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酚类

酚类是一大类化合物,它们主要特征是分子中含有一个羟基(-OH)直接连接在苯环上。这类化合物广泛存在于自然界中,并且具有重要的生物、医药及工业应用价值。

结构与分类

酚类化合物的基本结构为苯环上的氧原子与羟基相连。根据羟基的位置不同,可将酚分为单酚和多酚两大类:

  • 单酚:每个分子仅有一个酚羟基。
  • 多酚:含有两个或多个酚羟基的化合物。
生物学意义
  1. 天然来源:酚广泛存在于植物、动物以及微生物中,如咖啡因中的茶酚、儿茶素等。
  2. 抗氧化作用:许多酚类物质具有较强的抗氧化性,能够清除体内的自由基,保护细胞免受氧化损伤。
  3. 抗菌活性:部分酚类化合物展示出显著的抗菌效果,可用于食品保鲜或开发抗生素。
工业应用
  1. 农药和杀虫剂:利用某些酚类化合物对特定昆虫的选择性毒性进行害虫控制。
  2. 染料工业:许多天然及合成染料都基于酚结构设计而成。
  3. 医药领域:作为原料或药物成分,例如阿司匹林的核心成分水杨酸就属于苯酚衍生物。
工业生产

酚类可以通过多种途径制备:

  • 通过煤焦油蒸馏或石油裂解得到的粗酚进行精炼获得。
  • 以苯或其他芳烃为原料,在催化剂作用下与水反应生成苯酚,此过程称为菲林斯勒反应(Fischer–Strassmann反应)。
注意事项

