N-((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl)-3-(2,3,4-trihydroxyphenyl)propanamide | 1228675-84-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl)-3-(2,3,4-trihydroxyphenyl)propanamide
• CAS: 1228675-84-0
• 化学式: C₁₅H₂₃NO₉
• 分子量: 361.349
• InChiKey: DXBCFUXPRLICTB-UNNXFLIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.71
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  190.94
• 氢给体数：
  9.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N-((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl)-3-(2,3,4-trihydroxyphenyl)propanamide 在 Trametes versicolor laccase 作用下， 反应 48.0h， 以57%的产率得到
  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：

  7,8-dihydroxy-chroman-2-one 、 D-萄糖胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以98%的产率得到N-((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl)-3-(2,3,4-trihydroxyphenyl)propanamide
  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