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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
—— Ethyl 4-(4-hydroxy-2,3-dimethylphenyl)butanoate —— C14H20O3
Ethyl 4-(4-hydroxy-2,3-dimethylphenyl)butanoate
—— 2-[2-(2-Hydroxyphenyl)ethylsulfanyl]acetohydrazide —— C10H14N2O2S
2-[2-(2-Hydroxyphenyl)ethylsulfanyl]acetohydrazide
—— Benzyl 2-amino-2,6-dicyclohexyl-6-[[(2-hydroxy-4-nitrophenyl)-pyridin-4-ylmethyl]amino]-3-oxohexanoate —— C37H46N4O6
Benzyl 2-amino-2,6-dicyclohexyl-6-[[(2-hydroxy-4-nitrophenyl)-pyridin-4-ylmethyl]amino]-3-oxohexanoate
—— Methyl 2-[(2-chloro-4-hydroxyphenyl)methyl]-3-(dimethylamino)prop-2-enoate —— C13H16ClNO3
Methyl 2-[(2-chloro-4-hydroxyphenyl)methyl]-3-(dimethylamino)prop-2-enoate
—— 2-[[4-[2-(Cyclopropylmethoxy)ethyl]phenoxy]methyl]oxetane —— C16H22O3
2-[[4-[2-(Cyclopropylmethoxy)ethyl]phenoxy]methyl]oxetane
—— 6-(3-fluoro-4-hydroxy-5-methoxyphenyl)-4-methyl-2-oxo-5,6-dihydro-1H-pyrimidine-5-carboxylic acid —— C13H13FN2O5
6-(3-fluoro-4-hydroxy-5-methoxyphenyl)-4-methyl-2-oxo-5,6-dihydro-1H-pyrimidine-5-carboxylic acid
—— 2-[2-(2-Hydroxyethyl)pyrrol-2-yl]-4-methylphenol —— C13H15NO2
2-[2-(2-Hydroxyethyl)pyrrol-2-yl]-4-methylphenol
—— 3-Prop-1-ynylbenzene-1,2-diol —— C9H8O2
3-Prop-1-ynylbenzene-1,2-diol
—— (2E,5E)-2-[(2-chlorophenyl)imino]-5-(3,5-dibromo-2-hydroxybenzylidene)-1,3-thiazolidin-4-one —— C16H9Br2ClN2O2S
(2E,5E)-2-[(2-chlorophenyl)imino]-5-(3,5-dibromo-2-hydroxybenzylidene)-1,3-thiazolidin-4-one
—— Imino dopamine —— C8H10N2O2
Imino dopamine
—— 3-Methoxy-4-[2-[1-(2-sulfanylethyl)pyridin-1-ium-4-yl]ethenyl]phenol —— C16H18NO2S+
3-Methoxy-4-[2-[1-(2-sulfanylethyl)pyridin-1-ium-4-yl]ethenyl]phenol
—— 5-Decyl-2,3,4-trimethoxy-6-methylphenol —— C20H34O4
5-Decyl-2,3,4-trimethoxy-6-methylphenol
—— Bromomethane;ethane;phenol —— C9H15BrO
Bromomethane;ethane;phenol
—— 1-[6-(3-Chloro-4-hydroxyphenyl)-4-ethyl-2-hydroxy-1,2,5,6-tetrahydropyrimidin-5-yl]-2-(4-methylcyclohexyl)ethanone —— C21H29ClN2O3
1-[6-(3-Chloro-4-hydroxyphenyl)-4-ethyl-2-hydroxy-1,2,5,6-tetrahydropyrimidin-5-yl]-2-(4-methylcyclohexyl)ethanone
—— 2,3,5-Trichloro-6-pent-1-enylbenzene-1,4-diol —— C11H11Cl3O2
2,3,5-Trichloro-6-pent-1-enylbenzene-1,4-diol
—— 2-[(5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2,6-dimethylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]propanedinitrile —— C22H16BrN3O3S
2-[(5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2,6-dimethylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]propanedinitrile
—— 5-[2-(2-hydroxy-5-nitrophenyl)hydrazin-1-ylidene]-1,3-diazinane-2,4,6-trione —— C10H7N5O6
5-[2-(2-hydroxy-5-nitrophenyl)hydrazin-1-ylidene]-1,3-diazinane-2,4,6-trione
—— 2-[4-[2-[2-[2-[2-[2-[2-[10-(Cyclohex-3-en-1-ylmethylsulfanyl)decoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]butyl]-5-methylbenzene-1,4-diol —— C40H70O9S
2-[4-[2-[2-[2-[2-[2-[2-[10-(Cyclohex-3-en-1-ylmethylsulfanyl)decoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]butyl]-5-methylbenzene-1,4-diol
