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 |
|---|---|---|---|
| (2,2-二甲基-2,3-二氢-1-苯并呋喃-7-基)甲胺 | (2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-YL)methylamine | 868755-44-6 | C11H15NO |
| (2,2-二甲基-2,3-二氢-1-苯并呋喃-5-基)硼酸 | (2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)boronic acid | 1028748-08-4 | C10H13BO3 |
| (1Z,5Z,8S)-1,5-二甲基-8-(1-甲基乙烯基)环癸-1,5-二烯 | beta-Alanine, N-(((((2,3-dihydro-2,2-dimethyl-7-benzofuranyl)oxy)carbonyl)methylamino)thio)-N-hexyl-, ethyl ester | 82560-66-5 | C23H36N2O5S |
| (1R,2R)-2-(2,3-二氢-4-苯并呋喃基)环丙烷羧酸 | (1R-trans)-2-(2,3-dihydro-4-benzofuranyl)cyclopropanecarboxylic acid | 452324-76-4 | C12H12O3 |
| (1R,2R)-2-(2,3-二氢-4-苯并呋喃基)环丙烷甲酰胺 | (1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropane-1-carboxamide | 1161417-63-5 | C12H13NO2 |
| —— | (R,E)-ethyl 3-(7-methoxy-2,3-dihydrobenzofuran-2-yl)acrylate | 1177405-64-9 | C14H16O4 |
| —— | (3aS,9bS)-8-Methoxy-4,4-dimethyl-3a,9b-dihydro-4H-[1,3]dioxolo[4,5-c]chromen-2-one | 31298-66-5 | C13H14O5 |
| —— | 1,1,1,3,3,3-hexafluoropropan-2-yl 4-(bis(2,3-dihydrobenzofuran-5-yl)methyl)piperazine-1-carboxylate | 1446817-13-5 | C25H24F6N2O4 |
| —— | 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2',3',4',6',7',8',10',10a'-octahydro-1'H,3H-spiro[benzofuran-2,9'-pyrido[1,2-a]azepine] | 1258431-26-3 | C23H34BNO3 |
| —— | 4-Acetoxy-3-dimethylaminomethyl-4-phenyl-chroman | 94577-00-1 | C20H23NO3 |
| —— | 905454-86-6 | C18H19FO4 | |
| —— | diisopropyl (5aR,5bR,11aS,11bS)-6,12-dioxo-5b,6,11b,12-tetrahydrocyclobuta[1,2-b:3,4-b']dichromene-5a,11a-dicarboxylate | 1250416-23-9 | C26H24O8 |
| —— | N-Thio-(N'ME-O-tbu-carbamyl)carbofuran | 86569-98-4 | C18H26N2O5S |
| —— | 7,8-Dibromo-4b-methyl-10a-phenyl-4b,10a-dihydro-5,10-dioxa-benzo[b]biphenylene | 37895-71-9 | C21H14Br2O2 |
| —— | 1225021-75-9 | C12H14O3 | |
| —— | (2,3-dihydro-benzofuran-2-ylmethyl)-pyridin-3-yl-amine | 46824-21-9 | C14H14N2O |
| —— | 3c,4t-Dibrom-2r,6-dimethyl-chroman | 29392-85-6 | C11H12Br2O |
| —— | (R(P),R(P))-1,2-bis[(2,3-dihydro-2,2-dimethyl-7-methoxy-6-benzofuranyl)(phenyl)phosphino]ethane | 1152785-28-8 | C36H40O4P2 |
| —— | 2-(5-Hydroxy-6,7-dimethyl<2,3H>benzofuran-2-yl)-2-methoxy-propan | 31604-80-5 | C14H20O3 |
| —— | Acetic acid 5-acetoxy-6b-(4-butyl-phenyl)-7-oxo-6b,7-dihydro-12-oxa-benzo[4,5]pentaleno[2,1-a]naphthalen-11b-yl ester | 30654-54-7 | C33H28O6 |
| —— | Acetic acid 5-acetoxy-6b-(4-ethyl-phenyl)-7-oxo-6b,7-dihydro-12-oxa-benzo[4,5]pentaleno[2,1-a]naphthalen-11b-yl ester | 30654-52-5 | C31H24O6 |
| —— | Carbofuran,N-(N'-ME,isopr carbamidothio) | 86570-02-7 | C17H24N2O4S |
| —— | ethyl (1R,4aR,9aR)-2-(6-nitro-1,3,4,9a-tetrahydro-2H-1,4a-propanobenzofuro[2,3-c]pyridin-2-yl)carboxylate | 1058712-87-0 | C17H20N2O5 |
| —— | 1350910-92-7 | C27H34O6 | |
