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    首页 分子通 按分子结构分类 有机化合物 有机杂环化合物 香豆素

    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。

    相关化合物

    中文名称 英文名称 CAS号 化学式 结构式图片
    —— N-(3-aminopropoxy)-N-(3-aminopropyl)-2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-sulfonamide —— C19H33N3O4S
    N-(3-aminopropoxy)-N-(3-aminopropyl)-2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-sulfonamide
    —— (3aS,5R,5aS,10bR,10cR)-3,3-dimethoxy-5-(1-trimethylsilylethenyl)-2,3a,4,5a,10b,10c-hexahydro-1H-indeno[5,4-b][1]benzofuran-5-ol —— C22H32O4Si
    (3aS,5R,5aS,10bR,10cR)-3,3-dimethoxy-5-(1-trimethylsilylethenyl)-2,3a,4,5a,10b,10c-hexahydro-1H-indeno[5,4-b][1]benzofuran-5-ol
    —— 5-ethylidene-2,3a,4,5a,10b,10c-hexahydro-1H-indeno[5,4-b][1]benzofuran-3-one —— C17H18O2
    5-ethylidene-2,3a,4,5a,10b,10c-hexahydro-1H-indeno[5,4-b][1]benzofuran-3-one
    —— N-[7-chloro-2-(furan-2-ylmethylidene)-5-methyl-1-benzofuran-3-ylidene]hydroxylamine —— C14H10ClNO3
    N-[7-chloro-2-(furan-2-ylmethylidene)-5-methyl-1-benzofuran-3-ylidene]hydroxylamine
    —— 1-Methyl-4-piperidinyl (2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)(hydroxy)phenylacetate —— C24H29NO4
    1-Methyl-4-piperidinyl (2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)(hydroxy)phenylacetate
    —— 1-Azabicyclo[2.2.2]oct-3-yl 3-phenyl-2,3-dihydro-1-benzofuran-3-carboxylate —— C22H23NO3
    1-Azabicyclo[2.2.2]oct-3-yl 3-phenyl-2,3-dihydro-1-benzofuran-3-carboxylate
    —— Magnolignan H —— C36H34O6
    Magnolignan H
    —— Furo[2, 2,3,3a,8a-tetrahydro-5,7-diiodo-4,6-dimethoxy-, cis- —— C12H12I2O4
    Furo[2, 2,3,3a,8a-tetrahydro-5,7-diiodo-4,6-dimethoxy-, cis-
    —— Furo[2, 2,3,3a,8a-tetrahydro-6-methoxy-, cis- —— C11H12O4
    Furo[2, 2,3,3a,8a-tetrahydro-6-methoxy-, cis-
    —— S-Ethyl 2-methyl-2,3-dihydro-1-benzofuran-2-carbothioate —— C12H14O2S
    S-Ethyl 2-methyl-2,3-dihydro-1-benzofuran-2-carbothioate
    —— Ethyl 3-hydroxy-3-methyl-5-nitro-2,3-dihydro-1-benzofuran-2-carboxylate —— C12H13NO6
    Ethyl 3-hydroxy-3-methyl-5-nitro-2,3-dihydro-1-benzofuran-2-carboxylate
    —— 3(2H)-benzofuranone hydrazone 34823-97-7 C8H8N2O
    3(2H)-benzofuranone hydrazone
    —— 1-[1-(2,3-dihydrobenzo[b]furan-7-yl)piperid-4-yl]methylamine 170353-56-7 C14H20N2O
    1-[1-(2,3-dihydrobenzo[b]furan-7-yl)piperid-4-yl]methylamine
    —— 3-benzyl-3-methoxycarbonyl-2,3-dihydrobenzofuran 642096-20-6 C17H16O3
    3-benzyl-3-methoxycarbonyl-2,3-dihydrobenzofuran
    —— endo-3-ethyl-1,3,3a,8a-tetrahydro-2H-benzofuro[2,3-b]pyrrol-2-one —— C12H13NO2
    endo-3-ethyl-1,3,3a,8a-tetrahydro-2H-benzofuro[2,3-b]pyrrol-2-one
    —— ethyl (2,3-dihydrobenzofuran-5-yl)glyoxylate 79002-49-6 C12H12O4
    ethyl (2,3-dihydrobenzofuran-5-yl)glyoxylate