—— 3-[2-(3-Methyl-1,2,4-oxadiazol-5-yl)ethyl]phenol —— C11H12N2O2
3-[2-(3-Methyl-1,2,4-oxadiazol-5-yl)ethyl]phenol
—— [2-(5,5-Dimethyl-1,3-dioxan-2-yl)-2-methylpropyl] 3-(4-hydroxy-3,5-dimethylphenyl)propanoate;(5-ethyl-2,2-dimethyl-1,3-dioxan-5-yl)methyl 3-(4-hydroxy-3,5-dimethylphenyl)propanoate;furan-2-yl 3-(4-hydroxy-3,5-dimethylphenyl)propanoate —— C56H78O14
[2-(5,5-Dimethyl-1,3-dioxan-2-yl)-2-methylpropyl] 3-(4-hydroxy-3,5-dimethylphenyl)propanoate;(5-ethyl-2,2-dimethyl-1,3-dioxan-5-yl)methyl 3-(4-hydroxy-3,5-dimethylphenyl)propanoate;furan-2-yl 3-(4-hydroxy-3,5-dimethylphenyl)propanoate
—— 2-Amino-3-(2-hydroxyethyl)-4,6-dinitrophenol —— C8H9N3O6
2-Amino-3-(2-hydroxyethyl)-4,6-dinitrophenol
—— N-[1-cyano-4-(4-hydroxy-3,5-dimethoxyphenyl)buta-1,3-dienyl]-2-phenylpropanamide —— C22H22N2O4
N-[1-cyano-4-(4-hydroxy-3,5-dimethoxyphenyl)buta-1,3-dienyl]-2-phenylpropanamide
—— ethyl (2Z)-2-(2-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-5-[4-(prop-2-en-1-yloxy)phenyl]-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H26N2O6S
ethyl (2Z)-2-(2-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-5-[4-(prop-2-en-1-yloxy)phenyl]-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2,4-Bis(2,4-dihydroxyphenyl)cyclobutane-1,3-dione —— C16H12O6
2,4-Bis(2,4-dihydroxyphenyl)cyclobutane-1,3-dione
—— N-[(E)-1-(furan-2-yl)ethylideneamino]-3,4,5-trihydroxybenzamide —— C13H12N2O5
N-[(E)-1-(furan-2-yl)ethylideneamino]-3,4,5-trihydroxybenzamide
—— (5Z)-5-(2,3-dibromo-6-hydroxy-5-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one —— C11H7Br2NO3S2
(5Z)-5-(2,3-dibromo-6-hydroxy-5-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
—— 2,2-Diethyl-6,6-dimethyl-1-[2-[4-(oxiran-2-ylmethoxy)phenyl]ethoxy]-4,4-bis(phenylmethoxy)piperidine —— C36H47NO5
2,2-Diethyl-6,6-dimethyl-1-[2-[4-(oxiran-2-ylmethoxy)phenyl]ethoxy]-4,4-bis(phenylmethoxy)piperidine
—— 2-methoxy-5-[(Z)-[methyl(phenyl)hydrazinylidene]methyl]phenol —— C15H16N2O2
2-methoxy-5-[(Z)-[methyl(phenyl)hydrazinylidene]methyl]phenol
—— 2-[2-[5-[(4-Hydroxyphenyl)methyl]-2,5-dihydro-1,2-oxazol-3-yl]ethyl]phenol —— C18H19NO3
2-[2-[5-[(4-Hydroxyphenyl)methyl]-2,5-dihydro-1,2-oxazol-3-yl]ethyl]phenol
—— 2-Methoxy-5-[5-(2,4,5-trimethoxyphenyl)-1,2-oxazol-3-yl]phenol —— C19H19NO6
2-Methoxy-5-[5-(2,4,5-trimethoxyphenyl)-1,2-oxazol-3-yl]phenol
—— 4-[(4-Hydroxyphenoxy)-phenylmethoxymethyl]phenol —— C20H18O4
4-[(4-Hydroxyphenoxy)-phenylmethoxymethyl]phenol
—— N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-methylbutanamide —— C13H18N2O3
N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-methylbutanamide
—— 4-(Chloroamino)-2-methylphenol —— C7H8ClNO
4-(Chloroamino)-2-methylphenol
—— (6E)-4-bromo-6-[(2-hydroxy-4-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one —— C13H9BrN2O4
(6E)-4-bromo-6-[(2-hydroxy-4-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one
—— 3-[2-(5,6-Diphenylpyrazin-2-yl)-2-(2-methylpyrrol-2-yl)ethyl]phenol —— C29H25N3O
