6H-benzo[h]chromeno[4,3-b]quinolin-6-one | 5100-84-5

• 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: 6H-benzo[h]chromeno[4,3-b]quinolin-6-one
• 英文别名: 6H-Benzo[h][1]benzopyrano[4,3-b]quinolin-6-one；10-oxa-2-azapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1,3(12),4,6,8,13,15,17,19,21-decaen-11-one
• CAS: 5100-84-5
• 化学式: C₂₀H₁₁NO₂
• 分子量: 297.313
• InChiKey: FDQOYEWSAJWPLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 1-萘胺 在 air 作用下， 以 neat (no solvent) 为溶剂， 反应 24.0h， 生成 6H-benzo[h]chromeno[4,3-b]quinolin-6-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

• Carcinogenic nitrogen compounds. Part XLIX. Analogues of benzacridines and benzocarbazoles having an α-pyrone ring
  作者：N. P. Buu-Hoï、M. Mangane、P. Jacquignon

  DOI：10.1039/j39660000050

  日期：——

  and paraformaldehyde to give chromenoquinolines, which are analogues of the carcinogenic benzacridines and dibenzacridines. Isochromenoindoles, analogous to mono- and di-benzocarbazoles, were prepared by indolisation of aryl- and quinolylhydrazones of isochroman-1,4-dione. The electron-impact fragmentation of these compounds is discussed.

  显示4-羟基香豆素与伯芳基胺和多聚甲醛发生新的反应，生成色酚喹啉，它们是致癌的苯甲cr啶和二苯甲cr啶的类似物。异壬基吲哚类似于单-和二-苯并咔唑，是通过将异色满-1,4-二酮的芳基-和喹啉基hydr酮吲哚化而制得的。讨论了这些化合物的电子碰撞裂解。
• Substrate‐Induced Synthesis of Coumarin‐Fused Quinolinones from Anilines, 4‐Hydroxycoumarins and DMSO under Air
  作者：Xu Shi、Qingqing Zhang、Anan Wang、Tao‐Shan Jiang

  DOI：10.1002/adsc.202200284

  日期：2022.6.21

  Substrate-induced synthesis of 6H-Chromeno[4,3-b]quinolin-6-ones has been developed directly from anilines, 4-hydroxycoumarins and DMSO under air without any catalysts and additives in one pot. This protocol highlights dual roles of 4-hydroxycoumarins which were not only used as reactants but also activated DMSO to provide one-carbon unit in the desired products.

  6 H - Chromeno[4,3 - b ]quinolin-6-ones 的底物诱导合成直接由苯胺、4-羟基香豆素和 DMSO 在空气中开发，无需任何催化剂和添加剂。该协议强调了 4-羟基香豆素的双重作用，它们不仅用作反应物，而且还激活 DMSO 以在所需产品中提供单碳单元。
• Preparation of Chromeno[<i>b</i>]quinoline Derivatives and Their Application for Lipid Droplets Markers
  作者：Ming-Sen Zhu、Xiao-Qing Zhang、Ya-Nan Wang、Yu-Jie Xu、Ru Sun、Jian-Feng Ge

  DOI：10.1021/acs.joc.2c00667

  日期：2022.8.5

  Functional dyes with a chromeno[b]quinoline skeleton (3a–d) were synthesized by one-step cyclization between coumarin derivatives and aromatic amines under the promotion of anhydrous aluminum chloride in 41.2–45.8% yields. Their maximum absorption and emission wavelengths locate at 358–396 and 420–603 nm with large Stokes shifts (168–231 nm), and their intramolecular charge transfer has been corroborated

  在无水氯化铝的促进下，香豆素衍生物与芳香胺一步环合合成了具有色烯[ b ]喹啉骨架的功能染料（ 3a - d ），收率41.2-45.8%。它们的最大吸收和发射波长位于 358-396 和 420-603 nm，具有大的斯托克斯位移（168-231 nm），并且它们的分子内电荷转移已通过密度泛函理论计算得到证实。细胞实验证明，探针3a - c具有靶向脂滴的能力。
• Copper-Catalyzed Cyclization for Access to 6<i>H</i>-Chromeno[4,3-<i>b</i>]quinolin-6-ones Employing DMF as the Carbon Source
  作者：Yiyi Weng、Hao Zhou、Chen Sun、Yuanyuan Xie、Weike Su

  DOI：10.1021/acs.joc.7b01515

  日期：2017.9.1

  The first example of the copper-catalyzed cyclization of 4-(phenylamino)-2H-chromen-2-ones employing the N-methyl moiety of DMF as the source of the methine (CH) group has been developed, providing an efficient synthetic pathway to access novel functionalized 6H-chromeno[4,3-b]quinolin-6-ones in moderate to good yields.
• 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。