1-(4-fluorophenyl)-3-(2-hydroxy-5-methoxyphenyl)propane-1,3-dione | 312607-68-4

• 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-(4-fluorophenyl)-3-(2-hydroxy-5-methoxyphenyl)propane-1,3-dione
• CAS: 312607-68-4
• 化学式: C₁₆H₁₃FO₄
• 分子量: 288.275
• InChiKey: ABKONMXONQQXKA-UHFFFAOYSA-N

物化性质

• 沸点：
  471.0±40.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO：58 mg/mL (201.20 mM)；乙醇：7 mg/mL (24.28 mM)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 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：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-fluorophenyl)-3-(2-hydroxy-5-methoxyphenyl)propane-1,3-dione 在 维生素 C 作用下， 以87%的产率得到2-(4-fluorophenyl)-6-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  L-抗坏血酸：在常规和微波加热下绿色无溶剂合成黄酮和香豆素的促进剂

  摘要：

  背景：已经开发出一种快速的方法来合成两种不同类别的苯并吡喃酮。无溶剂条件下的黄酮和香豆素。发现L-抗坏血酸在微波辐射和常规加热下是有效的促进剂。合成了各种苯并-α-吡喃酮和苯并-γ-吡喃酮，总收率良好。本方案非常容易，不需要柱色谱法纯化，因此在微波辐射和常规加热下均可作为一种有效且兼容的方法。 结果：研究了L-抗坏血酸对黄酮和香豆素合成的催化能力。为此目的，选择了1-（2-羟苯基）-3-芳基-1，3-丙二酮的环脱水和Pechmann香豆素的合成反应。因此，据观察，完成反应需要一摩尔的L-抗坏血酸。在所有情况下，都能以良好至极佳的收率顺利产生所需的黄酮。表明其对各种官能团的优异耐受性。但是，在这些条件下，给电子基团有利于香豆素的合成。仔细分析了所有反应混合物，核磁共振表明转化率高，没有副产物。 结论：我们已经开发了L-抗坏血酸促进的，无溶剂的简单方法，该方法在微波辐射下以及常规加热条件下合成

  DOI：

  10.2174/1570178614666161116125148
• 作为产物：
  描述：

  2'-羟基-5'-甲氧基苯乙酮 在 吡啶 、 potassium hydroxide 、 三氯氧磷 作用下， 以 吡啶 为溶剂， 反应 4.0h， 生成 1-(4-fluorophenyl)-3-(2-hydroxy-5-methoxyphenyl)propane-1,3-dione
  参考文献：
  名称：

  Synthesis of novel 4,6-diaryl-2-aminopyrimidines as potential antiplasmodial agents

  摘要：

  A novel series of 4,6-diaryl-2-aminopyrimidines 8a-o has been synthesized and evaluated for in vitro antiplasmodial activity against Plasmodium falciparum. Out of the 15 compounds synthesized and tested, 6 compounds have shown IC50 values in the range of 1.61-9.53 mu g/mL. These compounds are several times more potent than chloroquine and quinine, the two standard drugs used for the purpose of comparison.

  DOI：

  10.1007/s00044-012-0328-z

文献信息

• L-Ascorbic Acid: A Green and Competent Promoter for Solvent-Free Synthesis of Flavones and Coumarins under Conventional as well as Microwave Heating
  作者：Rohit Arvind Dengale、Nitin Madhu Thorat、Shankar Ramchandra Thopate

  DOI：10.2174/1570178614666161116125148

  日期：2017.1.3

  Background: An expeditious approach has been developed for the synthesis of two distinct classes of benzopyrones viz. flavones and coumarins under solvent-free conditions. L-Ascorbic acid was found to be an effective promoter under microwave irradiation and conventional heating. Various benzo-α-pyrones and benzo-γ-pyrones were synthesized with overall good yields. The present protocol is highly facile and needs

