methyl 8,10-dihydroxy-3,4,9-trimethoxy-6-oxo-6H-dibenzo[b,d]pyran-1-carboxylate | 956031-04-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: methyl 8,10-dihydroxy-3,4,9-trimethoxy-6-oxo-6H-dibenzo[b,d]pyran-1-carboxylate
• 英文别名: Methyl 8,10-dihydroxy-3,4,9-trimethoxy-6-oxobenzo[c]chromene-1-carboxylate；methyl 8,10-dihydroxy-3,4,9-trimethoxy-6-oxobenzo[c]chromene-1-carboxylate
• CAS: 956031-04-2
• 化学式: C₁₈H₁₆O₉
• 分子量: 376.32
• InChiKey: LNFBWSIEYLNYKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 8,10-dihydroxy-3,4,9-trimethoxy-6-oxo-6H-dibenzo[b,d]pyran-1-carboxylate 以 甲醇 、 水 为溶剂， 反应 8.0h， 以100%的产率得到2,3,8-三邻甲基鞣花酸
  参考文献：
  名称：

  Total synthesis of 3,3′,4-tri-O-methylellagic acid from gallic acid

  摘要：

  Total synthesis of 3,3',4-tri-O-methylellagic acid has been described from commercially available gallic acid. Construction of the crucial unsymmetric Ar-Ar bond has been carried out in various methods such as Heck coupling, Heck coupling followed by oxidation or anionic Fries rearrangement, Suzuki cross-coupling, etc., but all the attempts were unsuccessful. Then, finally it has been achieved by intramolecular Ullmann coupling reaction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.103
• 作为产物：
  描述：

  2'-bromo-5',6'-dimethoxy-3'-methoxycarbonylphenyl 2-bromo-3,5-dibenzyloxy-4-methoxybenzoate 在 palladium on activated charcoal 氢气 、 铜 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 67.0h， 生成 methyl 8,10-dihydroxy-3,4,9-trimethoxy-6-oxo-6H-dibenzo[b,d]pyran-1-carboxylate
  参考文献：
  名称：

  Total synthesis of 3,3′,4-tri-O-methylellagic acid from gallic acid

  摘要：

  Total synthesis of 3,3',4-tri-O-methylellagic acid has been described from commercially available gallic acid. Construction of the crucial unsymmetric Ar-Ar bond has been carried out in various methods such as Heck coupling, Heck coupling followed by oxidation or anionic Fries rearrangement, Suzuki cross-coupling, etc., but all the attempts were unsuccessful. Then, finally it has been achieved by intramolecular Ullmann coupling reaction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.103

文献信息

• Total synthesis of 3,3′,4-tri-O-methylellagic acid from gallic acid
  作者：Ashraful Alam、Sadao Tsuboi

  DOI：10.1016/j.tet.2007.07.103

  日期：2007.10

  Total synthesis of 3,3',4-tri-O-methylellagic acid has been described from commercially available gallic acid. Construction of the crucial unsymmetric Ar-Ar bond has been carried out in various methods such as Heck coupling, Heck coupling followed by oxidation or anionic Fries rearrangement, Suzuki cross-coupling, etc., but all the attempts were unsuccessful. Then, finally it has been achieved by intramolecular Ullmann coupling reaction. (c) 2007 Elsevier Ltd. All rights reserved.