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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
—— 2,5-Bis{2-[ethyl(2-methoxybenzyl)amino]ethylamino}-[1,4]-benzoquinone —— C30H40N4O4
2,5-Bis{2-[ethyl(2-methoxybenzyl)amino]ethylamino}-[1,4]-benzoquinone
—— (2E)-3-[(2-hydroxy-5-methylphenyl)amino]-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one —— C19H21NO5
(2E)-3-[(2-hydroxy-5-methylphenyl)amino]-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
—— Ethane;phenol;propan-2-one —— C11H18O2
Ethane;phenol;propan-2-one
—— 1-Bromo-2,3,5-trimethylbenzene;methanesulfonamide;4-methylphenol —— C17H24BrNO3S
1-Bromo-2,3,5-trimethylbenzene;methanesulfonamide;4-methylphenol
—— 3-(1,2-Thiazolidin-2-yl)phenol —— C9H11NOS
3-(1,2-Thiazolidin-2-yl)phenol
—— (2E,5Z)-3-Cyclopentyl-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-2-(phenylimino)-1,3-thiazolidin-4-one —— C21H18Br2N2O2S
(2E,5Z)-3-Cyclopentyl-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-2-(phenylimino)-1,3-thiazolidin-4-one
—— (5Z)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-prop-2-enyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H15NO2S2
(5Z)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-prop-2-enyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (2E,5E)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-[(4-methylphenyl)imino]-1,3-thiazolidin-4-one —— C19H18N2O4S
(2E,5E)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-[(4-methylphenyl)imino]-1,3-thiazolidin-4-one
—— 2-[2-(2-Hydroxyethyl)pyrrol-2-yl]phenol —— C12H13NO2
2-[2-(2-Hydroxyethyl)pyrrol-2-yl]phenol
—— 5-[(4-hydroxyphenyl)methyl]-1,1-dioxo-2H-1,2,5-thiadiazol-3-ol —— C9H10N2O4S
5-[(4-hydroxyphenyl)methyl]-1,1-dioxo-2H-1,2,5-thiadiazol-3-ol
—— Adamantane;ethane;4-methylphenol —— C28H44O2
Adamantane;ethane;4-methylphenol
—— 2-Methoxy-4-[[methoxy(methyl)phosphoryl]oxymethyl]-6-methylphenol —— C11H17O5P
2-Methoxy-4-[[methoxy(methyl)phosphoryl]oxymethyl]-6-methylphenol
—— Methyl 4-[3-[2-(4-methylsulfonyloxyphenyl)ethoxy]phenyl]-3-(propoxyamino)but-3-enoate —— C23H29NO7S
Methyl 4-[3-[2-(4-methylsulfonyloxyphenyl)ethoxy]phenyl]-3-(propoxyamino)but-3-enoate
—— (1'R,4R,10'S)-1,1-dioxo-2-propylspiro[1,2,5-thiadiazolidine-4,13'-tricyclo[8.2.1.03,8]trideca-3(8),4,6-triene]-5'-ol —— C17H24N2O3S
(1'R,4R,10'S)-1,1-dioxo-2-propylspiro[1,2,5-thiadiazolidine-4,13'-tricyclo[8.2.1.03,8]trideca-3(8),4,6-triene]-5'-ol
—— 1-(2-Hydroxyphenyl)-3-pyridin-4-ylpropan-2-one —— C14H13NO2
1-(2-Hydroxyphenyl)-3-pyridin-4-ylpropan-2-one
—— 4-[[[(3S)-3-[[(3,4-dihydroxyphenyl)methylamino]methyl]cyclohexyl]methylamino]methyl]benzene-1,2-diol —— C22H30N2O4
4-[[[(3S)-3-[[(3,4-dihydroxyphenyl)methylamino]methyl]cyclohexyl]methylamino]methyl]benzene-1,2-diol
—— 4-[2-(5,5-Dimethyl-2-oxo-1,3,2lambda5-dioxaphosphinan-2-yl)-3-[(2,6-dimethylpyridin-3-yl)amino]prop-1-enyl]-2-methoxyphenol —— C22H29N2O5P
4-[2-(5,5-Dimethyl-2-oxo-1,3,2lambda5-dioxaphosphinan-2-yl)-3-[(2,6-dimethylpyridin-3-yl)amino]prop-1-enyl]-2-methoxyphenol
