3',4'-di-O-methyl-(-)-fisetinidol | 137299-03-7

• 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: 3',4'-di-O-methyl-(-)-fisetinidol
• 英文别名: (2R,3S)-2-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-chromene-3,7-diol
• CAS: 137299-03-7
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: ICCGKPVPYWOPKL-SUMWQHHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3',4'-di-O-methyl-(-)-fisetinidol 、 alkaline earth salt of/the/ methylsulfuric acid 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 3,7-di-O-acetyl-3',4'-di-O-methyl-(+)-fustin
  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：

  (-)-非瑟酮醇 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 3',4'-di-O-methyl-(-)-fisetinidol
  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

文献信息

• MALAN, JOHANNES C. S.;STEYNBERG, PETRUS J.;STEYNBERG, JAN P.;YOUNG, DESMO+, TETRAHEDRON, 46,(1990) N, C. 2883-2890
  作者：MALAN, JOHANNES C. S.、STEYNBERG, PETRUS J.、STEYNBERG, JAN P.、YOUNG, DESMO+

  DOI：——

  日期：——