2-甲基-3-(4-硝基苯甲酰基)色酮 | 854846-60-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 中文名称: 2-甲基-3-(4-硝基苯甲酰基)色酮
• 英文名称: 2-methyl-3-(4-nitrobenzoyl)chromone
• 英文别名: 2-methyl-3-(4-nitrobenzoyl)-4H-chromen-4-one；2-methyl-3-(4-nitro-benzoyl)-chromen-4-one；2-Methyl-3-(4-nitro-benzoyl)-chromen-4-on；2-Methyl-3-(4-nitrobenzoyl)chromen-4-one；2-methyl-3-(4-nitrobenzoyl)chromen-4-one
• CAS: 854846-60-9
• 化学式: C₁₇H₁₁NO₅
• 分子量: 309.278
• InChiKey: CIRVRQVWGOYBCG-UHFFFAOYSA-N

物化性质

• 熔点：
  202-204 °C
• 沸点：
  481.9±45.0 °C(Predicted)
• 密度：
  1.393±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-甲基-3-(4-硝基苯甲酰基)色酮 在 sodium tetrahydroborate 作用下， 以 吡啶 为溶剂， 以80%的产率得到
  参考文献：
  名称：

  Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones

  摘要：

  3-Acylchromones and 3-acylflavones, readily available by acylation of 2'-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate reduction with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The reduction is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO3H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This reduction-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.058
• 作为产物：
  描述：

  2-羟基苯乙酮 在 吡啶 、 sodium acetate 、 乙酸酐 、 potassium hydroxide 作用下， 反应 1.5h， 生成 2-甲基-3-(4-硝基苯甲酰基)色酮
  参考文献：
  名称：

  In vitro Photoprotective Evaluation and Development of Novel Nanoemulsion with Chromone Derivative

  摘要：

  合成了在UVA/UVB区域具有高吸光度值的香豆素衍生物，并评估了它们的光保护性能。根据已知文献程序制备了香豆素，并通过高分辨质谱、红外（IR）和核磁共振（NMR）光谱进行表征。通过Mansur方法确定了体外太阳防护因子（SPF），并使用sulforhodamine B测定了细胞毒性。合成的两种香豆素表现出合适的SPF值，并在测试浓度下对MRC-5人类成纤维细胞没有细胞毒性效应，表明在未来体内实验和临床试验中具有巨大潜力。最后，主要化合物被纳米乳化。纳米乳化剂显示出高液滴尺寸均一性和优异的稳定性。带有甲氧基取代基的香豆素被发现是最具前景的化合物，具有理想的光保护性能，适合用于防晒霜配方中的应用和合并。

  DOI：

  10.21577/0103-5053.20210072

文献信息

• Baker et al., Journal of the Chemical Society, 1952, p. 1294,1301
  作者：Baker et al.

  DOI：——

  日期：——
• Baker et al., Journal of the Chemical Society, 1294,1302
  作者：Baker et al.

  DOI：——

  日期：——
• Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones
  作者：David S. Clarke、Christopher D. Gabbutt、John D. Hepworth、B. Mark Heron

  DOI：10.1016/j.tetlet.2005.06.058

  日期：2005.8

  3-Acylchromones and 3-acylflavones, readily available by acylation of 2'-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate reduction with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The reduction is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO3H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This reduction-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones. (c) 2005 Elsevier Ltd. All rights reserved.
• In vitro Photoprotective Evaluation and Development of Novel Nanoemulsion with Chromone Derivative
  作者：Amanda Antunes、Ana Paula Gouveia、Gabriela Diogo、Jason Taylor、Lucas Sousa、Tatiane Amparo、Fernanda Perasoli、Orlando dos Santos、Thiago Cazati、Paula Vieira、Ricardo Penido、Viviane dos Santos

  DOI：10.21577/0103-5053.20210072

  日期：——

  Chromone derivatives exhibiting high absorbance values in the UVA/UVB region were synthesized, and their photoprotective properties were evaluated. Chromones were prepared according to known literature procedures and characterized by high resolution mass spectrometry, infrared (IR) and nuclear magnetic resonance (NMR) spectroscopy. The in vitro solar protection factor (SPF) was determined by the Mansur method and cytotoxicity was evaluated using the sulforhodamine B assay. Two of the chromones synthesized demonstrated suitable SPF values and displayed no cytotoxic effect towards MRC-5 human fibroblasts at the tested concentrations, indicating great potential for future in vivo assays and clinical trials. Finally, the lead compound was incorporated into a nanoemulsion. Nanoemulsions showed high droplet size homogeneity and excellent stability. Chromones bearing methoxy substituents were found to be the most promising compounds with ideal photoprotective properties desirable for utilization and incorporation in sunscreen formulations.

  合成了在UVA/UVB区域具有高吸光度值的香豆素衍生物，并评估了它们的光保护性能。根据已知文献程序制备了香豆素，并通过高分辨质谱、红外（IR）和核磁共振（NMR）光谱进行表征。通过Mansur方法确定了体外太阳防护因子（SPF），并使用sulforhodamine B测定了细胞毒性。合成的两种香豆素表现出合适的SPF值，并在测试浓度下对MRC-5人类成纤维细胞没有细胞毒性效应，表明在未来体内实验和临床试验中具有巨大潜力。最后，主要化合物被纳米乳化。纳米乳化剂显示出高液滴尺寸均一性和优异的稳定性。带有甲氧基取代基的香豆素被发现是最具前景的化合物，具有理想的光保护性能，适合用于防晒霜配方中的应用和合并。