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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
—— 2-[6-(4-Chlorophenyl)-2-[4-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-6-methoxyphenol —— C24H21ClF3N2O2+
2-[6-(4-Chlorophenyl)-2-[4-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-6-methoxyphenol
—— propan-2-yl 2-[(5-bromo-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21BrN2O4S
propan-2-yl 2-[(5-bromo-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 4-[(1R,2R)-2-amino-1-hydroxy-4-methylpentyl]benzene-1,2-diol —— C12H19NO3
4-[(1R,2R)-2-amino-1-hydroxy-4-methylpentyl]benzene-1,2-diol
—— 4-[(1S,2S)-2-amino-1-hydroxy-4-methylpentyl]benzene-1,2-diol —— C12H19NO3
4-[(1S,2S)-2-amino-1-hydroxy-4-methylpentyl]benzene-1,2-diol
—— 4-[(1R,2S)-2-amino-1-hydroxy-4-methylpentyl]benzene-1,2-diol —— C12H19NO3
4-[(1R,2S)-2-amino-1-hydroxy-4-methylpentyl]benzene-1,2-diol
—— 3-[(1S,2S)-2-amino-1-hydroxy-4-methylpentyl]phenol —— C12H19NO2
3-[(1S,2S)-2-amino-1-hydroxy-4-methylpentyl]phenol
—— 4-[(1R,2S)-2-amino-1-hydroxy-4-methylpentyl]phenol —— C12H19NO2
4-[(1R,2S)-2-amino-1-hydroxy-4-methylpentyl]phenol
—— 4-[(1S,2R)-2-amino-1-hydroxy-4-methylpentyl]-2-chlorophenol —— C12H18ClNO2
4-[(1S,2R)-2-amino-1-hydroxy-4-methylpentyl]-2-chlorophenol
—— [2-[[(2-Hydroxybenzoyl)hydrazinylidene]methyl]-6-methoxyphenyl]oxidanium;palladium(2+);hydroxide —— C15H16N2O5Pd+2
[2-[[(2-Hydroxybenzoyl)hydrazinylidene]methyl]-6-methoxyphenyl]oxidanium;palladium(2+);hydroxide
—— 13-[(1-Phenylethylimino)methyl]tricyclo [8.2.2.24,7] hexadeca-1(13),4,6,10(14),11,15-hexaen-5-ol —— C25H25NO
13-[(1-Phenylethylimino)methyl]tricyclo [8.2.2.24,7] hexadeca-1(13),4,6,10(14),11,15-hexaen-5-ol
—— 2-methoxy-6-(4,5,6,7-tetramethyl-2,3-dihydro-1H-benzimidazol-2-yl)phenol —— C18H22N2O2
2-methoxy-6-(4,5,6,7-tetramethyl-2,3-dihydro-1H-benzimidazol-2-yl)phenol
—— 4-[2,2-Bis(1,3-benzothiazol-2-yl)ethenyl]-2,6-dimethoxyphenol —— C24H18N2O3S2
4-[2,2-Bis(1,3-benzothiazol-2-yl)ethenyl]-2,6-dimethoxyphenol
—— 1-tert-butyl-6-cyclopropyl-N-[(3-hydroxy-4-methoxyphenyl)methyl]-3-methylpyrazolo[3,4-b]pyridine-4-carboxamide —— C23H28N4O3
1-tert-butyl-6-cyclopropyl-N-[(3-hydroxy-4-methoxyphenyl)methyl]-3-methylpyrazolo[3,4-b]pyridine-4-carboxamide
—— (2S)-2-(4-acetamidophenyl)sulfanyl-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide —— C19H22N2O4S
(2S)-2-(4-acetamidophenyl)sulfanyl-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide
—— (2R)-2-(2-chlorophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide —— C17H18ClNO4
(2R)-2-(2-chlorophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide
—— N-[(3-hydroxy-4-methoxyphenyl)methyl]-2-[2-(trifluoromethyl)phenoxy]acetamide —— C17H16F3NO4
N-[(3-hydroxy-4-methoxyphenyl)methyl]-2-[2-(trifluoromethyl)phenoxy]acetamide
—— 2-[2-(3,4-dimethoxyphenyl)-1,3-thiazol-4-yl]-N-[(3-hydroxy-4-methoxyphenyl)methyl]acetamide —— C21H22N2O5S
2-[2-(3,4-dimethoxyphenyl)-1,3-thiazol-4-yl]-N-[(3-hydroxy-4-methoxyphenyl)methyl]acetamide
—— 3-(2-bromophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide —— C17H18BrNO3
3-(2-bromophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide
