3-methoxycarbonyl-4-phenyl-2(1H)-quinolinone | 140842-02-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-methoxycarbonyl-4-phenyl-2(1H)-quinolinone
• 英文别名: 4-phenyl-2-quinolinone-3-carboxylic acid methyl ester；methyl 2-oxo-4-phenyl-1H-quinoline-3-carboxylate
• CAS: 140842-02-0
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: MNETVZHOUVQZPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methoxycarbonyl-4-phenyl-2(1H)-quinolinone 在 三氯氧磷 作用下， 反应 2.0h， 以90%的产率得到2-氯-4-苯基喹啉-3-羧酸甲酯
  参考文献：
  名称：

  Anzini; Cappelli; Vomero, Il Farmaco, 1991, vol. 46, # 12, p. 1435 - 1447

  摘要：

  DOI：
• 作为产物：
  描述：

  dimethyl 2-(2-nitrobenzylidene)malonate 在 ammonium peroxydisulfate 、 rose bengal 、 铁粉 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 50.0h， 生成 3-methoxycarbonyl-4-phenyl-2(1H)-quinolinone
  参考文献：
  名称：

  Visible Light‐Induced Metal‐free Arylation of Coumarin‐3‐carboxylates with Arylboronic Acids

  摘要：

  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.

  DOI：

  10.1002/asia.202400042

文献信息

• A general solid phase synthesis of 4-substituted quinolinones via Pd-catalyzed cross coupling
  作者：Caiding Xu、Lydie Yang、Ashok Bhandari、Christopher P. Holmes

  DOI：10.1016/j.tetlet.2006.05.032

  日期：2006.7

  A general method for the solid phase synthesis of 4-hydroxy quinolinones and subsequent Pd-catalyzed cross coupling to afford 4-substituted quinolinones has been developed. Conversion of support-bound 4-hydroxy quinolinones to 4-tosyl quinolinones and subsequent treatment with alkyl, aryl, benzylzinc halides, or arylboronic acids in the presence of catalytic amount of Pd(PPh3)4 provides 4-alkyl, aryl

  已经开发了固相合成4-羟基喹啉酮和随后的Pd催化的交叉偶联以提供4-取代的喹啉酮的通用方法。将结合有载体的4-羟基喹啉酮转化为4-甲苯磺酰基喹啉酮，然后在催化量的Pd（PPh 3）4存在下用烷基，芳基，苄基卤化锌或芳基硼酸处理，得到4-烷基，芳基或苄基喹啉酮。该方法允许在喹啉酮环的4位上引入烷基，芳基和苄基，是平行和组合化学文库合成的理想方法。
• Anzini; Cappelli; Vomero, Il Farmaco, 1991, vol. 46, # 12, p. 1435 - 1447
  作者：Anzini、Cappelli、Vomero、Campiani、Cagnotto、Skorupska

  DOI：——

  日期：——
• 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.