3-acetyl-4-phenyl-2H-chromen-2-one | 93327-76-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 3-acetyl-4-phenyl-2H-chromen-2-one
• 英文别名: 3-Acetyl-4-phenylchromen-2-one
• CAS: 93327-76-5
• 化学式: C₁₇H₁₂O₃
• 分子量: 264.28
• InChiKey: SVTUAIXAQRQWAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(hydroxy(phenyl)methyl)phenol 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 3-acetyl-4-phenyl-2H-chromen-2-one
  参考文献：
  名称：

  Mn3O4纳米颗粒催化一锅法合成3,4-二取代香豆素

  摘要：

  开发了由 Mn3O4 纳米颗粒催化的 β-酮酯取代 2-（羟甲基）苯酚一锅法合成 3,4-二取代香豆素。以良好的收率获得了一系列 3,4-二取代香豆素衍生物。

  DOI：

  10.1002/ejoc.201101578

文献信息

• The visible-light-induced acylation/cyclization of alkynoates with acyl oximes for the construction of 3-acylcoumarins
  作者：Quan Zhou、Fang-Ting Xiong、Pu Chen、Bi-Quan Xiong、Ke-Wen Tang、Yu Liu

  DOI：10.1039/d1ob01568k

  日期：——

  by the visible-light-induced acylation/cyclization of alkynoates with various acyl oxime compounds in acetonitrile. The difunctionalization of carbon–carbon triple bonds precedes the generation of iminyl radicals, which is followed by the formation of acyl radicals. The acyl radicals then attack the carbon–carbon triple bonds, followed by 5-exo-trig cyclization and 1,2-ester migration. This strategy

  描述了一种以氮为中心的自由基介导的碳-碳键断裂策略来合成功能化的 3-酰基香豆素。该策略是通过可见光诱导的炔酸酯与乙腈中的各种酰基肟化合物的酰化/环化来实现的。碳-碳三键的双官能化先于亚氨基自由基的产生，然后是酰基自由基的形成。然后酰基自由基攻击碳-碳三键，然后进行 5 -exo-trig环化和 1,2-酯迁移。该策略具有广泛的底物适应性和良好的取代基耐受性。
• KMnO₄/AcOH-mediated C3-selective direct arylation of coumarins with arylboronic acids
  作者：Jin-Wei Yuan、Liang-Ru Yang、Qiu-Yue Yin、Pu Mao、Ling-Bo Qu

  DOI：10.1039/c6ra04787d

  日期：——

  dehydrogenative direct radical arylation of coumarins with arylboronic acids to afford 3-arylcoumarin derivatives is described. A similar reaction system is also applicable to the 3-arylation of quinolinone derivatives. These KMnO4/AcOH-mediated coupling reactions occur regioselectively at the C3 position of coumarins and quinolinones. Some notable features of this method are high efficiency, moderate

  描述了一种有效的方案，用于香豆素与芳基硼酸的KMnO 4 / AcOH介导的脱氢直接自由基芳基化，以提供3-芳基香豆素衍生物。类似的反应系统也适用于喹啉酮衍生物的3-芳基化。这些KMnO 4 / AcOH介导的偶联反应在香豆素和喹啉酮的C3位置区域选择性地发生。该方法的一些显着特征是效率高，产量中等到良好以及广泛的群体耐受性。
• 一种可见光促进的3-酰基香豆素类化合物的合成方法
  申请人：湖南理工学院

  公开号：CN115057840A

  公开（公告）日：2022-09-16

  本发明公开了一种3‑酰基香豆素类化合物的合成新策略，提出一种以炔酸酯类化合物和酰基肟类化合物在可见光促进下的串联酰基化/环化反应，以NCR‑介导的C‑C键断裂策略合成各种结构的3‑酰基香豆素类化合物，碳碳叁键的双官能化经历了亚胺基自由基的生成、酰基自由基的生成、酰基自由基进攻碳碳叁键、5‑exo‑trig环化和1，2‑酯迁移的过程，该合成策略具有广泛的底物适应性和良好的取代基耐受性。
• Visible Light‐Induced Metal‐free Arylation of Coumarin‐3‐carboxylates with Arylboronic Acids
  作者：Swarnayu Banik、Aita Saikiran、Prathyusha Permula、K. S. Srivishnu、B. Sridhar、B. V. Subba Reddy

  DOI：10.1002/asia.202400042

  日期：2024.4.16

  The present work represents a novel methodology for the selective arylation of coumarin‐3‐carboxylates with arylboronic acids via a photochemical route, marking the first‐ever attempt for the direct alkenyl C−H arylation using rose bengal as a photocatalyst, which is a readily available and cost‐effective alternative to transition metal catalysis. The reaction proceeds smoothly in MeOH/H₂O solvent media in the presence of radical initiator affording the arylated products in good yields (60–80 %). The reaction parameters such as visible light, radical initiator, oxidant, anhydrous solvent, and inert atmosphere play a crucial role for the success of this methodology. The substituents present on the substrate show a significant effect on the conversion. This study provides a valuable contribution to the field of organic synthesis offering a new and efficient approach to the arylation of coumarin‐3‐carboxylic acid esters with a broad substrate scope and high functional group tolerance. It is a versatile method and provides a direct access to biologically relevant 4‐arylcoumarin‐3‐carboxylates.
• One-Pot Synthesis of 3,4-Disubstituted Coumarins under Catalysis of Mn3O4 Nanoparticles
  作者：Huayin Sun、Yonghui Zhang、Fengfeng Guo、Yizhe Yan、Changfeng Wan、Zhenggen Zha、Zhiyong Wang

  DOI：10.1002/ejoc.201101578

  日期：2012.1

  The one-pot synthesis of 3,4-disubstituted coumarins from substituted 2-(hydroxymethyl)phenols with β-keto esters catalyzed by Mn3O4 nanoparticles was developed. A series of 3,4-disubstituted coumarin derivatives were obtained in good yields.

  开发了由 Mn3O4 纳米颗粒催化的 β-酮酯取代 2-（羟甲基）苯酚一锅法合成 3,4-二取代香豆素。以良好的收率获得了一系列 3,4-二取代香豆素衍生物。