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 |
|---|---|---|---|
| —— | 3-hydroxy-2-methoxy-2-<i>p</i>-tolyl-2,3-dihydro-benzofuran-3-carboxylic acid | 42856-82-6 | C17H16O5 |
| —— | 5-methanesulfonyloxy-3,3,6-trimethyl-2-morpholin-4-yl-2,3-dihydro-benzofuran | 26225-71-8 | C16H23NO5S |
| —— | 1-(5-methoxy-2,2-dimethyl-2,3-dihydro-benzofuran-3-yl)-piperidine | 53903-28-9 | C16H23NO2 |
| —— | 2-[(benzyloxy)methyl]-5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran | 1243545-32-5 | C20H23BrO2 |
| —— | 3,8-dimethyl-5a-phenyl-benzo[<i>b</i>]benzo[4,5]furo[3,2-<i>d</i>]furan-10b-carboxylic acid ethyl ester | 32590-99-1 | C25H22O4 |
| —— | 1280210-06-1 | C24H27F2N7O2 | |
| —— | dimethyl 1',6-dimethyl-2-methylene-5',6'-dihydro-1'H-spiro[1-benzofuran-3,4'-pyridine]-2',3'-dicarboxylate | 1391817-59-6 | C19H21NO5 |
| —— | ethyl (Z)-2-(((4-chlorophenyl)sulfonyl)methylene)-6-ethyl-4-hydroxychromane-4-carboxylate | 1380746-02-0 | C21H21ClO6S |
| —— | 1,1-dimethylethyl-N-[((5aS,9aS)-9a-(hydroxyethyl)-4-(methyloxy)-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-1-yl)methyl]-N-methylcarbamate | 939438-14-9 | C22H31NO5 |
| —— | 2,3-dihydro-3,3-dimethyl-2-piperidino-benzofuran-5-yl methanesulphonate | 26225-62-7 | C16H23NO4S |
| —— | potassium;6,7-dichloro-5-(dimethylsulfamoyl)-2,3-dihydro-1-benzofuran-2-carboxylate | 103969-49-9 | C11H10Cl2NO5S*K |
| —— | 4-[(5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methyl]thiomorpholine 1,1-dioxide | 1243545-07-4 | C17H24BrNO3S |
| —— | (+)-(2R,3S)-2,3-dihydroxy-2,3-dihydro-2-methyl[b]benzofuran | 183812-30-8 | C9H10O3 |
| —— | 2,9-dimethyl-5a-phenyl-benzo[<i>b</i>]benzo[4,5]furo[3,2-<i>d</i>]furan-10b-carboxylic acid ethyl ester | 32590-96-8 | C25H22O4 |
| —— | 5-bromo-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran | 1243544-82-2 | C12H15BrO |
| —— | 4,4a,9,9a-Tetrahydro-2,5,7,9a-tetramethyl-4-methylen-xanthen-3-on | 40053-94-9 | C18H20O2 |
| —— | 52592-60-6 | C18H20O4 | |
| —— | (5a'R,7'R,8'S,10'S,10a'S)-10a'-(2-hydroxyethyl)-4'-methoxy-5a',7',8',9',10',10a'-hexahydrospiro[[1,3]dioxolane-2,6'-[7,10]methanocyclohepta[b]benzofuran]-8'-ol | 358753-72-7 | C19H24O6 |
| —— | 4,5,6-trichloro-2,3-dihydro-benzofuran | 52962-17-1 | C8H5Cl3O |
| —— | 1203447-61-3 | C12H12O | |
| —— | Acetic acid (3aS,8bS)-8-acetyl-5,6-dichloro-3a,8b-dihydro-1H-benzo[b]cyclopenta[d]furan-7-yl ester | 79756-08-4 | C15H12Cl2O4 |
| —— | 3-hexyl-5-methanesulfonyloxy-2-morpholin-4-yl-2,3-dihydro-benzofuran | 26225-70-7 | C19H29NO5S |
| —— | 1-ethyl-2-oxa-3,4-benzobicyclo<4.2.0>octan-8-one | 99477-39-1 | C13H14O2 |
| —— | ethyl (R)-4-((2R,4R)-7-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxy-5-methoxy-2-methylchroman-2-yl)-4-hydroxybutanoate | 1360932-92-8 | C34H44O7Si |
| —— | 7-ethoxy-2,4,6-trimethyl-2,3-dihydro-1-benzofuran | 1243544-37-7 | C13H18O2 |
