9-fluoro-6H-benzo[c]chromen-6-one | 1238196-74-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 9-fluoro-6H-benzo[c]chromen-6-one
• 英文别名: 9-Fluorobenzo[c]chromen-6-one；9-fluorobenzo[c]chromen-6-one
• CAS: 1238196-74-1
• 化学式: C₁₃H₇FO₂
• 分子量: 214.196
• InChiKey: XZHHYOTWGKRKDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-fluoro-[1,1'-biphenyl]-2-carboxylic acid 在 Iron(III) nitrate nonahydrate 、 sodium bromate 、 二甲基吡啶胺 作用下， 反应 16.0h， 以88%的产率得到9-fluoro-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  铁光催化实现分子内芳香CH酰氧基化。

  摘要：

  通过铁光催化已经实现了温和而有效的2-联苯基羧酸分子内芳族CH氧化的方案。在两个苯环上具有各种取代基的2-联苯羧酸可以很好的产率提供氧化产物。我们推测，在可见光照射下，芳基羧酸盐-铁（III）配合物应生成芳酰氧基和铁（II）。

  DOI：

  10.1021/acs.orglett.0c00002

文献信息

• Visible light mediated oxidative lactonization of 2-methyl-1,1′-biaryls for the synthesis of benzocoumarins
  作者：Zhi Luo、Zhong-Hua Gao、Zhi-Yong Song、You-Feng Han、Song Ye

  DOI：10.1039/c9ob00529c

  日期：——

  A visible light mediated C–H lactonization of 2-methyl-1,1′-biaryls with oxygen as the oxidant was developed, giving benzocoumarins in good yields.

  开发了一种可见光介导的2-甲基-1,1'-联苯基C-H内酯化反应，以氧氧化剂为氧化剂，产率较高地生成苯并香豆素。
• Novel and Efficient One-Step Parallel Synthesis of Dibenzopyranones via Suzuki−Miyaura Cross Coupling
  作者：Kodumuru Vishnumurthy、Alexandros Makriyannis

  DOI：10.1021/cc100068a

  日期：2010.9.13

  Microwave-promoted novel and efficient one-step parallel synthesis of dibenzopyranones and heterocyclic analogues from bromo arylcarboxylates and o-hydroxyarylboronic acids via Suzuki−Miyaura cross coupling reaction is described. Spontaneous lactonization gave dibenzopyranones and heterocyclic analogues bearing electron-donating and -withdrawing groups on both aromatic rings in good to excellent yields

  描述了通过微波促进的新型有效的一步苯并吡喃酮和杂环类似物通过Suzuki-Miyaura交叉偶联反应从溴代芳基羧酸盐和邻-羟基芳基硼酸平行合成的方法。自发的内酯化以良好或优异的产率得到了在两个芳族环上带有给电子和吸电子基团的二苯并吡喃酮和杂环类似物。
• Cobalt (II)‐catalyzed oxidation of 2‐aryl benzoic acids to access biaryl lactones
  作者：Mianran Chao、Hongyan Wang、Haixing Zhang、Fubi Zhong、Zhen Luo、Fengyun Wu、Feiyang Sun、Jiaojiao Jiang、Xuexue He、Shumiao Zhang、Peiwei Gong、Bin Wang、Duyi Shen

  DOI：10.1002/aoc.6809

  日期：2022.9

  Cobalt/peroxymonosulfate (Co/PMS) system is an efficient advanced oxidation process (AOP) for degradation of organic pollutants in wastewater, however, has limitations in organic synthesis. Herein, we employ a Co/PMS system to the preparation of biaryl lactones by the valorization of 2-aryl aromatic acids via intramolecular O-H/C-X oxidative coupling. This system exhibits intriguing advantages, such

  钴/过氧单硫酸盐（Co/PMS）体系是一种高效的高级氧化工艺（AOP），用于降解废水中的有机污染物，但在有机合成中存在局限性。在此，我们采用 Co/PMS 系统通过分子内 OH/CX 氧化偶联使 2-芳基芳香酸增值来制备联芳基内酯。该系统具有非贵金属催化剂、常用氧化剂、条件温和、易于后处理和产品分离等优点。机理研究，包括自由基猝灭实验和多探针底物，表明高价钴-氧代中间体应该是一种主要的活性物质。同时，过硫酸根阴离子（SO 4 •−) 和羟基自由基 (•OH) 存在于过程中并有助于有机反应。该工作不仅将Co/Oxone体系的合成应用扩展到环境领域之外，而且在已知的金属基AOPs中提供了比普遍接受的SO 4 •-更多的活性中间体。
• NIS-Mediated Oxidative Lactonization of 2-Arylbenzoic Acids for the Synthesis­ of Dibenzopyranones under Metal-Free Conditions
  作者：Yunyang Wei、Peng Gao

  DOI：10.1055/s-0033-1338568

  日期：——

  A series of dibenzopyranones were synthesized from 2-arylbenzoic acids by a radical oxidative cyclization procedure mediated by N-iodosuccinimide (NIS). The methodology is distinguished by its practicality in terms of its wide substrate scope, good functional group tolerance, and mild reaction conditions without the use of transition metals.
• Synthesis of dibenzopyranones and pyrazolobenzopyranones through copper(0)/Selectfluor system-catalyzed double CH activation/oxygen insertion of 2-arylbenzaldehydes and 5-arylpyrazole-4-carbaldehydes
  作者：Jian Zhang、Dongdong Shi、Haifeng Zhang、Zheng Xu、Hanyang Bao、Hongwei Jin、Yunkui Liu

  DOI：10.1016/j.tet.2016.11.069

  日期：2017.1

  A mild and efficient protocol for the synthesis of dibenzopyranones and pyrazolobenzopyranones was developed involving a copper(0)/Selectfluor system-catalyzed double C-H activation/oxygen insertion of 2-arylbenzaldehydes and 5-arylpyrazole-4-carbaldehydes. Preliminary mechanistic studies suggest that both water and dioxygen act as the oxygen source in the formation of pyranone scaffolds. (C) 2016 Elsevier Ltd. All rights reserved.