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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
—— methyl N-[(8Z)-8-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-7-oxonaphthalen-1-yl]carbamate —— C18H13N5O8
methyl N-[(8Z)-8-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-7-oxonaphthalen-1-yl]carbamate
—— (2Z,5E)-2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-5-[(3-nitrophenyl)methylidene]cyclopentan-1-one —— C21H19NO6
(2Z,5E)-2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-5-[(3-nitrophenyl)methylidene]cyclopentan-1-one
—— (2E,5Z)-2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-5-[(3-nitrophenyl)methylidene]cyclopentan-1-one —— C21H19NO6
(2E,5Z)-2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-5-[(3-nitrophenyl)methylidene]cyclopentan-1-one
—— (2Z,5Z)-2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-5-[(3-nitrophenyl)methylidene]cyclopentan-1-one —— C21H19NO6
(2Z,5Z)-2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-5-[(3-nitrophenyl)methylidene]cyclopentan-1-one
—— (2E,5Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-5-[(3-nitrophenyl)methylidene]cyclopentan-1-one —— C20H17NO5
(2E,5Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-5-[(3-nitrophenyl)methylidene]cyclopentan-1-one
—— (Z)-2-[1-(difluoromethyl)benzimidazol-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile —— C18H13F2N3O2
(Z)-2-[1-(difluoromethyl)benzimidazol-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile
—— 5-[(Z)-2-[1-(difluoromethyl)benzimidazol-2-yl]ethenyl]-2-methoxyphenol —— C17H14F2N2O2
5-[(Z)-2-[1-(difluoromethyl)benzimidazol-2-yl]ethenyl]-2-methoxyphenol
—— (2Z,5Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-5-[(3-nitrophenyl)methylidene]cyclopentan-1-one —— C20H17NO5
(2Z,5Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-5-[(3-nitrophenyl)methylidene]cyclopentan-1-one
—— (2Z,5E)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-5-[(3-nitrophenyl)methylidene]cyclopentan-1-one —— C20H17NO5
(2Z,5E)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-5-[(3-nitrophenyl)methylidene]cyclopentan-1-one
—— N'-{(E)-[4-(dimethylamino)phenyl]methylidene}-2-[(4-hydroxy-3,5-dimethylbenzyl)sulfanyl]acetohydrazide —— C20H25N3O2S
N'-{(E)-[4-(dimethylamino)phenyl]methylidene}-2-[(4-hydroxy-3,5-dimethylbenzyl)sulfanyl]acetohydrazide
—— 2-[(4-hydroxyphenyl)methylidene]-6,7-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidin-8-ium-3-one;acetate —— C15H16N2O4S
2-[(4-hydroxyphenyl)methylidene]-6,7-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidin-8-ium-3-one;acetate
—— 2-[(1R)-cyclopent-2-en-1-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide —— C15H19NO3
2-[(1R)-cyclopent-2-en-1-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide
—— 5-ethyl-3-[(2-hydroxyphenyl)methyl]-1,2-oxazole-4-carboxylic acid —— C13H13NO4
5-ethyl-3-[(2-hydroxyphenyl)methyl]-1,2-oxazole-4-carboxylic acid
—— 5-ethyl-3-[(3-hydroxyphenyl)methyl]-1,2-oxazole-4-carboxylic acid —— C13H13NO4
5-ethyl-3-[(3-hydroxyphenyl)methyl]-1,2-oxazole-4-carboxylic acid
—— 4-[(1S,9aR)-2,3,4,5,7,8,9,9a-octahydro-1H-pyrrolo[1,2-d][1,4]diazepin-1-yl]benzene-1,2-diol —— C14H20N2O2
4-[(1S,9aR)-2,3,4,5,7,8,9,9a-octahydro-1H-pyrrolo[1,2-d][1,4]diazepin-1-yl]benzene-1,2-diol
—— 4-[(5R,9aS)-2,3,4,5,7,8,9,9a-octahydro-1H-pyrrolo[1,2-d][1,4]diazepin-5-yl]benzene-1,2-diol —— C14H20N2O2
4-[(5R,9aS)-2,3,4,5,7,8,9,9a-octahydro-1H-pyrrolo[1,2-d][1,4]diazepin-5-yl]benzene-1,2-diol
—— 4-[(5R,9aR)-2,3,4,5,7,8,9,9a-octahydro-1H-pyrrolo[1,2-d][1,4]diazepin-5-yl]benzene-1,2-diol —— C14H20N2O2
4-[(5R,9aR)-2,3,4,5,7,8,9,9a-octahydro-1H-pyrrolo[1,2-d][1,4]diazepin-5-yl]benzene-1,2-diol
—— 4-[(1R,9aR)-2,3,4,5,7,8,9,9a-octahydro-1H-pyrrolo[1,2-d][1,4]diazepin-1-yl]benzene-1,2-diol —— C14H20N2O2
4-[(1R,9aR)-2,3,4,5,7,8,9,9a-octahydro-1H-pyrrolo[1,2-d][1,4]diazepin-1-yl]benzene-1,2-diol
—— 4-[(5S,9aR)-2,3,4,5,7,8,9,9a-octahydro-1H-pyrrolo[1,2-d][1,4]diazepin-5-yl]benzene-1,2-diol —— C14H20N2O2
4-[(5S,9aR)-2,3,4,5,7,8,9,9a-octahydro-1H-pyrrolo[1,2-d][1,4]diazepin-5-yl]benzene-1,2-diol
—— 4-[(5S,9aS)-2,3,4,5,7,8,9,9a-octahydro-1H-pyrrolo[1,2-d][1,4]diazepin-5-yl]benzene-1,2-diol —— C14H20N2O2
4-[(5S,9aS)-2,3,4,5,7,8,9,9a-octahydro-1H-pyrrolo[1,2-d][1,4]diazepin-5-yl]benzene-1,2-diol
—— ethyl (2E,5R)-5-(2,5-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H30N2O7S
ethyl (2E,5R)-5-(2,5-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5R)-5-(3,4-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H30N2O7S
ethyl (2E,5R)-5-(3,4-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-[(1R)-2-amino-1-[(2R)-1,4-dimethylpiperazin-2-yl]ethyl]phenol —— C14H23N3O
