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香豆素

香豆素 基本信息

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 结构式图片
—— 2-[6-bromo-2-hydroxy-5-(4-hydroxy-4-methylpent-2-enyl)-5,8a-dimethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-yl]-2,3-dihydro-1-benzofuran-5-carboxylic acid —— C27H37BrO5
2-[6-bromo-2-hydroxy-5-(4-hydroxy-4-methylpent-2-enyl)-5,8a-dimethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-yl]-2,3-dihydro-1-benzofuran-5-carboxylic acid
—— 7-Chloro-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-ol —— C11H13ClO3
7-Chloro-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-ol
—— 3-Hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid —— C12H14O5
3-Hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid
—— 7-(8-Hydroxy-1,2,3,4,4a,9b-hexahydrodibenzofuran-1-yl)-4-methoxy-6-methylhepta-2,4,6-trienoic acid —— C21H24O5
7-(8-Hydroxy-1,2,3,4,4a,9b-hexahydrodibenzofuran-1-yl)-4-methoxy-6-methylhepta-2,4,6-trienoic acid
—— 5-Methoxy-2-prop-1-en-2-yl-2,3-dihydro-1-benzofuran-6-ol —— C12H14O3
5-Methoxy-2-prop-1-en-2-yl-2,3-dihydro-1-benzofuran-6-ol
—— 2-(Hydroxymethyl)-5-(2-hydroxy-5-prop-2-enylphenyl)-2,3-dihydro-1-benzofuran-3-ol —— C18H18O4
2-(Hydroxymethyl)-5-(2-hydroxy-5-prop-2-enylphenyl)-2,3-dihydro-1-benzofuran-3-ol
—— 1-(5-Methoxy-2-prop-1-en-2-yl-2,3-dihydro-1-benzofuran-4-yl)ethanol —— C14H18O3
1-(5-Methoxy-2-prop-1-en-2-yl-2,3-dihydro-1-benzofuran-4-yl)ethanol
—— 7-(Hydroxymethyl)-2-(2-hydroxypropan-2-yl)-6-pentyl-2,3-dihydro-1-benzofuran-3-ol —— C17H26O4
7-(Hydroxymethyl)-2-(2-hydroxypropan-2-yl)-6-pentyl-2,3-dihydro-1-benzofuran-3-ol
—— 6a-hydroxy-3,9-dimethoxypterocarpan —— C17H18O5
6a-hydroxy-3,9-dimethoxypterocarpan
—— 2,3-dihydro-2-methylbenzofuran-4-carboxylic acid 1261963-74-9 C10H10O3
2,3-dihydro-2-methylbenzofuran-4-carboxylic acid
—— 6-methoxy-2,3,3-trimethyl-4-phenyl-2H-1-benzofuran —— C18H20O2
6-methoxy-2,3,3-trimethyl-4-phenyl-2H-1-benzofuran
—— 3-[2-(2-Hydroxypropan-2-yl)-4-[2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxy-2,3-dihydro-1-benzofuran-5-yl]propanoic acid —— C21H30O9
3-[2-(2-Hydroxypropan-2-yl)-4-[2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxy-2,3-dihydro-1-benzofuran-5-yl]propanoic acid
—— 2-(1-Acetyloxy-2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid —— C14H16O6
2-(1-Acetyloxy-2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid
—— 2-[5-(3-Hydroxyprop-1-enyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]propan-2-ol —— C15H20O4
2-[5-(3-Hydroxyprop-1-enyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]propan-2-ol
—— 1,1,4a,6-tetramethylspiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-6,7-dihydro-3H-furo[3,2-g][1]benzofuran]-2,4',7'-triol —— C23H32O5
1,1,4a,6-tetramethylspiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-6,7-dihydro-3H-furo[3,2-g][1]benzofuran]-2,4',7'-triol
—— Methyl 2-[2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-6-yl]acetate —— C14H18O4
Methyl 2-[2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-6-yl]acetate
—— Ethyl 4-hydroxy-3-(4-hydroxyphenyl)-2-[[2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]methyl]-5-oxofuran-2-carboxylate —— C25H26O8
Ethyl 4-hydroxy-3-(4-hydroxyphenyl)-2-[[2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]methyl]-5-oxofuran-2-carboxylate
—— 2-Prop-1-en-2-yl-2,3-dihydro-1-benzofuran-6-ol —— C11H12O2
