4-[(3,5-dimethylphenyl)amino]-2H-chromen-2-one | 799824-21-8

• 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-[(3,5-dimethylphenyl)amino]-2H-chromen-2-one
• 英文别名: 4-(3,5-dimethylanilino)chromen-2-one
• CAS: 799824-21-8
• 化学式: C₁₇H₁₅NO₂
• mdl: MFCD03682626
• 分子量: 265.312
• InChiKey: YOVLMGZZJVTLNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(3,5-dimethylphenyl)amino]-2H-chromen-2-one 在 palladium diacetate 、 溶剂黄146 作用下， 反应 24.0h， 以93%的产率得到7,9-dimethylchromeno[4,3-b]indol-6(11H)-one
  参考文献：
  名称：

  Access to Indole-Fused Polyheterocycles via Pd-Catalyzed Base-Free Intramolecular Cross Dehydrogenative Coupling

  摘要：

  A base-free process to access indole-fused polyheterocycles via a highly efficient and atom-economic palladium-catalyzed intramolecular cross dehydrogenetive coupling (CDC) reaction of 4-aniline substituted coumarins, quinolinones, and pyrones has been developed. A wide range of indolo[3,2-c]coumarins, indolo[3,2-c]quinolinones, and indolo[3,2-c]pyrones can be facilely afforded in good to excellent yields (up to 99%).

  DOI：

  10.1021/acs.joc.6b02160
• 作为产物：
  描述：

  4-羟基香豆素 、 1-氨基-3,5-二甲苯 以 neat (no solvent) 为溶剂， 生成 4-[(3,5-dimethylphenyl)amino]-2H-chromen-2-one
  参考文献：
  名称：

  Substrate‐induced Selective α‐C(sp³)−H Activation of N‐alkyl Amines: Synthesis of Coumarin‐fused Quinolinones under Air

  摘要：

  摘要 以N-烷基胺为溶剂和碳源，在空气条件下，不使用任何催化剂，通过底物诱导合成了4-(苯基氨基)-2H-色烯-2-酮类香豆素融合喹啉酮。该方案突出了 4-(苯基氨基)-2H-苯并吡喃-2-酮的特殊作用，它不仅可用作反应物，还可用作选择性活化 N-α-C(sp3)-H 键的内部氧化剂。该反应具有无需催化剂、底物范围广（N-烷基胺类 27 例和喹啉酮类 24 例）、一步合成操作简单以及溶剂回收和循环利用等特点。

  DOI：

  10.1002/adsc.202301352

文献信息

• A Novel and Facile Synthesis of N-Substituted 8-hydroxybenzo[g] chromeno[4, 3-b]indol-6(13H)-ones by a Nenitzescu Reaction
  作者：Zhiwei Chen、Xiaodong Wang、Weike Su

  DOI：10.2174/15701786113106660079

  日期：2014.2

  N-Substituted 8-hydroxybenzo[g]chromeno[4,3-b]indol-6(13H)-ones have been efficiently synthesized via a Nenitzescu reaction of naphthoquinone (or benzoquinone) and N-substituted 4-aminocoumarins in the presence of a catalytic amount of KHSO4 with a [bmim][BF4]/toluene system.

  N-取代的8-羟基苯并[g]色氨酸-6(13H)-酮通过在[bmim][BF4]/甲苯体系中，使用催化量的KHSO4进行萘醌（或苯醌）与N-取代的4-氨基香豆素的Nenitzescu反应高效合成。
• Access to Indole-Fused Polyheterocycles via Pd-Catalyzed Base-Free Intramolecular Cross Dehydrogenative Coupling
  作者：Chao Cheng、Wen-Wen Chen、Bin Xu、Ming-Hua Xu

  DOI：10.1021/acs.joc.6b02160

  日期：2016.11.18

  A base-free process to access indole-fused polyheterocycles via a highly efficient and atom-economic palladium-catalyzed intramolecular cross dehydrogenetive coupling (CDC) reaction of 4-aniline substituted coumarins, quinolinones, and pyrones has been developed. A wide range of indolo[3,2-c]coumarins, indolo[3,2-c]quinolinones, and indolo[3,2-c]pyrones can be facilely afforded in good to excellent yields (up to 99%).
• Substrate‐induced Selective <i>α</i>‐C(<i>sp</i>³)−H Activation of <i>N</i>‐alkyl Amines: Synthesis of Coumarin‐fused Quinolinones under Air
  作者：Zhou Zhang、Juan Wan、Lu Yin、Meitian Fu、Chao Huang

  DOI：10.1002/adsc.202301352

  日期：2024.3.19

  A substrate‐induced synthesis of coumarin‐fused quinolinones is achieved from 4‐(phenylamino)‐2H‐chromen‐2‐ones using N‐alkyl amines as the solvent and a carbon source under air conditions without any catalysts in one pot. This protocol highlights the special roles of 4‐(phenylamino)‐2H‐chromen‐2‐ones which were not only used as reactants but also as an internal oxidant selectively activated N‐α‐C(sp³)−H bond. This reaction features catalyst‐free, broad substrate scopes (N‐alkyl amines 27 examples and quinolinones 24 examples), operationally simple for the one‐step synthesis, and recovery and recycling of the solvent.

  摘要 以N-烷基胺为溶剂和碳源，在空气条件下，不使用任何催化剂，通过底物诱导合成了4-(苯基氨基)-2H-色烯-2-酮类香豆素融合喹啉酮。该方案突出了 4-(苯基氨基)-2H-苯并吡喃-2-酮的特殊作用，它不仅可用作反应物，还可用作选择性活化 N-α-C(sp3)-H 键的内部氧化剂。该反应具有无需催化剂、底物范围广（N-烷基胺类 27 例和喹啉酮类 24 例）、一步合成操作简单以及溶剂回收和循环利用等特点。