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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
—— 3-[(Z)-(diphenylphosphinothioylhydrazinylidene)methyl]phenol —— C19H17N2OPS
3-[(Z)-(diphenylphosphinothioylhydrazinylidene)methyl]phenol
—— (3Z)-3-[(4-hydroxyphenyl)methylidene]-2-oxoindolizine-1-carbonitrile —— C16H10N2O2
(3Z)-3-[(4-hydroxyphenyl)methylidene]-2-oxoindolizine-1-carbonitrile
—— 1-ethyl-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-methylbenzimidazole-5-carboxamide —— C19H20N4O3
1-ethyl-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-methylbenzimidazole-5-carboxamide
—— 3-chloro-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1-benzothiophene-2-carboxamide —— C17H13ClN2O3S
3-chloro-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1-benzothiophene-2-carboxamide
—— 2-methoxy-6-[[(2R,4R)-4-methyl-1,3-dioxolan-2-yl]methyl]phenol —— C12H16O4
2-methoxy-6-[[(2R,4R)-4-methyl-1,3-dioxolan-2-yl]methyl]phenol
—— 2-methoxy-6-[[(2S,4R)-4-methyl-1,3-dioxolan-2-yl]methyl]phenol —— C12H16O4
2-methoxy-6-[[(2S,4R)-4-methyl-1,3-dioxolan-2-yl]methyl]phenol
—— 2-methoxy-6-[[(2S,4S)-4-methyl-1,3-dioxolan-2-yl]methyl]phenol —— C12H16O4
2-methoxy-6-[[(2S,4S)-4-methyl-1,3-dioxolan-2-yl]methyl]phenol
—— 3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-methyl-5-phenylthieno[2,3-d]pyrimidin-4-one —— C21H17N3O3S
3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-methyl-5-phenylthieno[2,3-d]pyrimidin-4-one
—— 2-Fluoro-4-nitroresorcinol —— C6H4FNO4
2-Fluoro-4-nitroresorcinol
—— 4-(4,4,5,5,5-Pentafluoropentoxy)phenol —— C11H11F5O2
4-(4,4,5,5,5-Pentafluoropentoxy)phenol
—— 4-[(3R)-2,2,3,4,4,4-hexafluorobutoxy]phenol —— C10H8F6O2
4-[(3R)-2,2,3,4,4,4-hexafluorobutoxy]phenol
—— 4-(4-Bromo-3,3,4,4-tetrafluorobutoxy)phenol —— C10H9BrF4O2
4-(4-Bromo-3,3,4,4-tetrafluorobutoxy)phenol
—— 4-[(3S)-2,2,3,4,4,4-hexafluorobutoxy]phenol —— C10H8F6O2
4-[(3S)-2,2,3,4,4,4-hexafluorobutoxy]phenol
—— N-[(Z)-(3-hydroxyphenyl)methylideneamino]cyclopropanecarboxamide —— C11H12N2O2
N-[(Z)-(3-hydroxyphenyl)methylideneamino]cyclopropanecarboxamide
—— 2,6-dimethoxy-4-[[4-[(E)-3-phenylprop-2-enyl]piperazine-1,4-diium-1-yl]methyl]phenol —— C22H30N2O3+2
2,6-dimethoxy-4-[[4-[(E)-3-phenylprop-2-enyl]piperazine-1,4-diium-1-yl]methyl]phenol
—— N,N'-bis[(Z)-(3-hydroxyphenyl)methylideneamino]hexanediamide —— C20H22N4O4
N,N'-bis[(Z)-(3-hydroxyphenyl)methylideneamino]hexanediamide
—— 3-cyclohexyl-4-[(E)-(3-hydroxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione 500104-73-4 C15H18N4OS
3-cyclohexyl-4-[(E)-(3-hydroxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione
—— (2E)-2-[(Z)-benzylidenehydrazinylidene]-3-(4-hydroxyphenyl)-1,3-thiazolidin-4-one —— C16H13N3O2S
(2E)-2-[(Z)-benzylidenehydrazinylidene]-3-(4-hydroxyphenyl)-1,3-thiazolidin-4-one
—— (5E)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-1-phenylpyrimidine-2,4,6(1H,3H,5H)-trione —— C18H13BrN2O5
(5E)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-1-phenylpyrimidine-2,4,6(1H,3H,5H)-trione
—— 5-[(3-Bromo-2-chloro-4-hydroxy-5-methoxyphenyl)methylene]-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione —— C12H8BrClN2O4S
5-[(3-Bromo-2-chloro-4-hydroxy-5-methoxyphenyl)methylene]-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione
—— (5E)-5-(3,4-dihydroxybenzylidene)-3-(2,5-dimethyl-1H-pyrrol-1-yl)-2-thioxo-1,3-thiazolidin-4-one —— C16H14N2O3S2
(5E)-5-(3,4-dihydroxybenzylidene)-3-(2,5-dimethyl-1H-pyrrol-1-yl)-2-thioxo-1,3-thiazolidin-4-one
—— methyl (4Z)-1-[2-(cyclohex-1-en-1-yl)ethyl]-4-(2-hydroxybenzylidene)-2-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate —— C22H25NO4
methyl (4Z)-1-[2-(cyclohex-1-en-1-yl)ethyl]-4-(2-hydroxybenzylidene)-2-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate
—— (3Z)-3-[(2-hydroxyphenyl)methylidene]-5-phenylthiophen-2-one —— C17H12O2S
(3Z)-3-[(2-hydroxyphenyl)methylidene]-5-phenylthiophen-2-one
—— 4-[(E)-2-(1-ethyl-2H-pyridin-2-yl)ethenyl]-2-methoxyphenol —— C16H19NO2
4-[(E)-2-(1-ethyl-2H-pyridin-2-yl)ethenyl]-2-methoxyphenol
—— (5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(4-methoxyanilino)-2-phenylimidazol-4-one —— C24H21N3O4
(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(4-methoxyanilino)-2-phenylimidazol-4-one
