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 |
|---|---|---|---|
| —— | (3R)-4-iodo-2,3-dihydro-1-benzofuran-3-amine | 1212972-13-8 | C8H8INO |
| —— | 4-(1-(4-methoxyphenyl)vinyl)-5-methyl-2,3-dihydrobezofuran | 1582778-58-2 | C18H18O2 |
| —— | 2-(1,4-Dihydro-3-hydroxy-2-methyl-4-oxo-1-pyridinyl)ethyl 2,3-dihydro-5-hydroxy-4,6,7-trimethylbenzofuran-2-acetate | 272770-15-7 | C21H25NO6 |
| —— | 3-Benzofuranamine, 7-fluoro-2,3-dihydro-6-methyl-, (3R)- | 1272732-87-2 | C9H10FNO |
| —— | 2-(benzyloxymethyl)-2,3-dihydrobenzofuran | 1243273-41-7 | C16H16O2 |
| —— | 4-[(1R,2R,3aS,8bS)-2-Acetoxy-1-((E)-3-oxo-oct-1-enyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-butyric acid methyl ester | 94076-92-3 | C26H34O6 |
| —— | hydroxy-11 methoxy-6 dihydro-6,11 dibenzo<b,e>oxepinne | 92772-52-6 | C15H14O3 |
| —— | Acetic acid (S)-4,7-dihydroxy-6-(2-hydroxy-propyl)-2,2-dimethyl-2,3-dihydro-benzofuran-3-ylmethyl ester | 70901-57-4 | C16H22O6 |
| —— | 2,3-Dihydro-1-benzofuran-5-ylhydrazine hydrochloride | 197590-46-8 | C8H10N2O*ClH |
| —— | 2-(tert-butyl-dimethyl-silanyloxy)-11,14-dithia-spiro[4,5]-5,6,7,8-tetrahydro-benzo[c]chromen-9-ol | 874281-33-1 | C21H30O3S2Si |
| —— | 2-{[1-({[3-(2,3-dihydro-1-benzofuran-5-yl)propyl]amino}carbonyl)cyclopentyl]-methyl}-4-methoxybutanoic acid | 465527-90-6 | C23H33NO5 |
| —— | dimethyl 2,6'-dimethoxy-4,4,5,5-tetramethylspiro[1,3-dioxa-2λ5-phosphacyclopentane-2,2'-3,4-dihydro-1,2λ5-benzoxaphosphinine]-3',4'-dicarboxylate | 107905-84-0 | C20H29O9P |
| —— | (+/-)-N-[2-(aminomethyl)-2,3-dihydro-1-benzofuran-7-yl]-N-(3-methylphenyl)amine | 852115-06-1 | C16H18N2O |
| —— | N-(1'-cyclobutylspiro[4H-1,3-benzodioxine-2,4'-piperidine]-6-yl)morpholine-4-carboxamide | 1174721-67-5 | C21H29N3O4 |
| —— | (E)-1-(6-methyl-3,4-dihydro-2H-naphtho[1,8-bc]furan-5(2ah)-ylidene)butan-2-one | 1092108-10-5 | C16H18O2 |
| —— | 2-(Isopropylaminomethyl)-2,3-dihydrobenzofuran | 21130-03-0 | C12H17NO |
| —— | (R)-2-(4-methoxyphenyl)-2H-chromene-5,7-diyl bis(dimethylcarbamate) | 1255509-84-2 | C22H24N2O6 |
| —— | (R)-1-chloro-3-(5-(2,3-dihydrobenzofuryl))-2-propanol | 901235-77-6 | C11H13ClO2 |
| —— | Methyl 5-Fluoro-2,3-dihydrobenzofuran-3-acetate | 2070896-53-4 | C11H11FO3 |
| —— | 1-[4-(benzyloxy)-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl]ethanone | 1385690-78-7 | C19H20O3 |
| —— | methyl [(3S)-6-({(3S)-7-[(5-chloropyrimidin-2-yl)(propyl)amino]-2,3-dihydro-1-benzofuran-3-yl}amino)-2,3-dihydro-1-benzofuran-3-yl]acetate | 1258402-19-5 | C26H27ClN4O4 |
| —— | 7,8-dichloro-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxylic acid | 1415216-37-3 | C13H8Cl2O3S |
| —— | methyl 4-[2-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]benzoate | 503060-24-0 | C17H16O4 |
| —— | 4-anilinomethyl-6,9-dihydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-8-ylmethyl carbamate | 102409-70-1 | C20H22N4O5 |
| —— | methyl 3-[(1S,2R,3aS,8bS)-2-acetyloxy-1-(hydroxymethyl)-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-5-yl]propanoate | 123671-43-2 | C18H22O6 |
