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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
—— (2E,5E)-5-(4-hydroxy-3-nitrobenzylidene)-2-(phenylimino)-3-(tetrahydrofuran-2-ylmethyl)-1,3-thiazolidin-4-one —— C21H19N3O5S
(2E,5E)-5-(4-hydroxy-3-nitrobenzylidene)-2-(phenylimino)-3-(tetrahydrofuran-2-ylmethyl)-1,3-thiazolidin-4-one
—— 2-[3,5-Dihydroxy-2-[5-(3-nitrosobutyl)furan-2-yl]phenyl]acetic acid —— C16H17NO6
2-[3,5-Dihydroxy-2-[5-(3-nitrosobutyl)furan-2-yl]phenyl]acetic acid
—— (10S)-10,18-dihydroxy-15-(3-hydroxypropyl)-3-oxabicyclo[12.4.0]octadeca-1(18),5,12,14,16-pentaene-2,8-dione —— C20H24O6
(10S)-10,18-dihydroxy-15-(3-hydroxypropyl)-3-oxabicyclo[12.4.0]octadeca-1(18),5,12,14,16-pentaene-2,8-dione
—— [5-[Butyl-[(2-hydroxy-3-nitrophenyl)methyl]amino]-5-oxopentyl]carbamic acid —— C17H25N3O6
[5-[Butyl-[(2-hydroxy-3-nitrophenyl)methyl]amino]-5-oxopentyl]carbamic acid
—— 6-Cyclopentyl-6-[2-(5-ethyl-4-hydroxy-2-methoxyphenyl)ethyl]-3-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]oxane-2,4-dione —— C28H34N4O5
6-Cyclopentyl-6-[2-(5-ethyl-4-hydroxy-2-methoxyphenyl)ethyl]-3-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]oxane-2,4-dione
—— 2-Fluoro-3-[2-[(5-hydroxy-2,3-dihydronaphthalen-1-yl)oxy]ethoxy]-2-methylbut-3-enal —— C17H18FO4-
2-Fluoro-3-[2-[(5-hydroxy-2,3-dihydronaphthalen-1-yl)oxy]ethoxy]-2-methylbut-3-enal
—— Phenol, 4-[3-methyl-1-(2-methylpropyl)butyl] —— C15H24O
Phenol, 4-[3-methyl-1-(2-methylpropyl)butyl]
—— (2E,5E)-5-(3-bromo-4-hydroxy-5-nitrobenzylidene)-2-[(2,3-dichlorophenyl)imino]-1,3-thiazolidin-4-one —— C16H8BrCl2N3O4S
(2E,5E)-5-(3-bromo-4-hydroxy-5-nitrobenzylidene)-2-[(2,3-dichlorophenyl)imino]-1,3-thiazolidin-4-one
—— N-[(Z)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-methoxyanilino)acetamide —— C17H18BrN3O4
N-[(Z)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-methoxyanilino)acetamide
—— 2-Amino-5-ethylbenzene-1,3-diol —— C8H11NO2
2-Amino-5-ethylbenzene-1,3-diol
—— 5-[(3,5-Dibromo-4-hydroxyphenyl)methylidene]-3-methyl-2-methylideneimidazolidin-4-one —— C12H10Br2N2O2
5-[(3,5-Dibromo-4-hydroxyphenyl)methylidene]-3-methyl-2-methylideneimidazolidin-4-one
—— 3-[[2-(dimethylamino)-1,1,2,2-tetrahydroxyethoxy]-hydroxy-(2,3,5,6-tetrahydroxy-4-methylphenyl)methyl]-4-hydroxy-2-methyl-1H-pyrazol-5-one —— C16H23N3O12
3-[[2-(dimethylamino)-1,1,2,2-tetrahydroxyethoxy]-hydroxy-(2,3,5,6-tetrahydroxy-4-methylphenyl)methyl]-4-hydroxy-2-methyl-1H-pyrazol-5-one
—— (5E)-3-(2-hydroxy-4-nitrophenyl)-5-[(4-methylsulfanylphenyl)methylidene]-2-phenylimidazol-4-one —— C23H17N3O4S
(5E)-3-(2-hydroxy-4-nitrophenyl)-5-[(4-methylsulfanylphenyl)methylidene]-2-phenylimidazol-4-one
—— 3-Tri(propan-2-yl)silylbenzene-1,2-diol —— C15H26O2Si
3-Tri(propan-2-yl)silylbenzene-1,2-diol
—— 5-(5-cyclohexyl-1H-imidazol-2-yl)-4-ethyl-6-(3-fluoro-4-hydroxyphenyl)-5,6-dihydro-1H-pyrimidin-2-one —— C21H25FN4O2
5-(5-cyclohexyl-1H-imidazol-2-yl)-4-ethyl-6-(3-fluoro-4-hydroxyphenyl)-5,6-dihydro-1H-pyrimidin-2-one
—— 2-[3,5-Dihydroxy-2-[5-(3-methoxyiminobutyl)furan-2-yl]phenyl]acetic acid —— C17H19NO6
