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-Benzyl-5,7-di-tert.-butyl-1,2,3,4-tetrahydronaphthalin-1,4-endoxid | 37754-71-5 | C25H32O |
| —— | 2,7-Dimethyl-3-phenyl-3-(β-cyano-ethyl)-2-hydroxy-2,3-dihydro-benzofuran | 50519-11-4 | C19H19NO2 |
| —— | 7-acetoxy-2,3-dihydro-2,2-dimethyl-benzofuran-5-sulfonic acid N-cyclopropyl-amide | 1089210-13-8 | C15H19NO5S |
| —— | 41459-79-4 | C36H30N2O10 | |
| —— | isopropyl 2-cyano-3-phenyl-2,3-dihydronaphtho[1,2-b]furan-2-carbimidate | 1613306-47-0 | C23H20N2O2 |
| —— | 2-(2-Hydroxy-5-methoxy-phenyl)-7-methoxy-3-oxo-1,2a-diphenyl-1,2a,3,8b-tetrahydro-2H-4-oxa-cyclobuta[a]naphthalene-1-carboxylic acid methyl ester | 41508-83-2 | C33H28O7 |
| —— | [(3S)-6-({(3S)-7-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-dihydro-1-benzofuran-3-yl}amino)-2,3-dihydro-1-benzofuran-3-yl]acetic acid | 1258395-80-0 | C24H28N2O5 |
| —— | 2-methyl-4,6-dinitro-2,3-dihydro-benzofuran | 90417-82-6 | C9H8N2O5 |
| —— | N,N-dibenzyl-1-(5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methanamine | 1243545-03-0 | C27H30BrNO |
| —— | 6,7-dimethoxy-chroman-4-ylideneamine; hydrochloride | 37589-65-4 | C11H13NO3*ClH |
| —— | 2,2-Dimethyl-3,4-dibromchroman-6-carbonsaeure | 40310-21-2 | C12H12Br2O3 |
| —— | 1-[(5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methyl]pyrrolidine | 1243545-11-0 | C17H24BrNO |
| —— | 2.3-Dihydro-3.3-dimethyl-2-piperidino-5-hydroxy-benzofuran | 1746-07-2 | C15H21NO2 |
| —— | (1S,9R,13S)-9,11-Dimethyl-4-sulfo-8-oxa-10-aza-tricyclo[7.3.1.0<sup>2,7</sup>]trideca-2(7),3,5,11-tetraene-12,13-dicarboxylic acid dimethyl ester | 127827-75-2 | C17H19NO8S |
| —— | tert-butyl 2-(5-azido-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)acetate | 1335218-92-2 | C18H16BrIN4O3 |
| —— | 5-methanesulfonyloxy-3,3,6,7-tetramethyl-2-morpholin-4-yl-2,3-dihydro-benzofuran | 26225-69-4 | C17H25NO5S |
| —— | (Z)-tert-butyl 6-(2-{[(1,3-dioxolan-2-yl)methyl](methyl)amino}ethylidene)-2,2-dimethyl-4,4a-dihydro-[1,3]dioxepino[6,5,4-cd]isoindole-5(6H)-carboxylate | 1402461-39-5 | C24H34N2O6 |
| —— | 2,3-dihydrobenzofuran-6-nitrile | 1112184-64-1 | C9H7NO |
| —— | 2,8-Dimethoxy-6a,12a-diphenyl-6a,6b,12a,12b-tetrahydro-5,11-dioxa-dibenzo[a,b]biphenylene-6,12-dione | 41459-78-3 | C32H24O6 |
| —— | 114781-38-3 | C28H27DyO14 | |
| —— | 2-(5-trifluoracetamidopentoxy)-2-(1,2,2-trimethylpropoxy)-2-methyl-(4,6-di-tert-butyl)-1,3-dioxa-2λ(5)-benzophosphole | 245096-68-8 | C28H47F3NO5P |
| —— | 1415357-76-4 | C16H18O2 | |
| —— | (+/-)-{[7-(2,3-dimethoxyphenyl)-5-(trifluoromethyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852122-85-1 | C18H18F3NO3 |
| —— | β-(6,7-Dimethyl-3-phenyl-2-keto-2,3-dihydro-3-benzofuranyl)-propionsaeure | 50519-16-9 | C19H18O4 |
| —— | 6-isopropyl-5-methanesulfonyloxy-3,3-dimethyl-2-morpholin-4-yl-2,3-dihydro-benzofuran | 26225-73-0 | C18H27NO5S |