—— (2R)-2-(2-bromo-4-chlorophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide —— C17H17BrClNO4
(2R)-2-(2-bromo-4-chlorophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide
—— N-[(3-hydroxy-4-methoxyphenyl)methyl]-1-(3-phenoxypropanoyl)piperidine-4-carboxamide —— C23H28N2O5
N-[(3-hydroxy-4-methoxyphenyl)methyl]-1-(3-phenoxypropanoyl)piperidine-4-carboxamide
—— N-[(3-hydroxy-4-methoxyphenyl)methyl]-2-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]sulfanylacetamide —— C16H19N3O5S
N-[(3-hydroxy-4-methoxyphenyl)methyl]-2-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]sulfanylacetamide
—— 1-N,1-N-diethyl-4-N-[(3-hydroxy-4-methoxyphenyl)methyl]piperidine-1,4-dicarboxamide —— C19H29N3O4
1-N,1-N-diethyl-4-N-[(3-hydroxy-4-methoxyphenyl)methyl]piperidine-1,4-dicarboxamide
—— (2R)-N-[(3-hydroxy-4-methoxyphenyl)methyl]-2-phenyl-2-phenylsulfanylacetamide —— C22H21NO3S
(2R)-N-[(3-hydroxy-4-methoxyphenyl)methyl]-2-phenyl-2-phenylsulfanylacetamide
—— 5-(4-fluorophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]thiophene-2-carboxamide —— C19H16FNO3S
5-(4-fluorophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]thiophene-2-carboxamide
—— 4-(2-ethoxyphenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methyl]butanamide —— C20H25NO5
4-(2-ethoxyphenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methyl]butanamide
—— N-[(3-hydroxy-4-methoxyphenyl)methyl]-5-piperidin-1-ylsulfonylfuran-2-carboxamide —— C18H22N2O6S
N-[(3-hydroxy-4-methoxyphenyl)methyl]-5-piperidin-1-ylsulfonylfuran-2-carboxamide
—— 4-[(3S)-3-[(5-methyl-1H-imidazol-4-yl)methylamino]butyl]phenol —— C15H21N3O
4-[(3S)-3-[(5-methyl-1H-imidazol-4-yl)methylamino]butyl]phenol
—— (2S)-2-(2,4-dichlorophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide —— C17H17Cl2NO4
(2S)-2-(2,4-dichlorophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide
—— (2R)-2-(4-tert-butylphenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide —— C21H27NO4
(2R)-2-(4-tert-butylphenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide
—— (2R)-2-(2,4-dichlorophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide —— C17H17Cl2NO4
(2R)-2-(2,4-dichlorophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide
—— 6-cyclopropyl-N-[(3-hydroxy-4-methoxyphenyl)methyl]-3-propyl-[1,2]oxazolo[5,4-b]pyridine-4-carboxamide —— C21H23N3O4
6-cyclopropyl-N-[(3-hydroxy-4-methoxyphenyl)methyl]-3-propyl-[1,2]oxazolo[5,4-b]pyridine-4-carboxamide
—— (2R)-N-[(3-hydroxy-4-methoxyphenyl)methyl]-2-(3-methyl-4-propan-2-ylphenoxy)propanamide —— C21H27NO4
(2R)-N-[(3-hydroxy-4-methoxyphenyl)methyl]-2-(3-methyl-4-propan-2-ylphenoxy)propanamide
—— (2S)-2-(2-bromo-4-fluorophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide —— C17H17BrFNO4
(2S)-2-(2-bromo-4-fluorophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide
—— (3R)-1-[2-(4-fluorophenyl)acetyl]-N-[(3-hydroxy-4-methoxyphenyl)methyl]piperidine-3-carboxamide —— C22H25FN2O4
(3R)-1-[2-(4-fluorophenyl)acetyl]-N-[(3-hydroxy-4-methoxyphenyl)methyl]piperidine-3-carboxamide
—— (3S)-N-[(3-hydroxy-4-methoxyphenyl)methyl]-1-(thiophene-2-carbonyl)piperidine-3-carboxamide —— C19H22N2O4S
