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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
—— 3,7-Benzofurandiol, 2,3-dihyro-2,2-dimethyl-, 7-carbamate 98874-79-4 C11H13NO4
3,7-Benzofurandiol, 2,3-dihyro-2,2-dimethyl-, 7-carbamate
—— 2-dimethylhydroxymethylvinylidene-3-piperidino-3H-benzofuran 165402-24-4 C17H23NO2
2-dimethylhydroxymethylvinylidene-3-piperidino-3H-benzofuran
—— Carbamic acid, (((((2,4-dimethylphenyl)imino)methyl)methylamino)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 104946-77-2 C22H27N3O3S
Carbamic acid, (((((2,4-dimethylphenyl)imino)methyl)methylamino)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— Carbamic acid, methylnitroso-, 2,2-dimethyl-3-hydroxy-2,3-dihydro-7-benzofuranyl ester 100836-60-0 C12H14N2O5
Carbamic acid, methylnitroso-, 2,2-dimethyl-3-hydroxy-2,3-dihydro-7-benzofuranyl ester
—— 7-Benzofuranol, 2,3-dihydro-2,2-dimethyl-, N-hydroxycarbamate 100347-65-7 C11H13NO4
7-Benzofuranol, 2,3-dihydro-2,2-dimethyl-, N-hydroxycarbamate
—— 4-Benzofuranol, 2,3-dihydro-2,2-dimethyl-, carbamate 100347-64-6 C11H13NO3
4-Benzofuranol, 2,3-dihydro-2,2-dimethyl-, carbamate
—— 2-Ethyl-N-(3-methoxy-propyl)-<3>cumaranylmethylamin 94326-36-0 C15H23NO2
2-Ethyl-N-(3-methoxy-propyl)-<3>cumaranylmethylamin
—— 2-Ethyl-<3>cumaranylmethylamin 91245-86-2 C11H15NO
2-Ethyl-<3>cumaranylmethylamin
—— 2,3-dihydro-2,2-dimethyl-7-benzofuranyl(isopropoxysulfenyl)(methyl)carbamate 86627-64-7 C15H21NO4S
2,3-dihydro-2,2-dimethyl-7-benzofuranyl(isopropoxysulfenyl)(methyl)carbamate
—— 2,N-Diethyl-<3>cumaranylmethylamin 92195-77-2 C13H19NO
2,N-Diethyl-<3>cumaranylmethylamin
—— Carbamic acid, ((cyclohexyloxy)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 86627-66-9 C18H25NO4S
Carbamic acid, ((cyclohexyloxy)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— Carbamic acid, (((4-(1,1-dimethylethyl)phenyl)methoxy)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 86627-80-7 C23H29NO4S
Carbamic acid, (((4-(1,1-dimethylethyl)phenyl)methoxy)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— Carbamic acid, ((1,1-dimethylethoxy)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 86627-76-1 C16H23NO4S
Carbamic acid, ((1,1-dimethylethoxy)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— Carbamic acid, (ethoxythio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 86627-63-6 C14H19NO4S
Carbamic acid, (ethoxythio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— Carbamic acid, (methoxydithio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 86627-74-9 C13H17NO4S2
Carbamic acid, (methoxydithio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— Carbamic acid, ((dodecyloxy)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 86627-68-1 C24H39NO4S
Carbamic acid, ((dodecyloxy)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— Carbamic acid, ((decyloxy)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 86627-78-3 C22H35NO4S
Carbamic acid, ((decyloxy)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— Carbamic acid, ((hexyloxy)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 86627-65-8 C18H27NO4S
Carbamic acid, ((hexyloxy)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— Carbamic acid, methyl((octyloxy)thio)-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 86627-77-2 C20H31NO4S
