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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
—— 4-bromo-2-methoxy-5-[(Z)-(pyridin-2-ylhydrazinylidene)methyl]phenol —— C13H12BrN3O2
4-bromo-2-methoxy-5-[(Z)-(pyridin-2-ylhydrazinylidene)methyl]phenol
—— 2-(4-chlorophenyl)sulfanyl-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C16H15ClN2O3S
2-(4-chlorophenyl)sulfanyl-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— N'-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]oxamide —— C10H10BrN3O4
N'-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]oxamide
—— N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-methylbenzimidazol-1-yl)acetamide —— C18H18N4O3
N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-methylbenzimidazol-1-yl)acetamide
—— 2-(benzimidazol-1-yl)-N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C17H15BrN4O3
2-(benzimidazol-1-yl)-N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— (E)-N-[(2-hydroxy-5-nitrophenyl)methyl]-3-(1,3,5-trimethylpyrazol-4-yl)prop-2-enamide —— C16H18N4O4
(E)-N-[(2-hydroxy-5-nitrophenyl)methyl]-3-(1,3,5-trimethylpyrazol-4-yl)prop-2-enamide
—— 1-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-pyrrolidin-1-ylethanone —— C20H23N3O3S
1-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-pyrrolidin-1-ylethanone
—— 1-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-(4-methylpiperidin-1-yl)ethanone —— C22H27N3O3S
1-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-(4-methylpiperidin-1-yl)ethanone
—— 1-[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-morpholin-4-ylethanone —— C20H23N3O4S
1-[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-morpholin-4-ylethanone
—— (2-hydroxy-5-methoxyphenyl)-[5-(2H-[1,2,4]triazolo[4,3-a]pyridin-3-ylidene)pyrrol-3-yl]methanone —— C18H14N4O3
(2-hydroxy-5-methoxyphenyl)-[5-(2H-[1,2,4]triazolo[4,3-a]pyridin-3-ylidene)pyrrol-3-yl]methanone
—— 1-[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-pyrrolidin-1-ium-1-ylethanone —— C20H24N3O3S+
1-[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-pyrrolidin-1-ium-1-ylethanone
—— 1-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-pyrrolidin-1-ium-1-ylethanone —— C20H24N3O3S+
1-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-pyrrolidin-1-ium-1-ylethanone
—— 1-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-morpholin-4-ylethanone —— C20H23N3O4S
1-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-morpholin-4-ylethanone
—— [2-[(4-Hydroxy-3,5-dimethylphenyl)methylamino]-2-oxoethyl] 2-(4-fluorophenyl)sulfanylacetate —— C19H20FNO4S
[2-[(4-Hydroxy-3,5-dimethylphenyl)methylamino]-2-oxoethyl] 2-(4-fluorophenyl)sulfanylacetate
—— 3-(3,5-dimethyl-1H-pyrazol-4-yl)-N-(3-hydroxy-4-methoxyphenyl)propanamide —— C15H19N3O3
3-(3,5-dimethyl-1H-pyrazol-4-yl)-N-(3-hydroxy-4-methoxyphenyl)propanamide
—— 2-methoxy-5-[[(7R)-7-methyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-yl]amino]phenol —— C18H19N3O2S
2-methoxy-5-[[(7R)-7-methyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-yl]amino]phenol
—— 2-[[4-(1,3-Benzothiazol-2-ylmethyl)piperazine-1,4-diium-1-yl]methyl]-6-methoxy-4-prop-2-enylphenol —— C23H29N3O2S+2
