4',6-dimethoxy-isoflavone | 53847-88-4

• 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',6-dimethoxy-isoflavone
• 英文别名: 6-methoxy-3-(4-methoxyphenyl)-4H-chromen-4-one；6,4'-Dimethoxy-isoflavon；6-Methoxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one；6-methoxy-3-(4-methoxyphenyl)chromen-4-one
• CAS: 53847-88-4
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: PNFNTBYCHFOXSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2'-羟基-5'-甲氧基苯乙酮 在 吡啶 、 palladium 10% on activated carbon 、 碘 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 氯仿 、 水 为溶剂， 反应 20.0h， 生成 4',6-dimethoxy-isoflavone
  参考文献：
  名称：

  Synthesis, antimycobacterial evaluation and pharmacophore modeling of analogues of the natural product formononetin

  摘要：

  The synthesis and antimycobacterial activity of formononetin analogues is hereby reported. Formononetin and its analogue 11E showed 88% and 95% growth inhibition, respectively, against the H37Rv strain of Mycobacterium tuberculosis. Pharmacophore modeling studies indicated that the presence of a hydroxyl group in formononetin and its analogues, is crucial for maintaining activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.064

文献信息

• Stille coupling for the synthesis of isoflavones by a reusable palladium catalyst in water
  作者：Ya‐Ting Chang、Ling‐Jun Liu、Wen‐Sheng Peng、Lin‐Ting Lin、Yi‐Tsu Chan、Fu‐Yu Tsai

  DOI：10.1002/jccs.202000478

  日期：2021.3

  Isoflavones were synthesized from the reaction of 3‐bromochromone derivatives and aryltributylstannanes via Stille coupling catalyzed by a water‐soluble and reusable PdCl2(NH3)2/2,2′‐cationic bipyridyl system in aqueous solution. For prototype 3‐bromochromone, the coupling reaction was performed at 80°C for 24 hr with 2.5 mol% catalyst in water in the presence of tetrabutylammonium fluoride. After

  异黄酮是通过水溶性可重用的PdCl 2（NH 3）2 / 2,2'-阳离子联吡啶系统在水溶液中催化的Stille偶联反应，由3-溴色酮衍生物与芳基三丁基锡烷反应制得的。对于原型3-溴苯并二氢呋喃酮，偶合反应是在氟化四丁基铵存在下，在水中使用2.5 mol％催化剂，在80°C下进行24小时。反应后，该水溶液可重复使用几次，表明其活性仅略有下降。对于取代的3-溴色酮，添加NaHCO 3需要较高的反应温度（120°C）才能获得满意的结果。此外，该方案可通过一锅反应获得天然产物，如黄豆苷元。
• Pd-Catalyzed Efficient Cross-Couplings of 3-Iodochromones with Triaryl­bismuths as Substoichiometric Multicoupling Organometallic Nucleophiles
  作者：Maddali Rao、Varadhachari Venkatesh、Deepak Jadhav

  DOI：10.1055/s-0029-1217959

  日期：2009.10

  An efficient cross-coupling of 3-iodochromones with triarylbismuths under catalytic palladium conditions is reported. Triarylbismuths were employed as substoichiometric multicoupling nucleophiles for the synthesis of a variety of substituted isoflavones. Under the established protocol, cross-coupling reactions were found to be very efficient, furnishing high yields of products.

  报告了在钯催化条件下 3-碘色酮与三芳基铋的高效交叉偶联。三芳基铋被用作亚公倍数多偶联亲核物，用于合成多种取代的异黄酮。在既定的方案下，交叉耦合反应非常有效，产物收率高。
• Synthesis, antimycobacterial evaluation and pharmacophore modeling of analogues of the natural product formononetin
  作者：Peggoty Mutai、Elumalai Pavadai、Ian Wiid、Andile Ngwane、Bienyameen Baker、Kelly Chibale

  DOI：10.1016/j.bmcl.2015.04.064

  日期：2015.6

  The synthesis and antimycobacterial activity of formononetin analogues is hereby reported. Formononetin and its analogue 11E showed 88% and 95% growth inhibition, respectively, against the H37Rv strain of Mycobacterium tuberculosis. Pharmacophore modeling studies indicated that the presence of a hydroxyl group in formononetin and its analogues, is crucial for maintaining activity. (C) 2015 Elsevier Ltd. All rights reserved.