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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
—— N-cyclopropylmethyl-2,3-dihydro-7-benzofuranamine 61070-81-3 C12H15NO
N-cyclopropylmethyl-2,3-dihydro-7-benzofuranamine
—— 1-cyclopentylmethyl-1-(2,3-dihydro-6-benzofuranyl)urea 61070-42-6 C15H20N2O2
1-cyclopentylmethyl-1-(2,3-dihydro-6-benzofuranyl)urea
—— N-t-butyl-2,3-dihydro-7-benzofuranamine 61070-80-2 C12H17NO
N-t-butyl-2,3-dihydro-7-benzofuranamine
—— N-(Cyclopropylmethyl)-N-(2,3-dihydro-1-benzofuran-5-yl)urea 61090-75-3 C13H16N2O2
N-(Cyclopropylmethyl)-N-(2,3-dihydro-1-benzofuran-5-yl)urea
—— N-methallyl-2,3-dihydro-7-benzofuranamine 61070-79-9 C12H15NO
N-methallyl-2,3-dihydro-7-benzofuranamine
—— 1-cyclopropylmethyl-1-(2,3-dihydro-4-benzofuranyl)urea 61090-63-9 C13H16N2O2
1-cyclopropylmethyl-1-(2,3-dihydro-4-benzofuranyl)urea
—— 1-cyclopropylmethyl-1-(2,3-dihydro-6-benzofuranyl)urea 61070-41-5 C13H16N2O2
1-cyclopropylmethyl-1-(2,3-dihydro-6-benzofuranyl)urea
—— N-methallyl-2,3-dihydro-6-benzofuranamine 61070-35-7 C12H15NO
N-methallyl-2,3-dihydro-6-benzofuranamine
—— N-methallyl-2,3-dihydro-4-benzofuranamine 61090-58-2 C12H15NO
N-methallyl-2,3-dihydro-4-benzofuranamine
—— N-t-butyl-2,3-dihydro-6-benzofuranamine 61070-36-8 C12H17NO
N-t-butyl-2,3-dihydro-6-benzofuranamine
—— 1-isopropyl-1-(2,3-dihydro-7-benzofuranyl)urea 61090-55-9 C12H16N2O2
1-isopropyl-1-(2,3-dihydro-7-benzofuranyl)urea
—— N-tert-Butyl-2,3-dihydro-1-benzofuran-5-amine 61090-72-0 C12H17NO
N-tert-Butyl-2,3-dihydro-1-benzofuran-5-amine
—— 1-methallyl-1-(2,3-dihydro-6-benzofuranyl)urea 61070-39-1 C13H16N2O2
1-methallyl-1-(2,3-dihydro-6-benzofuranyl)urea
—— 1-isopropyl-1-(2,3-dihydro-5-benzofuranyl)urea 61090-43-5 C12H16N2O2
1-isopropyl-1-(2,3-dihydro-5-benzofuranyl)urea
—— N-cyclopentylmethyl-2,3-dihydro-6-benzofuranamine 61070-38-0 C14H19NO
N-cyclopentylmethyl-2,3-dihydro-6-benzofuranamine
—— 1-t-butyl-1-(2,3-dihydro-6-benzofuranyl)urea 61070-40-4 C13H18N2O2
1-t-butyl-1-(2,3-dihydro-6-benzofuranyl)urea
—— N-cyclopropylmethyl-2,3-dihydro-4-benzofuranamine 61090-60-6 C12H15NO
N-cyclopropylmethyl-2,3-dihydro-4-benzofuranamine
—— N-tert-Butyl-N-(2,3-dihydro-1-benzofuran-5-yl)urea 61090-74-2 C13H18N2O2
N-tert-Butyl-N-(2,3-dihydro-1-benzofuran-5-yl)urea
—— N-cyclopropylmethyl-2,3-dihydro-6-benzofuranamine 61070-37-9 C12H15NO
N-cyclopropylmethyl-2,3-dihydro-6-benzofuranamine
—— 6-[(5-Methoxy-1,5-dimethylheptyl)-oxy]-2,3-dihydrobenzofuran 51079-77-7 C18H28O3
6-[(5-Methoxy-1,5-dimethylheptyl)-oxy]-2,3-dihydrobenzofuran