2-[3,5-Dihydroxy-2-[5-(3-methoxyiminobutyl)furan-2-yl]phenyl]acetic acid
—— 4-[1-[(2R)-3-(4-hydroxy-3-methoxy-5-methylphenyl)-2-[4-(2-oxo-4,5-dihydro-1H-1,3-benzodiazepin-3-yl)piperidine-1-carbonyl]oxypropanoyl]piperidin-4-yl]piperidine-1-carboxylic acid —— C37H49N5O8
4-[1-[(2R)-3-(4-hydroxy-3-methoxy-5-methylphenyl)-2-[4-(2-oxo-4,5-dihydro-1H-1,3-benzodiazepin-3-yl)piperidine-1-carbonyl]oxypropanoyl]piperidin-4-yl]piperidine-1-carboxylic acid
—— Ethane;methanol;phenol —— C15H34O2
Ethane;methanol;phenol
—— N-[(5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]benzamide —— C18H13BrN2O4S2
N-[(5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]benzamide
—— 5-[4-hydroxy-2-methoxy-N-(1H-pyrazol-5-yl)anilino]pyrazine-2-carbonitrile —— C15H12N6O2
5-[4-hydroxy-2-methoxy-N-(1H-pyrazol-5-yl)anilino]pyrazine-2-carbonitrile
—— ethyl (2Z)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3-ethoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H29BrN2O7S
ethyl (2Z)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3-ethoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5E)-5-(3-bromo-4-hydroxy-5-nitrobenzylidene)-3-phenyl-1,3-thiazolidine-2,4-dione —— C16H9BrN2O5S
(5E)-5-(3-bromo-4-hydroxy-5-nitrobenzylidene)-3-phenyl-1,3-thiazolidine-2,4-dione
—— (4Z)-4-[(3-hydroxyphenyl)methylidene]-1-phenylpyrazolidine-3,5-dione —— C16H12N2O3
(4Z)-4-[(3-hydroxyphenyl)methylidene]-1-phenylpyrazolidine-3,5-dione
—— 6-Hydroxy-2-(3-hydroxy-4-methoxystyryl)-5-nitropyrimidin-4(3H)-one —— C13H11N3O6
6-Hydroxy-2-(3-hydroxy-4-methoxystyryl)-5-nitropyrimidin-4(3H)-one
—— 2-[1-[Di(propan-2-yl)amino]-4-ethylidenehept-5-en-3-yl]-4-methylphenol —— C22H35NO
2-[1-[Di(propan-2-yl)amino]-4-ethylidenehept-5-en-3-yl]-4-methylphenol
—— 4-[(6-Thiophen-3-yl-5,8-dihydroimidazo[1,2-a]pyrimidin-3-yl)methyl]phenol —— C17H15N3OS
4-[(6-Thiophen-3-yl-5,8-dihydroimidazo[1,2-a]pyrimidin-3-yl)methyl]phenol
—— N-[(Z)-(4-tert-butylphenyl)methylideneamino]-3,4,5-trihydroxybenzamide —— C18H20N2O4
N-[(Z)-(4-tert-butylphenyl)methylideneamino]-3,4,5-trihydroxybenzamide
—— (4aS,6R,7S,8S,8aR)-7,8-dihydroxy-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-6-(hydroxymethyl)-6,7,8,8a-tetrahydro-4aH-pyrano[3,2-b][1,4]oxathiin-2-one —— C17H20O9S
(4aS,6R,7S,8S,8aR)-7,8-dihydroxy-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-6-(hydroxymethyl)-6,7,8,8a-tetrahydro-4aH-pyrano[3,2-b][1,4]oxathiin-2-one
—— 4-(1-Methyloctyl)phenol-d5 —— C15H24O
4-(1-Methyloctyl)phenol-d5
—— (5E)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-2-phenylimino-3-prop-2-enyl-1,3-thiazolidin-4-one —— C19H15BrN2O2S
(5E)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-2-phenylimino-3-prop-2-enyl-1,3-thiazolidin-4-one
—— 5-{[5-(2-Hydroxy-4-nitrophenyl)furan-2-YL]methylidene}-1,3-dimethyl-1,3-diazinane-2,4,6-trione —— C17H13N3O7
5-{[5-(2-Hydroxy-4-nitrophenyl)furan-2-YL]methylidene}-1,3-dimethyl-1,3-diazinane-2,4,6-trione
—— Methyl 2-[2-(4-hydroxyphenyl)ethoxymethoxymethyl]-2-methylbutanoate —— C16H24O5
