy-2,3,1-benzodiazaborine
• CAS: 194552-63-1
• 化学式: C₇H₇BN₂O
• 分子量: 148.932
• InChiKey: VYLMBCVKHNTBIA-CWIKHUNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.69
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.62
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  苯甲醛-α-13C 在 N,N,N'-trimethylethylenediamine 、 n-BuLi 、 aq. HCl 、 aq. NaOH 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 [4-(13)C,2,3-(15)N2]-1,2-dihydro-1-hydroxy-2,3,1-benzodiazaborine
  参考文献：
  名称：

  Planar Boron Heterocycles with Nucleic Acid-Like Hydrogen-Bonding Motifs

  摘要：

  To promote the development of boron-containing purine analogues that exist in planar, non-zwitterionic dominant structural form in aqueous solution, rigorous solution and solid state structural analyses of 1-hydroxy-1H-2,3,1-benzoxazaborine (1), 1,2-dihydro-1-hydroxy-2,3,1-benzodiazaborine (2), and related 2,3,1-benzodiheteraborines were undertaken. With the aid of isotope-enriched compounds, a multisolvent H-1, C-13, B-11, and N-15 NMR spectroscopic analysis of 1 and 2 was conducted, providing structurally-diagnostic chemical shift data for all non-oxygen atoms that constitute their heterocyclic peripheries. In addition, single-crystal X-ray diffraction analyses of 1 and 2 were performed. In stark contrast to their 2,4,1 isomeric counterparts, the 2,3,1-benzoxaza- and benzodiazaborines exist in planar structural form in protic solution and in the solid state and display proton dissociative and associative tendencies reflective of the predominant Bronsted, yet still Lewis acidic-capable character of the B-OH group together with the basic one at the C4-N3 imine group. In the solid state, 1 and 2 display intermolecular hydrogen-bonding patterns not too dissimilar from the motifs of certain natural nucleic acid bases. Diazaborine 2 was shown by VT-NMR to undergo a triple hydrogen-bonding solution association with a 2',3',5'-tri-O-protected cytidine in a demonstration of one biomimetic potential held by a 1-hydroxy-2,3,1-diheteraborine periphery. In general, 1, 2, and related 1-hydroxy-2,3,1-benzodiheteraborine heterocycles were found to be characterized by an environment-dependent O1-->N3 Bronsted prototropy and B-OH group Bronsted/Lewis acid ambidency so sensitive and subtle that certain past difficulties encountered in attempts to delineate their physicochemical properties now become readily appreciated.

  DOI：

  10.1021/ja963784i