(3R,5R)-1,3,4,5-四[(3,4,5-三羟基苯甲酰基)氧基]环己烷-1-羧酸 | 109008-79-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (3R,5R)-1,3,4,5-四[(3,4,5-三羟基苯甲酰基)氧基]环己烷-1-羧酸
• 英文名称: 1,3,4,5-tetra-O-galloylquinic acid
• 英文别名: (3R,5R)-1,3,4,5-tetrakis[(3,4,5-trihydroxybenzoyl)oxy]cyclohexane-1-carboxylic acid
• CAS: 109008-79-9；123166-70-1
• 化学式: C₃₅H₂₈O₂₂
• 分子量: 800.594
• InChiKey: JQVXKQDWMIXILH-JHZIIMIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  57
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  385
• 氢给体数：
  13
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  4-Nitrobenzyl-1,3,4,5-tetrakis-O-tri-O-benzylgalloyl quinate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以90%的产率得到(3R,5R)-1,3,4,5-四[(3,4,5-三羟基苯甲酰基)氧基]环己烷-1-羧酸
  参考文献：
  名称：

  On the synthesis and chiroptical properties of the tri- and tetragalloylquinic acids

  摘要：

  A synthesis of the potential pharmaceutical agents 3,4,5-trigalloylquinic acid and 1,3,4,5-tetragalloylquinic acid is described. It involves three steps starting from commercially available quinic acid and provides overall yields of about 15%. The acylation of benzyl or 4-nitrobenzyl quinate with tribenzylgalloyl chloride is the key step. It leads selectively to the triacyl product in the case of benzyl quinate and can be either stopped at the triacyl stage or driven to the tetraacyl derivative in the case of the 4-nitrobenzyl quinate. From the chiroptical properties of the two compounds their stereochemistry was derived by means of the benzoate rule.

  DOI：

  10.1007/bf00824301

文献信息

• On the synthesis and chiroptical properties of the tri- and tetragalloylquinic acids
  作者：R. Altmann、H. Falk

  DOI：10.1007/bf00824301

  日期：1995.11

  A synthesis of the potential pharmaceutical agents 3,4,5-trigalloylquinic acid and 1,3,4,5-tetragalloylquinic acid is described. It involves three steps starting from commercially available quinic acid and provides overall yields of about 15%. The acylation of benzyl or 4-nitrobenzyl quinate with tribenzylgalloyl chloride is the key step. It leads selectively to the triacyl product in the case of benzyl quinate and can be either stopped at the triacyl stage or driven to the tetraacyl derivative in the case of the 4-nitrobenzyl quinate. From the chiroptical properties of the two compounds their stereochemistry was derived by means of the benzoate rule.