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 |
|---|---|---|---|
| —— | 1-((2R,3R,4R)-8-methoxy-2-methyl-4-(nitromethyl)chroman-3-yl)propan-1-one | 1627214-16-7 | C15H19NO5 |
| —— | 1-(2,3-dihydro-benzofuran-2-yl)-2-methylamino-ethanol; hydrochloride | 40749-30-2 | C11H15NO2*ClH |
| —— | 2,3-Dihydro-4,7-dimethoxy-2-methylbenzofuran | 105591-39-7 | C11H14O3 |
| —— | N-(2-cyanoethyl)-3-[3-(2,4-dichlorophenyl)-2,3-dihydro-1-benzofuran-5-yl]benzamide | 1202501-42-5 | C24H18Cl2N2O2 |
| —— | (+/-) 5-Chloro-2,3-dihydro-benzofuran-7-carboxylic acid (4-oxo-2-pyridin-4-yl-4,6,7,8,9,10-hexahydro-pyrimido[1,2-a]azepin-10-yl)-amide | 1036716-78-5 | C23H21ClN4O3 |
| —— | 2-(4-(5-bromo-2,3-dihydrobenzofuran-2-yl)piperidin-1-yl)-5-chloropyrimidine | 1602573-89-6 | C17H17BrClN3O |
| —— | 6-chloro-(4a<i>r</i>,9a<i>c</i>)-4a,9a-dihydro-4<i>H</i>-benzo[4,5]furo[2,3-<i>c</i>]pyridine-1,3-dione | 70554-61-9 | C11H8ClNO3 |
| —— | 3-Oxo-6,9β-dimethyl-1,2,3,4,4aβ,9b-hexahydrodibenzofuran | 68758-20-3 | C14H16O2 |
| —— | N-[1-[3-(6-fluoro-1,2-benzoxazol-3-yl)propyl]pyrrolidin-3-yl]-2,3-dihydrobenzofuran-6-sulphonamide | 1417307-94-8 | C22H24FN3O4S |
| —— | 1'-cyclobutyl-N-(thiophen-2-ylmethyl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-6-amine | 1174723-49-9 | C21H26N2O2S |
| —— | Cyclopentylmethyl-(7-methoxy-2,3-dihydro-benzofuran-2-ylmethyl)-amine | 62035-44-3 | C16H23NO2 |
| —— | trans-4-(3,3-dimethyl-2-oxobutyl)-3-ethyl-chroman-2-one | 136708-18-4 | C17H22O3 |
| —— | (3aR,9aR)-6-Chloro-2,3,9,9a-tetrahydro-3a(1H)-(1H-1,2,4-triazol-1-ylmethyl)cyclopenta [b][1]benzopyran | 164322-13-8 | C15H16ClN3O |
| —— | ethyl (E)-2,3-dihydro-5-(o-fluorobenzoyl)-6-hydroxy-7-methoxybenzofuran-2-carboxylate oxime | 90246-91-6 | C19H18FNO6 |
| —— | 1a-tert-butyl-1,1,1',1',3'-pentachlorospiro[7aH-cyclopropa[b]chromene-7,2'-cyclopropane] | 128343-03-3 | C16H15Cl5O |
| —— | 7-(Cyclopentyloxy)-6-methoxy-2,3-dihydrobenzofuran-3-ol | 1001061-67-1 | C14H18O4 |
| —— | 2'-methoxy-2-methyl-2H-spiro[benzofuran-3,1'-cyclohexa[2,5]diene] | 1053188-76-3 | C15H16O2 |
| —— | 1a-tert-butyl-2,2-dichloro-3-dichloromethyl-1a,2,2a,3-tetrahydrocyclopropa<b>-1-benzopyran | 128343-02-2 | C15H16Cl4O |
| —— | (+/-)-4a,8-dimethyl-(4a<i>r</i>,9b<i>c</i>)-3,4,4a,9b-tetrahydro-1<i>H</i>-dibenzofuran-2-one | 107620-59-7 | C14H16O2 |
| —— | 5-Methyl-2-(3-methoxypropylaminomethyl)-2,3-dihydro-benzofuran | 21130-16-5 | C14H21NO2 |
| —— | 8-(2,4,6-trichlorophenyl)-N,N-diethyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]-pyridin-6-amine | 488124-78-3 | C21H23Cl3N2O |
| —— | 6-Benzyloxy-7-iodo-4-methoxy-3a-<2-(trimethylsilyl)eth-1-oxy>-3a,8a-dihydrofuro<2,3-b>benzofuran-2(3H)-one | 139220-71-6 | C23H27IO6Si |
| —— | methyl 4-hydroxy-7-methoxy-5-benzo{b}pyranpropionate | 115678-85-8 | C14H16O5 |
| —— | (S)-5-difluoromethyl-1-(2,2-dimethyl-2,3-dihydro-benzofuran-3-yl)-1H-imidazole | 1034919-48-6 | C14H14F2N2O |
