1-(2-hydroxyphenyl)-3-(3-methoxyphenyl)-1,3-propanedione | 84634-65-1

• 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
• 英文名称: 1-(2-hydroxyphenyl)-3-(3-methoxyphenyl)-1,3-propanedione
• 英文别名: 1-(2-Hydroxyphenyl)-3-(3-methoxyphenyl)propane-1,3-dione
• CAS: 84634-65-1
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: YOXATDVHOFFCNI-UHFFFAOYSA-N

物化性质

• 熔点：
  83-84.5 °C
• 沸点：
  449.7±30.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxyphenyl)-3-(3-methoxyphenyl)-1,3-propanedione 在 硫酸 、 三溴化硼 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-羟基黄酮
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Substituted Flavones as Gastroprotective Agents

  摘要：

  Flavone (1) was found to protect against ethanol-induced gastric damage in rats; however, it is known that certain compounds in the flavone class, including flavone itself, are inducers of hepatic drug metabolizing enzymes. With the hope of identifying gastroprotective flavones that have minimal effects on drug metabolizing enzymes, we have synthesized and evaluated selected flavone analogs. Gastroprotective potency in the ethanol model was retained by methoxy substitution in the 5-position (4) and by methoxy (12) or methyl (14) substitution in the 7-position. A number of substituted analogs of the potent molecule 5-methoxyflavone (4) were also synthesized, and in many cases, these substitutions provided gastroprotective molecules. In order to assess liver enzyme induction potential, two of the gastroprotective flavones, 7-methoxyflavone (12) and 5-methoxy-4'-fluoroflavone (26), were examined for their effect on liver microsomal cytochrome P450 and 7-ethoxyresorufin O-dealkylase (CYP1A) activity. These two compounds caused minimal changes in the cytochrome P450 concentration and were considerably less potent than beta-naphthoflavone as inducers of CYP1A enzyme activity. Furthermore, following oral administration to rats, 5-methoxy-4'-fluoroflavone (26) was found to protect against indomethacin-induced gastric damage. These results indicate that, through appropriate substitution, flavones can be obtained that are gastroprotective but have minimal effects on drug-metabolizing enzymes.

  DOI：

  10.1021/jm00025a011
• 作为产物：
  描述：

  3-甲氧基苯甲酸 在 吡啶 、 氢氧化钾 、 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-(2-hydroxyphenyl)-3-(3-methoxyphenyl)-1,3-propanedione
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Substituted Flavones as Gastroprotective Agents

  摘要：

  Flavone (1) was found to protect against ethanol-induced gastric damage in rats; however, it is known that certain compounds in the flavone class, including flavone itself, are inducers of hepatic drug metabolizing enzymes. With the hope of identifying gastroprotective flavones that have minimal effects on drug metabolizing enzymes, we have synthesized and evaluated selected flavone analogs. Gastroprotective potency in the ethanol model was retained by methoxy substitution in the 5-position (4) and by methoxy (12) or methyl (14) substitution in the 7-position. A number of substituted analogs of the potent molecule 5-methoxyflavone (4) were also synthesized, and in many cases, these substitutions provided gastroprotective molecules. In order to assess liver enzyme induction potential, two of the gastroprotective flavones, 7-methoxyflavone (12) and 5-methoxy-4'-fluoroflavone (26), were examined for their effect on liver microsomal cytochrome P450 and 7-ethoxyresorufin O-dealkylase (CYP1A) activity. These two compounds caused minimal changes in the cytochrome P450 concentration and were considerably less potent than beta-naphthoflavone as inducers of CYP1A enzyme activity. Furthermore, following oral administration to rats, 5-methoxy-4'-fluoroflavone (26) was found to protect against indomethacin-induced gastric damage. These results indicate that, through appropriate substitution, flavones can be obtained that are gastroprotective but have minimal effects on drug-metabolizing enzymes.

  DOI：

  10.1021/jm00025a011

文献信息

• Mild and efficient organocatalytic method for the synthesis of flavones
  作者：Filip Stanek、Maciej Stodulski

  DOI：10.1016/j.tetlet.2016.07.042

  日期：2016.8

  A convenient and efficient organocatalytic procedure for the selective cyclization of 1,3-diketones to give aromatic substituted 4H-chromen-4-ones under mild reaction conditions using N-triflyl phosphoramide is described. Application of the described conditions is presented in a formal synthesis of (S)-flavanone.

