3,4-(fluoren-9-ylidenedioxy)-5-hydroxybenzoic acid | 146300-78-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3,4-(fluoren-9-ylidenedioxy)-5-hydroxybenzoic acid
• 英文别名: 7-hydroxyspiro[1,3-benzodioxole-2,9'-fluorene]-5-carboxylic acid
• CAS: 146300-78-9
• 化学式: C₂₀H₁₂O₅
• 分子量: 332.312
• InChiKey: BVSCZJYREWFNJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,4-(fluoren-9-ylidenedioxy)-5-hydroxybenzoic acid 在 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 3-(tert-butyldimethylsiloxy)-4,5-(fluoren-9-ylidenedioxy)benzoic acid
  参考文献：
  名称：

  Ellagitannin Chemistry. Preparative and Mechanistic Studies of the Biomimetic Oxidative Coupling of Galloyl Esters

  摘要：

  The construction of strictly the (S)-hexahydroxydiphenyl (HHDP) unit via biomimetic cyclization of suitably protected glucose-derived digalloyl esters has been achieved in good yield. Studies on substrates of increasing complexity utilizing a range of oxidants (Pb(OAc)(4), VOF3, Tl2O3) have helped define the scope and limitations of this approach to ellagitannin synthesis. Computer modeling of key cyclization precursors helped elucidate the molecular-level structural details which undergird the Haslam/Schmidt biosynthesis model for this class of naturally occurring secondary plant metabolites.

  DOI：

  10.1021/ja00087a022
• 作为产物：
  描述：

  methyl 3,4-(fluoren-9-ylidenedioxy)-5-hydroxybenzoate 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以99%的产率得到3,4-(fluoren-9-ylidenedioxy)-5-hydroxybenzoic acid
  参考文献：
  名称：

  Ellagitannin Chemistry. Preparative and Mechanistic Studies of the Biomimetic Oxidative Coupling of Galloyl Esters

  摘要：

  The construction of strictly the (S)-hexahydroxydiphenyl (HHDP) unit via biomimetic cyclization of suitably protected glucose-derived digalloyl esters has been achieved in good yield. Studies on substrates of increasing complexity utilizing a range of oxidants (Pb(OAc)(4), VOF3, Tl2O3) have helped define the scope and limitations of this approach to ellagitannin synthesis. Computer modeling of key cyclization precursors helped elucidate the molecular-level structural details which undergird the Haslam/Schmidt biosynthesis model for this class of naturally occurring secondary plant metabolites.

  DOI：

  10.1021/ja00087a022