4-(naphthalen-1-ylamino)-2H-chromen-2-one | 66647-00-5

• 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-(naphthalen-1-ylamino)-2H-chromen-2-one
• 英文别名: 4-(1-naphthylamino)coumarin；4-(Naphthalen-1-ylamino)chromen-2-one
• CAS: 66647-00-5
• 化学式: C₁₉H₁₃NO₂
• 分子量: 287.318
• InChiKey: JLCYUCSNEFRWDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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-(naphthalen-1-ylamino)-2H-chromen-2-one 在 水 、 N-氟代双苯磺酰胺 作用下， 以85 %的产率得到2,2-difluoro-3-(2-hydroxyphenyl)-N-(naphthalen-1-yl)-3-oxopropanamide
  参考文献：
  名称：

  Visible-light-initiated external photocatalyst-free synthesis of α,α-difluoro-β-ketoamides from 4-aminocoumarins

  摘要：

  一种开环二氟化策略已开发出来，用于从4-氨基香豆素、NFSI和水合成含羟基的α，α-二氟-β-酮酰胺。

  DOI：

  10.1039/d2ob01914k
• 作为产物：
  描述：

  4-羟基香豆素 、 1-萘胺 以 neat (no solvent) 为溶剂， 生成 4-(naphthalen-1-ylamino)-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

• 一种香豆素并[4,3-b]吡咯类衍生物及其合成方法和应用
  申请人：临沂大学

  公开号：CN113698412A

  公开（公告）日：2021-11-26

  本发明公开了一种香豆素并[4,3‑b]吡咯类衍生物及其合成方法，该合成方法的具体步骤为：以4‑氨基香豆素类化合物和呋喃醇类化合物为原料，加入有机溶剂和催化剂，催化合成得到如式(I)所示的香豆素并[4,3‑b]吡咯类衍生物。本发明制备方法无需贵金属催化，且对环境友好。本发明还公开了式(I)所示香豆素并[4,3‑b]吡咯类衍生物在制备抗菌、抗肿瘤、抗氧化、抗HIV或抗凝血药物中的应用。
• Visible-light-induced mesoporous graphitic carbon nitride-catalyzed trifluoromethylation and perfluoroalkylation of 4-aminocoumarins
  作者：Ning-Bo Li、Shuo Gu、Chu-Qian Hu、Yu-Xin Wang、Xue Zhou、Jie Qiao、Jun Jiang、Hong-Tao Ji、Wei-Min He

  DOI：10.1039/d2nj05304g

  日期：——

  A heterogeneous mesoporous graphitic carbon nitride (mpg-C₃N₄) photocatalytic 3-trifluoromethylation/perfluoroalkylation of 4-aminocoumarins was realized from 4-aminocoumarins and C_nF_2n+1SO₂Na under mild conditions.

  在温和条件下，以 4-氨基香豆素和 CnF2n+1SO2Na 为原料，实现了介孔石墨氮化碳（mpg-C3N4）对 4-氨基香豆素的 3-三氟甲基化/全氟烷基化的异相光催化。
• 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.
• Screening for In Vitro Antimycobacterial Activity and Three-Dimensional Quantitative Structure-Activity Relationship (3D-QSAR) Study of 4-(arylamino)coumarin Derivatives
  作者：Vijay Virsdoia、Mushtaque S. Shaikh、Atul Manvar、Bhavik Desai、Alpesh Parecha、Raju Loriya、Kinnari Dholariya、Gautam Patel、Vipul Vora、Kuldip Upadhyay、Karia Denish、Anamik Shah、Evans C. Coutinho

  DOI：10.1111/j.1747-0285.2010.00997.x

  日期：2010.11

  The resurgence of tuberculosis and the emergence of multidrug‐resistant strains of Mycobacteria necessitate the search for new classes of antimycobacterial agents. We have synthesized a small library of 50 analogues of 4‐(arylamino)coumarins with various aromatic amines at the C4‐ position of the coumarin scaffold. The compounds were evaluated for antimycobacterial activity against Mycobacterium tuberculosis H37Rv with rifampicin as the standard. Of the molecules synthesized, compound 9 was found to be most potent with a minimum inhibitory concentration >6.25 μg/mL for 100% inhibition. In an effort to develop new and more effective molecules in this series, the relationship between structure and activity was investigated by comparative molecular field analysis. Various models were generated using comparative molecular field analysis alone and comparative molecular field analysis plus a hydropathy field (HINT). In all, eight models were generated with atom‐fit and field‐fit alignment strategies. The comparative molecular field analysis models (Models 3a and 4a) based on field‐fit alignment were the best with statistically good correlation coefficients (r2) and cross‐validated q2. The values of r2pred for the validation set were 0.469 and 0.516. Based on the comparative molecular field analysis contours, some insights into the structure–activity relationship of the compounds could be gained.
• 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%).