2-(2-aminophenyl)-1,2-dihydro-4H-benzo[d][1,3,2,6]oxazadiborinin-4-ol | 157524-37-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(2-aminophenyl)-1,2-dihydro-4H-benzo[d][1,3,2,6]oxazadiborinin-4-ol
• CAS: 157524-37-3
• 化学式: C₁₂H₁₂B₂N₂O₂
• 分子量: 237.861
• InChiKey: NZRRVNOCJNEPSU-UHFFFAOYSA-N

物化性质

• 沸点：
  420.9±47.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.21
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.51
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(2-aminophenyl)-1,2-dihydro-4H-benzo[d][1,3,2,6]oxazadiborinin-4-ol 、 [(2,2-dimethylpenta-3,4-dienyloxy)methyl]benzene 在 2BF₄^(1-)*C₇₂H₆₂O₂P₄Pt₂⁽⁴⁺⁾ 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以64%的产率得到2-[5-(benzyloxy)-4,4-dimethylpent-1-en-2-yl]aniline
  参考文献：
  名称：

  基于分子内氨基甲酰基乙烯酮-烯烃[2 + 2]环加成反应的十溴氟胺B和E的全合成

  摘要：

  通过使用邻位氨基苯基硼酸与烯丙基的铂催化加成反应和分子内氨基甲酰乙烯酮-烯烃[2 + 2]环加成反应，可完成十溴氟乙胺B和E的全合成，从而构建目标生物碱的基本碳骨架作为关键步骤。

  DOI：

  10.1021/jo301817w
• 作为产物：
  描述：

  2-硝基苯基硼酸 在 H₂ 、 catalyst: Pd/C 作用下， 以 乙醇 为溶剂， 生成 2-(2-aminophenyl)-1,2-dihydro-4H-benzo[d][1,3,2,6]oxazadiborinin-4-ol
  参考文献：
  名称：

  Boron Heterocycles Bearing a Peripheral Resemblance to Naturally-Occurring Purines: Design, Syntheses, Structures, and Properties

  摘要：

  To test the design and initiate the development of a new class of boron-containing purine nucleoside and aglycon analogs, the benzo-fused boron heterocycles 1-hydroxy-1H-2,4,1-benzoxazaborine (2), 1,2-dihydro-1-hydroxy-2,4, 1-benzodiazaborine (3), and 3-amino-1,2-dihydro-1-hydroxy-2,4,1-benzodiazaborine (4) were synthesized, and their structural properties and chemical reactivities were investigated. The heterocyclic peripheries of these targets possess heteroatom, hydrogen atom, and in-plane lone-pair electron loci specifically selected to match closely those of the pyrimidine ring portions of the naturally-occurring purines adenine, hypoxanthine, and guanine. According to H-1 and B-11 NMR spectral analyses, 2-4 are stable to facile hydrolysis, but not to facile hydration, which occurs in a 1,4-fashion to give zwitterionic adducts. In addition, these benzo-fused boron heterocycles form bis-methanol adducts simply upon warming in methanol solution. A single-crystal X-ray diffraction analysis of the bis-methanol adduct (14) derived from 3 confirmed it to be a zwitterion comprised of tetrahedral berate anion and formamidinium cation molecular fragments. From NMR-based solution structure determinations made of 2-4 and a series of substituted derivatives, the facile 1,4-hydration property appears to be endemic to the 2,4,1-oxaza- and diazaborine classes of boron heterocycles and is projected to imbue certain future imidazo[5,4-e]-fused members with the requisite aqueous solution structural features for ''transition-state'' analog inhibition of the enzyme adenosine deaminase (EC 3.5.4.4). This work underscores the attraction of employing boron-for-carbon replacement strategies in the design of new, potentially bioactive agents.

  DOI：

  10.1021/ja00096a017