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.