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 |
|---|---|---|---|
| —— | ethyl (S)-4-((2R,4R)-7-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxy-5-methoxy-2-methylchroman-2-yl)-4-hydroxybutanoate | 1360933-02-3 | C34H44O7Si |
| —— | tert-butyl N-(tert-butoxycarbonyl)-(2,3-dihydrobenzofuran-3-yl)carbamate | 1410747-80-6 | C18H25NO5 |
| —— | butane-1-sulfonic acid 3,3-dimethyl-2-morpholin-4-yl-2,3-dihydro-benzofuran-5-yl ester | 26225-76-3 | C18H27NO5S |
| —— | methyl 4-((1R,2R,3aS,8bS)-2-hydroxy-1-(2-methylprop-1-enyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl)butanoate | 1352145-69-7 | C20H26O4 |
| —— | 3-methoxy-propane-1-sulfonic acid 3,3-dimethyl-2-morpholin-4-yl-2,3-dihydro-benzofuran-5-yl ester | 26322-72-5 | C18H27NO6S |
| —— | 1258401-88-5 | C33H34F3NO8S | |
| —— | 5-bromo-7-methoxy-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran | 1243544-54-8 | C13H17BrO2 |
| —— | E-5,5',7,7'-Tetra-tert-butyl-2,2,2',2'-tetraethoxy-Δ3,3'(2H,2'H)-bi<benzofuran> | 75540-61-3 | C40H60O6 |
| —— | 55038-05-6 | C25H22O2 | |
| —— | 1886-40-4 | C18H25NO2 | |
| —— | ethyl 2-((2R,3R,4R)-3-amino-3-methyl-4-(p-tolylthio)chroman-2-yl)acetate | 1258880-54-4 | C21H25NO3S |
| —— | cis-3,5-dichloro-2-fluoro-2,3-dihydrobenzofuran | 86324-93-8 | C8H5Cl2FO |
| —— | 2-(2,3-dihydrobenzofuran-5-ylethynyl)-6-methylpyridine | 428817-54-3 | C16H13NO |
| —— | 3-ethyl-5-methanesulfonyloxy-2-morpholin-4-yl-2,3-dihydro-benzofuran | 26322-69-0 | C15H21NO5S |
| —— | 3-Mercapto-2-benzo<b>furylidene-(p-methylphenyl)amine | 78096-40-9 | C16H13NOS |
| —— | Benzenemethanol,3-chloro-a-[[[(2,3-dihydro-7-benzofuranyl)methyl]methylamino]methyl]- | 389845-45-8 | C18H20ClNO2 |
| —— | spiro<2-(ethoxycarbonyl)-7-methoxybenzofuran-3-(2H),4'-1'-methyl-3'-methylene-2'-piperidinone> | 87903-04-6 | C18H21NO5 |
| —— | 7-(3,3-dimethylbut-1-ynyl)-2-(4-methoxyphenyl)-2,3-dimethyl-2,3-dihydrobenzofuran-5-ol | 1432504-82-9 | C23H26O3 |
| —— | 2-{[(1S)-10-phenylselanyl-4-isocaranylselanyl]methyl}-2,3-dihydrobenzofuran | 1202554-81-1 | C25H30OSe2 |
| —— | (R)-N-(1-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-1-oxopropan-2-yl)-2,2,2-trifluoroacetamide | 943899-34-1 | C15H13BrF3NO4 |
| —— | 4-[(5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methyl]morpholine | 1243545-04-1 | C17H24BrNO2 |
| —— | 5-methanesulfonyloxy-2-methoxycarbonyloxy-3,3-dimethyl-2,3-dihydro-benzofuran | 26244-26-8 | C13H16O7S |
| —— | 7-bromo-3,3-dimethyl-5-[(1S,2S)-3-hydroxy-1,2-methano-1-methl-propyl]-2,3-dihydro-benzofuran | 623176-44-3 | C15H19BrO2 |
| —— | 2-(3-Hydroxy-4,7-dimethyl-chroman-2-yl)-malonic acid diethyl ester | 43015-50-5 | C18H24O6 |
| —— | N-benzyl-2,2,4,7-tetramethyl-2,3-dihydro-1-benzofuran-5-amine | 1243545-19-8 | C19H23NO |