3-[2-(5,6-Diphenylpyrazin-2-yl)-2-(2-methylpyrrol-2-yl)ethyl]phenol
—— 3-[5-[2,4-Dihydroxy-6-(2-methoxy-2-oxoethyl)phenyl]furan-2-yl]propanoic acid —— C16H16O7
3-[5-[2,4-Dihydroxy-6-(2-methoxy-2-oxoethyl)phenyl]furan-2-yl]propanoic acid
—— ethyl (2Z)-2-(4-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-5-[2-(propan-2-yloxy)phenyl]-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H28N2O6S
ethyl (2Z)-2-(4-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-5-[2-(propan-2-yloxy)phenyl]-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-[(5S)-3-(4-hydroxyphenyl)-2,5-dihydro-1,2-oxazol-5-yl]acetic acid —— C11H11NO4
2-[(5S)-3-(4-hydroxyphenyl)-2,5-dihydro-1,2-oxazol-5-yl]acetic acid
—— 3-(2,5-dihydro-1H-imidazol-2-yl)phenol —— C9H10N2O
3-(2,5-dihydro-1H-imidazol-2-yl)phenol
—— (6E)-6-[(3-hydroxy-4-methylanilino)methylidene]cyclohexa-2,4-dien-1-one —— C14H13NO2
(6E)-6-[(3-hydroxy-4-methylanilino)methylidene]cyclohexa-2,4-dien-1-one
—— 2-methoxy-5-[(Z)-[(2-nitrophenyl)hydrazinylidene]methyl]phenol —— C14H13N3O4
2-methoxy-5-[(Z)-[(2-nitrophenyl)hydrazinylidene]methyl]phenol
—— (3E)-3-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-6-chloro-1H-indol-2-one —— C16H11BrClNO3
(3E)-3-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-6-chloro-1H-indol-2-one
—— (5E)-5-(3-bromo-5-chloro-4-hydroxybenzylidene)-3-(propan-2-yl)-1,3-thiazolidine-2,4-dione —— C13H11BrClNO3S
(5E)-5-(3-bromo-5-chloro-4-hydroxybenzylidene)-3-(propan-2-yl)-1,3-thiazolidine-2,4-dione
—— (5E)-5-[(3-chloro-4-hydroxyphenyl)methylidene]-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one —— C22H15ClN2O2S
(5E)-5-[(3-chloro-4-hydroxyphenyl)methylidene]-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one
—— 5-[2-(5-Chloro-2,4-dihydroxyphenyl)ethyl]-4-[(4-methoxyphenyl)methylamino]-1,2-oxazole-3-carboxamide —— C20H20ClN3O5
5-[2-(5-Chloro-2,4-dihydroxyphenyl)ethyl]-4-[(4-methoxyphenyl)methylamino]-1,2-oxazole-3-carboxamide
—— [1-(4-Hydroxy-3-methoxy-5-methylphenyl)-2-(1,3-thiazol-2-ylimino)ethyl]phosphonic acid —— C13H15N2O5PS
[1-(4-Hydroxy-3-methoxy-5-methylphenyl)-2-(1,3-thiazol-2-ylimino)ethyl]phosphonic acid
—— 5-[[[6-(4-Fluorophenyl)-7-methylthieno[3,2-d]pyrimidin-4-yl]diazenyl]methyl]-2-methoxyphenol —— C21H17FN4O2S
5-[[[6-(4-Fluorophenyl)-7-methylthieno[3,2-d]pyrimidin-4-yl]diazenyl]methyl]-2-methoxyphenol
—— 5-[[[4-(cycloheptylamino)-6-(3-fluoro-4-hydroxyanilino)-1,3,5-triazin-2-yl]amino]methyl]-4-hydroxy-3H-1,3-thiazol-2-one —— C20H24FN7O3S
5-[[[4-(cycloheptylamino)-6-(3-fluoro-4-hydroxyanilino)-1,3,5-triazin-2-yl]amino]methyl]-4-hydroxy-3H-1,3-thiazol-2-one
—— (5Z)-5-(2,3-dibromo-6-hydroxy-5-methoxybenzylidene)-1,3-thiazolidine-2,4-dione —— C11H7Br2NO4S
(5Z)-5-(2,3-dibromo-6-hydroxy-5-methoxybenzylidene)-1,3-thiazolidine-2,4-dione
—— [4-(2,4-Dihydroxyphenyl)sulfanyl-2,5-dimethyl-3-oxocyclohexyl] 3-phenylpropanoate —— C23H26O5S
[4-(2,4-Dihydroxyphenyl)sulfanyl-2,5-dimethyl-3-oxocyclohexyl] 3-phenylpropanoate