4β-methoxy-tri-O-methyl-3-O-acetyl-(-)-fisetinidol-(4α,8)-tetra-O-methyl-3-O-acetyl-(+)-catechin | 99260-77-2

• 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: 4β-methoxy-tri-O-methyl-3-O-acetyl-(-)-fisetinidol-(4α,8)-tetra-O-methyl-3-O-acetyl-(+)-catechin
• 英文别名: [(2R,3S)-8-[(2R,3R,4R)-3-acetyloxy-2-(3,4-dimethoxyphenyl)-4,7-dimethoxy-2,3-dihydrochromen-4-yl]-2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-3,4-dihydro-2H-chromen-3-yl] acetate
• CAS: 99260-77-2
• 化学式: C₄₂H₄₆O₁₄
• 分子量: 774.819
• InChiKey: HFHJOADPZUQHPA-MTGPOGRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 重原子数：
  56.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  144.9
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  4β-methoxy-tri-O-methyl-3-O-acetyl-(-)-fisetinidol-(4α,8)-tetra-O-methyl-3-O-acetyl-(+)-catechin 在 pyridinium hydrobromide perbromide 作用下， 以 甲醇 为溶剂， 生成 3-O-acetyl-8-bromo-3',4',5,7-tetra-O-methyl-(+)-catechin 、 [(2R,3R)-6-bromo-2-(3,4-dimethoxyphenyl)-4,4,7-trimethoxy-2,3-dihydrochromen-3-yl] acetate
  参考文献：
  名称：

  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)

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)82322-x
• 作为产物：
  描述：

  甲醇 、 (2R,3S,4R)-2,3-trans-3,4-cis-3-acetoxy-4-<(2R,3S)-2,3-trans-3-acetoxy-3,3',4',5,7-pentamethoxyflavan-8-yl>-3',4',7-trimethoxyflavan 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以36 mg的产率得到4β-methoxy-tri-O-methyl-3-O-acetyl-(-)-fisetinidol-(4α,8)-tetra-O-methyl-3-O-acetyl-(+)-catechin
  参考文献：
  名称：

  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)

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)82322-x