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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
—— [(E)-but-2-enyl] (4S,5R)-4-(4-hydroxy-3-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate —— C17H20N2O5
[(E)-but-2-enyl] (4S,5R)-4-(4-hydroxy-3-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate
—— 4-[(1R)-1-[[(1R)-2,2-dimethylcyclopropyl]amino]ethyl]benzene-1,3-diol —— C13H19NO2
4-[(1R)-1-[[(1R)-2,2-dimethylcyclopropyl]amino]ethyl]benzene-1,3-diol
—— 2-[(1S)-1-[[(1S)-2,2-dimethylcyclopropyl]amino]ethyl]benzene-1,4-diol —— C13H19NO2
2-[(1S)-1-[[(1S)-2,2-dimethylcyclopropyl]amino]ethyl]benzene-1,4-diol
—— 2-[(1S)-1-[[(1R)-2,2-dimethylcyclopropyl]amino]ethyl]benzene-1,4-diol —— C13H19NO2
2-[(1S)-1-[[(1R)-2,2-dimethylcyclopropyl]amino]ethyl]benzene-1,4-diol
—— 2-[(1S)-1-[[(1S)-2,2-dimethylcyclopropyl]amino]ethyl]phenol —— C13H19NO
2-[(1S)-1-[[(1S)-2,2-dimethylcyclopropyl]amino]ethyl]phenol
—— 4-[(1S)-1-[[(1R)-2,2-dimethylcyclopropyl]amino]ethyl]phenol —— C13H19NO
4-[(1S)-1-[[(1R)-2,2-dimethylcyclopropyl]amino]ethyl]phenol
—— 3-[(1S)-1-[[(1R)-2,2-dimethylcyclopropyl]amino]ethyl]phenol —— C13H19NO
3-[(1S)-1-[[(1R)-2,2-dimethylcyclopropyl]amino]ethyl]phenol
—— 4-[(1R)-1-[[(1S)-2,2-dimethylcyclopropyl]amino]ethyl]phenol —— C13H19NO
4-[(1R)-1-[[(1S)-2,2-dimethylcyclopropyl]amino]ethyl]phenol
—— 4-[(1S)-1-[[(1S)-2,2-dimethylcyclopropyl]amino]ethyl]benzene-1,3-diol —— C13H19NO2
4-[(1S)-1-[[(1S)-2,2-dimethylcyclopropyl]amino]ethyl]benzene-1,3-diol
—— 2-[(1R)-1-[[(1R)-2,2-dimethylcyclopropyl]amino]ethyl]benzene-1,4-diol —— C13H19NO2
2-[(1R)-1-[[(1R)-2,2-dimethylcyclopropyl]amino]ethyl]benzene-1,4-diol
—— 4-[(1S)-1-[[(1R)-2,2-dimethylcyclopropyl]amino]ethyl]benzene-1,3-diol —— C13H19NO2
4-[(1S)-1-[[(1R)-2,2-dimethylcyclopropyl]amino]ethyl]benzene-1,3-diol
—— 4-[(1R)-1-[[(1R)-2,2-dimethylcyclopropyl]amino]ethyl]phenol —— C13H19NO
4-[(1R)-1-[[(1R)-2,2-dimethylcyclopropyl]amino]ethyl]phenol
—— methyl (2S,7R)-5-amino-6-cyano-7-(4-hydroxyphenyl)-2-methyl-3-oxo-7H-[1,3]thiazolo[3,2-a]pyridine-8-carboxylate —— C17H15N3O4S
methyl (2S,7R)-5-amino-6-cyano-7-(4-hydroxyphenyl)-2-methyl-3-oxo-7H-[1,3]thiazolo[3,2-a]pyridine-8-carboxylate
—— N-[(5Z)-5-(4-hydroxy-3-methoxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]pyridine-3-carboxamide —— C17H13N3O4S2
N-[(5Z)-5-(4-hydroxy-3-methoxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]pyridine-3-carboxamide
—— 4-[4-[4-[(4-Chlorophenyl)methyl]piperazin-1-yl]butoxy]-2-propylphenol —— C24H33ClN2O2
4-[4-[4-[(4-Chlorophenyl)methyl]piperazin-1-yl]butoxy]-2-propylphenol
—— 5-methoxy-2-[2-[(3R)-3-(4-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-yl]phenol —— C24H21N3O3S2
5-methoxy-2-[2-[(3R)-3-(4-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-yl]phenol
—— 2-chloro-1-[(3R)-3-(4-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone —— C15H13ClN2O2S
2-chloro-1-[(3R)-3-(4-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone
—— 5-methoxy-2-[2-[(3S)-3-(4-nitrophenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-yl]phenol —— C23H18N4O4S2
5-methoxy-2-[2-[(3S)-3-(4-nitrophenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-yl]phenol
