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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
—— (2S)-2-(2-chloro-4-fluorophenoxy)-N-[(2R)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]propanamide —— C20H23ClFNO5
(2S)-2-(2-chloro-4-fluorophenoxy)-N-[(2R)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]propanamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[(5Z)-5-(2-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]propanamide —— C22H22N2O6S
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[(5Z)-5-(2-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]propanamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-5-[(4-fluorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C20H17FN2O5S
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-5-[(4-fluorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— (2R)-2-(2-chloro-4-fluorophenoxy)-N-[(2S)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]propanamide —— C20H23ClFNO5
(2R)-2-(2-chloro-4-fluorophenoxy)-N-[(2S)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]propanamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-5-(furan-2-ylmethylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C18H16N2O6S
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-5-(furan-2-ylmethylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— 3-(3-cyclopentyloxyphenyl)-N-[(2R)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]propanamide —— C25H33NO5
3-(3-cyclopentyloxyphenyl)-N-[(2R)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]propanamide
—— 3-(3-cyclopentyloxyphenyl)-N-[(2S)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]propanamide —— C25H33NO5
3-(3-cyclopentyloxyphenyl)-N-[(2S)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]propanamide
—— 5-[(Z)-{3-[chloro(difluoro)methyl]-6-methyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-ylidene}methyl]-2-methoxyphenol —— C14H11ClF2N4O2S
5-[(Z)-{3-[chloro(difluoro)methyl]-6-methyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-ylidene}methyl]-2-methoxyphenol
—— (5E)-3-(4-hydroxyphenyl)-5-[3-(4-hydroxyphenyl)-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H10N2O4S4
(5E)-3-(4-hydroxyphenyl)-5-[3-(4-hydroxyphenyl)-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-(3-hydroxyphenyl)imino-1,3-thiazolidin-4-one —— C17H14N2O4S
(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-(3-hydroxyphenyl)imino-1,3-thiazolidin-4-one
—— 2-[(5Z)-5-[(4-ethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)acetamide —— C20H17N3O6S2
2-[(5Z)-5-[(4-ethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)acetamide
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(3-methylphenyl)-1,3-thiazolidine-2,4-dione —— C18H15NO4S
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(3-methylphenyl)-1,3-thiazolidine-2,4-dione
—— diethyl 4-[(E)-2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate —— C23H29NO7
diethyl 4-[(E)-2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate
—— prop-2-enyl (2Z)-5-(4-butoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H30N2O6S
prop-2-enyl (2Z)-5-(4-butoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-methoxyethyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-[3-methoxy-4-(3-methylbutoxy)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C31H36N2O8S
2-methoxyethyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-[3-methoxy-4-(3-methylbutoxy)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— methyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-phenylmethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C31H28N2O7S
methyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-phenylmethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-methylpropyl (2Z)-5-(4-butoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C30H34N2O6S
2-methylpropyl (2Z)-5-(4-butoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— methyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H26N2O7S
methyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-methylpropyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-propoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H32N2O6S
2-methylpropyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-propoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-methylpropyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C30H32N2O7S
2-methylpropyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N-[(Z)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(4-fluoroanilino)acetamide —— C16H15BrFN3O3
N-[(Z)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(4-fluoroanilino)acetamide
—— (4Z)-4-(2-hydroxy-3-nitrobenzylidene)-2-phenyl-1,3-oxazol-5(4H)-one —— C16H10N2O5
(4Z)-4-(2-hydroxy-3-nitrobenzylidene)-2-phenyl-1,3-oxazol-5(4H)-one
—— 1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-prop-2-enylthiourea —— C12H15N3O2S
1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-prop-2-enylthiourea
—— methyl (2Z)-2-[(5-bromo-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C22H17BrN2O4S
methyl (2Z)-2-[(5-bromo-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-2-[(2-hydroxy-3,5-dinitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C17H14N4O8S
