2-羟基-6-甲氧基查尔酮 | 40524-67-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 2-羟基-6-甲氧基查尔酮
• 中文别名: 1-(2-羟基-5-甲基苯基)-1-丙酮
• 英文名称: (E)-1-(2-hydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one
• 英文别名: 2'-hydroxy-6'-methoxychalcone；2'-hydroxy-6'-methoxy-trans-chalcone；2'-Hydroxy-6'-methoxy-trans-chalkon
• CAS: 40524-67-2；42079-68-5
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: ZGXVPIGRFJUIEA-ZHACJKMWSA-N

物化性质

• 熔点：
  65.0-65.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  455.9±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-羟基-6-甲氧基查尔酮 在 碘 作用下， 以 二甲基亚砜 为溶剂， 生成 5-甲氧基黄酮
  参考文献：
  名称：

  Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives

  摘要：

  A series of chrysin derivatives were prepared and evaluated for their inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin production. Chrysin derivatives were prepared from 2-hydroxyacetophenone, 2,4-dihydroxyacetophenone and 2,6-dihydroxyacetophenone in 2 to 4 steps, respectively. Methxoylated chrysin derivatives were converted to the corresponding hydroxylated chrysin derivatives by the reaction with BBr3 in good yields. The inhibitory activity of the chrysin derivatives against prostaglandin production from lipopolysaccharide-treated RAW 264.7 cells was measured. We found that chrysin derivatives with 3',4'-dichloro substituents (5e, 6e and 7e) exhibited good inhibitory activity of prostaglandin production. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.087
• 作为产物：
  描述：

  5-甲氧基黄烷酮 以 1,4-二氧六环 、 水 为溶剂， 生成 2-羟基-6-甲氧基查尔酮
  参考文献：
  名称：

  碱性水溶液中一些2'-羟基查耳酮环化为黄烷酮的动力学和机理

  摘要：

  对于某些2'-羟基查耳酮，在其2'-羟基经过电离的pH范围（约8-11）中，查尔酮-黄酮平衡反应的速率系数已经确定。研究的查耳酮为母体2'-羟基查耳酮（I）及其以下衍生物：4'-OMe（II），6'-OMe（III），4'-OH（IV），4'，6'-Me 2（V）和5'，6'-苯并（VI）。伪一级速率系数（ķ OBS），其为有关可逆反应，是在正向和反向速率系数的总和，拟合动力学形式ķ OBS = KF甲+ ķ ' ˚F乙+ ķ “一OH –其中k和k '分别是中性和离子化查尔酮单分子环化的速率系数（ f A和f B是在相关pH下以中性和离子化形式存在的总查尔酮的分数），其中k ”是黄烷酮涉及氢氧根离子（活性为OH –）的逆反应的二级速率系数。数据分析给出了速率系数和p K a除查耳酮（IV）以外的所有分子具有不同的动力学形式。提出了一种共轭添加消除机制来解释pH值速率分布，其中一种[查尔酮

  DOI：

  10.1039/p29820001309

文献信息

• Kinetics and mechanism of the cyclisation of 2′,6′-dihydroxychalcone and derivatives
  作者：Christopher O. Miles、Lyndsay Main

  DOI：10.1039/p29890001623

  日期：——

  profiles are reported for the cyclisation in water to 5-hydroxyflavanones of 2′,6′-dihydroxychalcone (1) and its 4-methoxy (2), 3,4-dimethoxy (3), 3,4,5-trimethoxy (4), 2,4,6-trimethoxy (5), 4-chloro (6), and 3,4,4′-trimethoxy (8) derivatives. As for the previously studied 2′,6′-dihydroxy-4,4′-dimethoxychalcone (7), rate coefficients are established for acid-catalysed cyclisation of neutral chalcone, for

  报道了pH–速率曲线，表明在水中环化成2'，6'-二羟基查尔酮（1）及其4-甲氧基（2），3,4-二甲氧基（3），3,4,5-的5-羟基黄酮三甲氧基（4），2,4,6-三甲氧基（5），4-氯（6）和3,4,4'-三甲氧基（8）衍生物。至于先前研究的2'，6'-二羟基-4,4'-二甲氧基查尔酮（7）的速率系数是为中性查尔酮的酸催化环化，中性，单阴离子和二阴离子查尔酮的单分子环化以及碱催化的反向开环反应而确定的。2'，6'-二羟基查耳酮单阴离子的环化速度比2'-羟基-6'-甲氧基查耳酮的单阴离子的环化速度快40倍（10），并且据估计比2'，4'-二羟基查耳酮的反应性单阴离子快约十倍。这些是6'-OH基团提高单阴离子环化速率的首次计算。该作用仅很小，并且被认为主要是由于氢键合烯醇化氧而使酮化的过渡态稳定。还讨论了查耳酮单阴离子之间的其他反应性差异。报告了单阴离子环化（1），（2）和（4）–（6）
• Synthesis of Flavanones using Methane Sulphonic Acid as a Greencatalystand Comparision under Different Conditions
  作者：R. B. Kshatriya、G. M. Nazeruddin