2-[[4-(1,3-Benzothiazol-2-ylmethyl)piperazine-1,4-diium-1-yl]methyl]-6-methoxy-4-prop-2-enylphenol
—— 5-[[5-(4-Fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]amino]-2-methoxyphenol —— C19H14FN3O2S
5-[[5-(4-Fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]amino]-2-methoxyphenol
—— 2-[[4-(1,3-Benzothiazol-2-ylmethyl)piperazin-1-yl]methyl]-6-methoxy-4-prop-2-enylphenol —— C23H27N3O2S
2-[[4-(1,3-Benzothiazol-2-ylmethyl)piperazin-1-yl]methyl]-6-methoxy-4-prop-2-enylphenol
—— 2-(3-Hydroxy-4-methoxyanilino)-5-nitrobenzonitrile —— C14H11N3O4
2-(3-Hydroxy-4-methoxyanilino)-5-nitrobenzonitrile
—— 2-Methoxy-5-[(6-phenylthieno[2,3-d]pyrimidin-4-yl)amino]phenol —— C19H15N3O2S
2-Methoxy-5-[(6-phenylthieno[2,3-d]pyrimidin-4-yl)amino]phenol
—— (2R)-2-(4-hydroxyphenyl)-2-(4-methylpiperazine-1,4-diium-1-yl)acetonitrile —— C13H19N3O+2
(2R)-2-(4-hydroxyphenyl)-2-(4-methylpiperazine-1,4-diium-1-yl)acetonitrile
—— 1-[2-(4-Chlorophenyl)sulfanylethyl]-3-[(2-hydroxy-5-nitrophenyl)methyl]thiourea —— C16H16ClN3O3S2
1-[2-(4-Chlorophenyl)sulfanylethyl]-3-[(2-hydroxy-5-nitrophenyl)methyl]thiourea
—— 3-(2-hydroxyphenyl)-N-[[1-[[(1S)-1-phenylethyl]amino]cyclopentyl]methyl]propanamide —— C23H30N2O2
3-(2-hydroxyphenyl)-N-[[1-[[(1S)-1-phenylethyl]amino]cyclopentyl]methyl]propanamide
—— 3-(2-hydroxyphenyl)-N-[[1-[[(1R)-1-phenylethyl]amino]cyclopentyl]methyl]propanamide —— C23H30N2O2
3-(2-hydroxyphenyl)-N-[[1-[[(1R)-1-phenylethyl]amino]cyclopentyl]methyl]propanamide
—— (3R)-3-N-[(2-hydroxy-5-nitrophenyl)methyl]-1-N-phenylpiperidine-1,3-dicarboxamide —— C20H22N4O5
(3R)-3-N-[(2-hydroxy-5-nitrophenyl)methyl]-1-N-phenylpiperidine-1,3-dicarboxamide
—— 2-(3,4-dimethoxyphenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]-1,3-thiazole-4-carboxamide —— C19H17N3O6S
2-(3,4-dimethoxyphenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]-1,3-thiazole-4-carboxamide
—— (3S)-3-N-[(2-hydroxy-5-nitrophenyl)methyl]-1-N-phenylpiperidine-1,3-dicarboxamide —— C20H22N4O5
(3S)-3-N-[(2-hydroxy-5-nitrophenyl)methyl]-1-N-phenylpiperidine-1,3-dicarboxamide
—— 5-(2,5-dichlorophenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]furan-2-carboxamide —— C18H12Cl2N2O5
5-(2,5-dichlorophenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]furan-2-carboxamide
—— 5-acetyl-N-[(2-hydroxy-5-nitrophenyl)methyl]thiophene-2-carboxamide —— C14H12N2O5S
5-acetyl-N-[(2-hydroxy-5-nitrophenyl)methyl]thiophene-2-carboxamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-6-methyl-4-oxo-1-phenylpyridazine-3-carboxamide —— C19H16N4O5
N-[(2-hydroxy-5-nitrophenyl)methyl]-6-methyl-4-oxo-1-phenylpyridazine-3-carboxamide
—— (3R)-6-chloro-N-[(2-hydroxy-5-nitrophenyl)methyl]-3,4-dihydro-2H-chromene-3-carboxamide —— C17H15ClN2O5
(3R)-6-chloro-N-[(2-hydroxy-5-nitrophenyl)methyl]-3,4-dihydro-2H-chromene-3-carboxamide
—— 1-(4-chlorophenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]-6-methyl-4-oxopyridazine-3-carboxamide —— C19H15ClN4O5
1-(4-chlorophenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]-6-methyl-4-oxopyridazine-3-carboxamide
—— 3,6-dichloro-N-[(2-hydroxy-5-nitrophenyl)methyl]-1-benzothiophene-2-carboxamide —— C16H10Cl2N2O4S
3,6-dichloro-N-[(2-hydroxy-5-nitrophenyl)methyl]-1-benzothiophene-2-carboxamide
