[(2R,3S)-3,5,7-Tris-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-chroman-8-yl]-(2,4,6-tris-benzyloxy-phenyl)-methanone

• 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)-3,5,7-Tris-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-chroman-8-yl]-(2,4,6-tris-benzyloxy-phenyl)-methanone
• 化学式: C₇₈H₆₆O₁₀
• 分子量: 1163.38
• InChiKey: JEBBPTHZDUDKNY-LNCUWZICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.23
• 重原子数：
  88.0
• 可旋转键数：
  27.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  100.14
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  儿茶提取物 在 sodium chlorite 、 2-甲基-2-丁烯 、 磷酸 、 sodium hydride 、 三氟乙酸酐 、 三氯氧磷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 [(2R,3S)-3,5,7-Tris-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-chroman-8-yl]-(2,4,6-tris-benzyloxy-phenyl)-methanone
  参考文献：
  名称：

  Synthesis of modified proanthocyanidins: introduction of acyl substituents at C-8 of catechin. Selective synthesis of a C-4→O→C-3 ether-linked procyanidin-like dimer

  摘要：

  The regioselective introduction of substituents at C-8 of (+)-catechin is described, leading to the synthesis of several catechin derivatives with various substitution patterns to be used for the further synthesis of modified proanthocyanidins. Thereafter, a new 3-O-4 ether-linked procyanidin-like derivative was synthesized. Its formation was selectively achieved through TiCl4-catalyzed condensation of 4-(2-hydroxyethoxy)tetra-O-benzyl catechin with the 8-trifluoroacetyl adduct of tetra-O-benzyl catechin. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.046

文献信息

• Synthesis of modified proanthocyanidins: introduction of acyl substituents at C-8 of catechin. Selective synthesis of a C-4→O→C-3 ether-linked procyanidin-like dimer
  作者：Josiane Beauhaire、Nour-Eddine Es-Safi、François-Didier Boyer、Lucien Kerhoas、Christine le Guernevé、Paul-Henri Ducrot

  DOI：10.1016/j.bmcl.2004.11.046

  日期：2005.2

  The regioselective introduction of substituents at C-8 of (+)-catechin is described, leading to the synthesis of several catechin derivatives with various substitution patterns to be used for the further synthesis of modified proanthocyanidins. Thereafter, a new 3-O-4 ether-linked procyanidin-like derivative was synthesized. Its formation was selectively achieved through TiCl4-catalyzed condensation of 4-(2-hydroxyethoxy)tetra-O-benzyl catechin with the 8-trifluoroacetyl adduct of tetra-O-benzyl catechin. (C) 2004 Elsevier Ltd. All rights reserved.