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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
    —— 2,3-dihydro-2-(E-1-propenyl)benzofuran 175845-40-6 C11H12O
    2,3-dihydro-2-(E-1-propenyl)benzofuran
    —— ethyl 7-[6-(t-butyl)-2,3-dihydro-2,2-dimethylbenzo[b]furan-7-yl]-5-hydroxy-3-oxoheptanoate 149245-87-4 C23H34O5
    ethyl 7-[6-(t-butyl)-2,3-dihydro-2,2-dimethylbenzo[b]furan-7-yl]-5-hydroxy-3-oxoheptanoate
    —— 4-hydroxy-6-methoxy-2,3,3a,8a-tetrahydrofuro<2,3-b>benzofuran —— C11H12O4
    4-hydroxy-6-methoxy-2,3,3a,8a-tetrahydrofuro<2,3-b>benzofuran
    —— methyl 7-[5-benzylamino-2,3-dihydro-2,2,4,6-tetramethylbenzo[b]furan-7-yl]-3,5-dihydroxyheptanoate 149245-25-0 C27H37NO5
    methyl 7-[5-benzylamino-2,3-dihydro-2,2,4,6-tetramethylbenzo[b]furan-7-yl]-3,5-dihydroxyheptanoate
    —— ethyl 5-(cyclopent-2-en-1-yl)-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate 1352740-50-1 C18H22O3
    ethyl 5-(cyclopent-2-en-1-yl)-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate
    —— 3-(4-chlorophenyl)-5-methylbenzofuran-2(3H)-one 1312118-63-0 C15H11ClO2
    3-(4-chlorophenyl)-5-methylbenzofuran-2(3H)-one
    —— 5-methyl-3-[5-methyl-2-hydroxyphenyl]benzofuran-2-(3H)-one 3778-52-7 C16H14O3
    5-methyl-3-[5-methyl-2-hydroxyphenyl]benzofuran-2-(3H)-one
    —— 4a,9b-dihydro-8,9b-dimethyl-3-(4H)-dibenzofuranone (Pummerer's ketone) 546-24-7 C14H14O2
    4a,9b-dihydro-8,9b-dimethyl-3-(4H)-dibenzofuranone (Pummerer's ketone)
    —— N-[3-(7-fluoro-2,3-dihydro-benzofuran-4-yl)-propyl]-acetamide 199391-04-3 C13H16FNO2
    N-[3-(7-fluoro-2,3-dihydro-benzofuran-4-yl)-propyl]-acetamide
    —— 5-hydroxy-2-oxo-3-(4-(carboxymethoxy)phenyl)-2,3-dihydrobenzofuran 120618-10-2 C16H12O6
    5-hydroxy-2-oxo-3-(4-(carboxymethoxy)phenyl)-2,3-dihydrobenzofuran
    —— 7-Bromo-2,3-dihydro-5-benzofuranpropanenitrile 135634-52-5 C11H10BrNO
    7-Bromo-2,3-dihydro-5-benzofuranpropanenitrile
    —— 1'-benzyl-3-(4-isopropylphenyl)-4,6,7-trimethylspiro[benzofuran-2(3H),4'-piperidine]-5-ol 216989-66-1 C31H37NO2
    1'-benzyl-3-(4-isopropylphenyl)-4,6,7-trimethylspiro[benzofuran-2(3H),4'-piperidine]-5-ol
    —— 6-[(7-Methoxy-1,3,7-trimethyloctyl)-oxy]-2,3-dihydrobenzofuran 51079-60-8 C20H32O3
    6-[(7-Methoxy-1,3,7-trimethyloctyl)-oxy]-2,3-dihydrobenzofuran
    —— 6-[(1,3,5-trimethylhexyl)-oxy]-2,3-dihydrobenzofuran 51079-51-7 C17H26O2
    6-[(1,3,5-trimethylhexyl)-oxy]-2,3-dihydrobenzofuran
    —— 2,3-dihydro-7-sulfamoyl-benzo[b]furan 89819-27-2 C8H9NO3S
    2,3-dihydro-7-sulfamoyl-benzo[b]furan
    —— 3-(2-methyl-2,3-dihydro-benzofuran-5-yl)-3-oxo-propionic acid ethyl ester 861850-98-8 C14H16O4
    3-(2-methyl-2,3-dihydro-benzofuran-5-yl)-3-oxo-propionic acid ethyl ester
    —— (+/-)-5-benzyloxy-2,3-dihydro-4,6,7-trimethyl-2-benzofuranethanamine 134867-34-8 C20H25NO2
