1-O-[(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-yl] 4-O-methyl (2R,3R)-2,3-dibenzoyloxybutanedioate | 318949-09-6

• 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: 1-O-[(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-yl] 4-O-methyl (2R,3R)-2,3-dibenzoyloxybutanedioate
• CAS: 318949-09-6
• 化学式: C₆₂H₅₂O₁₃
• 分子量: 1005.09
• InChiKey: JDQYEEOXUUOSKW-YZEGPCJOSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  75
• 可旋转键数：
  25
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  151
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  1-O-[(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-yl] 4-O-methyl (2R,3R)-2,3-dibenzoyloxybutanedioate 在 palladium on activated charcoal 氢氧化钾 、 水 、 氢气 作用下， 以 甲醇 为溶剂， 生成 儿茶提取物
  参考文献：
  名称：

  Methods in synthesis of flavonoids.

  摘要：

  Resolution of racemic synthetic tetra-O-benzylcatechin 2 is described, through the formation of esters 5 and 6 derived from dibenzoyl-L-tartaric acid. The diastereoisomer of the natural series 6 was separated by crystallization, the other one being an oil. This process allowed us to prepare enantiomerically pure (+)-catechin 8 in high yield. The pure isomer in the ent-series 9 could be obtained, following the same scheme of reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01649-x
• 作为产物：
  描述：

  O,O'-dibenzoyl-L-tartaric acid 在 4-二甲氨基吡啶 、 乙酸酐 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 1-O-[(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-yl] 4-O-methyl (2R,3R)-2,3-dibenzoyloxybutanedioate
  参考文献：
  名称：

  Methods in synthesis of flavonoids.

  摘要：

  Resolution of racemic synthetic tetra-O-benzylcatechin 2 is described, through the formation of esters 5 and 6 derived from dibenzoyl-L-tartaric acid. The diastereoisomer of the natural series 6 was separated by crystallization, the other one being an oil. This process allowed us to prepare enantiomerically pure (+)-catechin 8 in high yield. The pure isomer in the ent-series 9 could be obtained, following the same scheme of reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01649-x