| —— | (+/-)-4ξ-amino-2<i>r</i>-(4-methoxy-phenyl)-6-methyl-chroman-3<i>t</i>-ol; acetate | 100195-42-4 | C2H4O2*C17H19NO3 |
| —— | (2S,3S)-3-Bromo-2-prop-2-ynyloxy-2,3-dihydro-benzofuran | 127773-54-0 | C11H9BrO2 |
| —— | 1609388-05-7 | C18H23NO8 | |
| —— | (2S,3S)-4-ethyl-2,3-dihydro-2-(2-hydroxyethyl)benzofuran-3-ol | 909532-90-7 | C12H16O3 |
| —— | 2,3-Dihydro-N,2-dimethyl-7-benzofurancarboxamid | 18058-31-6 | C11H13NO2 |
| —— | 7,8-dichloro-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide | 1415216-38-4 | C13H9Cl2NO2S |
| —— | rac-2,3-dihydro-benzofuran-4-carboxylic acid [3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-thiazolidin-2-ylmethyl]-amide | 1204583-56-1 | C25H25N3O3S2 |
| —— | (4S,4aR,9bS)-4-Hydroxy-6,9b-dimethyl-1,4,4a,9b-tetrahydro-2H-dibenzofuran-3-one | 68758-43-0 | C14H16O3 |
| —— | trimethyl(6,7,8,9-tetrachloro-4a-(2,3,4,5-tetrachloro-6-(trimethylsilyloxy)phenoxy)-3,4,4a,10a-tetrahydro-2H-benzo[b]pyrano[2,3-e][1,4]dioxin-10a-yloxy)silane | 1621232-92-5 | C23H24Cl8O6Si2 |
| —— | (Z)-3-(5-methyl-3-((triisopropylsilyl)oxy)benzofuran-2(3H)-ylidene)propan-1-ol | 1599372-17-4 | C21H34O3Si |
| —— | (2S,4R,5R)-methyl 5-(3-chlorophenylamino)-2-(2-methoxy-2-oxoethyl)-4-phenyl-4,5-dihydrobenzo[d][1,3]dioxepine-4-carboxylate | 1559074-32-6 | C26H24ClNO6 |
| —— | 1-[1-(3-tert-butoxy-2-pyrazinylmethyl)piperidin-4-yl]-2-(2,3-dihydrobenzofuran-7-yl)ethanone | 614727-61-6 | C24H31N3O3 |
| —— | 8-(2,4-dichlorophenyl)-N,N-diethyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]-pyridin-6-amine | 488124-77-2 | C21H24Cl2N2O |
| —— | 2-(azidomethyl)-2,3-dihydro-4,6-dimethylbenzofuran | 1311990-00-7 | C11H13N3O |
| —— | 2-[4-(2,3-dihydrobenzofuran-5-yl)benzyloxy]cyclohexylamine | 1236775-63-5 | C21H25NO2 |
| —— | 1-(6-Methoxymethoxy-2,3-dihydro-benzofuran-5-yl)-ethanone | 60237-55-0 | C12H14O4 |
| —— | (4aS,9bR)-8-(2,4-dichlorophenyl)-6-pyrrolidin-1-yl-1,2,3,4,4a,9b-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-90-5 | C21H22Cl2N2O |
| —— | 5-[[1-[5-(2,3-dihydro-1-benzofuran-5-yl)-4-hydroxythiophen-3-yl]ethylideneamino]carbamoyl]thiophene-2-carboxylic acid | 1294518-70-9 | C20H16N2O5S2 |
| —— | 3-Butyn-1-amine, 4-(2,3-dihydro-6-benzofuranyl)- | 1936255-33-2 | C12H13NO |
| —— | 3-[(<i>R</i>)-2-(α-hydroxy-isopropyl)-4-methoxy-2,3-dihydro-benzofuran-7-yl]-propionic acid | 880765-18-4 | C15H20O5 |
| —— | 2'-amino-6-(3-chloro-4-fluorophenyl)-1',3,3-trimethylspiro[chroman-4,4'-imidazol]-5'(1'H)-one | 1311262-05-1 | C20H19ClFN3O2 |
| —— | 3-phenyl-3a,8a-dihydro-benzo[4,5]furo[3,2-<i>d</i>]isoxazole | 66303-78-4 | C15H11NO2 |
| —— | 7-methoxy-2,5-dimethyl-2,3-dihydrobenzofuran | 1031715-92-0 | C11H14O2 |
| —— | Cyclohexylmethyl-(7-methoxy-2,3-dihydro-benzofuran-2-ylmethyl)-amine | 62035-46-5 | C17H25NO2 |
| —— | tert-Butyl 6-(cyclopentylthio)-8-(2,4-dichlorophenyl)-3,4,4a,9b-tetrahydro[1]benzofuro[3,2-c]pyridine-2(1H)-carboxylate | 488127-18-0 | C27H31Cl2NO3S |