3-benzoyl-2-methylchromone | 4919-77-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: 3-benzoyl-2-methylchromone
• 英文别名: 3-benzoyl-2-methyl-4H-chromen-4-one；3-Benzoyl-2-methylchromen-4-one
• CAS: 4919-77-1
• 化学式: C₁₇H₁₂O₃
• 分子量: 264.28
• InChiKey: MGOUCKCEGRQFEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzoyl-2-methylchromone 在 溴 作用下， 以 四氯化碳 为溶剂， 以81%的产率得到3-benzoyl-2-bromomethyl-1-benzopyran-4-one
  参考文献：
  名称：

  Ghosh, Chandra Kanta; Karak, Sumit Kumar; Chakravarty, Ajit Kumar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 11, p. 2401 - 2404

  摘要：

  DOI：
• 作为产物：
  描述：

  1-乙酰氧基-2-碘苯 在 镍 tris(dibenzylideneacetone)dipalladium (0) 、 三苯胂 、 氢气 、 sodium acetate 、 溶剂黄146 作用下， 反应 51.5h， 生成 3-benzoyl-2-methylchromone
  参考文献：
  名称：

  Ellemose, Steen; Kure, Niels; Torsell, Kurt B. G., Acta Chemica Scandinavica, 1995, vol. 49, # 7, p. 524 - 529

  摘要：

  DOI：

文献信息

• Rose Bengal-photosensitized oxidation of tertiary amines for the synthesis of bis-1,3-dicarbonyl compounds
  作者：Ling-Ling Wu、Li Tang、Shui-Gen Zhou、Yi-Jie Peng、Xiao-Dong He、Zhi Guan、Yan-Hong He

  DOI：10.1016/j.tet.2017.09.050

  日期：2017.11

  We report an example of Rose Bengal-photosensitized oxidation of tertiary amines for the synthesis of bis-1,3-dicarbonyl compounds. This protocol employs Rose Bengal as a visible-light absorbing photocatalyst without the need of a transition metal, and air as a green oxidant. Various functional groups were well tolerated to afford products with yields of up to 80% under mild reaction conditions.

  我们报告一个玫瑰的孟加拉国光敏的氧化叔胺合成bis-1,3-二羰基化合物的例子。该协议采用玫瑰红作为可见光吸收光催化剂，不需要过渡金属，而空气作为绿色氧化剂。在温和的反应条件下，各种官能团均具有良好的耐受性，可提供产率高达80％的产物。
• Synthesis of Multi-Functionalized Chromeno[2,3-c]pyrrol-9(2H)-ones: Investigation and Application of Baker-Venkataraman Rearrangement Involved Reactions Catalyzed by 4-(Dimethylamino)pyridine
  作者：Yanjun Yu、Yun Hu、Weiyan Shao、Jianing Huang、Yinglin Zuo、Yingpeng Huo、Linkun An、Jun Du、Xianzhang Bu

  DOI：10.1002/ejoc.201100435

  日期：2011.8

  An efficient one-pot synthesis of multi-functionalized chromeno[2,3-c]pyrrol-9(2H)-ones from 1,3-diaryl-1,3-diketones and amino acids is described. The synthesis is based on the 4-(dimethylamino)pyridine-catalyzed Baker–Venkataraman rearrangement and subsequent reactions.

  描述了从 1,3-二芳基-1,3-二酮和氨基酸中高效一锅合成多功能 chromeno[2,3-c]pyrrol-9(2H)-ones。该合成基于 4-（二甲氨基）吡啶催化的 Baker-Venkataraman 重排和后续反应。
• Benzopyrans. Part 41. Reactions of 2-(2-dimethylaminovinyl)-1-benzopyran-4-ones with various dienophiles
  作者：Chandra Kanta Ghosh、Samita Bhattacharyya、Chandreyi Ghosh、Amarendra Patra

  DOI：10.1039/a903145f

  日期：——

  propiolate (EP) ultimately gives xanthenones 33, 34 and 37, respectively, the latter being admixed with flavone 43. Enamine 2, cyclisable to xanthenone 11, gives 33 and 35 with DMAD, and 37 and 44 with EP. Reaction of 3 with DMAD affords 36 exclusively.

  二烯胺1与N-苯基马来酰亚胺和色酮14以及15通过最初的[4 + 2]环加成反应分别产生黄酮酮10和18。最初对色酮14和16的迈克尔加成反应以及乙酰二羧酸二甲酯（DMAD）分别触发了氧杂酮19、4-氮杂蒽酮26和富马酸酯49的形成。二烯胺1–3与亲电子乙炔的初始[2 + 2]环加合物始终会经历进一步的转化。因此，具有DMAD的1，二苯甲酰基乙炔和丙酸乙酯（EP）最终分别产生黄酮酮33、34和37，后者与黄酮43混合。烯胺2，可环化为黄酮酮11，产生33和35的DMAD，以及37和37带EP的44。3与DMAD的反应仅得到36。
• Synthesis and reactivity of 1-aryl-9H-thieno[3,4-b]chromon-9-ones
  作者：Mikhail M. Krayushkin、Konstantin S. Levchenko、Vladimir N. Yarovenko、Ludmila V. Christoforova、Valery A. Barachevsky、Yury A. Puankov、Tatyana M. Valova、Olga I. Kobeleva、K. Lyssenko

  DOI：10.1039/b9nj00237e

  日期：——

  Methods were developed for the synthesis of 1-aryl-9H-thieno[3,4-b]chromon-9-ones based on the reaction of bromo and dibromo derivatives of 2-methyl-4H-chromon-4-one with thioacetamide in DMF. The thienochromones were modified and their fluorescence properties were studied. Bis(thienochromones) were synthesized by the reaction of thienochromones with ketoaldehydes.

  根据 2-甲基-4H-色-4-酮的溴和二溴衍生物与硫代乙酰胺在 DMF 中的反应，开发了合成 1-芳基-9H-噻吩并[3,4-b]色-9-酮的方法。对这些噻吩一氢色酮进行了修饰，并研究了它们的荧光特性。双（噻吩一氢色酮）是通过噻吩一氢色酮与酮醛反应合成的。
• 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。