Carbamic acid, methyl((octyloxy)thio)-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— Carbamic acid, ((hexyloxy)dithio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 86627-73-8 C18H27NO4S2
Carbamic acid, ((hexyloxy)dithio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— Carbamic acid, methyl((octadecyloxy)thio)-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 86627-81-8 C30H51NO4S
Carbamic acid, methyl((octadecyloxy)thio)-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— Carbamic acid, ((1-ethylpropoxy)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 86627-75-0 C17H25NO4S
Carbamic acid, ((1-ethylpropoxy)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— Carbamic acid, methyl((phenylmethoxy)thio)-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 86627-67-0 C19H21NO4S
Carbamic acid, methyl((phenylmethoxy)thio)-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— ((2,6-Xylyl)sulfinyl)methylcarbamic acid 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 77248-44-3 C20H23NO5S
((2,6-Xylyl)sulfinyl)methylcarbamic acid 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— Benzofuran, 2,3-dihydro-2,2-dimethyl-7-(N-(N-methyl-N-pentoxycarbonylaminothio)-N-methylcarbamoyloxy)- 65907-31-5 C19H28N2O5S
Benzofuran, 2,3-dihydro-2,2-dimethyl-7-(N-(N-methyl-N-pentoxycarbonylaminothio)-N-methylcarbamoyloxy)-
—— Benzofuran, 2,3-dihydro-2,2-dimethyl-7-(N-(N-methyl-N-octyloxycarbonylaminothio)-N-methylcarbamoyloxy)- 65907-33-7 C22H34N2O5S
Benzofuran, 2,3-dihydro-2,2-dimethyl-7-(N-(N-methyl-N-octyloxycarbonylaminothio)-N-methylcarbamoyloxy)-
—— Benzofuran, 2,3-dihydro-2,2-dimethyl-7-(N-(N-methyl-N-heptyloxycarbonylaminothio)-N-methylcarbamoyloxy)- 65907-32-6 C21H32N2O5S
Benzofuran, 2,3-dihydro-2,2-dimethyl-7-(N-(N-methyl-N-heptyloxycarbonylaminothio)-N-methylcarbamoyloxy)-
—— Benzofuran, 2,3-dihydro-2,2-dimethyl-7-(N-(N-methyl-N-isopropoxycarbonylaminothio)-N-methylcarbamoyloxy)- 65907-29-1 C17H24N2O5S
Benzofuran, 2,3-dihydro-2,2-dimethyl-7-(N-(N-methyl-N-isopropoxycarbonylaminothio)-N-methylcarbamoyloxy)-
—— Benzofuran, 2,3-dihydro-2,2-dimethyl-7-(N-(N-methyl-N-propoxycarbonylaminothio)-N-methylcarbamoyloxy)- 65907-28-0 C17H24N2O5S
Benzofuran, 2,3-dihydro-2,2-dimethyl-7-(N-(N-methyl-N-propoxycarbonylaminothio)-N-methylcarbamoyloxy)-
—— (+)-2-isopropenyl-2,3-dihydrobenzofuran-5-methanol 63587-65-5 C12H14O2
(+)-2-isopropenyl-2,3-dihydrobenzofuran-5-methanol
—— Benzofuran, 2,3-dihydro-2,2-dimethyl-7-(N-(N-methyl-N-decyloxycarbonylaminothio)-N-methylcarbamoyloxy)- 65907-34-8 C24H38N2O5S
Benzofuran, 2,3-dihydro-2,2-dimethyl-7-(N-(N-methyl-N-decyloxycarbonylaminothio)-N-methylcarbamoyloxy)-
—— 3-[1-(Diethylamino)propan-2-yl]-3-phenyl-1-benzofuran-2(3H)-one--hydrogen chloride (1/1) 63917-62-4 C21H26ClNO2
3-[1-(Diethylamino)propan-2-yl]-3-phenyl-1-benzofuran-2(3H)-one--hydrogen chloride (1/1)
—— 3-[2-(Diethylamino)propyl]-3-phenyl-1-benzofuran-2(3H)-one--hydrogen chloride (1/1) 63917-63-5 C21H26ClNO2
3-[2-(Diethylamino)propyl]-3-phenyl-1-benzofuran-2(3H)-one--hydrogen chloride (1/1)
—— 3-<γ-Morpholinopropyl>-3-phenyl-2-benzofuranon-Hydrochlorid 63917-68-0 C21H23NO3*ClH
