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 |
|---|---|---|---|
| —— | 3H-5-(2-methyl-1,3-dioxolan-2-yl)-3H-spiro[benzofuran-2,1'-cyclopropan]-3-one O-allylcarbamoyl oxime | 95449-92-6 | C18H20N2O5 |
| —— | 7-(tert-butyl)-3-phenylbenzofuran-2(3H)-one | 55022-25-8 | C18H18O2 |
| —— | [3-(3-Cyclohex-1-enyl-3-methyl-ureido)-phenyl]-thiocarbamic acid S-isopropyl ester | 41402-49-7 | C18H25N3O2S |
| —— | (E)-6-<1-(4-cyanophenyl)-1-propen-3-yl>-2,3-dihydro-5-benzofuranol methoxymethyl ether | 124855-04-5 | C20H19NO3 |
| —— | 3,7-diphenyl-3,7-dihydrobenzo[1,2-b:4,5-b']difuran-2,6-dione | 69125-13-9 | C22H14O4 |
| —— | 5,7-diiodo-3,3-dimethyl-2,3-dihydrobenzofuran | 1246278-03-4 | C10H10I2O |
| —— | 5,5'-dimethyl-3,3'-diphenyl-3,3'-bibenzo-<b>furan-2,2'-(3H,3'H)-dione | 65425-11-8 | C30H22O4 |
| —— | ethyl 4,7-dichloro-2,3-dihydrobenzo<b>furan-2-carboxylate | 136741-42-9 | C11H10Cl2O3 |
| —— | methyl (R)-6,7-dichloro-2,3-dihydrobenzo<b>furan-2-carboxylate | 118166-28-2 | C10H8Cl2O3 |
| —— | 4,6-dimethyl-3-phenyl-3H-benzofuran-2-one | 50341-26-9 | C16H14O2 |
| —— | Benzofuran, 2,3-dihydro-2-methoxy-5-methyl-3-phenyl-, trans- | 111864-86-9 | C16H16O2 |
| —— | 4,7-dichloro-2,3-dihydro-5-(α-hydroxyiminobenzyl)benzo<b>furan-2-carboxylic acid | 107804-71-7 | C16H11Cl2NO4 |
| —— | (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1S,2S,3R,3aS,8bR)-6-(benzyloxy)-1,8b-dihydroxy-8-methoxy-3,3a-diphenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxylate | 1112993-23-3 | C42H46O7 |
| —— | (2α,3α,3aβ,4β,9bα)-2,3,3a,9b-Tetrahydro-2-phenyl-3,4-propano-4H-furo<3,2-c><1>benzopyran-2-carbonitril | 86661-41-8 | C21H19NO2 |
| —— | (2α,3α,3aβ,4α,9bα)-2,3,3a,9b-Tetrahydro-2-phenyl-3,4-propano-4H-furo<3,2-c><1>benzopyran-2-carbonitril | 86661-41-8 | C21H19NO2 |
| —— | 2-[2-oxo-3-(2-tolyl)-3-dihydrobenzofuranyl]-N,N-dimethylethylamine | 99484-58-9 | C19H21NO2 |
| —— | 1-(2,3-dihydro-1-benzofuran-5-yl)-5-(trifluoromethyl)-1H-tetrazole | 1345345-89-2 | C10H7F3N4O |
| —— | 267223-00-7 | C36H59NO3Si2 | |
| —— | (2α,3β,3aα,4α,9bα)-2,3,3a,9b-Tetrahydro-2-phenyl-3,4-pentano-4H-furo<3,2-c><1>benzopyran-2-carbonitril | 86661-43-0 | C23H23NO2 |
| —— | (2α,3α,3aβ,4β,9bα)-2,3,3a,9b-Tetrahydro-2-phenyl-3,4-pentano-4H-furo<3,2-c><1>benzopyran-2-carbonitril | 86661-43-0 | C23H23NO2 |
| —— | (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1R,2R,3S,3aR,8bS)-6-(benzyloxy)-1,8b-dihydroxy-8-methoxy-3,3a-diphenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxylate | 1112993-25-5 | C42H46O7 |
| —— | Piperazinohexahydrocycloheptabenzofuranol | 5117-24-8 | C18H26N2O2 |
| —— | 6-benzyloxy-4-chloro-2,3-dihydro-furo[3,2-<i>c</i>]pyridine | 21495-48-7 | C14H12ClNO2 |
| —— | 1016896-67-5 | C28H32BrNO7 | |