—— 5-methoxy-2-[2-[(3S)-3-(4-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-yl]phenol —— C24H21N3O3S2
5-methoxy-2-[2-[(3S)-3-(4-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-yl]phenol
—— (8S)-3-(3,4-dimethylphenyl)-8-(4-hydroxy-3-methoxyphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile —— C23H23N3O3S
(8S)-3-(3,4-dimethylphenyl)-8-(4-hydroxy-3-methoxyphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile
—— (8R)-3-(3,4-dimethylphenyl)-8-(4-hydroxy-3-methoxyphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile —— C23H23N3O3S
(8R)-3-(3,4-dimethylphenyl)-8-(4-hydroxy-3-methoxyphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile
—— diethyl-[3-[(5Z)-5-[(3-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propyl]azanium —— C17H23N2O2S2+
diethyl-[3-[(5Z)-5-[(3-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propyl]azanium
—— 1-[(2-hydroxyphenyl)methyl]-1-[[(2S)-oxolan-2-yl]methyl]-3-pyridin-3-ylurea —— C18H21N3O3
1-[(2-hydroxyphenyl)methyl]-1-[[(2S)-oxolan-2-yl]methyl]-3-pyridin-3-ylurea
—— 1-[(4-ethyl-1,2,4-triazol-3-yl)methyl]-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]urea —— C16H23N5O2
1-[(4-ethyl-1,2,4-triazol-3-yl)methyl]-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]urea
—— (12E)-12-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,2,8,10-tetrazatricyclo[7.3.0.03,7]dodeca-2,6,8-trien-11-one —— C16H14N4O3
(12E)-12-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,2,8,10-tetrazatricyclo[7.3.0.03,7]dodeca-2,6,8-trien-11-one
—— 5-bromo-N-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylideneamino]pyridine-3-carboxamide —— C14H11BrClN3O3
5-bromo-N-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylideneamino]pyridine-3-carboxamide
—— (5Z)-3-(3,4-dimethylphenyl)-5-(4-hydroxy-3-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one —— C19H17NO3S2
(5Z)-3-(3,4-dimethylphenyl)-5-(4-hydroxy-3-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
—— (2R,7R)-7-tert-butyl-2-(3-hydroxy-4-methoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C21H26N2O3S
(2R,7R)-7-tert-butyl-2-(3-hydroxy-4-methoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2S,7S)-7-tert-butyl-2-(3-hydroxy-4-methoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C21H26N2O3S
(2S,7S)-7-tert-butyl-2-(3-hydroxy-4-methoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (5Z)-5-[(2-hydroxyphenyl)methylidene]-3-(morpholin-4-ium-4-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H17N2O3S2+
(5Z)-5-[(2-hydroxyphenyl)methylidene]-3-(morpholin-4-ium-4-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 3-(3-Hydroxyphenyl)-5-(4-pyridylmethylene)-2-thioxo-1,3-thiazolidin-4-one —— C15H10N2O2S2
3-(3-Hydroxyphenyl)-5-(4-pyridylmethylene)-2-thioxo-1,3-thiazolidin-4-one
—— (5E)-5-[(4-hydroxyphenyl)methylidene]-3-[[(2S)-oxolan-2-yl]methyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H15NO3S2
(5E)-5-[(4-hydroxyphenyl)methylidene]-3-[[(2S)-oxolan-2-yl]methyl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(4-hydroxyphenyl)methylidene]-3-[[(2S)-oxolan-2-yl]methyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H15NO3S2
