4-(2,3,4-Trihydroxyphenyl)butanoic acid | 1228675-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(2,3,4-Trihydroxyphenyl)butanoic acid
• 英文别名: 4-(2,3,4-trihydroxyphenyl)butanoic acid
• CAS: 1228675-80-6
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: BIEDGINASLNEKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2,3,4-Trihydroxyphenyl)butanoic acid 在 Trametes versicolor laccase 作用下， 以51%的产率得到4-[1-(3-Carboxypropyl)-2,3,4,6-tetrahydroxy-5-oxobenzo[7]annulen-7-yl]butanoic acid
  参考文献：
  名称：

  An efficient chemo-enzymatic approach towards variably functionalized benzotropolones

  摘要：

  An efficient three-step synthesis for benzotropolones via three catalytic steps is presented. Pyrogallol phenones are formed in the first step starting from pyrogallol, which is acylated by proton-catalysis. Catalytic hydrogenation of the phenones yields the corresponding alkylated pyrogallyl dervatives. In the final enzyme-catalyzed step the pyrogallol derivatives are annulated to form the benzotropolone cores. An alternative pathway via the Pechmann reaction is also presented. The combination of the three catalytic steps gives access to a wide range of benzotropolone congeners. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.068
• 作为产物：
  描述：

  Methyl 4-oxo-4-(2,3,4-trihydroxyphenyl)butanoate 在 磷酸 、 1% Pd/C 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 以49%的产率得到4-(2,3,4-Trihydroxyphenyl)butanoic acid
  参考文献：
  名称：

  An efficient chemo-enzymatic approach towards variably functionalized benzotropolones

  摘要：

  An efficient three-step synthesis for benzotropolones via three catalytic steps is presented. Pyrogallol phenones are formed in the first step starting from pyrogallol, which is acylated by proton-catalysis. Catalytic hydrogenation of the phenones yields the corresponding alkylated pyrogallyl dervatives. In the final enzyme-catalyzed step the pyrogallol derivatives are annulated to form the benzotropolone cores. An alternative pathway via the Pechmann reaction is also presented. The combination of the three catalytic steps gives access to a wide range of benzotropolone congeners. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.068

文献信息

• An efficient chemo-enzymatic approach towards variably functionalized benzotropolones
  作者：Gabi Baisch、Barbara Wagner、Reinhold Öhrlein

  DOI：10.1016/j.tet.2010.03.068

  日期：2010.5

  An efficient three-step synthesis for benzotropolones via three catalytic steps is presented. Pyrogallol phenones are formed in the first step starting from pyrogallol, which is acylated by proton-catalysis. Catalytic hydrogenation of the phenones yields the corresponding alkylated pyrogallyl dervatives. In the final enzyme-catalyzed step the pyrogallol derivatives are annulated to form the benzotropolone cores. An alternative pathway via the Pechmann reaction is also presented. The combination of the three catalytic steps gives access to a wide range of benzotropolone congeners. (C) 2010 Elsevier Ltd. All rights reserved.