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 |
|---|---|---|---|
| —— | 4,7-Dimethoxy-6-(phenylmethoxy)-3(2H)-benzofuranone oxime | 101878-46-0 | C17H17NO5 |
| —— | 86657-86-5 | C21H25NO2 | |
| —— | [4-amino-2-[4-(2-diethylamino-ethoxy)-phenylamino]-thiazol-5-yl]-(2,3-dihydro-benzofuran-5-yl)-methanone | 627462-95-7 | C24H28N4O3S |
| —— | 2,3-Dihydro-5,7-dimethyl-2-benzofuranol | 343569-13-1 | C10H12O2 |
| —— | 3-bromo-2,12-dimethyl-7-nitro-3,4,4a,5-tetrahydro-10a,3-azaetheno-chromeno[2,3-<i>b</i>]pyridine | 70704-86-8 | C15H14BrN3O3 |
| —— | methyl N-[(4E)-4-(1H-imidazol-5-ylmethylidene)-2,3-dihydrochromen-6-yl]-N-propylcarbamate | 1049633-91-1 | C18H21N3O3 |
| —— | 2,3-Dihydro-2-hydroxy-3,3-dimethyl-5-benzofuranyl benzeneethanesulfonate | 134144-37-9 | C18H20O5S |
| —— | 9-[(1E)-3-methoxypropa-1-ene-1-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochloride | 1055879-15-6 | C13H17NO2*ClH |
| —— | (+/-)-[7-bromo-5-(trifluoromethyl)-2,3-dihydro-1-benzofuran-2-yl]methanol | 852112-71-1 | C10H8BrF3O2 |
| —— | ethyl 2-((2S,3R,4S)-3-benzyl-4-((2-hydroxyphenyl)amino)-3-nitrochroman-2-yl)acetate | 1266339-70-1 | C26H26N2O6 |
| —— | 60779-21-7 | C15H12O4 | |
| —— | 9-(2-methylphenyl)-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochloride | 1055878-71-1 | C16H17NO*ClH |
| —— | (2R,1'R)-2,3-dihydro-2-(2',2',4'-trimethyl-1',3'-dioxolan-4'-yl)-6-methoxybenzofuran | 470459-91-7 | C15H20O4 |
| —— | Spiro[1-benzoxepin-5(2H),4a(2)-imidazolidine] | 169-30-2 | C12H14N2O |
| —— | 2H-1-Benzopyran-3(4H)-one, 7,8-difluoro-5-hydroxy- | 1336947-30-8 | C9H6F2O3 |
| —— | 6-Benzofuranol, 2,3-dihydro-2-(1-methylethenyl)-, 6-acetate | 5207-54-5 | C13H14O3 |
| —— | 3-(3-methoxyphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-amine | 820259-66-3 | C18H21NO2 |
| —— | N-benzyl-3-(4-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1-benzofuran-5-amine | 820257-87-2 | C26H29NO |
| —— | 3-(4-isopropylphenyl)-2,2,4,7-tetramethyl-2,3-dihydro-1-benzofuran-5-amine hydrochloride | 820257-78-1 | C21H27NO*ClH |
| —— | 6-Amino-2-hydroxymethyl-5-methyl-2,3-dihydrobenzo[b]furan·hydrochloride | 170683-89-3 | C10H13NO2*ClH |
| —— | 2-hydroxy-5a-morpholin-4-yl-5a,6,7,8,9,9a-hexahydro-dibenzofuran-1-carboxylic acid methyl ester | 68085-24-5 | C18H23NO5 |
| —— | N-((3S)-1-(7-fluoro-2-methy1-2,3-dihydrobenzofuran-4-yl)pyrrolidin-3-yl)butyramide | 1258851-35-2 | C17H23FN2O2 |
| —— | diethyl-8,12-dioxa-33,37-dithia-20,21,23,24,30,31,35,36-octaazaheptacyclo(27.5.2.219,22.02,7.013,18.021,25.032,36)octatriaconta-2,4,6,13(18),14,16,22,24,29,31-decaene-34,38-dicarboxylate | 1446816-76-7 | C32H36N8O6S2 |
| —— | 3-(tert-Butyl-dimethyl-silanyloxy)-N2-[2-(2,3-dihydro-benzofuran-5-yl)-ethyl]-benzene-1,2-diamine | 938071-71-7 | C22H32N2O2Si |
| —— | N-((3S)-1-(7-fluoro-2-methyl-2,3-dihydrobenzofuran-4-yl)pyrrolidin-3-yl)pentanamide | 1258851-38-5 | C18H25FN2O2 |
| —— | ethyl 1-benzyl-4-hydroxy-9,10-dimethyl-11-oxo-8-oxa-10-azatricyclo[7.2.1.02,7]dodeca-2(7),3,5-triene-12-carboxylate | 78864-39-8 | C22H23NO5 |