尽管酚类化合物具有广泛的应用前景,但它们也可能带来毒性问题。例如强酸性的酚类物质会对皮肤造成刺激甚至腐蚀。因此在使用时需注意安全防护措施。

以上是对酚类的简单介绍,涵盖了其基本定义、生物学意义及工业应用等方面的内容。

中文名称 英文名称 CAS号 化学式 结构式图片
—— (2Z,5E)-5-(3-bromo-4-hydroxybenzylidene)-2-[(3-methylphenyl)imino]-1,3-thiazolidin-4-one —— C17H13BrN2O2S
(2Z,5E)-5-(3-bromo-4-hydroxybenzylidene)-2-[(3-methylphenyl)imino]-1,3-thiazolidin-4-one
—— 4-[(1S)-1-hydroxy-2-iminoethyl]phenol —— C8H9NO2
4-[(1S)-1-hydroxy-2-iminoethyl]phenol
—— 5-(3,3-Dihydroxypropeny)-3-methoxy-benzene-1,2-diol —— C10H12O5
5-(3,3-Dihydroxypropeny)-3-methoxy-benzene-1,2-diol
—— 4-[(1S)-1-hydroxy-2-iminoethyl]phenol;(2R,3S,4R,5S)-2-(hydroxymethyl)oxane-3,4,5-triol —— C14H21NO7
4-[(1S)-1-hydroxy-2-iminoethyl]phenol;(2R,3S,4R,5S)-2-(hydroxymethyl)oxane-3,4,5-triol
—— 5-(Dihydroxyamino)-2-nitrophenol —— C6H6N2O5
5-(Dihydroxyamino)-2-nitrophenol
—— (2E)-but-2-en-1-yl 4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate —— C17H20N2O5
(2E)-but-2-en-1-yl 4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
—— (4Z)-1-(3,4-dimethylphenyl)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]pyrazolidine-3,5-dione —— C20H20N2O5
(4Z)-1-(3,4-dimethylphenyl)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]pyrazolidine-3,5-dione
—— 5-[(4-Hydroxy-3-nitrophenyl)methylidene]-1,3-dimethyl-1,3-diazinane-2,4,6-trione —— C13H11N3O6
5-[(4-Hydroxy-3-nitrophenyl)methylidene]-1,3-dimethyl-1,3-diazinane-2,4,6-trione
—— ethyl (2E)-5-(4-chlorophenyl)-2-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H17Br2ClN2O4S
ethyl (2E)-5-(4-chlorophenyl)-2-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— Phenol, 2-(2-penten-4-yl)-4-methoxy- —— C12H16O2
Phenol, 2-(2-penten-4-yl)-4-methoxy-
—— ethyl (2Z)-5-amino-8-cyano-2-(4-hydroxybenzylidene)-7-(4-hydroxyphenyl)-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyridine-6-carboxylate —— C24H19N3O5S
ethyl (2Z)-5-amino-8-cyano-2-(4-hydroxybenzylidene)-7-(4-hydroxyphenyl)-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyridine-6-carboxylate
—— 4-[(4-hydroxy-2-methylanilino)methylidene]-5-methyl-2-(4-methylphenyl)pyrazol-3-one —— C19H19N3O2
4-[(4-hydroxy-2-methylanilino)methylidene]-5-methyl-2-(4-methylphenyl)pyrazol-3-one
—— (4E)-2-(3,4-dimethylphenyl)-4-[(2-hydroxy-4-nitroanilino)methylidene]-5-methylpyrazol-3-one —— C19H18N4O4
(4E)-2-(3,4-dimethylphenyl)-4-[(2-hydroxy-4-nitroanilino)methylidene]-5-methylpyrazol-3-one
—— 4-[(5-chloro-2-hydroxyanilino)methylidene]-5-methyl-2-(4-methylphenyl)pyrazol-3-one —— C18H16ClN3O2
4-[(5-chloro-2-hydroxyanilino)methylidene]-5-methyl-2-(4-methylphenyl)pyrazol-3-one
—— (5Z,5'Z)-2,2'-piperazine-1,4-diylbis[5-(5-bromo-2-hydroxybenzylidene)-1,3-thiazol-4(5H)-one] —— C24H18Br2N4O4S2
(5Z,5'Z)-2,2'-piperazine-1,4-diylbis[5-(5-bromo-2-hydroxybenzylidene)-1,3-thiazol-4(5H)-one]
—— (4E)-4-[(2-hydroxy-3,5-dinitroanilino)methylidene]-5-methyl-2-(2-methylphenyl)pyrazol-3-one —— C18H15N5O6
(4E)-4-[(2-hydroxy-3,5-dinitroanilino)methylidene]-5-methyl-2-(2-methylphenyl)pyrazol-3-one
—— (2Z)-2-(2-hydroxy-3,5-dinitrobenzylidene)-1-benzothiophen-3(2H)-one —— C15H8N2O6S
(2Z)-2-(2-hydroxy-3,5-dinitrobenzylidene)-1-benzothiophen-3(2H)-one
—— 5-Hydroxyconiferaldehyde —— C10H10O4
5-Hydroxyconiferaldehyde
—— (Z)-5-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)dec-4-en-3-one —— C17H24O4
(Z)-5-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)dec-4-en-3-one
—— 4-[(E)-2-[2-(3,4-dihydroxyphenyl)ethylamino]ethenyl]-2,3-dihydropyridine-2,6-dicarboxylic acid —— C17H18N2O6
4-[(E)-2-[2-(3,4-dihydroxyphenyl)ethylamino]ethenyl]-2,3-dihydropyridine-2,6-dicarboxylic acid
—— 3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-1-methyl-1-(pyridin-2-ylmethyl)urea —— C18H23N3O2
3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-1-methyl-1-(pyridin-2-ylmethyl)urea
—— 3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-1-methyl-1-(pyridin-2-ylmethyl)urea —— C18H23N3O2
3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-1-methyl-1-(pyridin-2-ylmethyl)urea
—— (2Z)-4-(3,5-dihydroxyphenyl)-5-hydroxy-2-[(4-hydroxyphenyl)methylidene]furan-3-one —— C17H12O6
(2Z)-4-(3,5-dihydroxyphenyl)-5-hydroxy-2-[(4-hydroxyphenyl)methylidene]furan-3-one
—— (2Z)-5-hydroxy-4-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]-2-[[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]methylidene]furan-3-one —— C27H28O5
(2Z)-5-hydroxy-4-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]-2-[[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]methylidene]furan-3-one
—— 3-methoxy-5-[(E)-2-[[(E)-styryl]sulfonylmethylsulfonyl]vinyl]benzene-1,2-diol —— C18H18O7S2
3-methoxy-5-[(E)-2-[[(E)-styryl]sulfonylmethylsulfonyl]vinyl]benzene-1,2-diol
