4-fluoro-6H-benzo[c]chromen-6-one | 158098-00-1

• 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: 4-fluoro-6H-benzo[c]chromen-6-one
• CAS: 158098-00-1
• 化学式: C₁₃H₇FO₂
• 分子量: 214.196
• InChiKey: KEYWNWZLRRWDBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.21
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3'-fluoro-[1,1'-biphenyl]-2-carbaldehyde 在 四丁基高氯酸铵 作用下， 以 氯仿 为溶剂， 以23.5 mg的产率得到4-fluoro-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  电化学连续氧化法合成内酯

  摘要：

  开发了一种电化学内酯合成方法，提供了从2-芳基苯甲醛快速合成各种二苯并吡喃酮的方法，此外，2-芳基苯甲酸也可以高效转化为相应的二苯并吡喃酮。已经进行了各种控制实验来验证这种电化学串联氧化的机制。

  DOI：

  10.1002/ejoc.202400557

文献信息

• Scalable Electrochemical Dehydrogenative Lactonization of C(sp²/sp³)–H Bonds
  作者：Sheng Zhang、Lijun Li、Huiqiao Wang、Qian Li、Wenmin Liu、Kun Xu、Chengchu Zeng

  DOI：10.1021/acs.orglett.7b03617

  日期：2018.1.5

  A practical, electrochemical method is developed for the direct dehydrogenative lactonization of C(sp2/sp3)–H bonds under external oxidant- and metal-free conditions, delivering diverse lactones, including coumarin derivatives with excellent regioselectivity. The scalable nature of this newly developed electrochemical process was demonstrated on a 40 g scale following an operationally simple protocol

  开发了一种实用的电化学方法，用于在无外部氧化剂和无金属的条件下对C（sp 2 / sp 3）–H键进行直接脱氢内酯化，从而提供多种内酯，包括具有优异区域选择性的香豆素衍生物。遵循操作简单的协议，以40 g规模展示了这种新开发的电化学过程的可扩展性。C（sp 3）-H键的远程内酯化将构成朝着电化学C-O键形成的重要合成进展。
• Cu-Catalyzed Mild C(sp²)–H Functionalization Assisted by Carboxylic Acids en Route to Hydroxylated Arenes
  作者：Joan Gallardo-Donaire、Ruben Martin

  DOI：10.1021/ja4047894

  日期：2013.6.26

  A formal Cu-catalyzed C(sp(2))-H hydroxylation assisted by benzoic acids is described. The procedure is characterized by its mild reaction conditions and wide substrate scope utilizing simple and cheap Cu catalysts, thus becoming a user-friendly and operationally simple protocol for C(sp(2))-H hydroxylation.
• Photocatalytic Dehydrogenative Lactonization of 2-Arylbenzoic Acids
  作者：Nieves P. Ramirez、Irene Bosque、Jose C. Gonzalez-Gomez

  DOI：10.1021/acs.orglett.5b02269

  日期：2015.9.18

  A metal-free dehydrogenative lactonization of 2-arylbenzoic acids at room temperature was developed. This work illustrates the first application of visible-light photoredox catalysis in the preparation of benzo-3,4-coumarins, an important structural motif in bioactive molecules. The combination of photocatalyst [Acr(+)-Mes] with (NH4)(2)S2O8 as a terminal oxidant provides an economical and environmentally benign entry to different substituted benzocoumarins. Preliminary mechanistic studies suggest that this reaction most likely occurs through a homolytic aromatic substitution pathway.