1-hydroxy-2-methyl-1H-2,4,1-benzodiazaborin-3-one | 179738-94-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 1-hydroxy-2-methyl-1H-2,4,1-benzodiazaborin-3-one
• 英文别名: 1-hydroxy-2-methyl-4H-2,4,1-benzodiazaborinin-3-one
• CAS: 179738-94-4
• 化学式: C₈H₉BN₂O₂
• 分子量: 175.983
• InChiKey: OMOZCICFDZGXLX-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.15
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  六甲基二硅氮烷 、 1-hydroxy-2-methyl-1H-2,4,1-benzodiazaborin-3-one 在 三甲基氯硅烷 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Boron-Containing Heterocycles:  Syntheses, Structures, and Properties of Benzoborauracils and a Benzoborauracil Nucleoside

  摘要：

  Benzo-fused boron-containing heterocycles (benzoborauracils), 1-hydroxy-1H-2,4,1-benzodiazaborin-3-one (3a), 1-hydroxy-2-methyl-1H-2,4,1-benzodiazaborin-3-one (3b), and 1-hydroxyy-phenyl-1H-2,4,1-benzodiazaborin-3-one (3c) were synthesized, and their structures were established on the basis of H-1, C-13, and B-11 NMR spectroscopies, mass spectrometry, and microelemental analyses. The structures of compounds 3b and 3e were unambiguously confirmed by X-ray crystallographic analyses. B-11 NMR spectral analyses of the methanolic solutions of benzoborauracils 3a-c confirmed the formation of the corresponding bis-methanol adducts 13a-c. The structure of the N-Ph bis-methanol adduct 13c was confirmed by X-ray crystallography. The stabilities of these bis-methanol adducts depend on the substituent at the N2 position of 3a-c. The bis-methanol adducts are readily reconverted to the corresponding benzoborauracils upon removal of methanol. The first stable benzoborauracil nucleoside, 4-[5-O-(tert-butyldimethylsilyl)-2,3-O-disopropylidene-alpha-D-ribofuranosyl]-1-hydroxy-2-methyl-1H-2,4,1-benzodiazaborin-3-one (25) was prepared in two steps by treatment of 2-aminophenylboronic acid with 5-O-(tert-butyldimethylsilyl)-2,3-O-diisopropylidene-D-ribofuranose followed by its reaction with methylisocyanate.

  DOI：

  10.1021/jo991176q
• 作为产物：
  描述：

  2-氨基苯硼酸 、 异氰酸甲酯 以 乙腈 为溶剂， 反应 6.0h， 以87%的产率得到1-hydroxy-2-methyl-1H-2,4,1-benzodiazaborin-3-one
  参考文献：
  名称：

  Boron-Containing Heterocycles:  Syntheses, Structures, and Properties of Benzoborauracils and a Benzoborauracil Nucleoside

  摘要：

  Benzo-fused boron-containing heterocycles (benzoborauracils), 1-hydroxy-1H-2,4,1-benzodiazaborin-3-one (3a), 1-hydroxy-2-methyl-1H-2,4,1-benzodiazaborin-3-one (3b), and 1-hydroxyy-phenyl-1H-2,4,1-benzodiazaborin-3-one (3c) were synthesized, and their structures were established on the basis of H-1, C-13, and B-11 NMR spectroscopies, mass spectrometry, and microelemental analyses. The structures of compounds 3b and 3e were unambiguously confirmed by X-ray crystallographic analyses. B-11 NMR spectral analyses of the methanolic solutions of benzoborauracils 3a-c confirmed the formation of the corresponding bis-methanol adducts 13a-c. The structure of the N-Ph bis-methanol adduct 13c was confirmed by X-ray crystallography. The stabilities of these bis-methanol adducts depend on the substituent at the N2 position of 3a-c. The bis-methanol adducts are readily reconverted to the corresponding benzoborauracils upon removal of methanol. The first stable benzoborauracil nucleoside, 4-[5-O-(tert-butyldimethylsilyl)-2,3-O-disopropylidene-alpha-D-ribofuranosyl]-1-hydroxy-2-methyl-1H-2,4,1-benzodiazaborin-3-one (25) was prepared in two steps by treatment of 2-aminophenylboronic acid with 5-O-(tert-butyldimethylsilyl)-2,3-O-diisopropylidene-D-ribofuranose followed by its reaction with methylisocyanate.

  DOI：

  10.1021/jo991176q