香豆素
香豆素
基本信息
香豆素（Coumarin）是一类具有独特芳香气味的化合物，化学式为C9H6O2。它们属于苯骈α-呋喃酮类化合物，在自然界中广泛存在。
结构特征香豆素的基本结构由苯环和呋喃酮构成，其中苯环与四个碳原子相连的呋喃酮单元形成独特的“香豆素环”。
自然来源香豆素存在于多种植物、真菌及动物体内。在植物界中，它主要作为天然防御机制的一部分，用作对昆虫的化学信号。著名的例子包括：天竺葵科（如紫花苜蓿）、唇形科（如薄荷）和芸香科（如柑橘属果实）。此外，在真菌、苔藓及藻类中也有发现。
化学性质 稳定性由于其独特的结构，香豆素表现出良好的化学稳定性。它们不易被氧化或还原，但可以与其他化合物发生多种类型的反应，包括缩合、取代等。
生物活性许多香豆素衍生物具有生物活性，能够引起抗菌、抗炎、抗氧化等多种作用。这些特性使它们成为医药、食品添加剂等多个领域的重要研究对象。
应用领域 医药行业在制药业中，某些结构类似物被开发为药物先导化合物。例如，香豆素类抗生素是最早的广谱抗生素之一；一些香豆素衍生物还表现出抗癌潜力。
食品工业由于其独特的香气和味道，在食品加工中也得到了广泛应用，常作为香精成分使用。
其他应用此外，它们还在染料生产、农药开发等多个领域展现出潜在价值。
生产方法香豆素可通过多种合成路径获得。传统的化学合成涉及从苯甲醛出发的反应；而近年来，通过生物转化技术，利用微生物发酵过程制备天然香豆素也成为一种可持续的方法。
总之，香豆素因其独特的结构和广泛的生物学应用，在多个领域中发挥着重要作用，并且仍然是有机化学研究中的一个重要课题。
相关化合物
| 中文名称 | 英文名称 | CAS号 | 化学式 | 结构式图片 |
|---|---|---|---|---|
| —— | 4-acetyl-N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]thiophene-2-carboxamide | —— | C17H17NO3S |
|
| —— | 1-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[1-[2-(dimethylamino)ethyl]pyrazol-4-yl]urea | —— | C18H25N5O2 |
|
| —— | 1-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[2-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)ethyl]urea | —— | C18H23N5O2 |
|
| —— | 1-[(3S)-5-methyl-2,3-dihydro-1-benzofuran-3-yl]-3-[2-(3-methylpyridin-4-yl)ethyl]urea | —— | C18H21N3O2 |
|
| —— | 1-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(2R)-2-methyl-3-(2-methylimidazol-1-yl)propyl]urea | —— | C19H26N4O2 |
|
| —— | 1-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[2-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)ethyl]urea | —— | C18H23N5O2 |
|
| —— | 1-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[2-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)ethyl]urea | —— | C18H23N5O2 |
|
| —— | 1-[(3R)-5-methyl-2,3-dihydro-1-benzofuran-3-yl]-3-[2-(3-methylpyridin-4-yl)ethyl]urea | —— | C18H21N3O2 |
|
| —— | 1-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(2R)-2-methyl-3-(2-methylimidazol-1-yl)propyl]urea | —— | C19H26N4O2 |
|
| —— | 1-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[1-[2-(dimethylamino)ethyl]pyrazol-3-yl]urea | —— | C18H25N5O2 |
|
| —— | 1-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(2S)-2-methyl-3-(2-methylimidazol-1-yl)propyl]urea | —— | C19H26N4O2 |
|
| —— | 1-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(2S)-2-methyl-3-(2-methylimidazol-1-yl)propyl]urea | —— | C19H26N4O2 |
|
| —— | 1-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[1-[2-(dimethylamino)ethyl]pyrazol-4-yl]urea | —— | C18H25N5O2 |
|
| —— | 1-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[1-[2-(dimethylamino)ethyl]pyrazol-4-yl]urea | —— | C18H25N5O2 |
|
| —— | 1-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[1-[2-(dimethylamino)ethyl]pyrazol-3-yl]urea | —— | C18H25N5O2 |
|
| —— | 1-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-(1-methyl-2-oxopyridin-3-yl)urea | —— | C17H19N3O3 |
|
| —— | 1-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-(1-methyl-2-oxopyridin-3-yl)urea | —— | C17H19N3O3 |
|
| —— | 1-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(1S)-1-(1,3-thiazol-2-yl)propyl]urea | —— | C17H21N3O2S |
|
| —— | 1-(2-cyclopropylpyrimidin-5-yl)-3-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]urea | —— | C18H20N4O2 |
|
| —— | 1-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(3S)-3-[(S)-methylsulfinyl]butyl]urea | —— | C16H24N2O3S |
|
| —— | 1-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(2R)-2-[(S)-methylsulfinyl]propyl]urea | —— | C15H22N2O3S |
|
| —— | 1-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(3S)-3-[(S)-methylsulfinyl]butyl]urea | —— | C16H24N2O3S |
|