ethyl (2Z)-2-[(2-hydroxy-3,5-dinitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-5-(4-chlorophenyl)-2-[4-hydroxy-3-methoxy-5-(prop-2-en-1-yl)benzylidene]-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H25ClN2O5S
ethyl (2Z)-5-(4-chlorophenyl)-2-[4-hydroxy-3-methoxy-5-(prop-2-en-1-yl)benzylidene]-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2E)-1-(4-chlorophenyl)-3-[(2-hydroxy-4-methylphenyl)amino]prop-2-en-1-one —— C16H14ClNO2
(2E)-1-(4-chlorophenyl)-3-[(2-hydroxy-4-methylphenyl)amino]prop-2-en-1-one
—— ethyl (2Z)-2-(4-hydroxy-3-nitrobenzylidene)-7-methyl-3-oxo-5-(thiophen-2-yl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H17N3O6S2
ethyl (2Z)-2-(4-hydroxy-3-nitrobenzylidene)-7-methyl-3-oxo-5-(thiophen-2-yl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (4Z)-2-(4-butoxyphenyl)-4-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-oxazol-5-one —— C20H18N2O6
(4Z)-2-(4-butoxyphenyl)-4-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-oxazol-5-one
—— 5-[(Z)-[(2,4-dinitrophenyl)hydrazinylidene]methyl]-2-methoxyphenol —— C14H12N4O6
5-[(Z)-[(2,4-dinitrophenyl)hydrazinylidene]methyl]-2-methoxyphenol
—— (6E)-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dien-1-one —— C14H13NO2
(6E)-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dien-1-one
—— N-[(5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-2-phenylacetamide —— C20H18N2O5S2
N-[(5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-2-phenylacetamide
—— (5Z)-3-butyl-2-butylimino-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C18H24N2O2S
(5Z)-3-butyl-2-butylimino-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 2-[(5Z)-5-[(2-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]ethanesulfonic acid —— C12H11NO5S3
2-[(5Z)-5-[(2-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]ethanesulfonic acid
—— 2-(2,4-dimethylphenoxy)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C18H20N2O4
2-(2,4-dimethylphenoxy)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— N-(3,4-dimethylphenyl)-2-[(5E)-5-(2-hydroxy-5-methyl-3-nitrobenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C21H19N3O6S
N-(3,4-dimethylphenyl)-2-[(5E)-5-(2-hydroxy-5-methyl-3-nitrobenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— (2E,5Z)-5-(4-hydroxy-3-methoxybenzylidene)-2-[(4-hydroxyphenyl)imino]-3-(prop-2-en-1-yl)-1,3-thiazolidin-4-one —— C20H18N2O4S
(2E,5Z)-5-(4-hydroxy-3-methoxybenzylidene)-2-[(4-hydroxyphenyl)imino]-3-(prop-2-en-1-yl)-1,3-thiazolidin-4-one
—— ethyl (2Z)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5-(3,4,5-trimethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H25N3O9S
ethyl (2Z)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5-(3,4,5-trimethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-(4-Hydroxybenzylidene)-3-(3-pyridinyl)-2-thioxo-1,3-thiazolidin-4-one —— C15H10N2O2S2
5-(4-Hydroxybenzylidene)-3-(3-pyridinyl)-2-thioxo-1,3-thiazolidin-4-one
—— ethyl (2Z)-2-[(1,3-dimethylpyrazol-4-yl)methylidene]-5-(4-hydroxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C22H22N4O4S
ethyl (2Z)-2-[(1,3-dimethylpyrazol-4-yl)methylidene]-5-(4-hydroxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (3Z)-3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylidenehydrazinylidene]-1H-indol-2-one —— C16H13N3O3
(3Z)-3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylidenehydrazinylidene]-1H-indol-2-one
—— ethyl (2Z)-5-(3,4-diethoxyphenyl)-2-(3-hydroxy-4-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C28H30N2O7S
ethyl (2Z)-5-(3,4-diethoxyphenyl)-2-(3-hydroxy-4-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5Z)-3-(4-hydroxyphenyl)-5-(1-methylpyridin-2-ylidene)-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H12N2O2S2
(5Z)-3-(4-hydroxyphenyl)-5-(1-methylpyridin-2-ylidene)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (2-acetamidovinyl)-2,5-dihydroxybenzene —— C10H11NO3
(2-acetamidovinyl)-2,5-dihydroxybenzene
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-[(4-methylanilino)methyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C19H18N2O3S2
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-[(4-methylanilino)methyl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 3-(3,4-dihydroxyphenyl)-N-[(Z)-[3-methoxy-4-(2-morpholin-4-ylethoxy)phenyl]methylideneamino]propanamide —— C23H29N3O6
3-(3,4-dihydroxyphenyl)-N-[(Z)-[3-methoxy-4-(2-morpholin-4-ylethoxy)phenyl]methylideneamino]propanamide
—— 2-[(5E)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(3,4-dimethylphenyl)acetamide —— C21H19ClN2O5S
2-[(5E)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(3,4-dimethylphenyl)acetamide
—— 5-[(Z)-(tert-butylhydrazinylidene)methyl]-2-methoxyphenol —— C12H18N2O2
5-[(Z)-(tert-butylhydrazinylidene)methyl]-2-methoxyphenol
—— (6Z)-3-(3,4-dihydroxyphenyl)-6-[(2-methoxyphenyl)methylene]thiazolo[2,3-b]thiazol-4-ium-5-one —— C19H14NO4S2+
(6Z)-3-(3,4-dihydroxyphenyl)-6-[(2-methoxyphenyl)methylene]thiazolo[2,3-b]thiazol-4-ium-5-one
—— N-[(Z)-(3-bromo-5-ethoxy-4-methoxyphenyl)methylideneamino]-2-hydroxy-5-nitrobenzamide —— C17H16BrN3O6
N-[(Z)-(3-bromo-5-ethoxy-4-methoxyphenyl)methylideneamino]-2-hydroxy-5-nitrobenzamide