  背景：已经开发出一种快速的方法来合成两种不同类别的苯并吡喃酮。无溶剂条件下的黄酮和香豆素。发现L-抗坏血酸在微波辐射和常规加热下是有效的促进剂。合成了各种苯并-α-吡喃酮和苯并-γ-吡喃酮，总收率良好。本方案非常容易，不需要柱色谱法纯化，因此在微波辐射和常规加热下均可作为一种有效且兼容的方法。 结果：研究了L-抗坏血酸对黄酮和香豆素合成的催化能力。为此目的，选择了1-（2-羟苯基）-3-芳基-1，3-丙二酮的环脱水和Pechmann香豆素的合成反应。因此，据观察，完成反应需要一摩尔的L-抗坏血酸。在所有情况下，都能以良好至极佳的收率顺利产生所需的黄酮。表明其对各种官能团的优异耐受性。但是，在这些条件下，给电子基团有利于香豆素的合成。仔细分析了所有反应混合物，核磁共振表明转化率高，没有副产物。 结论：我们已经开发了L-抗坏血酸促进的，无溶剂的简单方法，该方法在微波辐射下以及常规加热条件下合成
• Convenient One-Pot Synthesis of Chromone Derivatives and Their Antifungal and Antibacterial Evaluation
  作者：Sherif B. Abdel Ghani、Patrick J. Mugisha、Juliet C. Wilcox、Emad A. M. Gado、Erere O. Medu、Andrew J. Lamb、Richard C. D. Brown

  DOI：10.1080/00397911.2011.647222

  日期：2013.6.3

  one-pot method for the synthesis of chromone derivatives from the reaction of 2-hydroxyacetophenones with aliphatic or aromatic acid chlorides is reported. Esterification and Baker–Venkataraman rearrangement were promoted by t-BuOK, which was followed directly by acid-catalyzed cyclization in one pot. Some of 2-cyclohexyl- and 2-cyclohexylmethyl-substituted chromones displayed activity against plant pathogenic

  摘要 报道了一种由 2-羟基苯乙酮与脂肪族或芳香族酰氯反应合成色酮衍生物的一锅法。酯化和 Baker-Venkataraman 重排由 t-BuOK 促进，然后直接在一锅中进行酸催化环化。一些 2-环己基-和 2-环己基甲基-取代的色酮显示出抗植物病原真菌菌株的活性。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要
• Design, synthesis and structure–activity relationships of 3,5-diaryl-1H-pyrazoles as inhibitors of arylamine N-acetyltransferase
  作者：Elizabeth Fullam、James Talbot、Areej Abuhammed、Isaac Westwood、Stephen G. Davies、Angela J. Russell、Edith Sim

  DOI：10.1016/j.bmcl.2013.02.052

  日期：2013.5

  The synthesis and inhibitory potencies of a novel series of 3,5-diaryl-1H-pyrazoles as specific inhibitors of prokaryotic arylamine N-acetyltransferase enzymes is described. The series is based on hit compound 1 3,5-diaryl-1H-pyrazole identified from a high-throughout screen that has been carried out previously and found to inhibit the growth of Mycobacterium tuberculosis. (C) 2013 Elsevier Ltd. All rights reserved.
• Thorat, Nitin M.; Dengale, Rohit A.; Thopate, Shankar R., Letters in Organic Chemistry, 2015, vol. 12, # 8, p. 574 - 583
  作者：Thorat, Nitin M.、Dengale, Rohit A.、Thopate, Shankar R.、Rohokale, Sandeep V.

  DOI：——

  日期：——
• Assessment of antiplatelet activity of 2-aminopyrimidines
  作者：Rajani Giridhar、Riyaj S. Tamboli、R. Ramajayam、Dhaval G. Prajapati、M.R. Yadav

  DOI：10.1016/j.ejmech.2012.01.035

  日期：2012.4

  A series of 4,6-diaryl-2-aminopyrimidines was developed as antiplatelet agents and their potency was evaluated by in vitro assay. Compound 14k was found to be two times more potent than aspirin. These encouraging results could be helpful for the development of new antiplatelet compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.