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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
    —— methyl 4-[(1S,2S,7R,9S)-5-methyl-4,6,10-trioxatetracyclo[7.7.0.02,7.011,16]hexadeca-11,13,15-trien-12-yl]butanoate 88277-18-3 C19H24O5
    methyl 4-[(1S,2S,7R,9S)-5-methyl-4,6,10-trioxatetracyclo[7.7.0.02,7.011,16]hexadeca-11,13,15-trien-12-yl]butanoate
    —— 5-(2,4-Bisacetylaminophenyloxy)-3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran 216989-35-4 C32H38N2O4
    5-(2,4-Bisacetylaminophenyloxy)-3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran
    —— 1-[2-(2,3-Dihydro-benzofuran-5-yl)-2-oxo-ethyl]-3,5,7-triaza-1-azonia-tricyclo[3.3.1.1<sup>3,7</sup>]decane; bromide 151427-20-2 Br*C16H21N4O2
    1-[2-(2,3-Dihydro-benzofuran-5-yl)-2-oxo-ethyl]-3,5,7-triaza-1-azonia-tricyclo[3.3.1.1<sup>3,7</sup>]decane; bromide
    —— (3S,3aR,8bS)-(-)-2,3,3a,8b-Tetrahydro-3-hydroxy-3,3a,6,8b-tetramethyl-1H-cyclopenta<b>benzofuran 154800-88-1 C15H20O2
    (3S,3aR,8bS)-(-)-2,3,3a,8b-Tetrahydro-3-hydroxy-3,3a,6,8b-tetramethyl-1H-cyclopenta<b>benzofuran
    —— 1-[2-hydroxy-4(methanesulfonyl-2,3-dihydrobenzofuran-7-yl)-4-methyl-2-trifluoromethylpentyl]-3,5-dimethyl-1H-pyridin-4-one 727375-15-7 C23H28F3NO5S
    1-[2-hydroxy-4(methanesulfonyl-2,3-dihydrobenzofuran-7-yl)-4-methyl-2-trifluoromethylpentyl]-3,5-dimethyl-1H-pyridin-4-one
    —— (S)-2-acetyl-2-methyl-2,3-dihydrobenzofuran 221665-72-1 C11H12O2
    (S)-2-acetyl-2-methyl-2,3-dihydrobenzofuran
    —— 2-Benzylthiomethyl-5-formylamino-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran 142874-10-0 C21H25NO2S
    2-Benzylthiomethyl-5-formylamino-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran
    —— N-{2-[2-(4-fluorophenyl)ethyl]-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranyl}formamide 186039-28-1 C21H24FNO2
    N-{2-[2-(4-fluorophenyl)ethyl]-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranyl}formamide
    —— 2-[(2S)-6-methoxy-2,3-dihydro-1-benzofuran-2-yl]propan-2-ol 239445-75-1 C12H16O3
    2-[(2S)-6-methoxy-2,3-dihydro-1-benzofuran-2-yl]propan-2-ol
    —— 2-(4-Fluorophenyl) thiomethyl-5-formylamino-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran 142874-05-3 C20H22FNO2S
    2-(4-Fluorophenyl) thiomethyl-5-formylamino-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran
    —— 5-Formylamino-2,4,6,7-tetramethyl-2-propylthiomethyl-2,3-dihydrobenzofuran 142874-11-1 C17H25NO2S
    5-Formylamino-2,4,6,7-tetramethyl-2-propylthiomethyl-2,3-dihydrobenzofuran
    —— 6,12,19,25-Tetratert-butyl-2,15-dioxaheptacyclo[21.3.1.11,4.110,14.114,17.03,8.016,21]triaconta-3(8),4,6,10,12,16(21),17,19,23,25-decaene-27,29-dione 138899-86-2 C44H52O4
    6,12,19,25-Tetratert-butyl-2,15-dioxaheptacyclo[21.3.1.11,4.110,14.114,17.03,8.016,21]triaconta-3(8),4,6,10,12,16(21),17,19,23,25-decaene-27,29-dione