2-Prop-1-en-2-yl-2,3-dihydro-1-benzofuran-6-ol
—— 2-(2-Hydroxy-6-methylhept-5-en-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid —— C17H22O4
2-(2-Hydroxy-6-methylhept-5-en-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid
—— 3-Hydroxy-2-(1,2,3-trihydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde —— C12H14O6
3-Hydroxy-2-(1,2,3-trihydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde
—— 5-(2,3-dihydro-1-benzofuran-5-yl)-N-[3-(morpholin-4-yl)propyl]-1H-pyrazole-3-carboxamide —— C19H24N4O3
5-(2,3-dihydro-1-benzofuran-5-yl)-N-[3-(morpholin-4-yl)propyl]-1H-pyrazole-3-carboxamide
—— 2-Hydroxy-1-[4-hydroxy-7-(3-methylbut-2-enyl)-2-(3,3,5-trimethylhex-4-enyl)-2,3-dihydro-1-benzofuran-5-yl]ethanone —— C24H34O4
2-Hydroxy-1-[4-hydroxy-7-(3-methylbut-2-enyl)-2-(3,3,5-trimethylhex-4-enyl)-2,3-dihydro-1-benzofuran-5-yl]ethanone
—— 2-[5-(Hydroxymethyl)-2,3-dihydro-1-benzofuran-2-yl]propane-1,2-diol —— C12H16O4
2-[5-(Hydroxymethyl)-2,3-dihydro-1-benzofuran-2-yl]propane-1,2-diol
—— 2,3-Dihydro-N-[2-(1H-imidazol-5-yl)ethyl]-6-benzofuranacetamide —— C15H17N3O2
2,3-Dihydro-N-[2-(1H-imidazol-5-yl)ethyl]-6-benzofuranacetamide
—— Methyl 7-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylate —— C13H16O5
Methyl 7-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylate
—— 3,3a-Dimethyl-3,8b-dihydrocyclopenta[b][1]benzofuran —— C13H14O
3,3a-Dimethyl-3,8b-dihydrocyclopenta[b][1]benzofuran
—— Methyl 3-(3-(2-(2,3-dihydrobenzofuran-5-yl)ethoxy)-4-methoxyphenyl)-3-(1-(3,4-dihydroxyphenethyl)-4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)propanoate —— C35H37NO9
Methyl 3-(3-(2-(2,3-dihydrobenzofuran-5-yl)ethoxy)-4-methoxyphenyl)-3-(1-(3,4-dihydroxyphenethyl)-4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)propanoate
—— 9-Methoxy-11-oxatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraene —— C17H20O2
9-Methoxy-11-oxatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraene
—— N-(2,3-dihydro-1-benzofuran-2-ylmethyl)-2-[2-(4-methoxyphenyl)-5-methyl-7-oxo-7H-furo[3,2-b]pyran-3-yl]acetamide —— C26H23NO6
N-(2,3-dihydro-1-benzofuran-2-ylmethyl)-2-[2-(4-methoxyphenyl)-5-methyl-7-oxo-7H-furo[3,2-b]pyran-3-yl]acetamide
—— 3-Hydroxy-2-(2-hydroxypropan-2-yl)-7-(3-methylbut-2-enyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid —— C17H22O5
3-Hydroxy-2-(2-hydroxypropan-2-yl)-7-(3-methylbut-2-enyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid
—— 2-(2,3-dihydro-1-benzofuran-6-yl)-N-{[4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-yl]methyl}acetamide —— C23H27NO4
2-(2,3-dihydro-1-benzofuran-6-yl)-N-{[4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-yl]methyl}acetamide
—— 2-[6-bromo-2-hydroxy-5,8a-dimethyl-5-(4-methyl-3-oxopent-4-enyl)-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-yl]-2,3-dihydro-1-benzofuran-5-carboxylic acid —— C27H35BrO5
2-[6-bromo-2-hydroxy-5,8a-dimethyl-5-(4-methyl-3-oxopent-4-enyl)-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-yl]-2,3-dihydro-1-benzofuran-5-carboxylic acid
—— 1-(2-Prop-1-en-2-yl-2,3-dihydro-1-benzofuran-5-yl)propane-1,2-diol —— C14H18O3
1-(2-Prop-1-en-2-yl-2,3-dihydro-1-benzofuran-5-yl)propane-1,2-diol
—— 2-[6-bromo-2-hydroxy-5,8a-dimethyl-5-(4-methylpent-3-enyl)-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-yl]-2,3-dihydro-1-benzofuran-5-carboxylic acid —— C27H37BrO4
