2',4'-二羟基-7-甲氧基异黄酮 | 7622-53-9

• 物质功能分类: 天然产物 - 黄酮类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 中文名称: 2',4'-二羟基-7-甲氧基异黄酮
• 英文名称: 2',4'-dihydroxy-7-methoxyisoflavone
• 英文别名: 7-methoxy-2',4'-dihydroxyisoflavone；3-(2,4-dihydroxy-phenyl)-7-methoxy-chromen-4-one；2',4'-Dihydroxy-7-methoxy-isoflavon；2',4'-Dihydroxy-7-methoxyisoflavon；2',4'Dihydroxy-7-methoxy-isoflavon；7-MeO-2',4-di-OH-isoflavon；5-Deoxycajanin；3-(2,4-dihydroxyphenyl)-7-methoxychromen-4-one
• CAS: 7622-53-9
• 化学式: C₁₆H₁₂O₅
• 分子量: 284.268
• InChiKey: JZOYQACMFLYEJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  2',4'-二羟基-7-甲氧基异黄酮 在 吡啶 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 48.5h， 生成 pueranone
  参考文献：
  名称：

  从葛根属植物分离的生物遗传前体葛根素的简便合成方法

  摘要：

  使用查尔酮用三硝酸th（III）氧化查克酮，然后使用3-羟基异戊醛二甲基乙缩醛对所得的异黄酮进行镀铬，从而合成了葛根素。关键的脱甲基步骤是用三溴化硼实现的。

  DOI：

  10.1002/jhet.5570380434
• 作为产物：
  描述：

  丹皮酚 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 thallium(III) nitrate 、 氢气 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 15.0h， 生成 2',4'-二羟基-7-甲氧基异黄酮
  参考文献：
  名称：

  从葛根属植物分离的生物遗传前体葛根素的简便合成方法

  摘要：

  使用查尔酮用三硝酸th（III）氧化查克酮，然后使用3-羟基异戊醛二甲基乙缩醛对所得的异黄酮进行镀铬，从而合成了葛根素。关键的脱甲基步骤是用三溴化硼实现的。

  DOI：

  10.1002/jhet.5570380434

文献信息

• Insect Antifeedants, Pterocarpans and Pterocarpol, in Heartwood of<i>Pterocarpus macrocarpus</i>Kruz.
  作者：Masanori MORIMOTO、Hiromi FUKUMOTO、Masaru HIRATANI、Warinthorn CHAVASIRI、Koichiro KOMAI

  DOI：10.1271/bbb.60017

  日期：2006.8.23

  The insect antifeedant activities of pterocarpans and a sesquiterpene alcohol from the dichloromethane extract of Pterocarpus macrocarpus Kruz. (Leguminosae) were evaluated against the common cutworm, Spodoptera litura F. (Noctuidae), and the subterranean termite, Reticulitermes speratus (Kolbe)(Rhinotermitidae). Three pterocarpans, (−)-homopterocarpin (1), (−)-pterocarpin (2), and (−)-hydroxyhomopterocarpin (3) and the sesquiterpene alcohol, (+)-pterocarpol (5), were isolated from the dichloromethane extract of the heartwood of P. macrocarpus under guidance by a biological assay. Among these natural products, the most active insect antifeedant against both S. litura and R. speratus was 1. On the other hand, sesquiterpene alcohol 5 showed less insect antifeedant activity than the other pterocarpans against both insect species. While its methylated derivative, (−)-methoxyhomopterocarpin (4), showed high biological activity, 3 showed less insect antifeedant activity in this study. Interestingly, racemic 1 did not show insect antifeedant activity against S. litura. However, all of the test pterocarpans and isoflavones showed antifeedant activity against the test termites. Additionally, since these compounds were major constituents of P. macrocarpus, these antifeedant phenolics may act as chemical defense factors in this tree. In Thailand, lumber made from this tree is used to make furniture and in building construction due to its resistance to termite attack.

  对来自大果紫檀（Pterocarpus macrocarpus Kruz.）二氯甲烷提取物的紫檀苷和倍半萜醇（豆科）的昆虫拒食活性进行了评估，以对抗普通切根虫斜纹夜蛾（Spodoptera litura F.）（夜蛾科）和地下白蚁（Reticulitermes speratus (Kolbe)）（鼻白蚁科）。在生物测定指导下，从大果紫檀心材的二氯甲烷提取物中分离出三种紫檀苷（-）-紫檀苷（1）、（-）-紫檀苷（2）和（-）-羟基紫檀苷（3）以及倍半萜醇（+）-紫檀醇（5）。在这些天然产物中，对斜纹夜蛾和R. speratus最有效的昆虫拒食剂是1。另一方面，倍半萜醇5对这两种昆虫的昆虫拒食活性低于其他紫檀苷。虽然其甲基化衍生物（-）-甲氧基紫檀苷（4）显示出高生物活性，但在这项研究中，3的昆虫拒食活性较低。有趣的是，外消旋1对斜纹夜蛾没有表现出昆虫拒食活性。然而，所有
• Flavonoids from Eschscholtzia californica
  作者：L. Jain、M. Tripathi、V.B. Pandey、G. Rücker

  DOI：10.1016/0031-9422(95)00561-7

  日期：1996.2

  Abstract Two new isoflavones, together with quercitrin have been isolated from whole plants of Eschscholtzia californica . The structures of the new isoflavones were determined as 2′-methoxyformononetin and 7-methoxy-2′,4′-dihydroxyisoflavone by spectroscopic methods.

  摘要 从Eschscholtzia californica 的全株中分离到了两种新的异黄酮和槲皮苷。新异黄酮的结构通过光谱方法确定为2'-甲氧基香茅素和7-甲氧基-2',4'-二羟基异黄酮。
• Practical Synthesis of Lespedezol A₁
  作者：Rahul S. Khupse、Paul W. Erhardt

  DOI：10.1021/np070493m

  日期：2008.2.1

  A practical formal synthesis of lespedezol A(1) (1) was accomplished in 33% yield for four steps starting from formation of the substituted chalcone. Of particular note is a useful protocol for reduction of the 2-ene bond in the isoflavone intermediate. A significant improvement in the final ring closure when water was scavenged from the reaction is also noteworthy. The ready availability of lespedezol A, will provide material for further pharmacological evaluation and for exploration of the pterocarpene nucleus as a potential entry into various 6a-hydroxypterocarpans.
• Krishna Prasad, Awari V.; Kapil, Randhir S.; Popli, Satya P., Journal of the Chemical Society. Perkin transactions I, 1986, p. 1561 - 1564
  作者：Krishna Prasad, Awari V.、Kapil, Randhir S.、Popli, Satya P.

  DOI：——

  日期：——
• A facile synthesis of biogenetic precursor, puerarone, isolated from<i>Pueraria</i>sp
  作者：Riaz A. Khan、Randhir S. Kapil

  DOI：10.1002/jhet.5570380434

  日期：2001.7

  Puerarone was synthesized using chalcone oxidation with thallium (III) trinitrate and chromenation of the resulting isoflavone using 3-hydroxyisovaleraldehyde dimethylacetal. The key demethylation step was achieved with boron tribromide.

  使用查尔酮用三硝酸th（III）氧化查克酮，然后使用3-羟基异戊醛二甲基乙缩醛对所得的异黄酮进行镀铬，从而合成了葛根素。关键的脱甲基步骤是用三溴化硼实现的。