    (+/-)-5-benzyloxy-2,3-dihydro-4,6,7-trimethyl-2-benzofuranethanamine
    —— N-[6-Benzyloxy-2,3-dihydrobenzofuran-3-yl]-hydroxylamine 139149-23-8 C15H15NO3
    N-[6-Benzyloxy-2,3-dihydrobenzofuran-3-yl]-hydroxylamine
    —— (+/-)-N-hydroxy-N-[2,3-dihydro-6-(benzyloxy)benzofuran-3-yl]urea 184575-08-4 C16H16N2O4
    (+/-)-N-hydroxy-N-[2,3-dihydro-6-(benzyloxy)benzofuran-3-yl]urea
    —— 2,3-dihydro-4-methyl-6-(propen-3-yl)-5-benzofuranol 119795-39-0 C12H14O2
    2,3-dihydro-4-methyl-6-(propen-3-yl)-5-benzofuranol
    —— 2,3-Dihydro-4-methyl-5-benzofuranol 90536-02-0 C9H10O2
    2,3-Dihydro-4-methyl-5-benzofuranol
    —— (S)-N-(6-benzyloxy-2,3-dihydrobenzofuran-3-yl)hydroxylamine 162750-07-4 C15H15NO3
    (S)-N-(6-benzyloxy-2,3-dihydrobenzofuran-3-yl)hydroxylamine
    —— 2-(1'-methylpropoxy)-2,3-dihydro-3-methylenebenzofuran 1187956-17-7 C13H16O2
    2-(1'-methylpropoxy)-2,3-dihydro-3-methylenebenzofuran
    —— 2,3-Dihydro-6,7-dimethoxy-5-hydroxy-3-butylidene-4-(2-propenyl)benzofuran 135482-15-4 C17H22O4
    2,3-Dihydro-6,7-dimethoxy-5-hydroxy-3-butylidene-4-(2-propenyl)benzofuran
    —— 2,2'-[(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)imino]diethanol 1243545-15-4 C17H27NO3
    2,2'-[(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)imino]diethanol
    —— YT-15 142874-28-0 C13H19NO
    YT-15
    —— (2,3-dihydrobenzofuran-5-yl)magnesium bromide 134401-95-9 C8H7BrMgO
    (2,3-dihydrobenzofuran-5-yl)magnesium bromide
    —— 2,3-dihydro-2-morpholino-5-trifluoromethanesulfonyloxy-3,3,7-trimethylbenzofuran 131394-60-0 C16H20F3NO5S
    2,3-dihydro-2-morpholino-5-trifluoromethanesulfonyloxy-3,3,7-trimethylbenzofuran
    —— 2,3-dihydro-5-hydroxy-2-morpholino-3,3,7-trimethylbenzofuran 131395-00-1 C15H21NO3
    2,3-dihydro-5-hydroxy-2-morpholino-3,3,7-trimethylbenzofuran
    —— 6-(methylthio)-2,3-dihydro-1-benzofuran 1102467-20-8 C9H10OS
    6-(methylthio)-2,3-dihydro-1-benzofuran
    —— 4-({[({9aS}-8-Acetyl-1,7-dihydroxy-3-methoxy-9a-methyl-9-oxo-9,9a-dihydrodibenzo[b,d]furan-4-yl)carbonyl]amino}methyl)-2,3,5-trimethylbenzoic acid 925442-13-3 C28H27NO9
    4-({[({9aS}-8-Acetyl-1,7-dihydroxy-3-methoxy-9a-methyl-9-oxo-9,9a-dihydrodibenzo[b,d]furan-4-yl)carbonyl]amino}methyl)-2,3,5-trimethylbenzoic acid
    —— N-[(3aS,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-N-[(3S)-6-phenylmethoxy-2,3-dihydro-1-benzofuran-3-yl]hydroxylamine 182823-42-3 C27H33NO8
    N-[(3aS,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-N-[(3S)-6-phenylmethoxy-2,3-dihydro-1-benzofuran-3-yl]hydroxylamine
    —— 3,3-dimethyl-2,3-dihydrobenzofuran-7-carbaldehyde 1037764-40-1 C11H12O2
    3,3-dimethyl-2,3-dihydrobenzofuran-7-carbaldehyde
    —— 5-[1-(3-bromo-phenyl)-vinyl]-2,3-dihydro-benzofuran 1180015-46-6 C16H13BrO
    5-[1-(3-bromo-phenyl)-vinyl]-2,3-dihydro-benzofuran
