1,2-dihydro-1-hydroxy-2-propyl-2,4,1-benzodiazaborine | 157524-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 1,2-dihydro-1-hydroxy-2-propyl-2,4,1-benzodiazaborine
• CAS: 157524-30-6
• 化学式: C₁₀H₁₃BN₂O
• 分子量: 188.037
• InChiKey: XBYQXUZVTZTDQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.76
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.83
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-硝基苯基硼酸 在 H₂ 、 catalyst: Pd/C 、 H₂O 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 生成 1,2-dihydro-1-hydroxy-2-propyl-2,4,1-benzodiazaborine
  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