(2R,3S,4S,2'R,3'S,2''R,3''S,4''R)-2,2''-Bis-(3,4-dihydroxy-phenyl)-2'-(3-hydroxy-4-methoxy-phenyl)-3,4,3',4',3'',4''-hexahydro-2H,2'H,2''H-[4,6';8',4'']terchromene-3,7,3',5',7',3'',7''-heptaol | 182511-63-3

• 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: (2R,3S,4S,2'R,3'S,2''R,3''S,4''R)-2,2''-Bis-(3,4-dihydroxy-phenyl)-2'-(3-hydroxy-4-methoxy-phenyl)-3,4,3',4',3'',4''-hexahydro-2H,2'H,2''H-[4,6';8',4'']terchromene-3,7,3',5',7',3'',7''-heptaol
• CAS: 182511-63-3
• 化学式: C₄₆H₄₀O₁₆
• 分子量: 848.814
• InChiKey: DKBYMWXYYGNACG-FVJJOUCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.34
• 重原子数：
  62.0
• 可旋转键数：
  6.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  279.68
• 氢给体数：
  12.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,2'R,3'S,2''R,3''S,4''R)-2,2''-Bis-(3,4-dihydroxy-phenyl)-2'-(3-hydroxy-4-methoxy-phenyl)-3,4,3',4',3'',4''-hexahydro-2H,2'H,2''H-[4,6';8',4'']terchromene-3,7,3',5',7',3'',7''-heptaol 在 碳酸氢钠 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 5.5h， 生成 (2R,3S,8R,9R,10S)-10-(3,4-Dihydroxy-phenyl)-8-(2,4-dihydroxy-phenyl)-6-[(2R,3S,4S)-2-(3,4-dihydroxy-phenyl)-3,7-dihydroxy-chroman-4-yl]-2-(3-hydroxy-4-methoxy-phenyl)-3,4,9,10-tetrahydro-2H,8H-pyrano[2,3-f]chromene-3,5,9-triol 、 (2R,3S,8R,9R,10S)-10-(3,4-Dihydroxy-phenyl)-8-(2,4-dihydroxy-phenyl)-6-[(2R,3R,4S)-4-(3,4-dihydroxy-phenyl)-3,7-dihydroxy-chroman-2-yl]-2-(3-hydroxy-4-methoxy-phenyl)-3,4,9,10-tetrahydro-2H,8H-pyrano[2,3-f]chromene-3,5,9-triol 、 (2R,3S,4S,7S,8R)-2-(3,4-Dihydroxy-phenyl)-4-(2,4-dihydroxy-phenyl)-10-[(2R,3S,4R)-2-(3,4-dihydroxy-phenyl)-3,7-dihydroxy-chroman-4-yl]-8-(3-hydroxy-4-methoxy-phenyl)-3,4,7,8-tetrahydro-2H,6H-pyrano[3,2-g]chromene-3,5,7-triol 、 (2R,3S,4S,6R,7S,8R,10R,11S)-4,8-Bis-(2,4-dihydroxy-phenyl)-2,6-bis-(3,4-dihydroxy-phenyl)-10-(3-hydroxy-4-methoxy-phenyl)-3,4,7,8,11,12-hexahydro-2H,6H,10H-dipyrano[2,3-f;2',3'-h]chromene-3,7,11-triol
  参考文献：
  名称：

  Structure and synthesis of phlobatannins related to the (4α,6:4β,8)-bis-fisetinidol-catechin profisetinidin triflavanoid

  摘要：

  The natural class of phlobaphene condensed tannins is complemented by two functionalized hexahydrodipyrano[2,3-f:2',3'-h]chromene representing the products of stereoselective pyran ring rearrangement of the 2,3-trans-3,4-trans- and 2,3-trans-3,4-cis-flavan-3-ol moieties in the bis-fisetinidol-(4 alpha,6:4 beta,8)-catechin triflavanoid. Structural eludication of these complex natural products was effected by synthesis via base-catalysed conversion of the 4-O(E)-methyl ether of their presumed profisetinidin triflavanoid precursor. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0031-9422(96)00239-7
• 作为产物：
  描述：

  (-)-fisetidinol-(4β,8)-(+)-catechin-O-methyl ether 、 (+)-柔金合欢素 在 盐酸 作用下， 以 水 为溶剂， 反应 13.0h， 生成 (2R,3S,4R,2'R,3'S,2''R,3''S,4''R)-2,2''-Bis-(3,4-dihydroxy-phenyl)-2'-(3-hydroxy-4-methoxy-phenyl)-3,4,3',4',3'',4''-hexahydro-2H,2'H,2''H-[4,6';8',4'']terchromene-3,7,3',5',7',3'',7''-heptaol 、 (2R,3S,4S,2'R,3'S,2''R,3''S,4''R)-2,2''-Bis-(3,4-dihydroxy-phenyl)-2'-(3-hydroxy-4-methoxy-phenyl)-3,4,3',4',3'',4''-hexahydro-2H,2'H,2''H-[4,6';8',4'']terchromene-3,7,3',5',7',3'',7''-heptaol
  参考文献：
  名称：

  Structure and synthesis of phlobatannins related to the (4β,6:4α,8)-bis-fisetinidol-catechin profisetinidin triflavanoid

  摘要：

  Several members of the class of natural phlobatannins, representing the products of stereoselective pyran rearrangement of the 2,3-trans-3,4-trans- and 3,4-cis-flavan-3-ol units in the (4 beta,6:4 alpha,8)-bis-fisetinidol-catechin triflavanoid have been characterized. These comprise a functionalized hexahydro-dipyrano-[2,3-f:2',3'-h]-chromene, two fisetinidol-(4 alpha,10)-tetrahydropyrano[2,3-f]chromenes and a pair of fisetinidol-(4 alpha,10)-tetrahydropyrano[3,2-g]chromenes. The proposed structures of these novel compounds were confirmed by synthesis via base-catalysed conversion of the 4-O(E)-methyl ether of their presumed triflavanoid biogenetic precursor. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0031-9422(96)00114-8