tert-butyldimethylsilyl 3-(tert-butyldimethylsiloxy)-4,5-(fluoren-9-ylidenedioxy)benzoate | 146300-79-0

• 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: tert-butyldimethylsilyl 3-(tert-butyldimethylsiloxy)-4,5-(fluoren-9-ylidenedioxy)benzoate
• CAS: 146300-79-0
• 化学式: C₃₂H₄₀O₅Si₂
• 分子量: 560.838
• InChiKey: LISOPCLPBINRTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  583.8±50.0 °C(predicted)
• 密度：
  1.14±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.89
• 重原子数：
  39.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyldimethylsilyl 3-(tert-butyldimethylsiloxy)-4,5-(fluoren-9-ylidenedioxy)benzoate 在 4-二甲氨基吡啶 、 4-(dimethylamino)pyridine hydrochloride 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1,5-anhydro-2,3-dideoxy-D-erythro-hexitol bis(3-(tert-butyldimethylsiloxy)-4,5-(fluoren-9-ylidenedioxy)benzoate)
  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 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 tert-butyldimethylsilyl 3-(tert-butyldimethylsiloxy)-4,5-(fluoren-9-ylidenedioxy)benzoate
  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