(–)–3,5-di-O-feruloylquinic acid | 333753-65-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (–)–3,5-di-O-feruloylquinic acid
• 英文别名: (1s,3R,4s,5R)-3,5-di-O-feruloylquinic acid；(-)-3,5-di-O-feruloylquinic acid；3,5-di-O-caffeoylquinic acid；3,5-O-diferuloylquinic acid
• CAS: 333753-65-4
• 化学式: C₂₇H₂₈O₁₂
• 分子量: 544.512
• InChiKey: MOMSOBSYYRIFOP-JRCQBRFGSA-N

物化性质

• 沸点：
  773.7±60.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  189.28
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  3,3'-(((1R,2S,3R,5S)-5-carboxy-2,5-dihydroxycyclohexane-1,3-diyl)bis(oxy))bis(3-oxopropanoic acid) 、 香草醛 在 哌啶 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 192.0h， 以72%的产率得到(–)–3,5-di-O-feruloylquinic acid
  参考文献：
  名称：

  Total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives

  摘要：

  We report the first total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives, 3,5-O-diferuloylquinic acid and 3,5-(3,4-dimethoxycinnamyl)quinic acid, in a nine-step sequence. The key step involves Knoevenagel condensations between vanillin. 3,4-dimethoxybenzaldehyde or 4-hydroxy-3-methoxy-benzaldehyde and the dimalonate ester of quinic acid. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.127

文献信息

• Total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives
  作者：K. Saki Raheem、Nigel P. Botting、Gary Williamson、Denis Barron

  DOI：10.1016/j.tetlet.2011.10.127

  日期：2011.12

  We report the first total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives, 3,5-O-diferuloylquinic acid and 3,5-(3,4-dimethoxycinnamyl)quinic acid, in a nine-step sequence. The key step involves Knoevenagel condensations between vanillin. 3,4-dimethoxybenzaldehyde or 4-hydroxy-3-methoxy-benzaldehyde and the dimalonate ester of quinic acid. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.