| —— | 5-chloromethanesulfonyloxy-3,3-dimethyl-2-morpholin-4-yl-2,3-dihydro-benzofuran | 26322-73-6 | C15H20ClNO5S |
| —— | 6-(2,3-Dihydro-5-benzofuranyl)-3-morpholinone | 951626-34-9 | C12H13NO3 |
| —— | 7-methoxy-1,2,3,4,4a,9b-hexahydro-dibenzofuran | 1058159-86-6 | C13H16O2 |
| —— | 2-[1-(4-Chloro-phenylamino)-meth-(E)-ylidene]-benzofuran-3-thione | 78096-41-0 | C15H10ClNOS |
| —— | 114781-34-9 | C28H27NdO14 | |
| —— | [(3S)-6-({(3S)-7-[4-(cyclopropylmethoxy)-2,6-dimethylphenyl]-2,3-dihydro-1-benzofuran-3-yl}amino)-2,3-dihydro-1-benzofuran-3-yl]acetic acid | 1258396-31-4 | C30H31NO5 |
| —— | 4-(6-hydroxy-2,3-dihydro-benzofuran-5-yl)-2,4-dioxo-butyric acid ethyl ester | 860691-94-7 | C14H14O6 |
| —— | 8,10,11-Trioxa-tricyclo[7.2.2.0<sup>2,7</sup>]trideca-2(7),3,5,12-tetraene | 49836-47-7 | C10H8O3 |
| —— | 6-chloro-5-methanesulfonyloxy-3,3-dimethyl-2-morpholin-4-yl-2,3-dihydro-benzofuran | 26225-75-2 | C15H20ClNO5S |
| —— | 2,9-dimethyl-5a-phenyl-benzo[<i>b</i>]benzo[4,5]furo[3,2-<i>d</i>]furan-10b-carboxylic acid | 32590-97-9 | C23H18O4 |
| —— | 5-bromo-2-(methoxymethyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran | 1243544-88-8 | C14H19BrO2 |
| —— | 3-ethyl-5-methanesulfonyloxy-2-(4-methyl-piperazin-1-yl)-2,3-dihydro-benzofuran | 26322-77-0 | C16H24N2O4S |
| —— | (R)-methyl 3-(8-fluoro-1-methyl-2-oxo-2,4-dihydro-1H-benzo[d][1,3]oxazin-6-ylamino)-2-hydroxypropanoate | 946582-69-0 | C13H15FN2O5 |
| —— | 52206-20-9 | C15H21N3O4S | |
| —— | (R)-4,9b-Dimethyl-3,9b-dihydro-dibenzofuran-1-carboxylic acid methyl ester | 40801-38-5 | C16H16O3 |
| —— | 1-(5-Acetyl-4,6-dihydroxy-3,3-dimethyl-2-methylene-2,3-dihydro-benzofuran-7-yl)-ethanone | 53771-34-9 | C15H16O5 |
| —— | 42896-21-9 | C20H18O6 | |
| —— | (1S,14R)-6,12,19,25-tetratert-butyl-9,22-bis(methylsulfanyl)-2,15-dioxaheptacyclo[21.3.1.11,4.110,14.114,17.03,8.016,21]triaconta-3,5,7,10,12,16,18,20,23,25-decaene-27,29-dione | 460728-70-5 | C46H56O4S2 |
| —— | [(3S)-6-({(3S)-7-[4-(furan-2-ylmethoxy)-2,6-dimethylphenyl]-2,3-dihydro-1-benzofuran-3-yl}amino)-2,3-dihydro-1-benzofuran-3-yl]acetic acid | 1258396-34-7 | C31H29NO6 |
| —— | 6-hydroxy-3-(4-methoxy-phenyl)-3H-benzofuran-2-one | 31542-75-3 | C15H12O4 |
| —— | 2-iodomethyl-4-methoxy-2,3-dihydrobenzofuran | 862779-65-5 | C10H11IO2 |
| —— | 1-<3-(2H,3H-benzofurfuryl)>-2-methyl-2-propanol | 142041-18-7 | C12H16O2 |
| —— | 4-formyl-5-hydroxy-2-(2-oxoethyl)-2,3-dihydrobenzo<b>furan | 130663-58-0 | C11H10O4 |
| —— | β-(2,6,7-Trimethyl-3-phenyl-2-hydroxy-2,3-dihydro-3-benzofuranyl)-propionsaeure-lacton | 50519-13-6 | C20H20O3 |
| —— | tetra-<i>N</i>-methyl-4,4'-[6-nitro-4-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidenemethyl)-chroman-2,2-diyl]-bis-aniline | 58491-65-9 | C37H40N4O3 |