    —— [(2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]carbamic acid 105641-63-2 C12H15NO3
    [(2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]carbamic acid
    —— 3-(5-Nitro-2,3-dihydro-benzofuran-7-yl)-pyridine 181633-04-5 C13H10N2O3
    3-(5-Nitro-2,3-dihydro-benzofuran-7-yl)-pyridine
    —— 7-Pyridin-3-yl-2,3-dihydro-benzofuran-5-ylamine 181633-07-8 C13H12N2O
    7-Pyridin-3-yl-2,3-dihydro-benzofuran-5-ylamine
    —— N-(5-Ethoxy-2,3-dihydro-2-methyl-6-benzofuranyl)spiro[bicyclo[3.3.1]nonane-9,2a(2)-[1,3]dithiolane]-3-carboxamide 1060814-44-9 C23H31NO3S2
    N-(5-Ethoxy-2,3-dihydro-2-methyl-6-benzofuranyl)spiro[bicyclo[3.3.1]nonane-9,2a(2)-[1,3]dithiolane]-3-carboxamide
    —— Pummerer ketone 546-24-7 C14H14O2
    Pummerer ketone
    —— Methyl 2-[[(2,3-dihydro-2-benzofuranyl)carbonyl]amino]-5-thiazolecarboxylate 1060803-73-7 C14H12N2O4S
    Methyl 2-[[(2,3-dihydro-2-benzofuranyl)carbonyl]amino]-5-thiazolecarboxylate
    —— 2-(5-cyano-2,3-dihydro-benzofuran-3-yl)-ethyl amine 328125-17-3 C11H12N2O
    2-(5-cyano-2,3-dihydro-benzofuran-3-yl)-ethyl amine
    —— 2,3-dihydro-2-ethylbenzo[b]furan-2-carboxamidine hydrochloride 1041187-03-4 C11H14N2O*ClH
    2,3-dihydro-2-ethylbenzo[b]furan-2-carboxamidine hydrochloride
    —— 2-(2,3-dihydro-2-ethylbenzo[b]furan-2-yl)-5-nitro-pyrimidine 1041187-04-5 C14H13N3O3
    2-(2,3-dihydro-2-ethylbenzo[b]furan-2-yl)-5-nitro-pyrimidine
    —— 2,3-dihydro-2,3-dimethyl-2,3-epoxy-7-methoxybenzofuran 150969-69-0 C11H12O3
    2,3-dihydro-2,3-dimethyl-2,3-epoxy-7-methoxybenzofuran
    —— 3-(4-Isopropylphenyl)-5-(2,4-dinitrophenyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran 216989-34-3 C28H30N2O6
    3-(4-Isopropylphenyl)-5-(2,4-dinitrophenyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran
    —— 5-(4-Bromo-2-methylphenyl)-2,3-dihydrobenzofuran 227305-70-6 C15H13BrO
    5-(4-Bromo-2-methylphenyl)-2,3-dihydrobenzofuran
    —— 5-bromo-2,3-dihydrobenzofuran-7-amine 219963-64-1 C8H8BrNO
    5-bromo-2,3-dihydrobenzofuran-7-amine
    —— N-(6-chloro-4,5-dimethylpyridin-2-yl)-1-(2,3-dihydrobenzofuran-5-yl)cyclopropanecarboxamide 1083168-79-9 C19H19ClN2O2
    N-(6-chloro-4,5-dimethylpyridin-2-yl)-1-(2,3-dihydrobenzofuran-5-yl)cyclopropanecarboxamide
    —— 7-amino-2,2,4,6-tetramethyl-2,3-dihydrobenzofuran 153880-26-3 C12H17NO
    7-amino-2,2,4,6-tetramethyl-2,3-dihydrobenzofuran
    —— N-methyl-1-phenyl-N-[(2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methyl]methanamine 1243544-96-8 C21H27NO
    N-methyl-1-phenyl-N-[(2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methyl]methanamine
    —— tert-butyl-dimethyl-(2-methylene-2,3-dihydro-benzofuran-7-yloxy)-silane 680203-67-2 C15H22O2Si
    tert-butyl-dimethyl-(2-methylene-2,3-dihydro-benzofuran-7-yloxy)-silane
