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-Ethyl-5-methyl-cumaran | 7573-18-4 | C11H14O |
| —— | 1'-cyclobutyl-6-(2H-pyridazin-2-one-6-yl)-spiro[1,3-benzodioxine-2,4'-piperidine] | 1174923-90-0 | C20H23N3O3 |
| —— | 89908-61-2 | C15H16O3 | |
| —— | 7-hexyl-2,2-dimethyl-2,3-dihydrobenzofuran | 1398787-08-0 | C16H24O |
| —— | 7-(1-ethoxyethoxy)-2,2-dimethyl-6-(prop-2-enyl)-2,3-dihydrobenzofuran | 87386-30-9 | C17H24O3 |
| —— | (+/-)-{[7-(2,5-difluorophenyl)-5-methoxy-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-96-0 | C17H17F2NO2 |
| —— | 1-[1-(2,3-dihydro-1-benzofuran-5-yl)piperidin-4-yl]-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one | 1357591-45-7 | C26H25N5O2 |
| —— | 6-(hydroxypropyl)benzofuran-7-ol 7-ethoxyethyl ether | 87386-43-4 | C17H26O4 |
| —— | (4S)-5-(4-fluorophenyl)-7-propan-2-ylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-ol | 1266235-73-7 | C21H23FO2 |
| —— | 3-Chloro-N-((4R,9bS)-8,9b-dimethyl-6-nitro-3-oxo-1,2,3,4,4a,9b-hexahydro-dibenzofuran-4-yl)-propionamide | 61132-82-9 | C17H19ClN2O5 |
| —— | (R)-N-(tert-butyl)-3-((tert-butyldimethylsilyl)oxy)-7-((S)-2-hydroxypropyl)-5-methoxy-2,2-dimethylchroman-8-carboxamide | 1459804-96-6 | C26H45NO5Si |
| —— | (+/-)-{[7-(2,3-dichlorophenyl)-5-methoxy-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-93-7 | C17H17Cl2NO2 |
| —— | 8,9b-dimethyl-3-oxo-(4a<i>r</i>,9b<i>c</i>)-1,2,3,4,4a,9b-hexahydro-dibenzofuran-4-carboxylic acid 2-chloro-ethylamide | 61132-85-2 | C17H20ClNO3 |
| —— | 2,2-dimethyl-2,3-dihydrobenzofuran-7-yl diethylcarbamate | 1379516-35-4 | C15H21NO3 |
| —— | [(2S)-2-acetyloxy-2-[(2R)-5-(1-hydroxyethyl)-2,3-dihydro-1-benzofuran-2-yl]propyl] acetate | 850312-60-6 | C17H22O6 |
| —— | 4-[2-(3,5-Dichloro-4-pyridyl)-1-oxoethyl]-7-methoxy-spiro[2,3-dihydrobenzofuran-2,1'-cyclopentane] | 185407-91-4 | C20H19Cl2NO3 |
| —— | (2aS,7aR)-2aH-7-Oxa-cyclobuta[a]indene-1,7a-dicarboxylic acid dimethyl ester | 62250-76-4 | C14H12O5 |
| —— | 84824-27-1 | C42H55O2Ta | |
| —— | [(3S)-6-{[(3S)-7-{4-[2-(dimethylamino)ethoxy]-2,6-dimethylphenyl}-2,3-dihydro-1-benzofuran-3-yl]amino}-2,3-dihydro-1-benzofuran-3-yl]acetic acid | 1258396-33-6 | C30H34N2O5 |
| —— | 3-[(2-hydroxy-ethyl)-methyl-amino]-3-phenyl-3<i>H</i>-benzofuran-2-one | 55825-21-3 | C17H17NO3 |
| —— | 2,3-Dihydro-2-ethoxy-3-ethyl-5-hydroxybenzofuran | 111580-02-0 | C12H16O3 |
| —— | 2,9-dihydro-2,4a-ethano-xanthene-3,4-dicarboxylic acid dimethyl ester | 37568-90-4 | C19H18O5 |
| —— | (6aS,11bR)-3,9,10-tris(phenylmethoxy)-7,11b-dihydro-6H-indeno[2,1-c]chromen-6a-ol | 176302-38-8 | C37H32O5 |
| —— | 2-(2'-ethoxyethoxy)-2,3-dihydro-3-methylenebenzofuran | 1187956-36-0 | C13H16O3 |
| —— | 1'-(2-Methoxyphenyl)-spiro(naphthalene-1(2H),2'(1'H)-naphtho<2,1-b>furan)-2-one | 146382-44-7 | C28H20O3 |
| —— | [(3S)-6-{[(3S)-7-{2,6-dimethyl-4-[3-(pyridin-3-yl)propoxy]phenyl}-2,3-dihydro-1-benzofuran-3-yl]amino}-2,3-dihydro-1-benzofuran-3-yl]acetic acid | 1258396-37-0 | C34H34N2O5 |