3-[(1R)-2-amino-1-[(2R)-1,4-dimethylpiperazin-2-yl]ethyl]phenol
—— (5R)-2-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3-methoxyphenyl)-7-methyl-3-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide —— C29H24ClN3O5S
(5R)-2-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3-methoxyphenyl)-7-methyl-3-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
—— 2-[(1R)-2-amino-1-[(2R)-1,4-dimethylpiperazin-2-yl]ethyl]phenol —— C14H23N3O
2-[(1R)-2-amino-1-[(2R)-1,4-dimethylpiperazin-2-yl]ethyl]phenol
—— ethyl (2E,5S)-5-(3,4-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H30N2O7S
ethyl (2E,5S)-5-(3,4-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2S,3S)-2-(3,4-dihydroxyphenyl)azepane-3-carboxylic acid —— C13H17NO4
(2S,3S)-2-(3,4-dihydroxyphenyl)azepane-3-carboxylic acid
—— (E)-3-(1,3-benzoxazol-2-yl)-4-(3-hydroxy-4-methoxyphenyl)but-3-enoate —— C18H14NO5-
(E)-3-(1,3-benzoxazol-2-yl)-4-(3-hydroxy-4-methoxyphenyl)but-3-enoate
—— (E)-3-(1,3-benzoxazol-2-yl)-4-(3-hydroxy-4-methoxyphenyl)but-3-enoic acid —— C18H15NO5
(E)-3-(1,3-benzoxazol-2-yl)-4-(3-hydroxy-4-methoxyphenyl)but-3-enoic acid
—— 2-methoxy-6-[[4-[(E)-3-phenylprop-2-enyl]piperazin-1-yl]methyl]-4-prop-2-enylphenol —— C24H30N2O2
2-methoxy-6-[[4-[(E)-3-phenylprop-2-enyl]piperazin-1-yl]methyl]-4-prop-2-enylphenol
—— (E)-N-[(2-hydroxy-5-nitrophenyl)methyl]-3-thiophen-2-ylprop-2-enamide —— C14H12N2O4S
(E)-N-[(2-hydroxy-5-nitrophenyl)methyl]-3-thiophen-2-ylprop-2-enamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-2-(2-methylphenoxy)acetamide —— C16H16N2O5
N-[(2-hydroxy-5-nitrophenyl)methyl]-2-(2-methylphenoxy)acetamide
—— ethyl (2E,5S)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21BrN2O5S
ethyl (2E,5S)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5S)-2-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H16Br2N2O4S2
ethyl (2E,5S)-2-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-bromo-N-[(2-hydroxy-5-nitrophenyl)methyl]pyridine-3-carboxamide —— C13H10BrN3O4
5-bromo-N-[(2-hydroxy-5-nitrophenyl)methyl]pyridine-3-carboxamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-2-(2-methylphenyl)sulfanylacetamide —— C16H16N2O4S
N-[(2-hydroxy-5-nitrophenyl)methyl]-2-(2-methylphenyl)sulfanylacetamide
—— ethyl (2E,5R)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H20BrClN2O5S
ethyl (2E,5R)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 4-(4-bromophenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]butanamide —— C17H17BrN2O5
4-(4-bromophenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]butanamide
—— ethyl (2E,5S)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H23BrN2O6S
ethyl (2E,5S)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-(4-bromophenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C15H13BrN2O4
2-(4-bromophenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— 2-(4-ethylphenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C17H18N2O5
2-(4-ethylphenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— 2-(3-chlorophenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C15H13ClN2O5
2-(3-chlorophenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— 5-chloro-N-[(2-hydroxy-5-nitrophenyl)methyl]thiophene-2-carboxamide —— C12H9ClN2O4S
5-chloro-N-[(2-hydroxy-5-nitrophenyl)methyl]thiophene-2-carboxamide
—— 2-(4-fluorophenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C15H13FN2O5
2-(4-fluorophenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-2-[4-(4-methylphenyl)-2-sulfanylidene-1,3-thiazol-3-yl]acetamide —— C19H17N3O4S2
N-[(2-hydroxy-5-nitrophenyl)methyl]-2-[4-(4-methylphenyl)-2-sulfanylidene-1,3-thiazol-3-yl]acetamide
—— ethyl (2E,5S)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(2,5-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H25BrN2O7S
ethyl (2E,5S)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(2,5-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-2-[2-(3-methylanilino)-2-oxoethyl]sulfanylacetamide —— C18H19N3O5S
N-[(2-hydroxy-5-nitrophenyl)methyl]-2-[2-(3-methylanilino)-2-oxoethyl]sulfanylacetamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]pyridine-2-carboxamide —— C13H11N3O4
N-[(2-hydroxy-5-nitrophenyl)methyl]pyridine-2-carboxamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-3-phenylpropanamide —— C16H16N2O4
N-[(2-hydroxy-5-nitrophenyl)methyl]-3-phenylpropanamide
—— (E)-N-[(2-hydroxy-5-nitrophenyl)methyl]-3-(3-methylthiophen-2-yl)prop-2-enamide —— C15H14N2O4S
(E)-N-[(2-hydroxy-5-nitrophenyl)methyl]-3-(3-methylthiophen-2-yl)prop-2-enamide