4-chloro-6H-benzo[c]chromen-6-one | 90909-57-2

• 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-chloro-6H-benzo[c]chromen-6-one
• 英文别名: 4-chlorobenzo[c]chromen-6-one
• CAS: 90909-57-2
• 化学式: C₁₃H₇ClO₂
• 分子量: 230.65
• InChiKey: IWGVSBMJXGBEER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  2

反应信息

• 作为产物：
  描述：

  3-氯联苯-2-甲醛 在 水 、 铜 、 potassium carbonate 、 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以76%的产率得到4-chloro-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  Synthesis of dibenzopyranones and pyrazolobenzopyranones through copper(0)/Selectfluor system-catalyzed double CH activation/oxygen insertion of 2-arylbenzaldehydes and 5-arylpyrazole-4-carbaldehydes

  摘要：

  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.

  DOI：

  10.1016/j.tet.2016.11.069

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。
• Microwave-Assisted Cyclization under Mildly Basic Conditions: Synthesis of 6<i>H</i>-Benzo[<i>c</i>]chromen-6-ones and Their 7,8,9,10-Tetrahydro Analogues
  作者：Pham Duy Quang Dao、Son Long Ho、Ho-Jin Lim、Chan Sik Cho

  DOI：10.1021/acs.joc.8b00048

  日期：2018.4.6

  give the corresponding 6H-benzo[c]chromen-6-ones and their 7,8,9,10-tetrahydro analogues, respectively, in 50–72% yields. Aryl 3-bromoacrylates are also converted into 2H-chromen-2-ones under the employed conditions.

  在K 2 CO 3的存在下，在二甲基甲酰胺中通过微波辐照，将2-溴苯甲酸芳酯和2-溴环己-1-芳烷基芳酯环化，得到相应的6 H-苯并[ c ] chromen-6-one及其7,8， 9,10-四氢类似物，产率分别为50-72％。在所采用的条件下，将3-溴丙烯酸芳基酯也转化为2 H-铬-2-基。
• 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.
• Neumeister, Joachim; Griesbaum, Karl, Chemische Berichte, 1984, vol. 117, # 4, p. 1640 - 1642
  作者：Neumeister, Joachim、Griesbaum, Karl

  DOI：——

  日期：——
• NEUMEISTER, J.;GRIESBAUM, K., CHEM. BER., 1984, 117, N 4, 1640-1642
  作者：NEUMEISTER, J.、GRIESBAUM, K.

  DOI：——

  日期：——