3-(p-Bromphenyl)-4-hydroxycoumarin | 62497-36-3

• 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-(p-Bromphenyl)-4-hydroxycoumarin
• 英文别名: 3-(4-bromophenyl)-4-hydroxy-2H-chromen-2-one；3-(4-bromo-phenyl)-4-hydroxy-chromen-2-one；3-(4-Bromophenyl)-4-hydroxy-2H-1-benzopyran-2-one；3-(4-bromophenyl)-4-hydroxychromen-2-one
• CAS: 62497-36-3
• 化学式: C₁₅H₉BrO₃
• 分子量: 317.139
• InChiKey: RQHGTTKDFLSVHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3-(p-Bromphenyl)-4-hydroxycoumarin 在 iron(III) chloride 、 silica gel 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以50%的产率得到9-bromo-6H-benzofuro[3,2-c]chromen-6-one
  参考文献：
  名称：

  FeCl 3介导的4-羟基香豆素的氧化闭环合成Coumestan衍生物

  摘要：

  已经开发了一种简洁有效的方法来合成香豆素类似物。支撑策略涉及FeCl 3介导的4-羟基-3-苯基-2 H-铬烯-2-酮衍生物的分子内直接氧化烯丙基化反应。利用该合成方案，可以容易地从容易获得的试剂中获得多种香豆素衍生物。

  DOI：

  10.1021/jo2000644
• 作为产物：
  描述：

  水杨酸甲酯 在 吡啶 、 potassium hydroxide 、 三氯氧磷 作用下， 反应 9.5h， 生成 3-(p-Bromphenyl)-4-hydroxycoumarin
  参考文献：
  名称：

  Coumestan Inhibits Radical-Induced Oxidation of DNA: Is Hydroxyl a Necessary Functional Group?

  摘要：

  Coumestan is a natural tetracycle with a C═C bond shared by a coumarin moiety and a benzofuran moiety. In addition to the function of the hydroxyl group on the antioxidant activity of coumestan, it is worth exploring the influence of the oxygen-abundant scaffold on the antioxidant activity as well. In this work, seven coumestans containing electron-withdrawing and electron-donating groups were synthesized to evaluate the abilities to trap 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(•+)), 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively, and to inhibit the oxidations of DNA mediated by (•)OH, Cu(2+)/glutathione (GSH), and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH), respectively. It was found that all of the coumestans used herein can quench the aforementioned radicals and can inhibit (•)OH-, Cu(2+)/GSH-, and AAPH-induced oxidations of DNA. In particular, substituent-free coumestan exhibits higher ability to quench DPPH and to inhibit AAPH-induced oxidation of DNA than Trolox. In addition, nonsubstituted coumestan shows a similar ability to inhibit (•)OH- and Cu(2+)/GSH-induced oxidations of DNA relative to that of Trolox. The antioxidant effectiveness of the coumestan can be attributed to the lactone in the coumarin moiety and, therefore, a hydroxyl group may not be a necessary functional group for coumestan to be an antioxidant.

  DOI：

  10.1021/jf500013v

文献信息

• Synthesis of Coumestan Derivatives via FeCl₃-Mediated Oxidative Ring Closure of 4-Hydroxy Coumarins
  作者：Lina Tang、Yongle Pang、Qiao Yan、Liuqing Shi、Jianhui Huang、Yunfei Du、Kang Zhao

  DOI：10.1021/jo2000644

  日期：2011.4.15

  A concise and efficient approach to the syntheses of coumestan analogues has been developed. The underpinning strategy involves a FeCl3-mediated direct intramolecular oxidative annellation of 4-hydroxy-3-phenyl-2H-chromen-2-one derivatives. Utilizing this synthetic protocol, a variety of coumestan derivatives were conveniently obtained from readily available reagents.

  已经开发了一种简洁有效的方法来合成香豆素类似物。支撑策略涉及FeCl 3介导的4-羟基-3-苯基-2 H-铬烯-2-酮衍生物的分子内直接氧化烯丙基化反应。利用该合成方案，可以容易地从容易获得的试剂中获得多种香豆素衍生物。
• US4230850A
  申请人：——

  公开号：US4230850A

  公开（公告）日：1980-10-28
• Coumestan Inhibits Radical-Induced Oxidation of DNA: Is Hydroxyl a Necessary Functional Group?
  作者：Gao-Lei Xi、Zai-Qun Liu

  DOI：10.1021/jf500013v

  日期：2014.6.18

  Coumestan is a natural tetracycle with a C═C bond shared by a coumarin moiety and a benzofuran moiety. In addition to the function of the hydroxyl group on the antioxidant activity of coumestan, it is worth exploring the influence of the oxygen-abundant scaffold on the antioxidant activity as well. In this work, seven coumestans containing electron-withdrawing and electron-donating groups were synthesized to evaluate the abilities to trap 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(•+)), 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively, and to inhibit the oxidations of DNA mediated by (•)OH, Cu(2+)/glutathione (GSH), and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH), respectively. It was found that all of the coumestans used herein can quench the aforementioned radicals and can inhibit (•)OH-, Cu(2+)/GSH-, and AAPH-induced oxidations of DNA. In particular, substituent-free coumestan exhibits higher ability to quench DPPH and to inhibit AAPH-induced oxidation of DNA than Trolox. In addition, nonsubstituted coumestan shows a similar ability to inhibit (•)OH- and Cu(2+)/GSH-induced oxidations of DNA relative to that of Trolox. The antioxidant effectiveness of the coumestan can be attributed to the lactone in the coumarin moiety and, therefore, a hydroxyl group may not be a necessary functional group for coumestan to be an antioxidant.