7-methoxy-2-(4-trifluoromethylphenyl)-4H-chromen-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 7-methoxy-2-(4-trifluoromethylphenyl)-4H-chromen-4-one
• 英文别名: 7-Methoxy-2-[4-(trifluoromethyl)phenyl]chromen-4-one
• 化学式: C₁₇H₁₁F₃O₃
• 分子量: 320.268
• InChiKey: NIALVODYGCVRLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 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：
  6

反应信息

• 作为反应物：
  描述：

  7-methoxy-2-(4-trifluoromethylphenyl)-4H-chromen-4-one 在 吡啶盐酸盐 作用下， 反应 5.0h， 以88%的产率得到7-hydroxy-2-(4-(trifluoromethyl)phenyl)-4H-chromen-4-one
  参考文献：
  名称：

  基于磷酸盐和硫代磷酸黄酮类似物的类固醇硫酸酯酶抑制剂。

  摘要：

  临床前研究

  DOI：

  10.1002/ddr.21281
• 作为产物：
  描述：

  丹皮酚 在 碘 、 potassium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 5.0h， 生成 7-methoxy-2-(4-trifluoromethylphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  基于磷酸盐和硫代磷酸黄酮类似物的类固醇硫酸酯酶抑制剂。

  摘要：

  临床前研究

  DOI：

  10.1002/ddr.21281

文献信息

• 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
• Synthesis and anticancer effect of B-Ring trifluoromethylated flavonoids
  作者：Xing Zheng、Jian-Guo Cao、Wei-Dong Meng、Feng-Ling Qing

  DOI：10.1016/s0960-894x(03)00752-2

  日期：2003.10

  A series of B-ring trifluoromethylated flavonoids derivatives were prepared and tested in vitro against human gastric adenocarcinoma cell line (SGC-7901). Among these derivatives, 5,7-dipropoxy-2-(4'-trifluoromethylphenyl)-chromen-4-one 5c had the strongest activity against SGC-7901 cell.

  制备了一系列B环三氟甲基化类黄酮衍生物，并在体外针对人胃腺癌细胞系（SGC-7901）进行了测试。在这些衍生物中，5，7-二丙氧基-2-（4'-三氟甲基苯基）-铬-4--4-酮5c对SGC-7901细胞具有最强的活性。
• Formation of the unexpected 3-alkylated flavonoids in the alkylation of B-ring substituted 5,7-dihydroxy flavones
  作者：Cai-Ling Wang、Xing Zheng、Wei-Dong Meng、Hong-Qi Li、Feng-Ling Qing

  DOI：10.1016/j.tetlet.2005.05.144

  日期：2005.8

  Treatment of B-ring substituted 5,7-dihydroxy flavones with alkyl halides in the presence of potassium carbonate gave unexpected 3-alkylated flavonoids. Related experiments were carried out to explain the formation of 3-alkylated flavonoids and a ring opening followed by alkylation and ring closure mechanism was proposed. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of some novel 4H-benzopyran-4-one derivatives as nonsteroidal antiestrogens
  作者：Khadiga Ahmed Ismail、Tarek Abd El Aziem

  DOI：10.1016/s0223-5234(01)01218-1

  日期：2001.3

  The preparation and characterization of some novel 2- and 3-substituted-7-methoxy-4H-1-benzopyran-4-one are presented. The synthesized compounds were evaluated for their uterotrophic, antiuterotrophic and antiimplantation activities in mature female albino rats. 3-Benzyl-7-methoxy-4H-1-benzopyran-4-one (14) showed the highest uterotrophic activity (87%) based on dry uterine weight gain. The antifertility activity, as assessed by the post-coital antiimplantation activity test, was of weak potency for most compounds (14-29%). Among the products, the 2-(4'-methoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one (19) exhibited the highest antiestrogenic activity of 65%. It also elicited 31% of the uterotrophic activity of estradiol. (C) 2001 Editions scientifiques et medicales Elsevier SAS.