    —— 1-(3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-2-methyl-propan-1-ol 500165-23-1 C14H20O2
    1-(3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-2-methyl-propan-1-ol
    —— 2,3-dihydro-3,3-dimethyl-2-morpholino-5-hydroxybenzofuran 1623-76-3 C14H19NO3
    2,3-dihydro-3,3-dimethyl-2-morpholino-5-hydroxybenzofuran
    —— 7-methoxy-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran 1243544-52-6 C13H18O2
    7-methoxy-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran
    —— tert-butyl N-[4-[(2-chloropyrimidin-4-yl)-(2,3-dihydro-1-benzofuran-5-carbonyl)amino]butyl]carbamate 849751-90-2 C22H27ClN4O4
    tert-butyl N-[4-[(2-chloropyrimidin-4-yl)-(2,3-dihydro-1-benzofuran-5-carbonyl)amino]butyl]carbamate
    —— (R)-methyl 8-bromo-2-oxo-2,3,4,4a-tetrahydrodibenzo[b,d]furan-4a-carboxylate 1173425-29-0 C14H11BrO4
    (R)-methyl 8-bromo-2-oxo-2,3,4,4a-tetrahydrodibenzo[b,d]furan-4a-carboxylate
    —— (R)-methyl 8-chloro-2-oxo-2,3,4,4a-tetrahydrodibenzo[b,d]furan-4a-carboxylate 1173425-28-9 C14H11ClO4
    (R)-methyl 8-chloro-2-oxo-2,3,4,4a-tetrahydrodibenzo[b,d]furan-4a-carboxylate
    —— 7-tert-butyl-2,3-dihydro-1-benzofuran 131180-39-7 C12H16O
    7-tert-butyl-2,3-dihydro-1-benzofuran
    —— Ethanesulfonic acid 2-hydroxy-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl ester 68505-81-7 C12H16O5S
    Ethanesulfonic acid 2-hydroxy-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl ester
    —— 2,2,6,7-tetramethyl-5-nitrodihydrobenzofuran-2-ylmethyl methanesulfonate 936214-96-9 C14H19NO6S
    2,2,6,7-tetramethyl-5-nitrodihydrobenzofuran-2-ylmethyl methanesulfonate
    —— ethyl 6,7-dichloro-5-(N-ethyl-N-methylsulfamoyl)-2,3-dihydrobenzofuran-2-carboxylate 103969-25-1 C14H17Cl2NO5S
    ethyl 6,7-dichloro-5-(N-ethyl-N-methylsulfamoyl)-2,3-dihydrobenzofuran-2-carboxylate
    —— (3S*,4aS*,9bR*)-9b-<2-(N-formyl-N-methylamino)ethyl>-3-formyloxy-6-methoxy-1,2,3,4,4a,9b-hexahydrodibenzofuran 78167-06-3 C18H23NO5
    (3S*,4aS*,9bR*)-9b-<2-(N-formyl-N-methylamino)ethyl>-3-formyloxy-6-methoxy-1,2,3,4,4a,9b-hexahydrodibenzofuran
    —— 5-bromo-2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran 488834-30-6 C20H23BrO
    5-bromo-2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran
    —— 5-bromo-3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran 820257-30-5 C20H23BrO
    5-bromo-3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran
    —— anisoxide 78259-68-4 C14H18O
    anisoxide
    —— O-Allyl-N-[2-(5-carbamimidoyl-2,3-dihydro-benzofuran-3-yl)-ethyl]-carbamate Acetate Salt 328125-30-0 C2H4O2*C15H19N3O3
    O-Allyl-N-[2-(5-carbamimidoyl-2,3-dihydro-benzofuran-3-yl)-ethyl]-carbamate Acetate Salt
    —— 5-(benzyloxy)-6-<3-(4-cyanophenoxy)propyl>-2,3-dihydro-2-(2-phenylethyl)benzofuran 138854-19-0 C33H31NO3
    5-(benzyloxy)-6-<3-(4-cyanophenoxy)propyl>-2,3-dihydro-2-(2-phenylethyl)benzofuran