| —— | 1-(2-cyclopropylpyrimidin-5-yl)-3-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]urea | —— | C18H20N4O2 |
|
| —— | 1-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(3R)-3-[(S)-methylsulfinyl]butyl]urea | —— | C16H24N2O3S |
|
| —— | 1-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[1-[2-(dimethylamino)ethyl]pyrazol-3-yl]urea | —— | C18H25N5O2 |
|
| —— | 1-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(2R)-2-[(S)-methylsulfinyl]propyl]urea | —— | C15H22N2O3S |
|
| —— | 1-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(1S)-1-(5-methyl-1,2,4-oxadiazol-3-yl)propyl]urea | —— | C17H22N4O3 |
|
| —— | 1-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(1S)-2-methyl-1-(3-methyl-1,2,4-oxadiazol-5-yl)propyl]urea | —— | C18H24N4O3 |
|
| —— | 1-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(2S)-2-[(S)-methylsulfinyl]propyl]urea | —— | C15H22N2O3S |
|
| —— | 1-(2-cyclopropylpyrimidin-5-yl)-3-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]urea | —— | C18H20N4O2 |
|
| —— | 1-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[1-[2-(dimethylamino)ethyl]pyrazol-4-yl]urea | —— | C18H25N5O2 |
|
| —— | 1-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-(1-methyl-2-oxopyridin-3-yl)urea | —— | C17H19N3O3 |
|
| —— | 1-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(1S)-1-(1,3-thiazol-2-yl)propyl]urea | —— | C17H21N3O2S |
|
| —— | 1-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(1R)-1-(1,3-thiazol-2-yl)propyl]urea | —— | C17H21N3O2S |
|
| —— | 1-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(1R)-2-methyl-1-(3-methyl-1,2,4-oxadiazol-5-yl)propyl]urea | —— | C18H24N4O3 |
|
| —— | 1-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(2S)-2-[(S)-methylsulfinyl]propyl]urea | —— | C15H22N2O3S |
|
| —— | 1-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(1R)-1-(5-methyl-1,2,4-oxadiazol-3-yl)propyl]urea | —— | C17H22N4O3 |
|
| —— | 1-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-(1-methyl-2-oxopyridin-3-yl)urea | —— | C17H19N3O3 |
|
| —— | 1-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(1R)-2-methyl-1-(3-methyl-1,2,4-oxadiazol-5-yl)propyl]urea | —— | C18H24N4O3 |
|
| —— | 1-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(3R)-3-[(S)-methylsulfinyl]butyl]urea | —— | C16H24N2O3S |
|
| —— | 1-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(1R)-1-(5-methyl-1,2,4-oxadiazol-3-yl)propyl]urea | —— | C17H22N4O3 |
|
| —— | 1-(2-cyclopropylpyrimidin-5-yl)-3-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]urea | —— | C18H20N4O2 |
|
| —— | 1-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(1R)-1-(1,3-thiazol-2-yl)propyl]urea | —— | C17H21N3O2S |
|
| —— | 1-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[1-[2-(dimethylamino)ethyl]pyrazol-3-yl]urea | —— | C18H25N5O2 |
|
| —— | 1-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(1S)-2-methyl-1-(3-methyl-1,2,4-oxadiazol-5-yl)propyl]urea | —— | C18H24N4O3 |
|
| —— | 1-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(1-methylpyrrol-3-yl)methyl]urea | —— | C17H21N3O2 |
|
| —— | 1-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(1S)-1-(5-methyl-1,2,4-oxadiazol-3-yl)propyl]urea | —— | C17H22N4O3 |
|
| —— | 1-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[2-(2,4-dimethyl-1,3-thiazol-5-yl)ethyl]urea | —— | C18H23N3O2S |
|
| —— | 1-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[(1-methylpyrrol-3-yl)methyl]urea | —— | C17H21N3O2 |
|
| —— | 1-[(1R)-1-(4-cyanophenyl)ethyl]-3-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]urea | —— | C20H21N3O2 |
|
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