| —— | (+/-)-1-(5-chloro-7-isopropyl-4-methyl-2,3-dihydro-1-benzofuran-2-yl)methanamine | 852110-15-7 | C13H18ClNO |
| —— | 3-Dimethylaminomethyl-6-methoxy-4-phenyl-chroman-4-ol | 94914-92-8 | C19H23NO3 |
| —— | 1280224-97-6 | C24H34O4Si | |
| —— | 3-[1-(2-Amino-4-methyl-phenylamino)-meth-(Z)-ylidene]-5-hydroxy-2,2-dimethyl-7-pentyl-chroman-4-one | 35641-98-6 | C24H30N2O3 |
| —— | methyl 2-cyano-3-(4-nitrophenyl)-2,3-dihydronaphtho[1,2-b]furan-2-carbimidate | 1613306-50-5 | C21H15N3O4 |
| —— | 39891-59-3 | C10H12O2 | |
| —— | 7-bromo-4-methoxy-3-methyl-2,3-dihydro-benzofuran-6-ol | 51093-58-4 | C10H11BrO3 |
| —— | (1S,4aS,9aR)-(6-nitro-1,3,4,9a-tetrahydro-2H-1,4a-propanobenzofuro[2,3-c]pyridin-2-yl)-ethylcarboxylate | 1058712-71-2 | C17H20N2O5 |
| —— | 4,6-Dimethoxy-5-(2-methyl-cyclopentyl)-2,3,3a,8a-tetrahydro-benzo[b]furo[3,2-d]furan | 28126-52-5 | C18H24O4 |
| —— | 1033820-65-3 | C16H13NO5 | |
| —— | Carbofuran,N-(N'-ME,mecarbamidothio) | 68840-05-1 | C15H20N2O4S |
| —— | trans-4,8-diacetoxy-3,4-dihydro-3-hydroxy-2H-1-benzopyran | 106662-64-0 | C13H14O6 |
| —— | 3-methyl-3-(3-phenylprop-2-yn-1-yl)-2,3-dihydrobenzofuran | 1603105-46-9 | C18H16O |
| —— | N-tert-butyl-4-isopropyl-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine-5-carboxamide | 1290628-58-8 | C17H26N2O2 |
| —— | 6-chlorospiro[1,3-benzodioxine-4,1'-cyclohexane]-2-carboxylic acid | 73050-83-6 | C14H15ClO4 |
| —— | trans-4-[([1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]{4-[2-(2,5-dioxo-pyrrolidin-1-yl)ethoxy]-3-methoxy-benzyl}amino)methyl]cyclohexanecarboxylic acid | 1443019-04-2 | C32H40N2O7 |
| —— | 4-(5-bromo-2,3-dihydro-benzofuran-2-yl)-piperidine | 1346529-71-2 | C13H16BrNO |
| —— | trans-4,8-diacetoxy-3,4-dihydro-3-hydroxy-2H-1-benzopyran | 106662-64-0 | C13H14O6 |
| —— | 1,2,3,3a(R),8,9,9a(S),9b(S)-octahydro-7-chloro-9b-ethenyl-5-methoxy-3-(ethylenedioxy)phenanthro[4,4a,4b,5-bcd]furan | 186351-22-4 | C19H21ClO4 |
| —— | 2-(4-(5-bromo-2,3-dihydrobenzofuran-2-yl)piperidin-1-yl)-5-propylpyrimidine | 1346529-72-3 | C20H24BrN3O |
| —— | (4,6,7-trichloro-2,5-dihydroxy-2,3-dihydro-1-benzofuran-3-yl) N,N-diethylcarbamodithioate | 167321-30-4 | C13H14Cl3NO3S2 |
| —— | (9aS)-N-[4-(but-2-ynyloxy)-2,3,6-trimethylbenzyl]-1,7-dihydroxy-3-methoxy-8-[(1E)-N-methoxyethaneimidoyl]-9a-methyl-9-oxo-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide | 925440-54-6 | C32H34N2O8 |
| —— | 1-acetoxymercury(II) methyl-1,2-dihydrobenzofurane | 7146-62-5 | C11H12HgO3 |
| —— | 2-Acetoxymercurymethyl-5-methyl-2,3-dihydrobenzofuran | 66865-59-6 | C12H14HgO3 |
| —— | 2,2-dimethyl-4-imino-5-hydroxy-7-butoxy-2,3-dihydrobenzopyran | 136136-03-3 | C15H21NO3 |
| —— | (9aS)-8-acetyl-1-propyloxy-7-hydroxy-3-methoxy-9a-methyl-9-oxo-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide | 925441-82-3 | C20H21NO7 |