  DOI：10.13005/ojc/300264

  日期：2014.7.1

  Flavonoids are an important class of natural products with  wide   range activities.Flavonoids includes flavone,flavanone,flavane & flavanol.The synthetic route invovles synthesis of chalcone followed by ring closing to give flavanone.So many catalysts were mentioned in past literature.But most efficient catalyst is methane sulphonic acid.It is easy to handle,less reaction time &easily available.Flavanones were synthesized from chalcone using methane sulphonic acid under thermal condition,microw wave and ultrasound condition.Flavanones are syntheisized in very less time compared to other conditions.

  类黄酮是一类具有广泛活性的重要天然产物，其中包括黄酮、二氢黄酮、黄烷和黄烷醇。合成路线涉及先合成查耳酮，然后通过环合反应生成二氢黄酮。过去的文献中提到了许多催化剂，但最有效的催化剂是甲烷磺酸。它易于处理，反应时间短且易于获取。在热条件、微波和超声条件下，使用甲烷磺酸从查耳酮合成二氢黄酮。与其他条件相比，二氢黄酮的合成时间非常短。
• Flavonoids: structural requirements for antiproliferative activity on breast cancer cells
  作者：Christelle Pouget、Fabienne Lauthier、Alain Simon、Catherine Fagnere、Jean-Philippe Basly、Christiane Delage、Albert-José Chulia

  DOI：10.1016/s0960-894x(01)00617-5

  日期：2001.12

  Several classes of flavonoids (flavones, flavanones, 2'-hydroxychalcones and flavan-4-ols) having a variety of substituents on A ring were investigated for their antiproliferative activity against MCF-7 human breast cancer cells. Structure-activity relationships of these compounds were discussed. 2'-hydroxychalcones and methoxylated flavanones were found to be potent inhibitors of MCF-7 cells growth

  研究了在A环上具有各种取代基的几类类黄酮（类黄酮，黄烷酮，2'-羟基查耳酮和黄烷-4-醇）对MCF-7人乳腺癌细胞的抗增殖活性。讨论了这些化合物的构效关系。发现2'-羟基查耳酮和甲氧基黄酮是MCF-7细胞生长的有效抑制剂，而黄酮和flavan-4-ols除7,8-二羟基黄酮外似乎是弱抑制剂。
• Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride
  作者：Motofumi Miura、Karin Shigematsu、Masaharu Toriyama、Shigeyasu Motohashi

  DOI：10.1016/j.tetlet.2021.153480

  日期：2021.11

  flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.

  在温和条件下，从相应的羟基查耳酮与催化量的氟化铯水溶液通过氧杂-迈克尔加成容易合成总共 36 种黄烷酮，其中包括多环芳环和杂环。该方法可用于作为 SARS-CoV-2 刺突蛋白的已知强效抑制剂圣草酚的可扩展合成。
• Synthesis of 5-subsituted flavonols via the Algar-Flynn-Oyamada (AFO) reaction: The mechanistic implication
  作者：Xianyan Shen、Qiang Zhou、Wei Xiong、Wenchen Pu、Wei Zhang、Guolin Zhang、Chun Wang

  DOI：10.1016/j.tet.2017.06.064

  日期：2017.8

  Herein, we report a synthetic method with improved selectivity for 5-substituted flavonols via the Algar-Flynn-Oyamada reaction (AFO), by using of sodium carbonate/hydrogen peroxide A series of 5-substituted flavonols was obtained with moderate to high yields. The mechanism of the AFO reaction was elucidated. LCMS analysis and in situ 1H NMR analysis indicated that the epoxide was involved in the transformation

  本文中，我们报告了一种合成方法，该方法通过使用碳酸钠/过氧化氢，通过Algar-Flynn-Oyamada反应（AFO）对5-取代的黄酮醇进行了改进，具有中等至高收率的一系列5-取代的黄酮醇。阐明了AFO反应的机理。LCMS分析和原位1 H NMR分析表明，在碱性碱/过氧化物条件下，环氧化物参与了从查尔酮到黄酮醇和/或金酮的转化。