| —— | 6-bromo-2,2,4,7-tetramethyl-2,3-dihydro-1-benzofuran-5-amine | 1243545-20-1 | C12H16BrNO |
| —— | 3-(5-bromo-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-yl)pyridine | 1243543-48-7 | C15H14BrNO |
| —— | (1R,3R)-3-[([(S)-1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-{4-[2-(2,5-dioxo-pyrrolidin-1-yl)-ethoxy]-3-methoxy-benzyl}-amino)-methyl]-cyclopentanecarboxylic acid | 1443020-81-2 | C31H38N2O7 |
| —— | [4-Hydroxy-7-methoxy-5-methyl-chromen-(2E)-ylidene]-acetic acid methyl ester | 41607-36-7 | C14H14O5 |
| —— | 1-(6-hydroxy-4-methoxy-2,3-dihydro-benzofuran-7-yl)-butane-1,3-dione | 854461-81-7 | C13H14O5 |
| —— | (R)-1-Hydroxy-9-isopropenyl-6-methylene-3-pentyl-5a,6,7,8,9,9a-hexahydro-dibenzofuran-2-carboxylic acid methyl ester | 55623-76-2 | C23H30O4 |
| —— | 2-[[dichloro-(4-methoxyphenyl)-λ4-tellanyl]methyl]-2,3-dihydro-1-benzofuran | 115022-82-7 | C16H16Cl2O2Te |
| —— | 2-(2,2,2-trifluoroethyl)-2,3-dihydrobenzofuran | 1391001-60-7 | C10H9F3O |
| —— | 5-butyl-2-methyl-4-[2-(2-methylprop-1-enyl)phenyl]-2-(prop-1-en-2-yl)-2,3-dihydrofuran | 1234172-73-6 | C22H30O |
| —— | N-benzyl-1-(5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)-N-methylmethanamine | 1243544-97-9 | C21H26BrNO |
| —— | 2-(4'-Methylphenyl)-thiomethyl-2,3-dihydrobenzofuran | 101041-40-1 | C16H16OS |
| —— | 5-bromo-2,4,6-trimethyl-7-(1-methylethoxy)-2,3-dihydro-1-benzofuran | 1243544-43-5 | C14H19BrO2 |
| —— | 3,4,5-Tribromo-4-phenyl-2,3,4,5-tetrahydro-benzo[b]oxepine | 54562-97-9 | C16H13Br3O |
| —— | 1-(2,3-Dihydro-benzofuran-3-yl)-2-methanesulfinylmethyl-3,3-dimethyl-butan-2-ol | 63755-75-9 | C16H24O3S |
| —— | 2,3,8,9-tetramethyl-5a-phenyl-benzo[<i>b</i>]benzo[4,5]furo[3,2-<i>d</i>]furan-10b-carboxylic acid ethyl ester | 32590-84-4 | C27H26O4 |
| —— | (R)-7,9-Dimethoxy-4,9b-dimethyl-3,9b-dihydro-dibenzofuran-1,2-dicarboxylic acid dimethyl ester | 40801-29-4 | C20H22O7 |
| —— | ethyl 2-acetylamino-3-(7-bromo-3-phenyl-2,3-dihydrobenzofuran-3-yl)-3-oxopropionate | 217493-20-4 | C21H20BrNO5 |
| —— | 5-bromo-7-methoxy-2,4,6-trimethyl-2,3-dihydro-1-benzofuran | 1243544-40-2 | C12H15BrO2 |
| —— | 5-ethanesulfonyloxy-3,3-dimethyl-2-(4-methyl-piperazin-1-yl)-2,3-dihydro-benzofuran | 26322-74-7 | C17H26N2O4S |
| —— | 1,3,11,13-tetrabromo-5a,6,7,8,8a,9-hexahydro-5H-chromeno[3,2-d]xanthene | 1374221-23-4 | C20H16Br4O2 |
| —— | 2-Aminomethyl-2,3,7,8-tetrahydro-2,5,8,8-tetramethyl-6H-furo[2,3-e]indol-7-thione·hydrochloride | 170684-47-6 | C15H20N2OS*ClH |
| —— | 7-ethoxy-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran | 1243544-59-3 | C14H20O2 |
| —— | 2,3,4,6-Tetramethyl-7-propyl-2,3-dihydrofuro<3,2-c>pyridin | 22871-39-2 | C14H21NO |
| —— | 5-bromo-7-ethoxy-2,4,6-trimethyl-2,3-dihydro-1-benzofuran | 1243544-41-3 | C13H17BrO2 |
| —— | (R)-3-((R)-6,7-Dichloro-2,3-dihydro-benzofuran-2-carbonyl)-4-phenyl-oxazolidin-2-one | 118196-05-7 | C18H13Cl2NO4 |