(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-(2-hydroxy-4,6-dimethoxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol | 1258979-23-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-(2-hydroxy-4,6-dimethoxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 1258979-23-5
• 化学式: C₂₃H₂₂O₉
• 分子量: 442.422
• InChiKey: IVWBFRBINWGPIO-YTFSRNRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-(2-hydroxy-4,6-dimethoxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol 、 丙炔酸甲酯 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 methyl 2-(5-((2R,3R,4S)-3,5,7-trihydroxy-4-(2-hydroxy-4,6-dimethoxyphenyl)chroman-2-yl)benzo[d][1,3]dioxol-2-yl)acetate
  参考文献：
  名称：

  Sustainability from agricultural waste: chiral ligands from oligomeric proanthocyanidins via acid-mediated depolymerization

  摘要：

  Oligomeric proanthocyanidins (OPCs, Ar' = 3,4-(HO)(2)(C6H3) are abundant natural products found in agricultural and forestry waste such as pine bark, grape seeds, and the peels of mangosteen. We have demonstrated that the OPCs can be converted into small molecule chiral ligands by using proper nucleophiles for acid depolymerization of the OPCs. The chiral ligands may have potential for sustainable asymmetric catalysis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.123

文献信息

• METHOD OF PREPARING DERIVATIVES/OLIGOMERS OF EPICATECHIN AND APPLICATIONS THEREOF
  申请人：Huang Dejian

  公开号：US20120323016A1

  公开（公告）日：2012-12-20

  The present invention relates to the preparation of a class of novel, optically active compounds derived from oligomeric proanthocyanidins (OPCs), more particularly to oligomers of epicatechin. These compounds include multidentate ligands and their metal complexes for use in catalysis. Methods of depolymerising proanthocyanidins to form catechins, and particularly depolymerising proanthocyanidins derived from plant sources to form novel epicatechins having application in catalysis are disclosed.