Methyl 2-[2-(4-hydroxyphenyl)ethoxymethoxymethyl]-2-methylbutanoate
—— Methyl 2-[3-(4-hydroxyphenyl)-2,5-dihydro-1,2-oxazol-5-yl]cyclopentane-1-carboxylate —— C16H19NO4
Methyl 2-[3-(4-hydroxyphenyl)-2,5-dihydro-1,2-oxazol-5-yl]cyclopentane-1-carboxylate
—— 6-[(E)-2-(5-chloro-2-hydroxy-3-methoxyphenyl)ethenyl]-5-nitropyrimidine-2,4-diol —— C13H10ClN3O6
6-[(E)-2-(5-chloro-2-hydroxy-3-methoxyphenyl)ethenyl]-5-nitropyrimidine-2,4-diol
—— Ethane;4-methyl-1,3-oxazole;phenol —— C14H23NO2
Ethane;4-methyl-1,3-oxazole;phenol
—— (2E,5E)-3-ethyl-2-[(2-ethylphenyl)imino]-5-(4-hydroxybenzylidene)-1,3-thiazolidin-4-one —— C20H20N2O2S
(2E,5E)-3-ethyl-2-[(2-ethylphenyl)imino]-5-(4-hydroxybenzylidene)-1,3-thiazolidin-4-one
—— 2-(3-Hydroxyphenyl)-1-(methylamino)ethane-1,1,2-triol —— C9H13NO4
2-(3-Hydroxyphenyl)-1-(methylamino)ethane-1,1,2-triol
—— 2-Methylphenol;propane —— C10H16O
2-Methylphenol;propane
—— ethyl (2Z)-2-(5-chloro-2-hydroxybenzylidene)-5-(2-chlorophenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18Cl2N2O4S
ethyl (2Z)-2-(5-chloro-2-hydroxybenzylidene)-5-(2-chlorophenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 4-[2-[(2,4,6-Trimethoxyphenyl)methylsulfonyl]ethenyl]benzene-1,2-diol —— C18H20O7S
4-[2-[(2,4,6-Trimethoxyphenyl)methylsulfonyl]ethenyl]benzene-1,2-diol
—— 5-[(Z)-[(4,6-dianilino-1,3,5-triazin-2-yl)hydrazinylidene]methyl]-2-methoxyphenol —— C23H21N7O2
5-[(Z)-[(4,6-dianilino-1,3,5-triazin-2-yl)hydrazinylidene]methyl]-2-methoxyphenol
—— 4-[[1-[[3,5-Bis(trifluoromethyl)phenyl]methyl]pyrrolidin-1-ium-1-yl]methyl]-2-methoxyphenol —— C21H22F6NO2+
4-[[1-[[3,5-Bis(trifluoromethyl)phenyl]methyl]pyrrolidin-1-ium-1-yl]methyl]-2-methoxyphenol
—— 1-(4-chlorophenyl)-6-hydroxy-5-[3-(4-hydroxy-3,5-dimethoxyphenyl)propa-1,2-dienyl]-2-sulfanylidenepyrimidin-4-one —— C21H17ClN2O5S
1-(4-chlorophenyl)-6-hydroxy-5-[3-(4-hydroxy-3,5-dimethoxyphenyl)propa-1,2-dienyl]-2-sulfanylidenepyrimidin-4-one
—— 4-nitro-2-[2-(1,3,3-trimethylindol-2-ylidene)ethenyl]phenol —— C19H18N2O3
4-nitro-2-[2-(1,3,3-trimethylindol-2-ylidene)ethenyl]phenol
—— 3-hydroxy-4-nitrophenyl propionate —— C9H9NO5
3-hydroxy-4-nitrophenyl propionate
—— methyl (4Z)-4-(4-hydroxybenzylidene)-2-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate —— C14H13NO4
methyl (4Z)-4-(4-hydroxybenzylidene)-2-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate
—— 2-hydroxy-N'-[(E)-(3-hydroxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-5-nitrobenzohydrazide —— C14H11N3O6
2-hydroxy-N'-[(E)-(3-hydroxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-5-nitrobenzohydrazide
—— ethyl (5Z)-2-anilino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-4-oxothiophene-3-carboxylate —— C21H19NO5S
ethyl (5Z)-2-anilino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-4-oxothiophene-3-carboxylate
—— (2E,5E)-3-ethyl-5-(2-hydroxy-3-methoxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one —— C19H18N2O3S
(2E,5E)-3-ethyl-5-(2-hydroxy-3-methoxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one
—— 4-(1-Ethoxypropan-2-yl)phenol —— C11H16O2
4-(1-Ethoxypropan-2-yl)phenol