4',7-dimethoxyisoflavan | 4366-35-2

• 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: 4',7-dimethoxyisoflavan
• 英文别名: 4',7-dimethoxyflavane；7-methoxy-3-(4-methoxy-phenyl)-chroman；(+/-)-7-Methoxy-3-(4-methoxy-phenyl)-chroman；4',7-Dimethoxy-isoflavan；7,4'-Dimethoxy-isoflavan；(+/-)-O-Dimethylequol；7-methoxy-3-(4-methoxyphenyl)-3,4-dihydro-2H-chromene
• CAS: 4366-35-2
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: GQMFGWWADOSNMX-UHFFFAOYSA-N

物化性质

• 熔点：
  112.5-114 °C
• 沸点：
  395.5±42.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4',7-dimethoxyisoflavan 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 4',7-dimethoxyisoflavanone
  参考文献：
  名称：

  Anderson; Marrian, Journal of Biological Chemistry, 1939, vol. 127, p. 649,652

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基-2-(甲氧基甲氧基)苯甲醛 在 2,6-二甲基吡啶 、 盐酸 、 六甲基磷酰三胺 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 正丁基锂 、 N-环己基异丙基胺 、 三苯基膦 、 lithium bromide 、 偶氮二甲酸二乙酯 、 甲基磺酸酐 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 正己烷 为溶剂， 反应 33.33h， 生成 4',7-dimethoxyisoflavan
  参考文献：
  名称：

  The Direct Synthesis of Isoflavans via a-Alkylation of Phenylacetates

  摘要：

  DOI：

  10.3987/com-98-8149

文献信息

• Synthesis of isoflavanes and intermediates thereof
  申请人：System Biologie AG

  公开号：US10030003B2

  公开（公告）日：2018-07-24

  Subject of the invention is a method for enantioselective production of an isoflavane from an isoflavone, comprising the steps: (a) selectively reducing the isoflavone, such that the 4-keto group of the isoflavone is converted to a 4-hydroxy group, and the 2,3-double bond of the isoflavone is converted to a 2,3-single bond, thereby obtaining a 4-hydroxy intermediate, and (b) reacting the 4-hydroxy intermediate with a chiral reagent, such that a chiral group is covalently attached to the C4-position of the 4-hydroxy intermediate, thereby obtaining a chiral intermediate. The invention also relates to intermediates of formulae (IV), (V), (VI) and (VII) obtainable in the inventive process.

  本发明的主题是一种从异黄酮对映体选择性生产异黄烷的方法，包括以下步骤：(a) 选择性还原异黄酮，使异黄酮的 4-酮基转化为 4-羟基，异黄酮的 2，3-双键转化为 2，3-单键，从而得到 4-羟基中间体，以及 (b) 使 4-羟基中间体与手性试剂反应，使手性基团共价连接到 4-羟基中间体的 C4 位，从而得到手性中间体。本发明还涉及可在本发明工艺中获得的式 (IV)、(V)、(VI) 和 (VII) 的中间体。
• Synthesis, structure–activity relationship analysis and kinetics study of reductive derivatives of flavonoids as Helicobacter pylori urease inhibitors
  作者：Zhu-Ping Xiao、Zhi-Yun Peng、Jing-Jun Dong、Juan He、Hui Ouyang、Yu-Ting Feng、Chun-Lei Lu、Wan-Qiang Lin、Jin-Xiang Wang、Yin-Ping Xiang、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2013.03.016

  日期：2013.5

  In a continuing study for discovering urease inhibitors based on flavonoids, nineteen reductive derivatives of flavonoids were synthesized and evaluated against Helicobacter pylori urease. Analysis of structure-activity relationship disclosed that 4-deoxy analogues are more potent than other reductive products. Out of them, 4',7,8-trihydroxyl-2-isoflavene (13) was found to be the most active with IC50 of 0.85 mu M, being over 20-fold more potent than the commercial available urease inhibitor, acetohydroxamic acid (AHA). Kinetics study revealed that 13 is a competitive inhibitor of H. pylori urease with a K-i value of 0.641 mu M, which is well matched with the results of molecular docking. Biological evaluation and mechanism study of 13 suggest that it is a good candidate for discovering novel anti-gastritis and anti-gastric ulcer agent. (c) 2013 Elsevier Masson SAS. All rights reserved.
• o-Quinone methide based approach to isoflavans: application to the total syntheses of equol, 3′-hydroxyequol and vestitol
  作者：Santosh J. Gharpure、A.M. Sathiyanarayanan、Prasad Jonnalagadda

  DOI：10.1016/j.tetlet.2008.03.003

  日期：2008.4

  A concise strategy is developed for the synthesis of isoflavans employing a Diels-Alder reaction between o-quinone methides and aryl-substituted enol ethers followed by reductive cleavage of the acetal group. The method is extended towards the total syntheses of equol, 3'-hydroxyequol and vestitol. (C) 2008 Elsevier Ltd. All rights reserved.
• 179. The chemistry of subterranean clover. Part II. Synthesis and reduction of isoflavones related to genistein and formononetin
  作者：R. B. Bradbury、D. E. White

  DOI：10.1039/jr9530000871

  日期：——
• Wessely; Prillinger, Chemische Berichte, 1939, vol. 72, p. 629,632
  作者：Wessely、Prillinger

  DOI：——

  日期：——