4-Hydroxy-3-(2,3,4-trihydroxy-6-methoxycarbonyl-phenyl)-phenazine-2-carboxylic acid methyl ester | 198903-31-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-Hydroxy-3-(2,3,4-trihydroxy-6-methoxycarbonyl-phenyl)-phenazine-2-carboxylic acid methyl ester
• 英文别名: Methyl 4-hydroxy-3-(2,3,4-trihydroxy-6-methoxycarbonylphenyl)phenazine-2-carboxylate
• CAS: 198903-31-0
• 化学式: C₂₂H₁₆N₂O₈
• 分子量: 436.378
• InChiKey: OPEFCADVAYHJNU-UHFFFAOYSA-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：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  159
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-3-(2,3,4-trihydroxy-6-methoxycarbonyl-phenyl)-phenazine-2-carboxylic acid methyl ester 在 sodium dithionite 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以79%的产率得到dimethyl 4,4',5,5',6,6'-hexahydroxy-[1,1'-biphenyl]-2,2'-dicarboxylate
  参考文献：
  名称：

  Ellagitannin Chemistry. The First Synthesis of Dehydrohexahydroxydiphenoate Esters from Oxidative Coupling of Unetherified Methyl Gallate

  摘要：

  A simple o-chloranil-mediated oxidative dimerization of methyl gallate in anhydrous ether furnishes a dimethyl dehydrohexahydroxydiphenoate (DHHDP) product as a pale yellow precipitate in good yield. This methyl gallate dehydrodimer rapidly rearranges in acetone to give a mixture of two additional DHHDP regioisomers. One of these species corresponds to the isomer of the dehydrohexahydroxydiphenoyl group commonly observed in dehydroellagitannin natural products. Sodium dithionite-mediated reduction of the initially formed dimethyl dehydrohexahydroxydiphenoate and/or its derived regioisomers efficiently furnishes dimethyl hexahydroxydiphenoate (HHDP). Addition of N-(carbobenzyloxy)-L-cysteine benzyl ester to dimethyl dehydrohexahydroxydiphenoate(s) in THF solution produces two diastereomeric S-S-cysteinyl derivatives of dimethyl hexahydroxydiphenoate.

  DOI：

  10.1021/jo971354k
• 作为产物：
  描述：

  没食子酸甲酯 在 邻四氯苯醌 作用下， 以 乙醚 、 溶剂黄146 、 乙腈 为溶剂， 反应 18.0h， 生成 4-Hydroxy-3-(2,3,4-trihydroxy-6-methoxycarbonyl-phenyl)-phenazine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Ellagitannin Chemistry. The First Synthesis of Dehydrohexahydroxydiphenoate Esters from Oxidative Coupling of Unetherified Methyl Gallate

  摘要：

  A simple o-chloranil-mediated oxidative dimerization of methyl gallate in anhydrous ether furnishes a dimethyl dehydrohexahydroxydiphenoate (DHHDP) product as a pale yellow precipitate in good yield. This methyl gallate dehydrodimer rapidly rearranges in acetone to give a mixture of two additional DHHDP regioisomers. One of these species corresponds to the isomer of the dehydrohexahydroxydiphenoyl group commonly observed in dehydroellagitannin natural products. Sodium dithionite-mediated reduction of the initially formed dimethyl dehydrohexahydroxydiphenoate and/or its derived regioisomers efficiently furnishes dimethyl hexahydroxydiphenoate (HHDP). Addition of N-(carbobenzyloxy)-L-cysteine benzyl ester to dimethyl dehydrohexahydroxydiphenoate(s) in THF solution produces two diastereomeric S-S-cysteinyl derivatives of dimethyl hexahydroxydiphenoate.

  DOI：

  10.1021/jo971354k