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 |
|---|---|---|---|
| —— | (1S,4aS,9aR)-6-nitro-2-(2-phenethyl)-1,3,4,9a-tetrahydro-2H-1,4a-propanobenzofuro[2,3-c]pyridine | 1058712-75-6 | C22H24N2O3 |
| —— | (+/-)-N-[2-(aminomethyl)-2,3-dihydro-1-benzofuran-7-yl]-N-(4-chlorophenyl)amine | 852114-92-2 | C15H15ClN2O |
| —— | (S)-2-(5-tert-butyl-2-methyl-2,3-dihydrobenzofuran-2-yl)propan-2-ol | 1269598-94-8 | C16H24O2 |
| —— | 5-Iod-3-hydroxy-2-methyl-2,3-dihydrobenzo<b>furan | 60770-63-0 | C9H9IO2 |
| —— | 3,6-Epoxy-5-isobutyl-7-butyl-3,4,5,6-tetrahydro-2H-1,5-benzoxazocin | 59893-33-3 | C18H27NO2 |
| —— | 3-Chloro-4-(3-(7-propyl-3-methoxyimino-2H-benzofuran-6-yloxy)-propylthio)-phenylacetic acid | 194855-87-3 | C23H26ClNO5S |
| —— | 5-(2-Methoxy-ethoxymethoxy)-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid methyl ester | 77270-60-1 | C14H19NO6 |
| —— | N-[1-(4-Bromophenyl)ethyl]-2,3-dihydro-2-benzofuranmethanamine | 1182775-54-7 | C17H18BrNO |
| —— | 6-Bromo-2,3-dihydro-1-benzofuran-2-carboxylic acid | 1890906-32-7 | C9H7BrO3 |
| —— | (4aS,9bR)-8-(2,4,6-trichlorophenyl)-6-(benzylthio)-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-46-1 | C24H20Cl3NOS |
| —— | ethyl (3S)-1-(7-fluoro-2-methyl-2,3-dihydrobenzofuran-4-yl)pyrrolidin-3-ylcarbamate | 1258851-41-0 | C16H21FN2O3 |
| —— | 1-[4-oxo-4-(3,4,5-trimethoxyphenyl)butyl]-4-piperidinyl 4-amino-5-chloro-2,3-dihydro-2,2-dimethyl-7-benzofurancarboxylate | 178759-80-3 | C29H37ClN2O7 |
| —— | 3,8-dimethoxy-(5ar,10bc)-5a,10b-dihydrobenzo<b>benzo<4,5>furo<3,2-d>furan | 124483-04-1 | C16H14O4 |
| —— | [(3S)-6-{[(3S)-7-{4-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)oxy]-2,6-dimethylphenyl}-2,3-dihydro-1-benzofuran-3-yl]amino}-2,3-dihydro-1-benzofuran-3-yl]acetic acid | 1258395-88-8 | C31H33NO7S |
| —— | 2-(6-bromo-2,2-diethyl-4,4-dimethylchroman-8-yl)propan-2-ol | 960591-74-6 | C18H27BrO2 |
| —— | (4aS,9bR)-8-(2,4-dichlorophenyl)-6-butyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-06-3 | C21H23Cl2NO |
| —— | 5-<(tert-butyldiphenylsilyl)oxy>-2-carbethoxymethyl-2,3-dihydro-3,3-dimethyl-6-propylbenzofuran | 139201-30-2 | C33H42O4Si |
| —— | 1072855-83-4 | C19H15ClN4O2 | |
| —— | 7-bromo-6-hydroxy-4-methoxy-3-methyl-2,3-dihydro-benzofuran-5-carbaldehyde | 35616-64-9 | C11H11BrO4 |
| —— | 2,3-Dihydro-3-(4-pyridyl)-5-chlor-3-benzofuranol | 59214-73-2 | C13H10ClNO2 |
| —— | 52193-46-1 | C14H11Br3O3 | |
| —— | [(3S)-6-{[(3S)-7-{2,6-dimethyl-4-[(5-methylisoxazol-3-yl)methoxy]phenyl}-2,3-dihydro-1-benzofuran-3-yl]amino}-2,3-dihydro-1-benzofuran-3-yl]acetic acid | 1258396-44-9 | C31H30N2O6 |
| —— | 10b-Methyl-5a,10b-dihydro-benzo[b]benzo[4,5]furo[3,2-d]furan-2,9-diol | 104830-37-7 | C15H12O4 |
| —— | (4Z,4aS,9bR)-4-[[2-[[(Z)-[(4aS,9bR)-8,9b-dimethyl-3-oxo-2,4a-dihydro-1H-dibenzofuran-4-ylidene]methyl]amino]ethylamino]methylidene]-8,9b-dimethyl-2,4a-dihydro-1H-dibenzofuran-3-one | 86658-27-7 | C32H36N2O4 |
| —— | 2,2-Diethyl-7-methoxy-4-[2-(4-pyridyl)ethyl]-2,3-dihydrobenzofuran-hydrochloride | 185400-60-6 | C20H25NO2*ClH |