| —— | 2,3-dihydro-2-hydroxy-5-trifluoromethanesulfonyloxy-3,3,7-trimethylbenzofuran | 131394-61-1 | C12H13F3O5S |
| —— | (S)-N-[2-(2,3,-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine hydrochloride | 241136-31-2 | C20H32N2O3S*ClH |
| —— | 8-hydroxy-1,1-diphenyl-1H-naphtho[2,1-b]furan-2-one | 860744-02-1 | C24H16O3 |
| —— | 2,3-dihydro-benzofuran-2-carboxylic acid {5-[3-(3-fluoro-benzyl)-ureido]-[1,2,4]thiadiazol-3-ylmethyl}-methyl-amide | 1108711-26-7 | C21H20FN5O3S |
| —— | 3,3-dimethyl-7-(2,2-dimethyl-propyl)-2,3-dihydro-benzofuran-5-boronic acid | 623176-09-0 | C15H23BO3 |
| —— | 1-methyl-(3a<i>r</i>,9b<i>c</i>)-1,3a,4,9b-tetrahydro-3<i>H</i>-chromeno[3,4-<i>d</i>]isoxazole-3<i>c</i>-carboxylic acid methyl ester | 28809-13-4 | C13H15NO4 |
| —— | 7-cyclohexylmethyl-3,3-dimethyl-5-(3-hydroxy-1-methyl-prop-(1Z)-enyl)-2,3-dihydro-benzofuran | 623176-28-3 | C21H30O2 |
| —— | 5-(2,6-dichloro-phenyl)-7,8-dimethoxy-3-methyl-2,3-dihydro-benzo[<i>f</i>][1,4]oxazepine | 62539-23-5 | C18H17Cl2NO3 |
| —— | 9-Allyl-3,6-dimethyl-7-nitro-2,3-dihydro-benzo[de]chromen-3-ol | 873426-20-1 | C17H17NO4 |
| —— | 2,3-Dihydro-3-ethyl-5-hydroxybenzofuran | 111580-03-1 | C10H12O2 |
| —— | 4-[4-(2,3-dihydro-1-benzofuran-5-yl)-1H-pyrazol-1-yl]-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide | 1402637-10-8 | C17H21N3O5S |
| —— | 2-(2-chloro-phenyl)-cyclopropanecarboxylic acid [1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-amide | 701913-64-6 | C20H20ClNO2 |
| —— | 2,9-dibromo-(5ar,10bc)-5a,10b-dihydrobenzo<b>benzo<4,5>furo<3,2-d>furan | 124483-06-3 | C14H8Br2O2 |
| —— | (R)-2-acetyl-6-[2-(benzylthio)acetyl]-3,9-dihydroxy-7-methoxy-8,9b-dimethyldibenzo[b,d]furan-1(9bH)-one | 1609950-08-4 | C26H24O7S |
| —— | 2,3-dihydro-3,3-dimethyl-7-fluoro-5-hydroxybenzofuran | 131395-04-5 | C10H11FO2 |
| —— | 2-amino-2,3-dihydro-3,3-dimethyl-5-trifluoromethanesulfonyloxy benzofuran | 131394-59-7 | C11H12F3NO4S |
| —— | 5-(2-Phenyl-2,3-dihydro-benzofuran-5-ylmethyl)-thiazolidine-2,4-dione | 109209-12-3 | C18H15NO3S |
| —— | cis-1-methyl-1,3a,4,9b-tetrahydro-3H-<1>benzopyrano<4,3-c>isoxazole | 28082-02-2 | C11H13NO2 |
| —— | 3-methoxy-10,10-dimethyl-6,6a,7,8,10,10a-hexahydro-benzo[<i>c</i>]chromen-9-one | 31582-22-6 | C16H20O3 |
| —— | 4-tert-butyl-5-hydroxy-2-octyl-2,3-dihydrobenzofuran | 157360-53-7 | C20H32O2 |
| —— | [(3S)-6-{[(3S)-7-{4-[2-(azepan-1-yl)ethoxy]-2,6-dimethylphenyl}-2,3-dihydro-1-benzofuran-3-yl]amino}-2,3-dihydro-1-benzofuran-3-yl]acetic acid | 1258396-42-7 | C34H40N2O5 |
| —— | 4-amino-2,3-dihydro-1-benzofuran-7-carboxylic acid methyl ester | 1620412-64-7 | C10H11NO3 |
| —— | trans-2,3-Dibromo-3-deuterio-2,3-dihydrobenzofuran | 68051-08-1 | C8H6Br2O |
| —— | 4-(1-(3-chlorophenyl)vinyl)-5-methyl-2,3-dihydrobenzofuran | 1582778-64-0 | C17H15ClO |