    —— 6,12,19,25-Tetratert-butyl-2,16-dioxaheptacyclo[21.3.1.11,4.114,17.117,21.03,8.010,15]triaconta-3(8),4,6,10(15),11,13,18,20,23,25-decaene-27,28-dione 138899-87-3 C44H52O4
    6,12,19,25-Tetratert-butyl-2,16-dioxaheptacyclo[21.3.1.11,4.114,17.117,21.03,8.010,15]triaconta-3(8),4,6,10(15),11,13,18,20,23,25-decaene-27,28-dione
    —— 5-Formylamino-2,4,6,7-tetramethyl-2-(pyridin-4-yl)thiomethyl-2,3-dihydrobenzofuran 142874-09-7 C19H22N2O2S
    5-Formylamino-2,4,6,7-tetramethyl-2-(pyridin-4-yl)thiomethyl-2,3-dihydrobenzofuran
    —— 2,2,6,7-Tetramethyl-4-nitro-2,3-dihydro-benzofuran-5-ylamine 693769-60-7 C12H16N2O3
    2,2,6,7-Tetramethyl-4-nitro-2,3-dihydro-benzofuran-5-ylamine
    —— 5-Formylamino-2-(2-hydroxyethyl)thiomethyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran 142874-12-2 C16H23NO3S
    5-Formylamino-2-(2-hydroxyethyl)thiomethyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran
    —— 6-(7-tert-Butyl-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-2,3-dihydro-imidazo[2,1-b]thiazole 1-oxide 194592-49-9 C19H24N2O2S
    6-(7-tert-Butyl-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-2,3-dihydro-imidazo[2,1-b]thiazole 1-oxide
    —— 5-Formylamino-2,4,6,7-tetramethyl-2-phenylthiomethyl-2,3-dihydrobenzofuran 142874-04-2 C20H23NO2S
    5-Formylamino-2,4,6,7-tetramethyl-2-phenylthiomethyl-2,3-dihydrobenzofuran
    —— 7-Methoxy-2,3,3a,8a-tetrahydro-benzo[b]furo[3,2-d]furan-2-ol 214423-20-8 C11H12O4
    7-Methoxy-2,3,3a,8a-tetrahydro-benzo[b]furo[3,2-d]furan-2-ol
    —— 4-{(1R,2R,3aS,8bS)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl}-butyric acid methyl ester 163565-89-7 C36H62O5Si2
    4-{(1R,2R,3aS,8bS)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl}-butyric acid methyl ester
    —— (Z)-3-{7-[3-(2-tert-Butoxycarbonylamino-ethyl)-1H-indol-4-yl]-3-phenyl-2,3-dihydro-benzofuran-3-yl}-acrylic acid methyl ester 918304-74-2 C33H34N2O5
    (Z)-3-{7-[3-(2-tert-Butoxycarbonylamino-ethyl)-1H-indol-4-yl]-3-phenyl-2,3-dihydro-benzofuran-3-yl}-acrylic acid methyl ester
    —— (5'aR,9'aS)-2'-bromospiro[1,3-dioxolane-2,7'-5a,6,8,9-tetrahydrodibenzofuran]-9'a-carbaldehyde 1334171-22-0 C15H15BrO4
    (5'aR,9'aS)-2'-bromospiro[1,3-dioxolane-2,7'-5a,6,8,9-tetrahydrodibenzofuran]-9'a-carbaldehyde
    —— (5aR,9aR)-2-bromo-7-oxo-5a,6,8,9-tetrahydrodibenzofuran-9a-carbonitrile 1334171-20-8 C13H10BrNO2
    (5aR,9aR)-2-bromo-7-oxo-5a,6,8,9-tetrahydrodibenzofuran-9a-carbonitrile
    —— {2-[4-(3-Phenyl-3-triisopropylsilanyloxymethyl-2,3-dihydro-benzofuran-7-yl)-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester 217493-26-0 C39H52N2O4Si
    {2-[4-(3-Phenyl-3-triisopropylsilanyloxymethyl-2,3-dihydro-benzofuran-7-yl)-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester
    —— 2-isopropenyl-6-(methoxymethyl)oxy-2,3-dihydrobenzofuran-5-carbaldehyde 581096-54-0 C14H16O4