| —— | (S)-N-[2-(2,3-Dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-[1-(pyrrolidine-1-sulfonyl)piperidin-4-ylmethyl]amine hydrochloride | 241137-08-6 | C23H37N3O3S*ClH |
| —— | (S)-2,3-dihydro-benzofuran-4-carboxylic acid {1-[5-(2-fluoro-phenyl)-2-m-tolyl-thiazole-4-carbonyl]-piperidin-2-ylmethyl}-amide | 1137129-40-8 | C32H30FN3O3S |
| —— | 2,3-Dihydro-2,3-dihydroxy-6-methyl-benzo<b>furan-2,3-dicarbonsaeure-methylester | 342819-34-5 | C13H14O7 |
| —— | 2,3-Dihydro-2,2-dimethyl-7-benzofuranyl N-piperidinocarbonyl-N-methyl-carbamate | 77249-06-0 | C18H24N2O4 |
| —— | (4aS,9bR)-8-(2,4,6-trichlorophenyl)-6-[(1-ethylpropyl)thio]-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-43-8 | C22H24Cl3NOS |
| —— | 3-Methyl-2,3-dihydro-1-benzofuran-3-amine hydrochloride | 2680540-57-0 | C9H12ClNO |
| —— | (R,S)-5-(methanesulfonylamino-methyl)-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester | 847949-09-1 | C12H15NO5S |
| —— | 2-Aethyl-3,4-dihydro-8-methoxy-3-methyl-2-morpholino-4-(nitromethyl)-2H-1-benzopyran | 40697-23-2 | C18H26N2O5 |
| —— | 6-bromo-2-ethyl-2,3-dihydro-1-benzofuran-3-amine hydrochloride, Mixture of diastereomers | 2680537-29-3 | C10H13BrClNO |
| —— | 6-bromo-2-(2-methylpropyl)-2,3-dihydro-1-benzofuran-3-amine hydrochloride, Mixture of diastereomers | 2680542-06-5 | C12H17BrClNO |
| —— | ethyl ((2-((3S)-6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethyl)sulfanyl)acetate | 1452477-24-5 | C21H22Cl2O4S |
| —— | (4aS,9bR)-8-(2,6-difluoro-4-chlorophenyl)-6-(benzyloxy)-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-83-6 | C24H20ClF2NO2 |
| —— | 1,2,3,4,4a,9b-Hexahydro-8,9b-dimethyl-4-methylaminomethylendibenzofuran-3-on | 86658-17-5 | C16H19NO2 |
| —— | (R,S)-7-bismethanesulfonylamino-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester | 847949-00-2 | C12H15NO7S2 |
| —— | 5-Amino-2,3-dihydro-1-benzofuran-2-carboxamidehydrochloride | 2551117-08-7 | C9H11ClN2O2 |
| —— | acetic acid (R)-1-((2R,3R)-7-bromo-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydrobenzofuran-3-yl)-but-3-enyl ester | 628299-78-5 | C25H39BrO4Si |
| —— | 7-(o-nitrophenylazo)-6-hydroxy-2,4-dimethyl-1,3-benzodioxane | 87973-70-4 | C16H15N3O5 |
| —— | 2-[7-(Methoxycarbonyl)-2,3-dihydro-1-benzofuran-5-yl]acetic acid | 2758001-38-4 | C12H12O5 |
| —— | Bis(2,3-dihydro-1-benzofuran-5-ylmethyl)amine | 1951444-97-5 | C18H19NO2 |
| —— | (S)-2,2-bis(fluoromethyl)-8-(trifluoromethoxy)chroman-4-ol | 1221444-07-0 | C12H11F5O3 |
| —— | (S)-2,2-dimethyl-8-(trifluoromethoxy)chroman-4-ol | 1221444-36-5 | C12H13F3O3 |
| —— | (S)-N-[2-(2,3-Dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-[1-(thiomorpholine-4-sulfonyl)piperidin-4-ylmethyl]amine hydrochloride | 241137-10-0 | C23H37N3O3S2*ClH |
| —— | annullatin A | 1370709-00-4 | C17H24O3 |
| —— | 2-phenethyl-2,3-dihydrobenzofuran-2-carboxylic acid | 89197-66-0 | C17H16O3 |
| —— | (S)-2,2-diethyl-8-(trifluoromethyl)chroman-4-ol | 1221443-87-3 | C14H17F3O2 |