    —— 2-<<(4-methoxyphenyl)thio>methyl>-2,3-dihydrobenzofuran 111017-50-6 C16H16O2S
    2-<<(4-methoxyphenyl)thio>methyl>-2,3-dihydrobenzofuran
    —— 2-((3S)-6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethanol 1452479-57-0 C17H16Cl2O3
    2-((3S)-6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethanol
    —— (4aS*,9bR*)-9b-cyanomethyl-6-methoxy-1,4,4a,9b-tetrahydrodibenzofuran-3(2H)-one ethylene acetal 115262-35-6 C17H19NO4
    (4aS*,9bR*)-9b-cyanomethyl-6-methoxy-1,4,4a,9b-tetrahydrodibenzofuran-3(2H)-one ethylene acetal
    —— (2-Methyl-2,3-dihydro-1-benzofuran-5-yl)acetic acid 889939-89-3 C11H12O3
    (2-Methyl-2,3-dihydro-1-benzofuran-5-yl)acetic acid
    —— 7-Ethylthio-2,3-dihydro-2,2-dimethyl-5-(2-methyl-1-propenyl)benzofuran 363185-39-1 C16H22OS
    7-Ethylthio-2,3-dihydro-2,2-dimethyl-5-(2-methyl-1-propenyl)benzofuran
    —— 3-(Biphenyl-4-yl)-5-bromo-4,6,7-trimethyl-2,3-dihydro-1-benzofuran 820259-06-1 C23H21BrO
    3-(Biphenyl-4-yl)-5-bromo-4,6,7-trimethyl-2,3-dihydro-1-benzofuran
    —— 3-(4-isopropylphenyl)-4,7-dimethyl-2,3-dihydro-1-benzofuran 820259-01-6 C19H22O
    3-(4-isopropylphenyl)-4,7-dimethyl-2,3-dihydro-1-benzofuran
    —— 7-nitro-2,3-dihydrobenzofuran-5-sulfonyl chloride 874781-18-7 C8H6ClNO5S
    7-nitro-2,3-dihydrobenzofuran-5-sulfonyl chloride
    —— tert-Butyl-((S)-3,6-dimethyl-2-vinyl-2,3-dihydro-benzofuran-5-yloxy)-dimethyl-silane 914086-83-2 C18H28O2Si
    tert-Butyl-((S)-3,6-dimethyl-2-vinyl-2,3-dihydro-benzofuran-5-yloxy)-dimethyl-silane
    —— (E)-4-[(S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,6-dimethyl-2,3-dihydro-benzofuran-2-yl]-2-methyl-but-3-en-2-ol 914086-85-4 C21H34O3Si
    (E)-4-[(S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,6-dimethyl-2,3-dihydro-benzofuran-2-yl]-2-methyl-but-3-en-2-ol
    —— benzofuran-3-one oxime 82415-84-7 C8H7NO2
    benzofuran-3-one oxime
    —— 7-ethoxy-2,3-dihydro-2,2-dimethyl-5-(2-methyl-1-propenyl)benzofuran 363185-22-2 C16H22O2
    7-ethoxy-2,3-dihydro-2,2-dimethyl-5-(2-methyl-1-propenyl)benzofuran
    —— 2,3-dihydro-7-methoxy-5-(2-methyl-1-propenyl)benzofuran 521068-45-1 C13H16O2
    2,3-dihydro-7-methoxy-5-(2-methyl-1-propenyl)benzofuran
    —— 3-(bromomethyl)-2,3-dihydrobenzofuran 78739-85-2 C9H9BrO
    3-(bromomethyl)-2,3-dihydrobenzofuran
    —— ethyl 2,2-dimethyl-5-(methylsulfonyl)-2,3-dihydrobenzofuran-7-carboxylate 1352740-14-7 C14H18O5S
    ethyl 2,2-dimethyl-5-(methylsulfonyl)-2,3-dihydrobenzofuran-7-carboxylate
    —— (2,2-dimethyl-2,3-dihydrobenzofuran-4-yI)methanol 209256-59-7 C11H14O2
    (2,2-dimethyl-2,3-dihydrobenzofuran-4-yI)methanol
    —— 3-(5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-propionic acid 623176-75-0 C13H15BrO3
    3-(5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-propionic acid