    2-isopropenyl-6-(methoxymethyl)oxy-2,3-dihydrobenzofuran-5-carbaldehyde
    —— benzodifurantrione 157462-65-2 C16H8O5
    benzodifurantrione
    —— (5'aR,9'aR)-2'-bromospiro[1,3-dioxolane-2,7'-5a,6,8,9-tetrahydrodibenzofuran]-9'a-carbonitrile 1334171-21-9 C15H14BrNO3
    (5'aR,9'aR)-2'-bromospiro[1,3-dioxolane-2,7'-5a,6,8,9-tetrahydrodibenzofuran]-9'a-carbonitrile
    —— (1R,7S,9S,17R)-7,9,12,17-tetramethyl-6,10,18-trioxatetracyclo[13.2.1.05,17.011,16]octadeca-4,11,13,15-tetraen-3-one 208708-82-1 C19H22O4
    (1R,7S,9S,17R)-7,9,12,17-tetramethyl-6,10,18-trioxatetracyclo[13.2.1.05,17.011,16]octadeca-4,11,13,15-tetraen-3-one
    —— (3aR,8bS)-3a,6,8b-Trimethyl-1,2,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-3-one 362057-03-2 C14H16O2
    (3aR,8bS)-3a,6,8b-Trimethyl-1,2,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-3-one
    —— methyl (2S)-2-ethyl-5-hydroxy-2,3-dihydro-1-benzofuran-2-carboxylate 653578-63-3 C12H14O4
    methyl (2S)-2-ethyl-5-hydroxy-2,3-dihydro-1-benzofuran-2-carboxylate
    —— (-)-(3R,3aR,8bS)-cis-3a,7,8b-trimethyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-3-yl acetate 681035-73-4 C16H20O3
    (-)-(3R,3aR,8bS)-cis-3a,7,8b-trimethyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-3-yl acetate
    —— (R)-2-(1,1-dimethyl-2-p-tolyl-ethyl)-2,3-dihydrobenzofuran 647033-36-1 C19H22O
    (R)-2-(1,1-dimethyl-2-p-tolyl-ethyl)-2,3-dihydrobenzofuran
    —— 4-(2-Chlorophenylamino)-2-(2,3-dihydrobenzofuran-5-yl)thiazole-5-carboxylic acid 861708-34-1 C18H13ClN2O3S
    4-(2-Chlorophenylamino)-2-(2,3-dihydrobenzofuran-5-yl)thiazole-5-carboxylic acid
    —— 4-(2-chlorophenylamino)-2-(2,3-dihydrobenzofuran-5-yl)thiazole-5-carboxylic acid amide 861708-36-3 C18H14ClN3O2S
    4-(2-chlorophenylamino)-2-(2,3-dihydrobenzofuran-5-yl)thiazole-5-carboxylic acid amide
    —— (-)-(3aR,8bS)-cis-3a,7,8b-trimethyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-3-one 681035-74-5 C14H16O2
    (-)-(3aR,8bS)-cis-3a,7,8b-trimethyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-3-one
    —— 6,12,18,24,30,36-Hexatert-butyl-39,40,41,42-tetrahydroxy-2-oxaoctacyclo[32.3.1.11,4.110,14.116,20.122,26.128,32.03,8]tritetraconta-3(8),4,6,10,12,14(42),16,18,20(41),22(40),23,25,28(39),29,31,34,36-heptadecaen-38-one 171668-14-7 C66H82O6
    6,12,18,24,30,36-Hexatert-butyl-39,40,41,42-tetrahydroxy-2-oxaoctacyclo[32.3.1.11,4.110,14.116,20.122,26.128,32.03,8]tritetraconta-3(8),4,6,10,12,14(42),16,18,20(41),22(40),23,25,28(39),29,31,34,36-heptadecaen-38-one
    —— tert-butyl N-[(5S)-6-azido-5-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylcarbamothioylamino]hexyl]carbamate 869735-67-1 C25H40N6O5S2
    tert-butyl N-[(5S)-6-azido-5-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylcarbamothioylamino]hexyl]carbamate
    —— Ethyl 2,3-dihydro-2-methyl-7-benzofurancarboxylate 183673-67-8 C12H14O3
