6-hydroxy-4-methyl-5,7-dinitrocoumarin | 102589-06-0

• 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: 6-hydroxy-4-methyl-5,7-dinitrocoumarin
• 英文别名: 6-hydroxy-4-methyl-5,7-dinitro-coumarin；6-Hydroxy-4-methyl-5,7-dinitro-cumarin；6-hydroxy-4-methyl-5,7-dinitrochromen-2-one
• CAS: 102589-06-0
• 化学式: C₁₀H₆N₂O₇
• 分子量: 266.167
• InChiKey: CHGOKYJXASGLFU-UHFFFAOYSA-N

物化性质

• 熔点：
  220 °C (decomp)(Solv: acetic acid (64-19-7); ethanol, 50% (64-17-5))
• 沸点：
  410.9±45.0 °C(Predicted)
• 密度：
  1.693±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-hydroxy-4-methyl-5,7-dinitrocoumarin 在 palladium on activated charcoal 甲酸 作用下， 以 乙醇 、 水 、 叔丁醇 为溶剂， 反应 2.0h， 以70%的产率得到5,7-Diamino-6-hydroxy-4-methylchromen-2-one
  参考文献：
  名称：

  Mashelkar; Audi, Journal of the Indian Chemical Society, 2005, vol. 82, # 3, p. 258 - 261

  摘要：

  DOI：
• 作为产物：
  描述：

  对苯二酚 在 硫酸 、 硝酸 作用下， 反应 1.0h， 生成 6-hydroxy-4-methyl-5,7-dinitrocoumarin
  参考文献：
  名称：

  Synthesis of novel amino and acetyl amino-4-methylcoumarins and evaluation of their antioxidant activity

  摘要：

  The six novel 4-methylcoumarins bearing different functionalities such as amino, hydroxy, N-acetyl, acetoxy and nitro have been synthesized and confirmed on the basis of their spectral data ((1)H-, (13)C-NMR, UV, IR and El mass). They were examined for the first time for their effect on NADPH dependent liver microsomal lipid peroxidation in vitro, and the results were compared with other model 4-methylcoumarin derivatives to establish the structure-activity relationship. Our studies demonstrated that amino group is an effective substitute for the hydroxyl group for antioxidant property and produced a dramatic inhibition of lipid peroxidation. Ortho dihydroxy and ortho hydroxy-amino coumarins were found to possess highest antioxidant and radical scavenging activities. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.09.002

文献信息

• Studies on Regioselectivity of Nitration of Coumarins with Cerium(IV) Ammonium Nitrate: Solid-State Nitration of 6-Hydroxy-Coumarins on Montmorillonite K-10 Clay Support Under Microwave Irradiation
  作者：Nemai C. Ganguly、Mrityunjoy Datta、Prithwiraj De、Romaprosad Chakravarty

  DOI：10.1081/scc-120015821

  日期：2003.1.4

  in acetic acid and acetonitrile in acceptable-to-excellent yields. Acetonitrile was found to be a better solvent for regioselective nitration than acetic acid. Use of CAN on montmorillonite K-10 clay under microwave irradiation for expeditious solvent-free regioselective nitration has been revealed for the first time.

  摘要 6-羟基香豆素及其 O-甲基醚在碳环中选择性硝化，即使在 2-吡喃酮环中存在活化 4-Me 基团的情况下，醋酸和乙腈中的铈 (IV) 硝酸铵 (CAN) 在可接受的范围内也能被硝化。 - 优异的产量。发现乙腈是比乙酸更好的区域选择性硝化溶剂。首次揭示了在微波辐射下在蒙脱石 K-10 粘土上使用 CAN 进行快速无溶剂区域选择性硝化。
• Mashelkar; Audi, Journal of the Indian Chemical Society, 2005, vol. 82, # 3, p. 258 - 261
  作者：Mashelkar、Audi

  DOI：——

  日期：——
• Borsche, Chemische Berichte, 1907, vol. 40, p. 2732
  作者：Borsche

  DOI：——

  日期：——
• Mewada; Shah, Chemische Berichte, 1956, vol. 89, p. 2209
  作者：Mewada、Shah

  DOI：——

  日期：——
• Synthesis of novel amino and acetyl amino-4-methylcoumarins and evaluation of their antioxidant activity
  作者：Yogesh K. Tyagi、Ajit Kumar、Hanumantharao G. Raj、Parag Vohra、Garima Gupta、Ranju Kumari、Pankaj Kumar、Rajinder K. Gupta

  DOI：10.1016/j.ejmech.2004.09.002

  日期：2005.4

  The six novel 4-methylcoumarins bearing different functionalities such as amino, hydroxy, N-acetyl, acetoxy and nitro have been synthesized and confirmed on the basis of their spectral data ((1)H-, (13)C-NMR, UV, IR and El mass). They were examined for the first time for their effect on NADPH dependent liver microsomal lipid peroxidation in vitro, and the results were compared with other model 4-methylcoumarin derivatives to establish the structure-activity relationship. Our studies demonstrated that amino group is an effective substitute for the hydroxyl group for antioxidant property and produced a dramatic inhibition of lipid peroxidation. Ortho dihydroxy and ortho hydroxy-amino coumarins were found to possess highest antioxidant and radical scavenging activities. (c) 2005 Elsevier SAS. All rights reserved.