5-benzoyl-6-C-(2'',3'',4'',6''-tetra-O-benzyl-β-D-glucopyranosyl)-4'-hydroxy-7-methoxyflavone | 1437307-72-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 5-benzoyl-6-C-(2'',3'',4'',6''-tetra-O-benzyl-β-D-glucopyranosyl)-4'-hydroxy-7-methoxyflavone
• CAS: 1437307-72-6
• 化学式: C₅₇H₅₀O₁₁
• 分子量: 911.017
• InChiKey: XJRXVRWXRXAGAP-ZUZWOGPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.81
• 重原子数：
  68.0
• 可旋转键数：
  18.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  132.12
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  5-benzoyl-6-C-(2'',3'',4'',6''-tetra-O-benzyl-β-D-glucopyranosyl)-4'-hydroxy-7-methoxyflavone 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 silver carbonate 作用下， 以 喹啉 为溶剂， 反应 3.0h， 以70%的产率得到5-benzoyl-6-C-(2'',3'',4'',6''-tetra-O-benzyl-β-D-glucopyranosyl)-4'-O-(2''',3''',4''',6'''-tetra-O-acetyl-β-D-glucopyranosyl)-7-methoxyflavone
  参考文献：
  名称：

  Concise synthesis of flavocommelin, 7-O-methylapigenin 6-C-, 4′-O-bis-β-d-glucoside, a component of the blue supramolecular pigment from Commelina communis

  摘要：

  Flavocommelin, 7-O-methylapigenin 6-C-, 4 '-O-bis-beta-D-glucoside, was synthesized in 9 steps from the C-glycosylation of 6-O-benzy-4-O-methylphloroacetophenone via the introduction of a cinnamoyl residue by aldol condensation and the formation of a C-ring by regioselective and oxidative ring-closure to regio-and stereoselective O-glycosylation for an overall yield of 31%. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.03.016
• 作为产物：
  描述：

  5-benzoyl-4'-benzyloxy-6-C-(2'',3'',4'',6''-tetra-O-benzyl-β-D-glucopyranosyl)-7-methoxyflavone 在 5%-palladium/activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 以68%的产率得到5-benzoyl-6-C-(2'',3'',4'',6''-tetra-O-benzyl-β-D-glucopyranosyl)-4'-hydroxy-7-methoxyflavone
  参考文献：
  名称：

  Concise synthesis of flavocommelin, 7-O-methylapigenin 6-C-, 4′-O-bis-β-d-glucoside, a component of the blue supramolecular pigment from Commelina communis

  摘要：

  Flavocommelin, 7-O-methylapigenin 6-C-, 4 '-O-bis-beta-D-glucoside, was synthesized in 9 steps from the C-glycosylation of 6-O-benzy-4-O-methylphloroacetophenone via the introduction of a cinnamoyl residue by aldol condensation and the formation of a C-ring by regioselective and oxidative ring-closure to regio-and stereoselective O-glycosylation for an overall yield of 31%. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.03.016