—— 6-[(5-ethoxy-1,5-dimethylhexyl)-oxy]-2,3-dihydrobenzofuran 51079-75-5 C18H28O3
6-[(5-ethoxy-1,5-dimethylhexyl)-oxy]-2,3-dihydrobenzofuran
—— 6-[(7-Methoxy-3,7-dimethyloctyl)-oxy]-2,3-dihydrobenzofuran 51079-55-1 C19H30O3
6-[(7-Methoxy-3,7-dimethyloctyl)-oxy]-2,3-dihydrobenzofuran
—— 6-[(7-Ethoxy-3,7-dimethyloctyl)oxy]-2,3-dihydro-1-benzofuran 51079-69-7 C20H32O3
6-[(7-Ethoxy-3,7-dimethyloctyl)oxy]-2,3-dihydro-1-benzofuran
—— 2,3-dihydro-3,3-dimethyl-2-(1,1-dimethylpropoxy)benzofuran-5-yl methanesulphonate 58740-98-0 C16H24O5S
2,3-dihydro-3,3-dimethyl-2-(1,1-dimethylpropoxy)benzofuran-5-yl methanesulphonate
—— 3-chloropropyl 2,2-dimethyl-2,3-dihydrobenzofur-7-yl ether 256372-40-4 C13H17ClO2
3-chloropropyl 2,2-dimethyl-2,3-dihydrobenzofur-7-yl ether
—— (S)-N-[2-(2,3,-dihydrobenzofuran-5-yl)-1-methylethyl]-ethylamine hydrochloride 241138-41-0 C13H19NO*ClH
(S)-N-[2-(2,3,-dihydrobenzofuran-5-yl)-1-methylethyl]-ethylamine hydrochloride
—— (S)-N-[2-(2,3,-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-methanesulfonylpiperidin-4-ylcarbonyl)amine 241136-78-7 C20H30N2O4S
(S)-N-[2-(2,3,-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-methanesulfonylpiperidin-4-ylcarbonyl)amine
—— 7-amino-2,3-dihydro-2,2-dimethylbenzofuran hydrochloride 82277-70-1 C10H13NO*ClH
7-amino-2,3-dihydro-2,2-dimethylbenzofuran hydrochloride
—— 2,3-dihydro-5,6,7-trimethylbenzo[b]furan-4-carboxaldehyde 89240-32-4 C12H14O2
2,3-dihydro-5,6,7-trimethylbenzo[b]furan-4-carboxaldehyde
—— 7-Chloro-2,3-dihydro-4,5-dimethylbenzo[b]furan-6-carboxaldehyde 89240-28-8 C11H11ClO2
7-Chloro-2,3-dihydro-4,5-dimethylbenzo[b]furan-6-carboxaldehyde
—— 2,3-Dihydro-4,5,7-trimethylbenzo[b]furan-6-carboxaldehyde 89240-18-6 C12H14O2
2,3-Dihydro-4,5,7-trimethylbenzo[b]furan-6-carboxaldehyde
—— 2,3-Dihydro-4,6,7-trimethylbenzo[b]furan-5-carboxaldehyde 89240-22-2 C12H14O2
2,3-Dihydro-4,6,7-trimethylbenzo[b]furan-5-carboxaldehyde
—— 2,3-dihydro-6,7-dimethylbenzo[b]furan-5-carboxaldehyde 89240-30-2 C11H12O2
2,3-dihydro-6,7-dimethylbenzo[b]furan-5-carboxaldehyde
—— 2,3-dihydro-5,6,7-trimethylbenzo[b]furan 89240-31-3 C11H14O
2,3-dihydro-5,6,7-trimethylbenzo[b]furan
—— Aethyl-5-phenyl-2,3-dihydrobenzofuran-2-carboxylat 59962-91-3 C17H16O3
Aethyl-5-phenyl-2,3-dihydrobenzofuran-2-carboxylat
—— 2a-(Acetyloxymethyl)-2a,7b-dihydro-7b-methyl-1,2-dioxeto(3,4-b)benzofuran 128753-96-8 C12H12O5
2a-(Acetyloxymethyl)-2a,7b-dihydro-7b-methyl-1,2-dioxeto(3,4-b)benzofuran
—— 2a,7b-Dihydro-2a,7b-bis(hydroxymethyl)-1,2-dioxeto(3,4-b)benzofuran 128753-94-6 C10H10O5
2a,7b-Dihydro-2a,7b-bis(hydroxymethyl)-1,2-dioxeto(3,4-b)benzofuran
