9-Chlorobenzo-4H-furo[3,2-c][1]benzopyran-6-one

• 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: 9-Chlorobenzo-4H-furo[3,2-c][1]benzopyran-6-one
• 英文别名: 9-chloro-6H-benzofuro[3,2-c]chromen-6-one；9-Chloro-[1]benzofuro[3,2-c]chromen-6-one
• 化学式: C₁₅H₇ClO₃
• 分子量: 270.672
• InChiKey: IHPIAAYAFLDZNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(4-氯苯基)苯并吡喃-2-酮 在 dipotassium peroxodisulfate 、 palladium diacetate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 、 三氟乙酸 为溶剂， 反应 25.0h， 生成 9-Chlorobenzo-4H-furo[3,2-c][1]benzopyran-6-one
  参考文献：
  名称：

  Palladium-Catalyzed Weakly Coordinating Lactone-Directed C–H Bond Functionalization of 3-Arylcoumarins: Synthesis of Bioactive Coumestan Derivatives

  摘要：

  DOI：

  10.1021/acs.joc.1c01097

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。
• Synthesis of Furocoumarins via Rhodium(II)-Catalysed Heterocyclisation of 3-Diazobenzopyran-2,4-(3H)-dione with Terminal Alkynes
  作者：Stefano Tollari、Giovanni Palmisano、Sergio Cenini、Giancarlo Cravotto、Giovanni B. Giovenzana、Andrea Penoni

  DOI：10.1055/s-2001-12765

  日期：——

  The rhodium (II) acetate-catalysed decomposition of 3-diazobenzopyran-2,4(3H)-dione in the presence of a terminal alkyne gave rise to a mixture of isomeric 2-substituted furo[3,2-c]coumarin and furo[2,3-b]coumarin, resulting from a formal [3+2] cycloaddition.

  在末端炔存在下，乙酸铑 (II) 催化分解 3-重氮苯并吡喃-2,4(3H)-二酮，生成异构体 2-取代呋喃并[3,2-c]香豆素和呋喃的混合物[2,3-b]香豆素，由正式的[3+2]环加成反应产生。
• 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.
• Palladium-Catalyzed Weakly Coordinating Lactone-Directed C–H Bond Functionalization of 3-Arylcoumarins: Synthesis of Bioactive Coumestan Derivatives
  作者：Vikki N. Shinde、Krishnan Rangan、Dalip Kumar、Anil Kumar

  DOI：10.1021/acs.joc.1c01097

  日期：2021.7.16