—— 2-(Oxan-4-yl)benzene-1,3-diol —— C11H14O3
2-(Oxan-4-yl)benzene-1,3-diol
—— 4-[2,4-bis(2-methylbutan-2-yl)phenoxy]-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]butanamide —— C28H40N2O4
4-[2,4-bis(2-methylbutan-2-yl)phenoxy]-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]butanamide
—— Ethenyl 2-(2-bromo-5-hydroxy-4-methoxyphenyl)acetate —— C11H11BrO4
Ethenyl 2-(2-bromo-5-hydroxy-4-methoxyphenyl)acetate
—— 3-(5-Bromo-2-iminopyridine-1-carboximidoyl)phenol —— C12H10BrN3O
3-(5-Bromo-2-iminopyridine-1-carboximidoyl)phenol
—— 1,2-dimethoxy-4-[2-(2-methylcyclohexyl)oxyethyl]benzene;(3R)-1-[2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexyl]-3-[2-(4-phenylmethoxyphenyl)ethoxy]pyrrolidine —— C52H71NO8
1,2-dimethoxy-4-[2-(2-methylcyclohexyl)oxyethyl]benzene;(3R)-1-[2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexyl]-3-[2-(4-phenylmethoxyphenyl)ethoxy]pyrrolidine
—— (2E)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-6,7-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidin-3-one —— C14H14N2O3S
(2E)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-6,7-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidin-3-one
—— (E)-ethyl 2-((1-ethyl-3-methyl-1H-pyrazol-4-yl)methylene)-5-(4-hydroxyphenyl)-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H24N4O4S
(E)-ethyl 2-((1-ethyl-3-methyl-1H-pyrazol-4-yl)methylene)-5-(4-hydroxyphenyl)-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N-[(Z)-[3-ethoxy-4-[(4-nitrophenyl)methoxy]phenyl]methylideneamino]-2-hydroxy-5-nitrobenzamide —— C23H20N4O8
N-[(Z)-[3-ethoxy-4-[(4-nitrophenyl)methoxy]phenyl]methylideneamino]-2-hydroxy-5-nitrobenzamide
—— (4Z)-4-[(4-hydroxy-2-methylanilino)methylidene]-3-(trifluoromethyl)-1H-pyrazol-5-one —— C12H10F3N3O2
(4Z)-4-[(4-hydroxy-2-methylanilino)methylidene]-3-(trifluoromethyl)-1H-pyrazol-5-one
—— Amino 3-(3,5-dibromo-4-hydroxyphenyl)propanoate —— C9H9Br2NO3
Amino 3-(3,5-dibromo-4-hydroxyphenyl)propanoate
—— cis,cis-1,3,5-Tris[(2,3-dihydroxybenzylamino)aminomethyl]cyclohexane —— C30H42N6O6
cis,cis-1,3,5-Tris[(2,3-dihydroxybenzylamino)aminomethyl]cyclohexane
—— cyclohexylmethyl 6-ethyl-4-(3-hydroxy-4-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate —— C22H29NO5
cyclohexylmethyl 6-ethyl-4-(3-hydroxy-4-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate
—— 6-(3-chloro-4-hydroxyphenyl)-4-(2-cyclopentylethyl)-5-propanoyl-5,6-dihydro-1H-pyrimidin-2-one —— C20H25ClN2O3
6-(3-chloro-4-hydroxyphenyl)-4-(2-cyclopentylethyl)-5-propanoyl-5,6-dihydro-1H-pyrimidin-2-one
—— 1-Chloro-3-(5-chloro-2,4-dihydroxyphenyl)propan-2-one —— C9H8Cl2O3
1-Chloro-3-(5-chloro-2,4-dihydroxyphenyl)propan-2-one
—— N-[(E)-[(3-hydroxyphenyl)-morpholin-4-ylmethylidene]amino]hexadecane-1-sulfonamide —— C27H47N3O4S
N-[(E)-[(3-hydroxyphenyl)-morpholin-4-ylmethylidene]amino]hexadecane-1-sulfonamide
—— 3,3-Diamino-3-(2-hydroxyphenyl)propanal —— C9H12N2O2
3,3-Diamino-3-(2-hydroxyphenyl)propanal