| —— | 3-[(5aR,9aS)-2-(2-Methoxycarbonyl-ethyl)-7-oxo-6,7,8,9-tetrahydro-5aH-dibenzofuran-9a-yl]-propionic acid methyl ester | 38390-54-4 | C20H24O6 |
| —— | Acetic acid 5-acetoxy-7-oxo-6b-p-tolyl-6b,7-dihydro-12-oxa-benzo[4,5]pentaleno[2,1-a]naphthalen-11b-yl ester | 30654-51-4 | C30H22O6 |
| —— | 7-acetoxy-2,3-dihydro-2,2-dimethyl-benzofuran-5-sulfonyl chloride | 1089210-09-2 | C12H13ClO5S |
| —— | 2-(2,3-dihydro-1-benzofuran-5-yl)-5-(methylsulfanyl)-1,3,4-oxadiazole | 1005200-17-8 | C11H10N2O2S |
| —— | Carbofuran,N-(N'-ME,PR carbamidothio) | 86570-01-6 | C17H24N2O4S |
| —— | 2-Furan-2-yl-1,9b-dihydro-5-oxa-3,3a-diaza-cyclopenta[a]naphthalen-4-one | 153685-72-4 | C14H10N2O3 |
| —— | (2S)-2-{[1-({[3-(2,3-dihydro-1-benzofuran-5-yl)propyl]amino}carbonyl)cyclopentyl]-methyl}-4-methoxybutanoic acid | 465528-04-5 | C23H33NO5 |
| —— | 3-[(5aR,9aR)-2-(2-Methoxycarbonyl-ethyl)-7-oxo-6,7-dihydro-5aH-dibenzofuran-9a-yl]-propionic acid methyl ester | 33405-30-0 | C20H22O6 |
| —— | 2-(2-bromoethyl)-5-<(tert-butyldiphenylsilyl)oxy>-2,3-dihydro-3,3-dimethyl-6-propylbenzofuran | 139201-31-3 | C31H39BrO2Si |
| —— | tert-butyl benzyl(4-iodo-2,3-dihydrobenzofuran-3-yl)carbamate | 1410747-89-5 | C20H22INO3 |
| —— | 1260760-81-3 | C14H20O | |
| —— | 2-[1-(5,6,7,8-Tetrachloro-3a,9a-dihydro-benzo[b]furo[2,3-e][1,4]dioxin-2-yl)-propyl]-malononitrile | 31700-98-8 | C16H10Cl4N2O3 |
| —— | 5-hydroxy-3,3-dimethyl-2-morpholino-4-propionylbenzo<b>furan | 116074-75-0 | C17H23NO4 |
| —— | (2R,3R)-3-Ethyl-2-methyl-6-nitro-chroman | 26005-27-6 | C12H15NO3 |
| —— | 5-methoxy-N-[(3S)-5-(6-methoxypyridin-3-yl)-3,4-dihydro-2H-chromen-3-yl]pyrazine-2-carboxamide | 1072852-90-4 | C21H20N4O4 |
| —— | N-[(3S)-5-pyridin-3-yl-3,4-dihydro-2H-chromen-3-yl]-5-(3,3,3-trifluoropropoxy)pyrazine-2-carboxamide | 1072852-84-6 | C22H19F3N4O3 |
| —— | Methyl-(2E)-2-cyano-3-(2,3-dihydro-1-benzofuran-5-yl)-2-butenoate | 465529-68-4 | C14H13NO3 |
| —— | methyl 2-cyano-3-(4-cyanophenyl)-2,3-dihydronaphtho[1,2-b]furan-2-carbimidate | 1613306-55-0 | C22H15N3O2 |
| —— | 3-[1-(2-Amino-5-methyl-phenylamino)-meth-(Z)-ylidene]-5-hydroxy-2,2-dimethyl-7-pentyl-chroman-4-one | 35692-83-2 | C24H30N2O3 |
| —— | 2,2-diallyl-2,3-dihydrobenzofuran-3,4-diol | 1146968-62-8 | C14H16O3 |
| —— | 1,1,2,2,-Tetracyan-11-methoxy-4-methyl-1,2,3,11-tetrahydrodibenzofuran | 33562-18-4 | C18H12N4O2 |
| —— | 2-[3-Methyl-1-(5,6,7,8-tetrachloro-3a,9a-dihydro-benzo[b]furo[2,3-e][1,4]dioxin-2-yl)-butyl]-malononitrile | 31700-99-9 | C18H14Cl4N2O3 |
| —— | (3aS,8aR)-4-(tert-butyldimethylsilyloxy)-3a,8a-dihydro-6-methoxyfuro[2,3-b]benzofuran | 1268615-40-2 | C17H24O4Si |
| —— | 1138675-08-7 | C18H16F3N5O4S | |
| —— | 267223-83-6 | C25H34O5 | |
| —— | Acetic acid 5-acetoxy-7-oxo-6b-phenyl-6b,7-dihydro-12-oxa-benzo[4,5]pentaleno[2,1-a]naphthalen-11b-yl ester | 30502-01-3 | C29H20O6 |