3-<γ-Morpholinopropyl>-3-phenyl-2-benzofuranon-Hydrochlorid
—— 3-[11-(Diethylamino)undecyl]-3-phenyl-1-benzofuran-2(3H)-one--hydrogen chloride (1/1) 63917-65-7 C29H42ClNO2
3-[11-(Diethylamino)undecyl]-3-phenyl-1-benzofuran-2(3H)-one--hydrogen chloride (1/1)
—— 3-<β-Morpholinoaethyl>-3-phenyl-2-benzofuranon Hydrochlorid 63917-67-9 C20H21NO3*ClH
3-<β-Morpholinoaethyl>-3-phenyl-2-benzofuranon Hydrochlorid
—— 3-[3-(Diethylamino)propyl]-3-phenyl-1-benzofuran-2(3H)-one--hydrogen chloride (1/1) 63917-64-6 C21H26ClNO2
3-[3-(Diethylamino)propyl]-3-phenyl-1-benzofuran-2(3H)-one--hydrogen chloride (1/1)
—— 3-[3-(Dibutylamino)propyl]-3-phenyl-1-benzofuran-2(3H)-one--hydrogen chloride (1/1) 63917-60-2 C25H34ClNO2
3-[3-(Dibutylamino)propyl]-3-phenyl-1-benzofuran-2(3H)-one--hydrogen chloride (1/1)
—— 3-[2-(Dimethylamino)ethyl]-3-phenyl-1-benzofuran-2(3H)-one--hydrogen chloride (1/1) 63917-66-8 C18H20ClNO2
3-[2-(Dimethylamino)ethyl]-3-phenyl-1-benzofuran-2(3H)-one--hydrogen chloride (1/1)
—— 3-[2-(Diethylamino)ethyl]-5-methyl-3-phenyl-1-benzofuran-2(3H)-one--hydrogen chloride (1/1) 63917-61-3 C21H26ClNO2
3-[2-(Diethylamino)ethyl]-5-methyl-3-phenyl-1-benzofuran-2(3H)-one--hydrogen chloride (1/1)
—— 3-Phenyl-3-[2-(piperidin-1-yl)ethyl]-1-benzofuran-2(3H)-one--hydrogen chloride (1/1) 63917-69-1 C21H24ClNO2
3-Phenyl-3-[2-(piperidin-1-yl)ethyl]-1-benzofuran-2(3H)-one--hydrogen chloride (1/1)
—— Methyl((2-methylphenyl)sulfinyl)carbamic acid 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 57020-68-5 C19H21NO4S
Methyl((2-methylphenyl)sulfinyl)carbamic acid 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— 2,3-Dihydro-2,2-dimethyl-7-benzofuranyl (3-methylphenylthio)(methyl)carbamate 50539-68-9 C19H21NO3S
2,3-Dihydro-2,2-dimethyl-7-benzofuranyl (3-methylphenylthio)(methyl)carbamate
—— Carbamic acid, thiobis(methyl-, bis(2,3-dihydro-2,2-dimethyl-7-benzofuranyl) ester 50673-14-8 C24H28N2O6S
Carbamic acid, thiobis(methyl-, bis(2,3-dihydro-2,2-dimethyl-7-benzofuranyl) ester
—— Carbamic acid, ((4-chlorophenyl)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 50539-73-6 C18H18ClNO3S
Carbamic acid, ((4-chlorophenyl)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— Carbamic acid, ((p-bromophenyl)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 50539-74-7 C18H18BrNO3S
Carbamic acid, ((p-bromophenyl)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— Carbamic acid, ((4-cyanophenyl)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 50539-77-0 C19H18N2O3S
Carbamic acid, ((4-cyanophenyl)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— Carbamic acid, ((p-tert-butylphenyl)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 50539-70-3 C22H27NO3S
Carbamic acid, ((p-tert-butylphenyl)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— Carbamic acid, (ethylthio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester 50539-81-6 C14H19NO3S
Carbamic acid, (ethylthio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester
—— 2,3-Dihydro-2,2-dimethyl-7-benzofuranyl (methyl)(pentachlorophenylthio)carbamate 50539-76-9 C18H14Cl5NO3S
2,3-Dihydro-2,2-dimethyl-7-benzofuranyl (methyl)(pentachlorophenylthio)carbamate