(3S)-N-[(3-hydroxy-4-methoxyphenyl)methyl]-1-(thiophene-2-carbonyl)piperidine-3-carboxamide
—— N-[(3-hydroxy-4-methoxyphenyl)methyl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)propanamide —— C19H19N3O4
N-[(3-hydroxy-4-methoxyphenyl)methyl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)propanamide
—— (3R)-1-(1,3-benzothiazol-2-yl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]piperidine-3-carboxamide —— C21H23N3O3S
(3R)-1-(1,3-benzothiazol-2-yl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]piperidine-3-carboxamide
—— 3-[(1R)-1-(1,3-thiazol-5-ylmethylamino)ethyl]phenol —— C12H14N2OS
3-[(1R)-1-(1,3-thiazol-5-ylmethylamino)ethyl]phenol
—— 5-[(3-Bromo-4-hydroxy-5-nitrophenyl)methylidene]-2-(2-chlorophenyl)imino-1,3-thiazolidin-4-one —— C16H9BrClN3O4S
5-[(3-Bromo-4-hydroxy-5-nitrophenyl)methylidene]-2-(2-chlorophenyl)imino-1,3-thiazolidin-4-one
—— (3S)-N-[(1R)-1-(4-hydroxyphenyl)ethyl]-N-methyloxane-3-carboxamide —— C15H21NO3
(3S)-N-[(1R)-1-(4-hydroxyphenyl)ethyl]-N-methyloxane-3-carboxamide
—— (3R)-N-[(1R)-1-(4-hydroxyphenyl)ethyl]-N-methyloxane-3-carboxamide —— C15H21NO3
(3R)-N-[(1R)-1-(4-hydroxyphenyl)ethyl]-N-methyloxane-3-carboxamide
—— 3-[(1R)-1-(1H-imidazol-5-ylmethylamino)ethyl]phenol —— C12H15N3O
3-[(1R)-1-(1H-imidazol-5-ylmethylamino)ethyl]phenol
—— 3-[(1S)-1-(1H-imidazol-5-ylmethylamino)ethyl]phenol —— C12H15N3O
3-[(1S)-1-(1H-imidazol-5-ylmethylamino)ethyl]phenol
—— 5-[(5-Bromo-2-hydroxyphenyl)methylidene]-3-(4-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H12BrNO2S2
5-[(5-Bromo-2-hydroxyphenyl)methylidene]-3-(4-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 3,5-Dimethyl 1-[2-(adamantan-1-yloxy)ethyl]-4-(4-hydroxy-3,5-dimethoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate —— C29H37NO8
3,5-Dimethyl 1-[2-(adamantan-1-yloxy)ethyl]-4-(4-hydroxy-3,5-dimethoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate
—— Cyclopenta-1,3-diene;3-cyclopenta-2,4-dien-1-yl-1-(2-hydroxy-4-methylphenyl)prop-2-en-1-one;iron —— C20H10FeO2-10
Cyclopenta-1,3-diene;3-cyclopenta-2,4-dien-1-yl-1-(2-hydroxy-4-methylphenyl)prop-2-en-1-one;iron
—— 2-Cyano-3-(2-hydroxy-4-oxo-1,5-dioxaspiro[5.5]undec-2-en-3-yl)-3-(4-hydroxyphenyl)propanethioamide —— C19H20N2O5S
2-Cyano-3-(2-hydroxy-4-oxo-1,5-dioxaspiro[5.5]undec-2-en-3-yl)-3-(4-hydroxyphenyl)propanethioamide
—— 3-[3-Amino-2-cyano-1-(4-hydroxyphenyl)-3-sulfanylidenepropyl]-4-oxo-1,5-dioxaspiro[5.5]undec-2-en-2-olate —— C19H19N2O5S-
3-[3-Amino-2-cyano-1-(4-hydroxyphenyl)-3-sulfanylidenepropyl]-4-oxo-1,5-dioxaspiro[5.5]undec-2-en-2-olate
—— Oxidanium;cobalt;2-fluoro-6-[2-[(3-fluoro-2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol;propan-2-one —— C19H22CoF2N2O4
Oxidanium;cobalt;2-fluoro-6-[2-[(3-fluoro-2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol;propan-2-one
—— 2,8,14,20-Tetrakis(2-methylpropyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,5,6,10,11,12,16,17,18,22,24-undecol —— C44H56O11
2,8,14,20-Tetrakis(2-methylpropyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,5,6,10,11,12,16,17,18,22,24-undecol