—— (4Z)-4-[(5E)-5-(anilinomethylidene)-3-(4-hydroxy-3-methoxyphenyl)-4-nitrofuran-2-ylidene]-2-methoxycyclohexa-2,5-dien-1-one —— C25H20N2O7
(4Z)-4-[(5E)-5-(anilinomethylidene)-3-(4-hydroxy-3-methoxyphenyl)-4-nitrofuran-2-ylidene]-2-methoxycyclohexa-2,5-dien-1-one
—— (3,4-Dihydroxy-phenyl)-triphenyl-arsonium —— C24H20AsO2+
(3,4-Dihydroxy-phenyl)-triphenyl-arsonium
—— 1,3-diethyl-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione —— C17H20N2O5S
1,3-diethyl-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione
—— 2-(2-tert-butylphenoxy)-N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide —— C19H21N3O5
2-(2-tert-butylphenoxy)-N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide
—— (4Z)-4-[(2-bromo-5-hydroxyphenyl)methylidene]-1-phenylpyrazolidine-3,5-dione —— C16H11BrN2O3
(4Z)-4-[(2-bromo-5-hydroxyphenyl)methylidene]-1-phenylpyrazolidine-3,5-dione
—— ethyl (2Z,5S)-5-(3-ethoxy-4-methoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H28N2O7S
ethyl (2Z,5S)-5-(3-ethoxy-4-methoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-(2,4-dimethylanilino)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C18H21N3O3
2-(2,4-dimethylanilino)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— (2S)-2-ethyl-5-(2-hydroxy-5-nitroanilino)-5-oxopentanoic acid —— C13H16N2O6
(2S)-2-ethyl-5-(2-hydroxy-5-nitroanilino)-5-oxopentanoic acid
—— 4-tert-butyl-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide —— C19H22N2O3
4-tert-butyl-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide
—— (5E)-2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C17H20N2O4S
(5E)-2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— 5-[(4-Hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione —— C15H14N2O4S
5-[(4-Hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
—— (5Z)-1-tert-butyl-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-diazinane-2,4,6-trione —— C17H20N2O6
(5Z)-1-tert-butyl-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-diazinane-2,4,6-trione
—— tert-butyl N-[(Z)-(3-hydroxyphenyl)methylideneamino]carbamate 162739-81-3 C12H16N2O3
tert-butyl N-[(Z)-(3-hydroxyphenyl)methylideneamino]carbamate
—— 2-hydroxy-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C10H12N2O4
2-hydroxy-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-(4-methoxyphenoxy)acetamide —— C17H18N2O5
N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-(4-methoxyphenoxy)acetamide
—— N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-phenoxyacetamide —— C16H16N2O4
N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-phenoxyacetamide
—— (2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-1-benzothiophen-3-one —— C15H10O3S
(2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-1-benzothiophen-3-one
—— (4R)-6-amino-3-(3-hydroxyphenyl)-4-phenyl-2,4-dihydro-[1,2]oxazolo[5,4-b]pyridine-5-carbonitrile —— C19H14N4O2
(4R)-6-amino-3-(3-hydroxyphenyl)-4-phenyl-2,4-dihydro-[1,2]oxazolo[5,4-b]pyridine-5-carbonitrile
—— (5Z)-3-ethyl-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C14H16N2O4S
(5Z)-3-ethyl-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— 3-(3,5-dioxo-2H-1,2,4-triazin-6-yl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]propanamide —— C14H15N5O5
3-(3,5-dioxo-2H-1,2,4-triazin-6-yl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]propanamide
—— 4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-6-methyl-3-sulfanylidene-2H-1,2,4-triazin-5-one —— C12H12N4O3S
4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-6-methyl-3-sulfanylidene-2H-1,2,4-triazin-5-one
—— (6E)-4-bromo-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dien-1-one —— C14H12BrNO2
(6E)-4-bromo-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dien-1-one
—— 4-bromo-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide —— C15H13BrN2O3
4-bromo-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide
—— 4-[[[(4-hydroxy-3-methoxyphenyl)-[[(E)-(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]amino]methyl]amino]methylidene]-2-methoxycyclohexa-2,5-dien-1-one —— C24H24N2O6
4-[[[(4-hydroxy-3-methoxyphenyl)-[[(E)-(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]amino]methyl]amino]methylidene]-2-methoxycyclohexa-2,5-dien-1-one
—— 4-[(Z)-2-(hydroxyamino)-1-nitrosoprop-1-enyl]phenol —— C9H10N2O3
4-[(Z)-2-(hydroxyamino)-1-nitrosoprop-1-enyl]phenol