—— 5-(2,4-dichlorophenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]furan-2-carboxamide —— C18H12Cl2N2O5
5-(2,4-dichlorophenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]furan-2-carboxamide
—— 5-(2-chlorophenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]furan-2-carboxamide —— C18H13ClN2O5
5-(2-chlorophenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]furan-2-carboxamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-5-methoxy-3-methyl-1-benzofuran-2-carboxamide —— C18H16N2O6
N-[(2-hydroxy-5-nitrophenyl)methyl]-5-methoxy-3-methyl-1-benzofuran-2-carboxamide
—— (1Z,4S)-1-[(2-hydroxyphenyl)methylidene]-4-methylpyrazolidin-1-ium-3-one —— C11H13N2O2+
(1Z,4S)-1-[(2-hydroxyphenyl)methylidene]-4-methylpyrazolidin-1-ium-3-one
—— (1Z,4R)-1-[(2-hydroxyphenyl)methylidene]-4-methylpyrazolidin-1-ium-3-one —— C11H13N2O2+
(1Z,4R)-1-[(2-hydroxyphenyl)methylidene]-4-methylpyrazolidin-1-ium-3-one
—— 2-methoxy-5-[[[(1S,3R)-3-methyl-2,3-dihydro-1H-inden-1-yl]amino]methyl]phenol —— C18H21NO2
2-methoxy-5-[[[(1S,3R)-3-methyl-2,3-dihydro-1H-inden-1-yl]amino]methyl]phenol
—— 5-[[[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]amino]methyl]-2-methoxyphenol —— C18H21NO3
5-[[[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]amino]methyl]-2-methoxyphenol
—— 2-methoxy-5-[[[(1S,3S)-3-methyl-2,3-dihydro-1H-inden-1-yl]amino]methyl]phenol —— C18H21NO2
2-methoxy-5-[[[(1S,3S)-3-methyl-2,3-dihydro-1H-inden-1-yl]amino]methyl]phenol
—— 2-methoxy-5-[[[(1R)-1-(1,3,5-trimethylpyrazol-4-yl)ethyl]amino]methyl]phenol —— C16H23N3O2
2-methoxy-5-[[[(1R)-1-(1,3,5-trimethylpyrazol-4-yl)ethyl]amino]methyl]phenol
—— 5-[[[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]amino]methyl]-2-methoxyphenol —— C18H21NO3
5-[[[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]amino]methyl]-2-methoxyphenol
—— 2-methoxy-5-[[[(1R,3S)-3-methyl-2,3-dihydro-1H-inden-1-yl]amino]methyl]phenol —— C18H21NO2
2-methoxy-5-[[[(1R,3S)-3-methyl-2,3-dihydro-1H-inden-1-yl]amino]methyl]phenol
—— 2-methoxy-5-[[[(1R,3R)-3-methyl-2,3-dihydro-1H-inden-1-yl]amino]methyl]phenol —— C18H21NO2
2-methoxy-5-[[[(1R,3R)-3-methyl-2,3-dihydro-1H-inden-1-yl]amino]methyl]phenol
—— 2-methoxy-5-[[[(1S)-1-(1,3,5-trimethylpyrazol-4-yl)ethyl]amino]methyl]phenol —— C16H23N3O2
2-methoxy-5-[[[(1S)-1-(1,3,5-trimethylpyrazol-4-yl)ethyl]amino]methyl]phenol
—— (8S,9S)-4-tert-butyl-10-(4-fluorophenyl)-8-(4-hydroxy-3,5-dimethoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one —— C25H26FN5O4
(8S,9S)-4-tert-butyl-10-(4-fluorophenyl)-8-(4-hydroxy-3,5-dimethoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one
—— (4R)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-13-(methoxymethyl)-11-methyl-8-thia-3,5,10-triazatricyclo[7.4.0.02,7]trideca-1(13),2(7),9,11-tetraen-6-one —— C19H18ClN3O4S
(4R)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-13-(methoxymethyl)-11-methyl-8-thia-3,5,10-triazatricyclo[7.4.0.02,7]trideca-1(13),2(7),9,11-tetraen-6-one
—— (8S,9R)-4-tert-butyl-10-(4-fluorophenyl)-8-(4-hydroxy-3,5-dimethoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one —— C25H26FN5O4
(8S,9R)-4-tert-butyl-10-(4-fluorophenyl)-8-(4-hydroxy-3,5-dimethoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one