—— 1H-Cyclopenta(b)benzofuran-3a-ol, 7-methoxy-2,3,3a,8b-tetrahdro- 59701-69-8 C12H14O3
1H-Cyclopenta(b)benzofuran-3a-ol, 7-methoxy-2,3,3a,8b-tetrahdro-
—— 11-Aethoxycarbonyl-2,5a,8-trimethyl-benzofuro<2,3-b>benzofuran 1569-28-4 C20H20O4
11-Aethoxycarbonyl-2,5a,8-trimethyl-benzofuro<2,3-b>benzofuran
—— N-(1-Azabicyclo(2.2.2)octan-3-yl)-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxamide 125363-06-6 C20H25ClN2O2
N-(1-Azabicyclo(2.2.2)octan-3-yl)-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxamide
—— N-[(1-butylpyrrolidin-2-yl)methyl]-2-methyl-5-sulfamoyl-2,3-dihydro-1-benzofuran-7-carboxamide;hydron;chloride —— C19H30ClN3O4S
N-[(1-butylpyrrolidin-2-yl)methyl]-2-methyl-5-sulfamoyl-2,3-dihydro-1-benzofuran-7-carboxamide;hydron;chloride
—— (3-hydroxy-2,2-dimethyl-3H-1-benzofuran-7-yl) N-(hydroxymethyl)carbamate 17781-14-5 C12H15NO5
(3-hydroxy-2,2-dimethyl-3H-1-benzofuran-7-yl) N-(hydroxymethyl)carbamate
—— SB 210661 162750-10-9 C16H14F2N2O4
SB 210661
—— 2-Ethyl-N-(2-methoxy-ethyl)-<3>cumaranylmethylamin 92322-53-7 C14H21NO2
2-Ethyl-N-(2-methoxy-ethyl)-<3>cumaranylmethylamin
—— 3-[2-(Dibutylamino)ethyl]-3-phenyl-1-benzofuran-2(3H)-one--hydrogen chloride (1/1) 63917-59-9 C24H32ClNO2
3-[2-(Dibutylamino)ethyl]-3-phenyl-1-benzofuran-2(3H)-one--hydrogen chloride (1/1)
—— Carbamic acid, methyl(methylthio)-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 50539-80-5 C13H17NO3S
Carbamic acid, methyl(methylthio)-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— Carbamic acid, ((4-(1,1-dimethylethyl)-2-methylphenyl)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 50539-71-4 C23H29NO3S
Carbamic acid, ((4-(1,1-dimethylethyl)-2-methylphenyl)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— beta-Alanine, N-(((((2,3-dihydro-2,2-dimethyl-7-benzofuranyl)oxy)carbonyl)methylamino)dithio)-N-(1-methylethyl)-, ethyl ester 98859-42-8 C20H30N2O5S2
beta-Alanine, N-(((((2,3-dihydro-2,2-dimethyl-7-benzofuranyl)oxy)carbonyl)methylamino)dithio)-N-(1-methylethyl)-, ethyl ester
—— beta-Alanine, N-(((((2,3-dihdryo-2,2-dimethyl-7-benzofuranyl)oxy)carbonyl)methylamino)sulfonyl)-N-(1-methylethyl)-, ethyl ester 98874-78-3 C20H30N2O7S
beta-Alanine, N-(((((2,3-dihdryo-2,2-dimethyl-7-benzofuranyl)oxy)carbonyl)methylamino)sulfonyl)-N-(1-methylethyl)-, ethyl ester
—— beta-Alanine, N-(((((2,3-dihydro-3-hydroxy-2,2-dimethyl-7-benzofuranyl)oxy)carbonyl)methylamino)thio)-N-(1-methylethyl)-, ethyl ester 98859-43-9 C20H30N2O6S
beta-Alanine, N-(((((2,3-dihydro-3-hydroxy-2,2-dimethyl-7-benzofuranyl)oxy)carbonyl)methylamino)thio)-N-(1-methylethyl)-, ethyl ester