—— 2-hydroxy-5-nitro-N'-[(E)-(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]benzohydrazide —— C14H10N4O7
2-hydroxy-5-nitro-N'-[(E)-(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]benzohydrazide
—— (2Z)-5-(4-ethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide —— C30H27N3O5S
(2Z)-5-(4-ethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
—— [1-(4-Hydroxy-3-methoxy-5-methylphenyl)-2-pyrazin-2-yliminoethyl]phosphonic acid —— C14H16N3O5P
[1-(4-Hydroxy-3-methoxy-5-methylphenyl)-2-pyrazin-2-yliminoethyl]phosphonic acid
—— 8-(3-Chloro-5-hydroxyphenyl)-12-methyl-11-[[4-(2-methylpentanoyl)cyclohexa-1,3-dien-1-yl]methyl]-3-propan-2-yl-7-azaspiro[5.6]dodec-7-en-9-one —— C34H46ClNO3
8-(3-Chloro-5-hydroxyphenyl)-12-methyl-11-[[4-(2-methylpentanoyl)cyclohexa-1,3-dien-1-yl]methyl]-3-propan-2-yl-7-azaspiro[5.6]dodec-7-en-9-one
—— ethyl (2Z)-2-(2-hydroxy-3-nitrobenzylidene)-5-(3-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21N3O7S
ethyl (2Z)-2-(2-hydroxy-3-nitrobenzylidene)-5-(3-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N-[(Z)-(2-chlorophenyl)methylideneamino]-2-hydroxy-5-nitrobenzamide —— C14H10ClN3O4
N-[(Z)-(2-chlorophenyl)methylideneamino]-2-hydroxy-5-nitrobenzamide
—— 2-fluoro-6-[3-methyl-1,5-bis(2-phenylethyl)-4H-pyridazin-4-yl]phenol —— C27H27FN2O
2-fluoro-6-[3-methyl-1,5-bis(2-phenylethyl)-4H-pyridazin-4-yl]phenol
—— ethyl (2Z)-5-(4-fluorophenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21FN2O5S
ethyl (2Z)-5-(4-fluorophenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— Ethane;4-ethylphenol —— C10H16O
Ethane;4-ethylphenol
—— N-[2-[(3,4,5-trihydroxyphenyl)methylamino]ethyl]formamide —— C10H14N2O4
N-[2-[(3,4,5-trihydroxyphenyl)methylamino]ethyl]formamide
—— 1-(2-Hydroxyphenyl)-3-pyridin-2-ylpropan-2-one —— C14H13NO2
1-(2-Hydroxyphenyl)-3-pyridin-2-ylpropan-2-one
—— 4-Hydroxy-5-[(4-hydroxyphenyl)methyl]-1,3-bis(oxiran-2-ylmethyl)imidazol-2-one —— C16H18N2O5
4-Hydroxy-5-[(4-hydroxyphenyl)methyl]-1,3-bis(oxiran-2-ylmethyl)imidazol-2-one
—— (3-Hydroxy-2-pentadecylphenyl)sulfanylphosphonic acid —— C21H37O4PS
(3-Hydroxy-2-pentadecylphenyl)sulfanylphosphonic acid
—— 2-Chloro-5-[trideuteriomethoxy-[5-(trideuteriomethoxy)-2-adamantylidene]methyl]phenol —— C19H23ClO3
2-Chloro-5-[trideuteriomethoxy-[5-(trideuteriomethoxy)-2-adamantylidene]methyl]phenol
—— 2-(1,7-Dimethyl-2,3,4,5,6,7,8,8a-octahydro-1-benzazecin-1-ium-2-yl)-4-[2-(1-hydroxy-2-methylprop-2-enoxy)ethyl]phenol —— C27H38NO3+
2-(1,7-Dimethyl-2,3,4,5,6,7,8,8a-octahydro-1-benzazecin-1-ium-2-yl)-4-[2-(1-hydroxy-2-methylprop-2-enoxy)ethyl]phenol
—— 4-[(E)-2-(4-hydroxy-3-methoxy-phenyl)vinyl]-5,5-dimethyl-2-oxo-furan-3-carbonitrile —— C16H15NO4
4-[(E)-2-(4-hydroxy-3-methoxy-phenyl)vinyl]-5,5-dimethyl-2-oxo-furan-3-carbonitrile
—— (5S)-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-5,9-dimethyldecan-2-one —— C19H30O4
(5S)-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-5,9-dimethyldecan-2-one