[2-[N-(D-ribofuranosyl)amino]phenyl]boronic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-[N-(D-ribofuranosyl)amino]phenyl]boronic acid
• 英文别名: [2-[[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]amino]phenyl]boronic acid
• 化学式: C₁₁H₁₆BNO₆
• 分子量: 269.062
• InChiKey: TXSBXYKYKKQCOW-QHPFDFDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.78
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  122
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  卡培他滨杂质25 、 2-氨基苯硼酸 以 乙醇 为溶剂， 反应 24.0h， 以97%的产率得到[2-[N-(D-ribofuranosyl)amino]phenyl]boronic acid
  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

文献信息

• Boron-Containing Heterocycles:  Syntheses, Structures, and Properties of Benzoborauracils and a Benzoborauracil Nucleoside
  作者：Jin-Cong Zhuo、Albert H. Soloway、John C. Beeson、Weihua Ji、Beverly A. Barnum、Feng-Guang Rong、Werner Tjarks、Glenn T. Jordan、Jianping Liu、Sheldon G. Shore

  DOI：10.1021/jo991176q

  日期：1999.12.1

  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.