—— 4-[(E)-2-[[(E)-2-(3,4-dihydroxyphenyl)vinyl]sulfonylmethylsulfonyl]vinyl]benzene-1,2-diol —— C17H16O8S2
4-[(E)-2-[[(E)-2-(3,4-dihydroxyphenyl)vinyl]sulfonylmethylsulfonyl]vinyl]benzene-1,2-diol
—— 5-[(E)-2-[[(E)-2-(3,4-dihydroxy-5-methoxy-phenyl)vinyl]sulfonylmethylsulfonyl]vinyl]-3-methoxy-benzene-1,2-diol —— C19H20O10S2
5-[(E)-2-[[(E)-2-(3,4-dihydroxy-5-methoxy-phenyl)vinyl]sulfonylmethylsulfonyl]vinyl]-3-methoxy-benzene-1,2-diol
—— 5-[(E)-2-[[(E)-2-(3,4,5-trihydroxyphenyl)ethenyl]sulfonylmethylsulfonyl]ethenyl]benzene-1,2,3-triol 862097-17-4 C17H16O10S2
5-[(E)-2-[[(E)-2-(3,4,5-trihydroxyphenyl)ethenyl]sulfonylmethylsulfonyl]ethenyl]benzene-1,2,3-triol
—— 1-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-3-[[3-(pyrazol-1-ylmethyl)phenyl]methyl]urea —— C22H26N4O2
1-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-3-[[3-(pyrazol-1-ylmethyl)phenyl]methyl]urea
—— 2-[[4-[(3R)-1,1-dioxothiolan-3-yl]piperazin-1-yl]methyl]-4-ethoxy-6-prop-2-enylphenol —— C20H30N2O4S
2-[[4-[(3R)-1,1-dioxothiolan-3-yl]piperazin-1-yl]methyl]-4-ethoxy-6-prop-2-enylphenol
—— N-cyclohexyl-2,4,6-trihydroxy-3-nitro-benzamide —— C13H16N2O6
N-cyclohexyl-2,4,6-trihydroxy-3-nitro-benzamide
—— 2,4,6-trihydroxy-3-nitro-N-phenethyl-benzamide —— C15H14N2O6
2,4,6-trihydroxy-3-nitro-N-phenethyl-benzamide
—— N-heptyl-2,4,6-trihydroxy-3-nitro-benzamide —— C14H20N2O6
N-heptyl-2,4,6-trihydroxy-3-nitro-benzamide
—— 1-<(1,3-dihydroxy-2-propoxy)methyl>-5-(4-hydroxybenzyl)-6-azauracil —— C14H17N3O6
1-<(1,3-dihydroxy-2-propoxy)methyl>-5-(4-hydroxybenzyl)-6-azauracil
—— 1-<(2-hydroxyethoxy)methyl>-5-(4-hydroxybenzyl)-6-azauracil —— C13H15N3O5
1-<(2-hydroxyethoxy)methyl>-5-(4-hydroxybenzyl)-6-azauracil
—— 1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[[(1S,3S)-3-methylcyclohexyl]methyl]urea —— C18H28N2O3
1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[[(1S,3S)-3-methylcyclohexyl]methyl]urea
—— 1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[[(1R,3R)-3-methylcyclohexyl]methyl]urea —— C18H28N2O3
1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[[(1R,3R)-3-methylcyclohexyl]methyl]urea
—— [(E)-[3-[(Z)-(carbamothioylhydrazinylidene)methyl]-5-hydroxy-4-methoxyphenyl]methylideneamino]thiourea —— C11H14N6O2S2
[(E)-[3-[(Z)-(carbamothioylhydrazinylidene)methyl]-5-hydroxy-4-methoxyphenyl]methylideneamino]thiourea
—— N-[(3-hydroxy-4-methoxyphenyl)methyl]-3-(2,3,4-trimethoxyphenyl)propanamide —— C20H25NO6
N-[(3-hydroxy-4-methoxyphenyl)methyl]-3-(2,3,4-trimethoxyphenyl)propanamide
—— 3,4,5-trihydroxy-N-[(3-hydroxy-2,2-dimethylpropylidene)amino]benzamide —— C12H16N2O5
3,4,5-trihydroxy-N-[(3-hydroxy-2,2-dimethylpropylidene)amino]benzamide
—— 2,6-Bis[(4-methylphenyl)sulfonylmethyl]-4-nitrophenol —— C22H21NO7S2
2,6-Bis[(4-methylphenyl)sulfonylmethyl]-4-nitrophenol
—— S-(3,4-dihydroxyphenyl)-isothiourea —— C7H8N2O2S
S-(3,4-dihydroxyphenyl)-isothiourea
—— 5-[(5-Bromo-2-hydroxyphenyl)methylidene]-3-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-4-one —— C13H12BrNO2S2
5-[(5-Bromo-2-hydroxyphenyl)methylidene]-3-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-5-(5-methylfuran-2-yl)-N-(2-methylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide 7061-52-1 C28H25N3O5S
2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-5-(5-methylfuran-2-yl)-N-(2-methylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
—— 2-[(2-hydroxy-5-nitrophenyl)methylidene]-7-methyl-5-(5-methylfuran-2-yl)-N-(2-methylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide —— C27H22N4O6S
2-[(2-hydroxy-5-nitrophenyl)methylidene]-7-methyl-5-(5-methylfuran-2-yl)-N-(2-methylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
—— 5-[(2-Hydroxyphenyl)methylidene]-3-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-4-one —— C13H13NO2S2
5-[(2-Hydroxyphenyl)methylidene]-3-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-5-(5-methylfuran-2-yl)-N-(2-methylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide —— C28H25N3O5S
2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-5-(5-methylfuran-2-yl)-N-(2-methylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
—— ethyl 5-(4-bromophenyl)-2-[(2-hydroxy-5-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18BrN3O6S
ethyl 5-(4-bromophenyl)-2-[(2-hydroxy-5-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl 2-[(5-bromo-2-hydroxyphenyl)methylidene]-5-(4-bromophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18Br2N2O4S
ethyl 2-[(5-bromo-2-hydroxyphenyl)methylidene]-5-(4-bromophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— phenol;tungsten —— C36H36O6W
phenol;tungsten