tetra-O-methyl-3-O-acetyl-(-)-epicatechin-(4β,8)-tetra-O-methyl-3-O-acetyl-(+)-catechin | 3888-39-9

• 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: tetra-O-methyl-3-O-acetyl-(-)-epicatechin-(4β,8)-tetra-O-methyl-3-O-acetyl-(+)-catechin
• 英文别名: [(2R,3S)-8-[(2R,3R,4R)-3-acetyloxy-2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-3,4-dihydro-2H-chromen-4-yl]-2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-3,4-dihydro-2H-chromen-3-yl] acetate
• CAS: 3888-39-9；7700-79-0；14617-31-3；17941-25-2；17947-27-2；28699-22-1；41093-86-1；67253-07-0；67253-08-1；97233-63-1
• 化学式: C₄₂H₄₆O₁₄
• 分子量: 774.819
• InChiKey: GZPWRAWXXKSBOE-UHWUVZTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  56
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  原花青素(OPC) 生成 tetra-O-methyl-3-O-acetyl-(-)-epicatechin-(4β,8)-tetra-O-methyl-3-O-acetyl-(+)-catechin
  参考文献：
  名称：

  KOLODZIEJ, HERBERT, PHYTOCHEMISTRY, 28,(1989) N2, C. 3487-3492

  摘要：

  DOI：

文献信息

• Synthesis and characterization of procyanidin dimers as their peracetates and octamethyl ether diacetates
  作者：Herbert Kolodziej

  DOI：10.1016/s0031-9422(00)81582-4

  日期：1986.4
• Regio- and stereoselective oxidation of flavan-3-ol- 4-arylflavan-3-ol- and biflavanoid derivatives with 2,3-dichloro-56-dicyano-1,4-benzoquinone (DDQ)
  作者：Jacobus A. Steenkamp、C.Hendrik L. Mouton、Daneel Ferreira

  DOI：10.1016/s0040-4020(01)82322-x

  日期：1991.8

  The phenolic methyl ethers of flavan-3-ols, 4-beta-arylflavan-3-ols, and (-)-fisetinidol-(4-beta,8)-(+)-catechin biflavanoids are susceptible to regio- and stereoselective methoxylation at C-4 in moderate yields with DDQ in CHCl3-MeOH solution. The observed asymmetric induction with exclusive formation of 2,4-trans products is compatible with the intermediacy of a diastereogenic donor-acceptor interaction, DDQ acting as the acceptor and oxidant. The 4-funtionalized analogues are of both synthetic and degradative significance in condensed tannin chemistry.