| —— | 3-(2,2-dimethyl-2,3-dihydro-1-benzofuran-6-yl)pyridine | 1243543-47-6 | C15H15NO |
| —— | 5-bromo-2,2,4,7-tetramethyl-2,3-dihydro-1-benzofuran | 1243544-62-8 | C12H15BrO |
| —— | 2,2'-[(6-bromo-2,2,4,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)imino]diethanol | 1243545-21-2 | C16H24BrNO3 |
| —— | methyl 6,8-ditert-butyl-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate | 1354632-94-2 | C20H25F3O4 |
| —— | 5-bromo-7-ethoxy-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran | 1243544-60-6 | C14H19BrO2 |
| —— | Acetic acid 2,3,3a,8a-tetrahydro-benzo[b]furo[3,2-d]furan-2-yl ester | 53737-93-2 | C12H12O4 |
| —— | 4-((2',3'-dihydrobenzofuran-7'-carbonyl)amino)-1-methyl-3-n-propylpyrazole-5-carboxamide | 258270-58-5 | C17H20N4O3 |
| —— | 3a,8b-cis-dihydro-3H-5-bromocyclopenta<b>benzofuran | 84599-03-1 | C11H9BrO |
| —— | 1-(2,3-dihydro-benzofuran-5-yl)-3-(6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-7-yl)urea | 1234375-63-3 | C19H19N5O2 |
| —— | 1-[2,3-Dihydro-5H-benzo[b]oxepin-(4Z)-ylidenemethyl]-piperidine | 86896-80-2 | C16H21NO |
| —— | [2,3-Dihydro-5H-benzo[b]oxepin-(4Z)-ylidenemethyl]-diethyl-amine | 86896-77-7 | C15H21NO |
| —— | N-[1-(2,3-dihydro-1-benzofuran-5-yl)-3-phenylpropylidene]hydroxylamine | 115063-25-7 | C17H17NO2 |
| —— | 7,8-Dichloro-5-(thiophene-2-carbonyl)-2,3-dihydro-benzo[1,4]dioxine-2-carboxylic acid | 103830-27-9 | C14H8Cl2O5S |
| —— | 2,10-dimethyl-6,12-ethano-12H-dibenzo[2,1-d:1',2'-g][1,3]dioxocine | 1256601-79-2 | C18H18O2 |
| —— | 2-(1-hydroxy-1-methyl-ethyl)-4-methoxy-2,3-dihydro-benzofuran-7-carbaldehyde | 54776-78-2 | C13H16O4 |
| —— | dimethyl 3-hydroxy-2-methyl-2,3-dihydro-1-benzofuran-2-ylphosphonate | 1010732-99-6 | C11H15O5P |
| —— | Isopropyl-sulfamic acid 2-hydroxy-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl ester | 55530-97-7 | C13H19NO5S |
| —— | 1-[2,3-Dihydro-5H-benzo[b]oxepin-(4Z)-ylidenemethyl]-pyrrolidine | 86896-79-9 | C15H19NO |
| —— | 7-Methyl-2-p-tolylsulfanylmethyl-2,3-dihydro-benzofuran | 101041-41-2 | C17H18OS |
| —— | 3-(2-methoxyphenyl)-2,3-dihydrobenzofuran-3-ol | 1048361-28-9 | C15H14O3 |
| —— | 2-Methoxy-5-methoxymethyl-4,4,7,8-tetramethyl-6-chromanol | 50442-82-5 | C16H24O4 |
| —— | 2.6-Dihydroxy-8-methyl-2.3.5.6-tetrahydro-benzo<1.2-b,5.4-b'>difuran | 22304-83-2 | C11H12O4 |
| —— | Ethyl-sulfamic acid 2-hydroxy-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl ester | 55530-95-5 | C12H17NO5S |
| —— | (1S)-1-[(2R)-5-fluoro-6-phenylmethoxy-3,4-dihydro-2H-chromen-2-yl]ethane-1,2-diol | 905454-78-6 | C18H19FO4 |
| —— | bromo-7 diphenyl-5b,13a dihydro-5b,13a dinaphto <2',3'-e:2",3"-3,4> cyclobuta <1,2-b> <dioxinne-1,4> | 76742-28-4 | C34H21BrO2 |