4-(m-tolyl)quinolin-2(1H)-one

• 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: 4-(m-tolyl)quinolin-2(1H)-one
• 英文别名: 4-(3-methylphenyl)-1,2-dihydroquinolin-2-one；4-(3-methylphenyl)-1H-quinolin-2-one
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: CVTJFFCSQDWFQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-碘乙酰苯胺 在 palladium diacetate potassium acetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 4-(m-tolyl)quinolin-2(1H)-one
  参考文献：
  名称：

  4-Aryl-2-quinolones via a Domino Heck Reaction / Cyclization Process

  摘要：

  DOI：

  10.3987/com-06-s(o)30

文献信息

• Palladium catalysed hydrolysis-free arylation of aliphatic nitriles for the synthesis of 4-arylquinolin-2-one/pyrazolone derivatives
  作者：Singarajanahalli Mundarinti Krishna Reddy、Subramaniyan Prasanna Kumari、Subramaniapillai Selva Ganesan

  DOI：10.1016/j.tetlet.2021.153296

  日期：2021.8

  Palladium catalysed addition of arylboronic acid to the readily available 2-cyano-(N-aryl)-acetamide or ethyl-2-cyanoacetate followed by subsequent reaction transform them into the biologically significant 4-arylquinolin-2-one or pyrazolone derivatives. The reaction conditions are robust enough to prevent the hydrolysis of ester/amide moiety during arylation. In addition, the unactivated nitrile moiety

  钯催化芳基硼酸加成到容易获得的 2-氰基-( N-芳基)-乙酰胺或 2-氰基乙酸乙酯中，随后反应将它们转化为具有生物学意义的 4-芳基喹啉-2-酮或吡唑啉酮衍生物。反应条件足以防止芳基化过程中酯/酰胺部分的水解。此外，乙腈中未活化的腈部分也转化为相应的苯乙酮衍生物。
• A straight forward synthesis of 4-aryl substituted 2-quinolones via Heck reaction
  作者：Sumanta Gupta、Bhaskar Ganguly、Sajal Das

  DOI：10.1039/c4ra06284a

  日期：——

  Pd–NHC catalyzed one pot synthesis of 4-aryl-2-quinolones through the Heck reaction followed by cyclization. Additionally an efficient methodology has been developed for Heck reaction with a wide range of arylhalides and olefins.

  Pd-NHC催化的一锅法合成4-芳基-2-喹啉酮，首先进行Heck反应，然后进行环化。此外，还开发了一种高效的方法，用于进行Heck反应，可以使用广泛范围的芳基卤代物和烯烃。
• An efficient synthesis of 4-arylquinolin-2(1<i>H</i>)-ones and 3-alkenyl-4-arylquinolin-2(1<i>H</i>)-one using a Pd/NiFe₂O₄-catalyzed consecutive Heck reaction
  作者：Sanjay R. Borhade、Suresh B. Waghmode

  DOI：10.1139/v11-103

  日期：2011.11

  A convenient one-pot method for the synthesis of 4-arylquinolin-2(1H)-ones and 4-arylcoumarins has been described. The successive Heck reaction on substituted 2-iodoaniline and 2-iodophenol catalyzed by a Pd/nickel ferrite catalyst followed by in situ cyclization was the key step. The scope of this methodology was extended to the synthesis of bioactive 3-alkenyl derivatives of 4-arylquinolin-2(1H)-ones.

  已描述了一种合成4-芳基喹啉-2(1H)-酮和4-芳基香豆素的便捷一锅法。由Pd/镍铁氧体催化的取代2-碘苯胺和2-碘酚的连续Heck反应，随后进行原位环化是关键步骤。这种方法的范围已扩展到合成生物活性的4-芳基喹啉-2(1H)-酮的3-烯基衍生物。
• Palladium-catalyzed arylation/cyclization/desulfonation cascades toward 4-aryl quinolin-2(1 H )-ones with diaryliodonium salts
  作者：Jianwei Han、Xunshen Wu、Zhiang Zhang、Limin Wang

  DOI：10.1016/j.tetlet.2017.07.065

  日期：2017.8

  Palladium-catalyzed cascades of arylation/cyclization/desulfonation of ortho-aminocinnamate esters by using diaryliodonium salts afforded a wide range of 4-aryl quinolin-2(1H)-ones. As such, the desired 4-aryl quinolin-2(1H)-ones with potential biological activity has been synthesized in the yields of 34–96%.

  通过使用二芳基碘鎓盐，钯催化的邻氨基肉桂酸酯的芳基化/环化/脱硫级联反应提供了广泛的4-芳基喹啉-2（1 H）-酮。因此，已经合成了所需的具有潜在生物活性的4-芳基喹啉-2（1 H）-一，产率为34-96％。
• Cobalt-catalyzed carbonylative cyclization of N-(2-Vinylphenyl)nicotinamides to access (NH)-quinolin-2(1H)-ones
  作者：Yiwen Zhu、Jun Ying、Xiao-Feng Wu

  DOI：10.1016/j.mcat.2022.112267

  日期：2022.5