6-hydroxy-4-methyl-5-nitro-2H-chromen-2-one | 5255-54-9

• 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-nitro-2H-chromen-2-one
• 英文别名: 6-hydroxy-4-methyl-5-nitrocoumarin；6-hydroxy-5-nitro-4-methylcoumarin；6-hydroxy-4-methyl-5-nitro-chromen-2-one；6-hydroxy-4-methyl-5-nitro-coumarin；6-Hydroxy-4-methyl-5-nitro-cumarin；2H-1-Benzopyran-2-one, 6-hydroxy-4-methyl-5-nitro-；6-hydroxy-4-methyl-5-nitrochromen-2-one
• CAS: 5255-54-9
• 化学式: C₁₀H₇NO₅
• 分子量: 221.169
• InChiKey: PUOSYPRBKCKJNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 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：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  6-hydroxy-4-methyl-5-nitro-2H-chromen-2-one 在 sodium dithionite 、 氨 作用下， 以 水 为溶剂， 反应 3.0h， 以75%的产率得到5-amino-6-hydroxy-4-methyl-coumarin
  参考文献：
  名称：

  具有分子内氢键的新型氨基香豆素 knightletin 的光谱特性和建模

  摘要：

  Knightletin 是一种新型的、高量子产率的取代香豆素，属于荧光 7-氨基香豆素组。该分子通过其吸光度-荧光特性和与几种初始溶剂的相互作用揭示了邻羟基对氨基香豆素结构的影响。香豆素苯环上的取代影响电子态、分子偶极矩并且涉及分子内和分子间氢键。本报告描述了 knightletin 的合成、其在不同极性和氢键能力的三种溶剂中的吸光度-荧光特性，以及从密度泛函理论模型中对其构象的见解。在甲醇中 0.81 的量子产率是显着的。建模表明具有金字塔形 NH 的基态几何2基团与 OH 在 NH-供体氢键中相互作用，并预测与实验观察一致的光谱特征。

  DOI：

  10.1016/j.jphotochem.2022.114286
• 作为产物：
  描述：

  6-methoxy-4-methyl-5-nitrocoumarin 在 水 、 氢溴酸 作用下， 反应 3.0h， 以85%的产率得到6-hydroxy-4-methyl-5-nitro-2H-chromen-2-one
  参考文献：
  名称：

  [EN] DEVELOPMENT OF FLUOROGENIC SUBSTRATES FOR MONOAMINE OXIDASES (MAO-A AND MAO-B)
  [FR] MISE AU POINT DE SUBSTRATS FLUOROGENES DESTINES AUX MONOAMINE OXYDASES (MAO-A AND MAO-B)

  摘要：

  公开号：

  WO2006026368A3

文献信息

• Synthesis of Fused Oxazolocoumarins from <i>o</i> -Hydroxynitrocoumarins and Benzyl Alcohol Under Gold Nanoparticles or FeCl₃ Catalysis
  作者：Evangelia-Eirini N. Vlachou、Gerasimos S. Armatas、Konstantinos E. Litinas

  DOI：10.1002/jhet.2842

  日期：2017.7

  Synthesis of fused oxazolocoumarins has been achieved from the one‐pot tandem reactions of o‐hydroxynitrocoumarins with benzyl alcohol in toluene under catalysis in a sealed tube at 150°C. The catalysis was performed by gold nanoparticles supported on TiO2 (0.4 mol% Au) or FeCl3 (5%) or silver nanoparticles supported on TiO2 (1.7 mol% Ag).

  邻羟基硝基香豆素与苯甲醇在甲苯中在150°C的密闭管催化下的单锅串联反应可实现稠合的恶唑香豆素的合成。通过负载在TiO 2（0.4 mol％Au）或FeCl 3（5％）上的金纳米颗粒或负载在TiO 2（1.7 mol％Ag）上的银纳米颗粒进行催化。
• Development of Fluorogenic Substrates For Monoamine Oxidases (Mao-A and Mao-B)
  申请人：Chen Gong

  公开号：US20080194522A1

  公开（公告）日：2008-08-14

  The present invention relates to compounds useful for detecting the activity of monoamine oxidases, compounds useful for competitively inhibiting monoamine oxidases, for determining inhibitors of monoamine oxidases and compounds useful for treating monoamine oxidase-related nervous system pathologies, as well as pharmaceutical compositions and methods of manufacture thereof.

  本发明涉及用于检测单胺氧化酶活性的化合物，用于竞争性抑制单胺氧化酶的化合物，用于确定单胺氧化酶抑制剂和用于治疗与单胺氧化酶相关的神经系统病理的化合物，以及制药组合物和制造方法。
• 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.
• Borsche, Chemische Berichte, 1907, vol. 40, p. 2732
  作者：Borsche

  DOI：——

  日期：——
• Reddy; Somayajulu, Journal of the Indian Chemical Society, 1981, vol. 58, # 6, p. 599 - 601
  作者：Reddy、Somayajulu

  DOI：——

  日期：——