(5Z)-5-[(4-hydroxyphenyl)methylidene]-3-[[(2S)-oxolan-2-yl]methyl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(3-hydroxyphenyl)methylidene]-2-[(3S)-3-methylpiperidin-1-yl]-1,3-thiazol-4-one —— C16H18N2O2S
(5Z)-5-[(3-hydroxyphenyl)methylidene]-2-[(3S)-3-methylpiperidin-1-yl]-1,3-thiazol-4-one
—— (5E)-5-[(3-hydroxyphenyl)methylidene]-2-[(3S)-3-methylpiperidin-1-yl]-1,3-thiazol-4-one —— C16H18N2O2S
(5E)-5-[(3-hydroxyphenyl)methylidene]-2-[(3S)-3-methylpiperidin-1-yl]-1,3-thiazol-4-one
—— ethyl (2Z,5S)-2-[(5-bromo-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H19BrN2O4S
ethyl (2Z,5S)-2-[(5-bromo-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5E)-5-[(3-hydroxyphenyl)methylidene]-2-[(3R)-3-methylpiperidin-1-yl]-1,3-thiazol-4-one —— C16H18N2O2S
(5E)-5-[(3-hydroxyphenyl)methylidene]-2-[(3R)-3-methylpiperidin-1-yl]-1,3-thiazol-4-one
—— methyl (2Z,5S)-2-[(3-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C22H18N2O4S
methyl (2Z,5S)-2-[(3-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidine-2,4-dione —— C12H11NO4S
(5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidine-2,4-dione
—— methyl (4E)-4-[(4-hydroxyphenyl)methylidene]-1-(3-methoxypropyl)-2-methyl-5-oxopyrrole-3-carboxylate —— C18H21NO5
methyl (4E)-4-[(4-hydroxyphenyl)methylidene]-1-(3-methoxypropyl)-2-methyl-5-oxopyrrole-3-carboxylate
—— (5Z)-3-[(2S)-2-ethylhexyl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C19H25NO3S2
(5Z)-3-[(2S)-2-ethylhexyl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— ethyl (2E,5R)-5-(4-chlorophenyl)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21ClN2O5S
ethyl (2E,5R)-5-(4-chlorophenyl)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5R)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H22N2O5S
ethyl (2E,5R)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z,5R)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H22N2O5S
ethyl (2Z,5R)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (Z)-3-Amino-4,4,4-trifluoro-1-(2-hydroxy-5-methoxy-phenyl)-but-2-en-1-one —— C11H10F3NO3
(Z)-3-Amino-4,4,4-trifluoro-1-(2-hydroxy-5-methoxy-phenyl)-but-2-en-1-one
—— 2-(4-bromophenyl)-4-{2-hydroxy-5-nitrobenzylidene}-1,3-oxazol-5(4H)-one —— C16H9BrN2O5
2-(4-bromophenyl)-4-{2-hydroxy-5-nitrobenzylidene}-1,3-oxazol-5(4H)-one
—— tert-butyl N-[(2,4,6-tribromo-3-hydroxyphenyl)methylideneamino]carbamate —— C12H13Br3N2O3
tert-butyl N-[(2,4,6-tribromo-3-hydroxyphenyl)methylideneamino]carbamate
—— N-cyclohexyl-N-[(2-hydroxyphenyl)methyl]-2-(1-thiophen-2-ylethenylamino)oxyacetamide —— C21H26N2O3S
N-cyclohexyl-N-[(2-hydroxyphenyl)methyl]-2-(1-thiophen-2-ylethenylamino)oxyacetamide
—— 3-[4-[(5E)-5-[(4-hydroxyphenyl)methylidene]-4-oxo-1,3-thiazol-2-yl]piperazin-1-ium-1-yl]propanenitrile —— C17H19N4O2S+
3-[4-[(5E)-5-[(4-hydroxyphenyl)methylidene]-4-oxo-1,3-thiazol-2-yl]piperazin-1-ium-1-yl]propanenitrile
—— (2Z,5Z)-5-(3-bromo-4-hydroxy-5-nitrobenzylidene)-2-[(3,5-dimethylphenyl)imino]-1,3-thiazolidin-4-one —— C18H14BrN3O4S
(2Z,5Z)-5-(3-bromo-4-hydroxy-5-nitrobenzylidene)-2-[(3,5-dimethylphenyl)imino]-1,3-thiazolidin-4-one