    Ethyl 2,3-dihydro-2-methyl-7-benzofurancarboxylate
    —— tert-butyl N-[(5S)-5-azido-6-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylcarbamothioylamino]hexyl]carbamate 869736-03-8 C25H40N6O5S2
    tert-butyl N-[(5S)-5-azido-6-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylcarbamothioylamino]hexyl]carbamate
    —— 5-chloro-6-methyl-2-(4-methyl)phenyldihydrobenzofuranol 842169-04-4 C16H15ClO2
    5-chloro-6-methyl-2-(4-methyl)phenyldihydrobenzofuranol
    —— (3S)-1-(4-methylphenyl)-3-[(3S)-2-oxo-3-phenyl-1-benzofuran-3-yl]pyrrolidine-2,5-dione 1258326-10-1 C25H19NO4
    (3S)-1-(4-methylphenyl)-3-[(3S)-2-oxo-3-phenyl-1-benzofuran-3-yl]pyrrolidine-2,5-dione
    —— (S)-6,7-dichloro-5-(N,N-dimethylsulfamoyl)-2,3-dihydrobenzo<b>furan-2-carboxylic acid 108940-99-4 C11H11Cl2NO5S
    (S)-6,7-dichloro-5-(N,N-dimethylsulfamoyl)-2,3-dihydrobenzo<b>furan-2-carboxylic acid
    —— Methyl 1-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)azetidine-3-carboxylate 1392442-68-0 C13H15NO5S
    Methyl 1-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)azetidine-3-carboxylate
    —— (11S)-25-(methoxymethyl)-8-methyl-11-phenyl-9,13,28-trioxa-4,7,25-triazaheptacyclo[18.6.1.12,5.06,10.011,15.014,19.024,27]octacosa-1(26),2,4,6(10),7,14(19),15,17,20(27),21,23-undecaene 405519-85-9 C31H23N3O4
    (11S)-25-(methoxymethyl)-8-methyl-11-phenyl-9,13,28-trioxa-4,7,25-triazaheptacyclo[18.6.1.12,5.06,10.011,15.014,19.024,27]octacosa-1(26),2,4,6(10),7,14(19),15,17,20(27),21,23-undecaene
    —— 2-(5,7-difluoro-2,3-dihydrobenzofuran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 1395284-03-3 C14H17BF2O3
    2-(5,7-difluoro-2,3-dihydrobenzofuran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
    —— 7-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1-benzofuran 1154740-44-9 C14H18BClO3
    7-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1-benzofuran
    —— 4,4,5,5-Tetramethyl-2-(4-methyl-2,3-dihydrobenzofuran-5-yl)-1,3,2-dioxaborolane 1154740-64-3 C15H21BO3
    4,4,5,5-Tetramethyl-2-(4-methyl-2,3-dihydrobenzofuran-5-yl)-1,3,2-dioxaborolane
    —— 1-(5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)-N,N-dimethylmethanamine 1243544-95-7 C15H22BrNO
    1-(5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)-N,N-dimethylmethanamine
    —— 1-(5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methanamine 1243544-94-6 C13H18BrNO
    1-(5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methanamine
    —— (1S,14R,27R,29S)-6,12,19,25-tetratert-butyl-2,15-dioxaheptacyclo[21.3.1.11,4.110,14.114,17.03,8.016,21]triaconta-3(8),4,6,10,12,16(21),17,19,23,25-decaene-27,29-diol 379707-54-7 C44H56O4
    (1S,14R,27R,29S)-6,12,19,25-tetratert-butyl-2,15-dioxaheptacyclo[21.3.1.11,4.110,14.114,17.03,8.016,21]triaconta-3(8),4,6,10,12,16(21),17,19,23,25-decaene-27,29-diol