| —— | (Z)-3-(5-nitro-3-((triisopropylsilyl)oxy)benzofuran-2(3H)-ylidene)propan-1-ol | 1599372-13-0 | C20H31NO5Si |
| —— | (E)-3-(2,3-dihydrobenzofuran-3-yl)-1-phenylpropene | 113002-45-2 | C17H16O |
| —— | 2,3-dihydro-benzofuran-4-carboxylic acid {(1S,3S,5S)-2-[5-(2,3-dimethyl-phenyl)-2-methyl-thiazole-4-carbonyl]-2-aza-bicyclo[3.1.0]hex-3-ylmethyl}-amide | 1038507-90-2 | C28H29N3O3S |
| —— | (7-Methoxy-2,3-dihydro-benzofuran-2-ylmethyl)-(1-phenyl-ethyl)-amine | 57024-03-0 | C18H21NO2 |
| —— | 7-bromo-3-(4-isopropylphenyl)-5-methoxy-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran | 820257-95-2 | C22H27BrO2 |
| —— | 5-bromo-2,4,6-trimethyl-2,3-dihydro-1-benzofuran | 820258-90-0 | C11H13BrO |
| —— | (S)-7-Bromo-2,3-dihydrobenzofuran-3-amine hydrochloride | 2055848-77-4 | C8H9BrClNO |
| —— | 5-bromo-2,3-dihydro-2,2-dimethyl-7-(3-chloro-propoxy)-benzofuran | 1089210-22-9 | C13H16BrClO2 |
| —— | 4-{8-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)methyl]-2-oxo-1-oxa-3,8-diazaspiro[4.5]dec-3-yl}benzoic acid trifluoroacetate | 1360915-18-9 | C2HF3O2*C25H28N2O5 |
| —— | -W(CHCMe3)[O-2,6-C6H3(CMe2CH2)-(CMe3)][O-2,6-C6H3(CMe3)2]Cl | 91229-84-4 | C33H51ClO2W |
| —— | methyl 2-[(5aS,7S,9aR)-7-[tert-butyl(dimethyl)silyl]oxy-4-methoxy-1-[[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]methyl]-6,7,8,9-tetrahydro-5aH-dibenzofuran-9a-yl]acetate | 137718-82-2 | C29H47NO7Si |
| —— | (7-Methoxy-2,3-dihydro-benzofuran-2-ylmethyl)-(1-methyl-allyl)-amine | 62035-33-0 | C14H19NO2 |
| —— | 2,3-dihydro-8-methoxy-2,2,6-trimethyl-1,5-benzoxazepin-4(5H)-one | 156965-45-6 | C13H17NO3 |
| —— | 2-[4-(2,3-Dihydro-benzofuran-2-ylmethyl)-piperazin-1-yl]-ethanol | 21130-08-5 | C15H22N2O2 |
| —— | 2,2-Diethyl 4-chloro-6-methoxy-2,2(3H)-benzofurandicarboxylate | 116475-69-5 | C15H17ClO6 |
| —— | 5-bromo-3-(4-isopropylphenyl)-3,6,7-trimethyl-2,3-dihydro-1-benzofuran | 820257-42-9 | C20H23BrO |
| —— | 3a-<2-(trimethylsilyl)eth-1-oxy>-3a,8a-dihydrofuro<2,3b>benzofuran-2(3H)-one | 126680-41-9 | C15H20O4Si |
| —— | 2.3-Dihydro-benzofuran-carbonsaeure-(2)-methylamid | 112689-09-5 | C10H11NO2 |
| —— | N-((2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-oxotetrahydrofuran-2-yl)methyl)-4-nitrobenzenesulfonamide | 1338575-90-8 | C19H18N2O8S |
| —— | 2,3-dihydro-2,2-dimethyl-7-benzofuranyl [(N-di-ethoxyphosphinyl) (N-n-propyl)aminosulfenyl][methyl]carbamate | 64354-05-8 | C19H31N2O6PS |
| —— | 2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran-5-yldiethylaminosulfonate | 55530-99-9 | C14H21NO5S |
| —— | 1-(5-methyl-2,3-dihydro-benzofuran-7-yl)-propan-1-one-(2,4-dinitro-phenylhydrazone) | 101788-53-8 | C18H18N4O5 |
| —— | 1,2,3,4,4a,9b-Hexahydro-8-hydroxy-3-oxo-dibenzofuran | 91963-16-5 | C12H12O3 |
| —— | 4-(4-hydroxy-phenyl)-4-methyl-chroman-2-one | 101110-36-5 | C16H14O3 |
| —— | methyl 2-(6-hydroxy-2,3-dihydro-1-benzofuran-3-yl)butanoate | 652983-23-8 | C13H16O4 |
| —— | (3E)-3-benzylidene-7-iodo-2,2-dimethyl-1-benzofuran-5-carbaldehyde | 1204570-85-3 | C18H15IO2 |