| —— | [(3S)-6-{[(3S)-7-{2,6-dimethyl-4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}-2,3-dihydro-1-benzofuran-3-yl]amino}-2,3-dihydro-1-benzofuran-3-yl]acetic acid | 1258396-40-5 | C33H39N3O5 |
| —— | 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-2-carboxylic acid | 885069-04-5 | C15H19BO5 |
| —— | [Zn2(μ,η1-ddbfo)2Cl2(py)2] | 292616-95-6 | C30H32Cl2N2O4Zn2 |
| —— | 1-[1-(2,3-Dihydro-1-benzofuran-5-carbonyl)-2,3-dihydroimidazo[1,2-b]pyrazol-6-yl]-3-methylurea | 1209487-36-4 | C16H17N5O3 |
| —— | 2-(5-coumaranyl)-2-oxoethylammonium bromide | 151427-22-4 | BrH*C10H11NO2 |
| —— | (4aS,9bR)-8-(2,6-difluoro-4-chlorophenyl)-6-butoxy-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-79-0 | C21H22ClF2NO2 |
| —— | 3,8-dinitro-4b,9b-dihydro-benzofuro[3,2-<i>b</i>]benzofuran | 108880-03-1 | C14H8N2O6 |
| —— | 1-[(3R)-3-(4-bromophenyl)-2,3-dihydro-2-oxo-3-benzofuranyl]-1,2-hydrazinedicarboxylic acid,1,2-bis(phenylmethyl) ester | 1314114-34-5 | C30H23BrN2O6 |
| —— | 2,3-diacetoxy-8-methoxy-3-methylsulfanyl-chroman-4-one | 66395-41-3 | C15H16O7S |
| —— | (4bR,9bR)-2,7-Dimethoxy-4b,9b-dimethyl-4b,9b-dihydro-benzo[b]benzo[4,5]furo[2,3-d]furan | 105314-87-2 | C18H18O4 |
| —— | (4bR,9bR)-4,9-Dimethoxy-4b,9b-dimethyl-4b,9b-dihydro-benzo[b]benzo[4,5]furo[2,3-d]furan | 105314-89-4 | C18H18O4 |
| —— | 2,9-dichloro-(10b<i>c</i>,10c<i>c</i>)-10b,10c-dihydro-dibenzo[<i>d</i>,<i>d</i>']cyclobuta[1,2-<i>b</i>;4,3-<i>b</i>']difuran-5a<i>r</i>,5b<i>c</i>-dicarboxylic acid | 67194-01-8 | C18H10Cl2O6 |
| —— | N-((3S)-1-(2-methyl-2,3-dihydrobenzofuran-4-yl)pyrrolidin-3-yl)propionamide | 1258851-45-4 | C16H22N2O2 |
| —— | N-(4'-amino-5'-methyl-spiro[chromane-4,2'-imidazole]-6-yl)-5-methyl-thiophene-2-carboxamide | 1383982-56-6 | C18H18N4O2S |
| —— | (2-Benzyl-3,3-diethoxy-2,3-dihydro-benzofuran-2-yl)-[1-phenyl-meth-(E)-ylidene]-amine | 130268-11-0 | C26H27NO3 |
| —— | methyl (3S)-1-(7-fluoro-2-methyl-2,3-dihydrobenzofuran-4-yl)pyrrolidin-3-ylcarbamate | 1258851-40-9 | C15H19FN2O3 |
| —— | 5-Methyl-2-(2-methyl-propenyl)-3-phenyl-2,3-dihydro-benzofuran-3-ol | 130155-79-2 | C19H20O2 |
| —— | 6,7-Dichloro-5-{2-[3-methyl-3H-thiazol-(2E)-ylidene]-acetyl}-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester | 126201-11-4 | C16H13Cl2NO4S |
| —— | N-(2-chlorophenyl)-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepine-2-carbohydrazonamide | 1246616-23-8 | C18H15ClN4OS |
| —— | (2R,1'S)-2,3-dihydro-2-(2',2',4'-trimethyl-1',3'-dioxolan-4'-yl)-6-hydroxybenzofuran | 470459-84-8 | C14H18O4 |
| —— | (4aS,9bR)-8-(2,6-difluoro-4-chlorophenyl)-6-butyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-24-5 | C21H22ClF2NO |
| —— | [(3S)-6-({(3S)-7-[2,6-dimethyl-4-(pyridin-3-ylmethoxy)phenyl]-2,3-dihydro-1-benzofuran-3-yl}amino)-2,3-dihydro-1-benzofuran-3-yl]acetic acid | 1258396-35-8 | C32H30N2O5 |
| —— | (4aS,9bR)-8-(2,4,6-trichlorophenyl)-6-ethyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-12-1 | C19H18Cl3NO |
| —— | Acetic acid (3R,3aR,8bR)-7-bromo-3-chloro-3,6,8b-trimethyl-1,2,3,8b-tetrahydro-benzo[b]cyclopenta[d]furan-3a-yl ester | 74552-44-6 | C16H18BrClO3 |