3-(4-methoxyphenyl)-6-methyl-4H-chromen-4-one | 130252-75-4

• 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: 3-(4-methoxyphenyl)-6-methyl-4H-chromen-4-one
• 英文别名: 3-(4-Methoxyphenyl)-6-methylchromen-4-one
• CAS: 130252-75-4
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: KYWFITXYAMPJAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-羟基-5-甲基苯乙酮 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 3-(4-methoxyphenyl)-6-methyl-4H-chromen-4-one
  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

• Arylation of <i>ortho</i>-Hydroxyarylenaminones by Sulfonium Salts and Arenesulfonyl Chlorides: An Access to Isoflavones
  作者：Satenik Mkrtchyan、Viktor O. Iaroshenko

  DOI：10.1021/acs.joc.0c02294

  日期：2021.4.2

  diversities of bench-stable and easy-to-use sulfonium salts and arenesulfonyl chlorides. Both developed methods, namely the light-mediated photoredox and electrophilic arylation, showed good efficiency, and are feasible for the preparation of 3-arylchromones in good-to-excellent yields. This work showcases the first described attempt where the sulfonium salts and arenesulfonyl chlorides were successfully utilized

  本文中，我们公开了三种新方法，这些方法可通过大量稳定和易于使用的sulf盐和芳烃磺酰氯将邻羟基羟基亚胺基芳基化后，直接有效地合成3-芳基色酮。两种开发的方法，即光介导的光氧化还原和亲电芳基化，均显示出良好的效率，并且对于以良好至优异的产率制备3-芳基色酮是可行的。这项工作展示了首次描述的尝试，其中成功地利用了salts盐和芳烃磺酰氯来构建色酮杂环系统。
• Oxidative 1,2-aryl rearrangement in flavanones using thallium(III) -tolylsulphonate (TTS)= A new useful route to isoflavones
  作者：Om V. Singh、C.P. Garg、R.P. Kapoor

  DOI：10.1016/s0040-4039(00)94689-6

  日期：1990.1

  Oxidation of flavanones using thallium(III) -tolylsulphonate (prepared by the reaction of thallium(III) acetate and -toluene sulphonic acid) in propionitrile leads to 1,2-aryl shift providing a new useful route to the synthesis of isoflavones.

  在丙腈中使用甲苯磺酸th （III）（由乙酸III（III）和-甲苯磺酸反应制得）对黄烷酮进行氧化可导致1,2-芳基转移，为异黄酮的合成提供了一条新的有用途径。
• 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。
• Mechanochemical Ni‐Catalysed Arylation of <i>ortho</i> ‐Hydroxyarylenaminones: Synthesis of Isoflavones
  作者：Satenik Mkrtchyan、Michał Jakubczyk、Suneel Lanka、Muhammad Yar、Tariq Mahmood、Khurshid Ayub、Mika Sillanpää、Christine M. Thomas、Viktor O. Iaroshenko

  DOI：10.1002/adsc.202200645

  日期：2022.10.18

  describes two new synthetic methods for the preparation of isoflavones following the Ni-catalysed domino arylation reactions of the vast range of ortho-hydroxyarylenaminones utilising aromatic bromides as well as carboxylic acids. The presented protocols tolerated significant variation of all coupling partners and enabled synthesis of isoflavone library of twenty-three representatives. This is the first

  这项工作描述了两种新的合成方法，用于在镍催化的多米诺芳基化反应之后利用芳香族溴化物和羧酸对大量邻羟基亚芳基胺进行多米诺芳基化反应。所提出的协议允许所有耦合伙伴的显着变化，并能够合成 23 个代表的异黄酮库。这是第一个在多米诺环化模式后利用机械能合成异黄酮的先例。
• Khanna, Mahavir S.; Singh, Om V.; Garg, Chandra P., Journal of the Chemical Society. Perkin transactions I, 1992, # 19, p. 2565 - 2568
  作者：Khanna, Mahavir S.、Singh, Om V.、Garg, Chandra P.、Kapoor, Ram P.

  DOI：——

  日期：——