4-[(3-nitrophenyl)amino]-2H-chromen-2-one

• 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-nitrophenyl)amino]-2H-chromen-2-one
• 英文别名: 4-(3'-nitrophenylamino)coumarin；4-(3-Nitroanilino)chromen-2-one
• 化学式: C₁₅H₁₀N₂O₄
• 分子量: 282.255
• InChiKey: WPFJVRWSJCBASD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[(3-nitrophenyl)amino]-2H-chromen-2-one 在 palladium diacetate 、 copper(II) acetate monohydrate 、 caesium carbonate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 30.0h， 生成 2-methyl-1-(3-nitrophenyl)chromeno[4,3-b]pyrrol-4(1H)-one
  参考文献：
  名称：

  Pd-Catalyzed N–H or C–H Functionalization/Oxidative Cyclization for the Efficient Synthesis of N-Aryl-Substituted [3,4]-Fused Pyrrolo­coumarins

  摘要：

  摘要：通过在Cu(OAc)2存在下，在醋酸中加热Pd催化的3-烯丙基-4-芳基氨基香豆素的分子内aza-Wacker型环化反应或N-烯丙基-N-芳基-4-氨基香豆素的C-H插入/氧化环化反应，分别制备了1-芳基-2-甲基或3-甲基色诺[4,3-b]吡咯-4(1H)-酮，收率极高。起始的烯丙基香豆素通过在Cs2CO3存在下，在CH3CN中使用烯丙基溴代物与4-芳基氨基香豆素进行烯丙基化反应制备。初步的生物测试表明，这些化合物具有有趣的抗氧化活性和显著的大豆脂氧化酶抑制活性。

  DOI：

  10.1055/s-0037-1610793
• 作为产物：
  描述：

  4-羟基香豆素 在 四丁基溴化铵 、 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 9.0h， 生成 4-[(3-nitrophenyl)amino]-2H-chromen-2-one
  参考文献：
  名称：

  Pd-Catalyzed Efficient Synthesis of Azacoumestans Via Intramolecular Cross Coupling of 4-(Arylamino)coumarins in the Presence of Copper Acetate under Microwaves

  摘要：

  Azacoumestans通过Pd催化的氧化偶联合成在乙酸中Cu(OAc)2存在下在微波辐射下以优异产率合成。4-(芳胺基)香豆素，甚至那些带有电子吸引基团的化合物，通过芳胺与4-溴香豆素在水中或在加热条件下通过Pd催化的C-N偶联反应几乎定量制备。初步生物测试表明对大豆脂氧化酶和抗脂质过氧化有显著抑制作用。

  DOI：

  10.1055/s-0036-1588955

文献信息

• Magnetically Retrievable Nano Crystalline Nickel Ferrite- Catalyzed Aerobic, Ligand-Free CN, CO and CC Cross- Coupling Reactions for the Synthesis of a Diversified Library of Heterocyclic Molecules
  作者：Sanjay Paul、Koyel Pradhan、Sirshendu Ghosh、S. K. De、Asish R. Das

  DOI：10.1002/adsc.201300686

  日期：2014.4.14

  A new nickel ferrite nano‐crystal‐catalyzed, ligand‐free strategy for the construction of CN, CO, and CC bonds is presented, in which easily available nitrogen and oxygen nucleophiles, aryl/heteroaryl halides and arylboronic acids are used for the cross‐coupling reactions. The reactions can be performed at low catalyst loadings with excellent functional group tolerance and chemoselectivity. A variety

  提出了一种新的镍铁氧体纳米晶催化，无配体的CN，CO和CC键构建策略，其中容易获得的氮和氧亲核试剂，芳基/杂芳基卤化物和芳基硼​​酸用于交叉偶联反应。该反应可以在低催化剂负载下以优异的官能团耐受性和化学选择性进行。各种官能团均与反应条件兼容，包括硝基，甲氧基以及对酸和碱敏感的杂芳族基团。这种前所未有的化学性质很好地补充了胺/杂胺（O）的N-芳基化的经典方法酚/羟基香豆素和联芳基/杂芳基的芳基化反应。低成本，易于处理的性质以及该催化系统的简单性使得该方法可与需要复杂配体存在的基于铜和钯的可比方案竞争。通过简单的水热法制备了镍铁氧体磁性纳米粒子，并通过XRD，TEM图像，能量色散X射线分析，XPS和FT-IR对其进行了表征。催化剂的容易回收和产物的高收率使得该方案具有吸引力，可持续性和经济性。将该催化剂再利用五个循环，其催化活性几乎保持不变。
• 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.
• Chavan, Abhijit P., Journal of Chemical Research, 2006, # 3, p. 179 - 181
  作者：Chavan, Abhijit P.

  DOI：——

  日期：——
• Chavda, Mausami; Shah, Anamik; Bhatt, Surendra, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 6, p. 1502 - 1507
  作者：Chavda, Mausami、Shah, Anamik、Bhatt, Surendra、Deo, Keshav、Kundu, Pareshnath

  DOI：——

  日期：——
• Pd-Catalyzed Efficient Synthesis of Azacoumestans Via Intramolecular Cross Coupling of 4-(Arylamino)coumarins in the Presence of Copper Acetate under Microwaves
  作者：Thomas Balalas、Alaa Abdul-Sada、Dimitra Hadjipavlou-Litina、Konstantinos Litinas

  DOI：10.1055/s-0036-1588955

  日期：2017.6

  Azacoumestans have been synthesized in excellent yields by the Pd-catalyzed oxidative coupling of 4-(arylamino)coumarins in the presence of Cu(OAc)2 in acetic acid under microwave irradiation. 4-(Arylamino)coumarins, even those substituted with an electron-withdrawing group, have been prepared almost quantitatively by the reaction of arylamines with 4-bromocoumarin under microwave irradiation in water or by Pd-catalyzed C–N coupling under heating. Preliminary biological tests indicated significant inhibition of soybean lipoxygenase and antilipid peroxidation.

  Azacoumestans通过Pd催化的氧化偶联合成在乙酸中Cu(OAc)2存在下在微波辐射下以优异产率合成。4-(芳胺基)香豆素，甚至那些带有电子吸引基团的化合物，通过芳胺与4-溴香豆素在水中或在加热条件下通过Pd催化的C-N偶联反应几乎定量制备。初步生物测试表明对大豆脂氧化酶和抗脂质过氧化有显著抑制作用。