  描述了一种方便有效的有机催化方法，该方法用于在温和的反应条件下使用N-三氟乙磷酰胺选择性环化1,3-二酮以生成芳族取代的4 H-铬4-酮。所述条件的应用以（S）-黄烷酮的形式合成给出。
• Synthesis and antibacterial activity of substituted flavones, 4-thioflavones and 4-iminoflavones
  作者：Ehsan Ullah Mughal、Muhammad Ayaz、Zakir Hussain、Aurangzeb Hasan、Amina Sadiq、Muhammad Riaz、Abdul Malik、Samreen Hussain、M. Iqbal Choudhary

  DOI：10.1016/j.bmc.2006.03.031

  日期：2006.7.15

  Synthesis of flavones, 4-thioflavones and 4-iminoflavones was carried out with the substitution of variable halogens, methyl, methoxy and nitro groups in the A, B and AB rings of the respective compounds and we also report here their antibacterial activity. Most of the synthesized compounds were found to be active against Escherichia coli, Bacillus subtilis, Shigella flexnari, Salmonella aureus, Salmonella

  黄酮，4-硫代黄酮和4-亚氨基黄酮的合成是通过取代相应化合物的A，B和AB环中的可变卤素，甲基，甲氧基和硝基进行的，我们在此也报告了它们的抗菌活性。发现大多数合成的化合物对大肠杆菌，枯草芽孢杆菌，弗氏志贺氏菌，金黄色沙门氏菌，伤寒沙门氏菌和铜绿假单胞菌具有活性。发现4-硫代黄酮和4-亚氨基黄酮的活性高于其相应的黄酮类似物的活性。在环B的4'-位具有取代基（如F，OMe和NO2）的被研究化合物显示出增强的活性，所研究化合物中负电基团的存在与抗菌活性直接相关。
• CF3SOCl-promoted intramolecular cyclization of β-diketones: An efficient synthesis of flavones
  作者：Dong-Wei Sun、Yong-Yan Zhou、Min Jiang、Tang Nian、Jin-Tao Liu

  DOI：10.1016/j.tet.2021.132226

  日期：2021.7

  An efficient intramolecular cyclization reaction of β-diketones containing a phenyl group with an ortho-hydroxyl substituent was achieved. Using CF3SOCl as an additive, the reaction took place under transition-metal-free and mild conditions. A series of flavones were synthesized in moderate to excellent yields.

  实现了含有苯基和邻羟基取代基的β-二酮的有效分子内环化反应。使用CF 3 SOCl 作为添加剂，反应在无过渡金属和温和条件下进行。以中等至极好的收率合成了一系列黄酮。
• A Facile Preparation of Flavones Using Nonaqueous Cation-Exchange Resin
  作者：Yukio Hoshino、Noboru Takeno

  DOI：10.1246/bcsj.60.1919

  日期：1987.5

  Flavone was prepared from 1-(2-hydroxyphenyl)-3-phenyl-1,3-propanedione by using nonaqueous cationexchange resin in a nearly quantitative yield. Of several reaction media, isopropyl alcohol gave the best result. Eight substituted flavones were also synthesized from the corresponding diketones in satisfactory yields.

  黄酮是通过使用无水阳离子交换树脂从1-(2-羟基苯基)-3-苯基-1,3-丙二酮制备的，几乎具有定量的产率。在几种反应介质中，异丙醇给出了最佳结果。还从相应的二酮合成了八种取代的黄酮，并且产率令人满意。
• FeCl3 CATALYZED DEHYDRATIVE CYCLISATION of 1,3-(DIARYL DIKETONES) to FLAVONES
  作者：P. K. Zubaidha、A. M. Hashmi、R. S. Bhosale

  DOI：10.1515/hc.2005.11.1.97

  日期：2005.1

  required synthesis of substituted flavones on large scale. Currently there are number of methods available to synthesize flavones, among them Baker Venkatraman strategy represents the most convenient route from 2hydroxy acetophenone. In this method, acid induced dehydrative cyclisation of 1,3 ( diaryl diketones ) obtained by intramolecular Claisen condensation of Ο benzoyl acetophenone to flavones in 75%

  催化量的FeCh影响取代的1(2羟基苯基)3苯基1、3丙二醇以高产率平滑转化为相应的黄酮。简介 : 黄酮是最丰富、最重要的黄酮类化合物，具有广泛的生物活性。最近对黄酮的兴趣源于它们抑制逆转录病毒转录酶的能力以及它们抑制蛋白质酪氨酸激酶和丝氨酸/苏氨酸激酶的能力。我们对研究黄酮作为醛糖还原酶抑制剂的兴趣需要大规模合成取代的黄酮。目前有多种方法可用于合成黄酮，其中 Baker Venkatraman 策略代表了从 2-羟基苯乙酮合成最便捷的路线。在该方法中，酸诱导脱水环化 1，3（二芳基二酮）通过 Ο 苯甲酰基苯乙酮分子内克莱森缩合得到黄酮，产率为 75%。上述脱水环化的最新进展包括在 MW 辐射下使用 Amberlyst 15、Co(Sulpr) OH、Br2/CHCl3、EtOH/HCl、粘土、NaOAc/AcOH 和 H2SO4。这些程序在操作简单性、反应时间、产率和试剂成本方面受到影响