cis-2,3-dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-benzopyran-4-ol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: cis-2,3-dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-benzopyran-4-ol
• 英文别名: cis-tetrahydrodaidzein；cis-4',7-dihydroxyisoflavan-4-ol；cis-4-Hydroxyequol；(3S,4S)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-4,7-diol
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: YOSDNAMJVOLJKI-UKRRQHHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-2,3-dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-benzopyran-4-ol 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 60.0 ℃ 、700.01 kPa 条件下， 反应 4.0h， 以89.4%的产率得到
  参考文献：
  名称：

  JP2015/44770

  摘要：

  公开号：
• 作为产物：
  描述：

  大豆甙元 在 palladium on activated charcoal 锂硼氢 、 ammonium formate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 cis-2,3-dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-benzopyran-4-ol
  参考文献：
  名称：

  Experimental and DFT ¹H NMR Study of Conformational Equilibria in trans-4‘,7-Dihydroxyisoflavan-4-ol and trans-Isoflavan-4-ol

  摘要：

  The solution-state conformational equilibria of trans-4',7-dihydroxyisoflavan-4-ol (1) and trans-isoflavan-4-ol (2) were assessed based on the temperature dependence of their vicinal coupling constants J(H-2alpha,H-3) and J(H-3,H-4) in comparison to values calculated with density functional theory (DFT) methods at the B3LYP/cc-pVTZ//B3LYP/6-31G(d,p) level of theory. For each half-chair conformer, several rotamers with respect to the C-4 hydroxyl and C-3 phenyl were calculated and the overall diequatorial-to-diaxial ratio at 298 K was assessed as 66:34 for 1 and 73:27 for 2. The syntheses of 1 and 2 are described.

  DOI：

  10.1021/jo0301200

文献信息

• Production of isoflavone derivatives
  申请人：Heaton Andrew

  公开号：US20050143588A1

  公开（公告）日：2005-06-30

  Methods for the hydrogenation of isoflavones are described which provide access to workable quantities of isoflavan-4-ols, isoflav-3-enes, and isoflavans. The isoflavone derivatives can be obtained in high purity and in near quantitative yields whilst employing pharmaceutically acceptable reagents and solvents.

  描述了异黄酮氢化的方法，可以获得可操作数量的异黄烷-4-醇、异黄烯和异黄烷。在使用药用可接受的试剂和溶剂时，可以高纯度地获得异黄酮衍生物，并且产率接近定量。
• The Synthesis, Structure, and Anticancer Activity of <i>cis</i>- and <i>trans</i>-4‘,7-Dihydroxyisoflavan-4-ols
  作者：Kristiina Wähälä、Jorma K. Koskimies、Markku Mesilaakso、Auli K. Salakka、Tero K. Leino、Herman Adlercreutz

  DOI：10.1021/jo970892u

  日期：1997.10.1

  cis-4',7-Dihydroxyisoflavan-4-ol (4) and trans-4',7-dihydroxyisoflavan-4-ol (5), two proposed metabolites of daidzein (4',7-dihydroxyisoflavone), have been synthesized and fully characterized for the first time. The vicinal coupling constants of the pyran ring protons are compatible with a half-chair conformation. The cis isomer is anancomeric while the trans isomer consists of a 68:32 mixture of two ring inversion conformers. Molecular mechanical calculations are in agreement with the half-chair conformation of the pyran ring and suggest that the cis isomer is biased because of an unfavorable gauche interaction of the equatorial hydroxyl and the axial phenyl group. The isoflavanols 4 and 5 are comparable to genistein (4',5,7-trihydroxyisoflavone) in antitumor activity against human prostate cancer cells.