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。
中文名称 | 英文名称 | CAS号 | 化学式 | 结构式图片 |
---|---|---|---|---|
—— | 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(1R,3S)-3-(trifluoromethyl)cyclohexyl]acetamide | —— | C19H24F3NO3 |
|
—— | 3-[acetyl(3-methylbutyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C24H34N2O7 |
|
—— | 3-[cyclopentyl(3-methylbutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H38N2O7 |
|
—— | 3-[furan-3-ylmethyl(hept-6-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H32N2O6 |
|
—— | Ethyl 2-(5-chloropyrimidin-2-yl)oxy-2-(2,3-dihydro-1-benzofuran-5-yl)acetate | —— | C16H15ClN2O4 |
|
—— | 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-methylpropanoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H40N2O8 |
|
—— | 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-methoxyethyl(pent-4-enoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H32N2O8 |
|
—— | 3-[(3,4-dichlorophenyl)methyl-(oxolane-3-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H30Cl2N2O8 |
|
—— | 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-methoxyethyl(2-methylpropanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C24H34N2O8 |
|
—— | 3-[cyclopropylmethyl(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O8 |
|
—— | 3-[(3,4-dichlorophenyl)methyl-pent-2-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H28Cl2N2O5 |
|
—— | 8-formyl-3-[hexyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H40N2O7 |
|
—— | 3-[(3,4-dichlorophenyl)methyl-pentanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H34Cl2N2O7 |
|
—— | 3-[benzyl(cyclopropanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H28N2O5 |
|
—— | 3-[cyclopentanecarbonyl-[2-(3-fluorophenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H33FN2O5 |
|
—— | 3-[cyclopropanecarbonyl(hexyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H34N2O5 |
|
—— | 3-[cyclohexylmethyl-(2-cyclopentylacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H42N2O7 |
|
—— | 3-[dodecanoyl-[(4-methylphenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C37H52N2O7 |
|
—— | (2S)-5-chloro-N-[3-[2-methoxyethyl(methyl)amino]propyl]-2,3-dihydro-1-benzofuran-2-carboxamide | —— | C16H23ClN2O3 |
|
—— | 3-[cyclohexyl(3-methoxypropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H34N2O6 |
|
—— | 3-[cyclohexylmethyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O5 |
|
—— | 3-[cycloheptyl(2-oxobutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H34N2O6 |
|
—— | 3-[cyclopentanecarbonyl(hexyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H40N2O7 |
|
—— | 3-[cyclopropylmethyl(oxolane-2-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H32N2O8 |
|
—— | 3-[cyclopropylmethyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H34N2O7 |
|
—— | 3-[hexyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H40N2O7 |
|
—— | 3-[3-cyclopentylpropanoyl(cyclopropylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O5 |
|
—— | (2R)-5-chloro-N-[3-(1,2,4-triazol-1-yl)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide | —— | C14H15ClN4O2 |
|
—— | (2S)-5-chloro-N-[3-(1,2,4-triazol-1-yl)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide | —— | C14H15ClN4O2 |
|
—— | 3-[furan-3-ylmethyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H34N2O8 |
|
—— | 8-formyl-3-[hept-6-enoyl(hexyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H42N2O7 |
|
—— | 3-[cyclopentanecarbonyl-[2-(2-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C32H40N2O8 |
|
—— | (2R)-N-[(2R)-2-(dimethylamino)-2-(3-methoxyphenyl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide | —— | C20H24N2O3 |
|
—— | 3-[2-(3-fluorophenyl)ethyl-pent-4-enoylamino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H33FN2O7 |
|
—— | (2S)-N-[(2R)-2-(dimethylamino)-2-(3-methoxyphenyl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide | —— | C20H24N2O3 |
|
—— | (2R)-N-[(2S)-2-(dimethylamino)-2-(3-methoxyphenyl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide | —— | C20H24N2O3 |
|
—— | N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(pyridin-3-ylmethylsulfanyl)acetamide | —— | C20H24N2O3S |
|
—— | 3-[(4-chlorophenyl)methyl-(cyclopentanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H35ClN2O7 |
|
—— | 8-formyl-3-[furan-3-ylmethyl(octanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H38N2O8 |
|
—— | N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-(3-methyl-1,2,4-oxadiazol-5-yl)butanamide | —— | C19H25N3O4 |
|
—— | (3R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(pyrrolidine-1-carbonyl)piperidine-3-carboxamide | —— | C23H33N3O4 |
|
—— | (3S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(pyrrolidine-1-carbonyl)piperidine-3-carboxamide | —— | C23H33N3O4 |
|
—— | (3S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(pyrrolidine-1-carbonyl)piperidine-3-carboxamide | —— | C23H33N3O4 |
|
—— | 5-[1-(4-Chlorophenyl)ethenyl]-2,3-dihydro-1-benzofuran | —— | C16H13ClO |
|
—— | 3-[cyclopentyl(pent-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O7 |
|
—— | 3-[butanoyl(2,2,2-trifluoroethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C21H25F3N2O5 |
|
—— | 3-[(3,4-Difluorophenyl)methyl]-2-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazolidin-4-one | —— | C18H15F2NO2S |
|
—— | 2-(2,3-Dihydro-1-benzofuran-5-yl)-3-(thiophen-2-ylmethyl)-1,3-thiazolidin-4-one | —— | C16H15NO2S2 |
|
—— | 3-[dodecanoyl(2-methoxyethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H46N2O6 |
|
—— | 3-[cyclopentanecarbonyl(cyclopentyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H34N2O5 |
|