2-bromo-3-dehydroshikimic acid | 202416-29-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-3-dehydroshikimic acid
• 英文别名: (4S,5R)-2-bromo-4,5-dihydroxy-3-oxocyclohexene-1-carboxylic acid
• CAS: 202416-29-3
• 化学式: C₇H₇BrO₅
• 分子量: 251.034
• InChiKey: SZFVEAGZDIZWAT-WUJLRWPWSA-N

物化性质

• 熔点：
  176-178 °C
• 沸点：
  425.6±45.0 °C(Predicted)
• 密度：
  2.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-bromo-3-dehydroshikimic acid 在 deuterated potassium phosphate buffer 、 shikimate dehydroge 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 水 为溶剂， 反应 24.0h， 以90%的产率得到(3S,4S,5R)-2-bromo-3,4,5-trihydroxycyclohexene-1-carboxylic acid
  参考文献：
  名称：

  Synthesis of 2-Bromo- and 2-Fluoro-3-dehydroshikimic Acids and 2-Bromo- and 2-Fluoroshikimic Acids Using Synthetic and Enzymatic Approaches

  摘要：

  The syntheses of 2-bromo-3-dehydroshikimic acid(1) (5) and 2-bromoshikimic acid(2) (8), are described. Their formation from (2R)-2-bromo-3-dehydroquinic acid (2) using dehydroquinase and shikimate dehydrogenase is also reported. The corresponding enzymatic formation of 2-fluoro-3-dehydroshikimic acid(1) (6) and 2-fluoroshikimic acid(2) (9) from (2R)-2-fluoro-3-dehydroquinic acid (3) are reported.

  DOI：

  10.1021/jo971858i
• 作为产物：
  描述：

  (1S,2R,4S,5R)-2-bromo-4-[tert-butyl(dimethyl)silyl]oxy-1-hydroxy-6-oxabicyclo[3.2.1]octane-3,7-dione 在 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 为溶剂， 反应 76.0h， 生成 2-bromo-3-dehydroshikimic acid
  参考文献：
  名称：

  Synthesis of 2-Bromo- and 2-Fluoro-3-dehydroshikimic Acids and 2-Bromo- and 2-Fluoroshikimic Acids Using Synthetic and Enzymatic Approaches

  摘要：

  The syntheses of 2-bromo-3-dehydroshikimic acid(1) (5) and 2-bromoshikimic acid(2) (8), are described. Their formation from (2R)-2-bromo-3-dehydroquinic acid (2) using dehydroquinase and shikimate dehydrogenase is also reported. The corresponding enzymatic formation of 2-fluoro-3-dehydroshikimic acid(1) (6) and 2-fluoroshikimic acid(2) (9) from (2R)-2-fluoro-3-dehydroquinic acid (3) are reported.

  DOI：

  10.1021/jo971858i

文献信息

• Synthesis of 2-Bromo- and 2-Fluoro-3-dehydroshikimic Acids and 2-Bromo- and 2-Fluoroshikimic Acids Using Synthetic and Enzymatic Approaches
  作者：C. González-Bello、M. K. Manthey、J. H. Harris、A. R. Hawkins、J. R. Coggins、C. Abell

  DOI：10.1021/jo971858i

  日期：1998.3.1

  The syntheses of 2-bromo-3-dehydroshikimic acid(1) (5) and 2-bromoshikimic acid(2) (8), are described. Their formation from (2R)-2-bromo-3-dehydroquinic acid (2) using dehydroquinase and shikimate dehydrogenase is also reported. The corresponding enzymatic formation of 2-fluoro-3-dehydroshikimic acid(1) (6) and 2-fluoroshikimic acid(2) (9) from (2R)-2-fluoro-3-dehydroquinic acid (3) are reported.