2-[6-bromo-2-hydroxy-5,8a-dimethyl-5-(4-methylpent-3-enyl)-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-yl]-2,3-dihydro-1-benzofuran-5-carboxylic acid
—— 5-(2,3-dihydro-1-benzofuran-5-yl)-N-[2-(4-hydroxyphenyl)ethyl]-1H-pyrazole-3-carboxamide —— C20H19N3O3
5-(2,3-dihydro-1-benzofuran-5-yl)-N-[2-(4-hydroxyphenyl)ethyl]-1H-pyrazole-3-carboxamide
—— 3-[5-(3-Methoxybuta-1,3-dienyl)-2,3-dihydro-1-benzofuran-2-yl]pentan-3-ol —— C18H24O3
3-[5-(3-Methoxybuta-1,3-dienyl)-2,3-dihydro-1-benzofuran-2-yl]pentan-3-ol
—— methyl 2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-5-carboxylate —— C13H14O3
methyl 2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-5-carboxylate
—— 1-[5-Hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-4-yl]-2-methylpropan-1-one —— C15H20O4
1-[5-Hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-4-yl]-2-methylpropan-1-one
—— Methyl 3-(2-prop-1-en-2-yl-2,3-dihydro-1-benzofuran-5-yl)prop-2-enoate —— C15H16O3
Methyl 3-(2-prop-1-en-2-yl-2,3-dihydro-1-benzofuran-5-yl)prop-2-enoate
—— 1-[3-(3-Methylbutanoyloxy)-2-(3-oxoprop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-yl]ethyl 2-methylbutanoate —— C23H30O6
1-[3-(3-Methylbutanoyloxy)-2-(3-oxoprop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-yl]ethyl 2-methylbutanoate
—— 1-[2-(3-Oxoprop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-yl]ethyl 2-methylbut-2-enoate —— C18H20O4
1-[2-(3-Oxoprop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-yl]ethyl 2-methylbut-2-enoate
—— methyl3-[5-[2-(2,3-dihydro-1-benzofuran-5-yl)ethoxy]-4-methoxycyclohepta-1,3,6-trien-1-yl]-3-[2-[6,7-dihydroxy-4-(4,5-dihydroxycyclohexa-1,3-dien-1-yl)cyclohexa-1,5-dien-1-yl]ethyl-hydroxy-5-oxo-1-azacyclohepta-3,6-dien-4-yl]propanoate —— C35H37NO9
methyl3-[5-[2-(2,3-dihydro-1-benzofuran-5-yl)ethoxy]-4-methoxycyclohepta-1,3,6-trien-1-yl]-3-[2-[6,7-dihydroxy-4-(4,5-dihydroxycyclohexa-1,3-dien-1-yl)cyclohexa-1,5-dien-1-yl]ethyl-hydroxy-5-oxo-1-azacyclohepta-3,6-dien-4-yl]propanoate
—— 2-(5-Formyl-2,3-dihydro-1-benzofuran-2-yl)prop-2-enyl 2-methylpropanoate —— C16H18O4
2-(5-Formyl-2,3-dihydro-1-benzofuran-2-yl)prop-2-enyl 2-methylpropanoate
—— 4-(2-hydroxy-5,7-dimethyl-3H-1-benzofuran-2-yl)piperidine-2,6-dione —— C15H17NO4
4-(2-hydroxy-5,7-dimethyl-3H-1-benzofuran-2-yl)piperidine-2,6-dione
—— 2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-5-carbaldehyde 69745-01-3 C12H12O2
2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-5-carbaldehyde
—— [2-(Hydroxymethyl)-6-[3-(hydroxymethyl)-2-methoxy-2,3-dihydro-1-benzofuran-6-yl]-2,3-dihydro-1-benzofuran-3-yl]methanol —— C20H22O6
[2-(Hydroxymethyl)-6-[3-(hydroxymethyl)-2-methoxy-2,3-dihydro-1-benzofuran-6-yl]-2,3-dihydro-1-benzofuran-3-yl]methanol
—— 2-Hydroxy-1-(2-prop-1-en-2-yl-2,3-dihydro-1-benzofuran-5-yl)propan-1-one —— C14H16O3
2-Hydroxy-1-(2-prop-1-en-2-yl-2,3-dihydro-1-benzofuran-5-yl)propan-1-one
—— 1-[7-(Hydroxymethyl)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-6-yl]propane-1,2-diol —— C15H22O5
1-[7-(Hydroxymethyl)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-6-yl]propane-1,2-diol
—— methyl 2-methyl-2,3-dihydrobenzofuran-7-carboxylate 41176-57-2 C11H12O3
methyl 2-methyl-2,3-dihydrobenzofuran-7-carboxylate
—— 2-(2,3-Dihydro-1-benzofuran-6-YL)-N-[3-(morpholin-4-YL)propyl]acetamide —— C17H24N2O3
2-(2,3-Dihydro-1-benzofuran-6-YL)-N-[3-(morpholin-4-YL)propyl]acetamide