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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
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-phenyl-3-[(E)-(3,5,5-trimethylcyclohex-3-en-1-ylidene)amino]imidazol-4-one —— C26H27N3O3
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-phenyl-3-[(E)-(3,5,5-trimethylcyclohex-3-en-1-ylidene)amino]imidazol-4-one
—— 2-(3,4-dimethylphenoxy)-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]acetohydrazide —— C18H20N2O4
2-(3,4-dimethylphenoxy)-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]acetohydrazide
—— N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]benzohydrazide —— C15H14N2O3
N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]benzohydrazide
—— 1-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-(4-methylphenyl)thiourea —— C16H17N3O2S
1-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-(4-methylphenyl)thiourea
—— 2-(4-chloro-3-methylphenoxy)-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]acetohydrazide —— C17H17ClN2O4
2-(4-chloro-3-methylphenoxy)-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]acetohydrazide
—— N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-methylbenzamide —— C16H16N2O3
N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-methylbenzamide
—— N'-[(E)-(3-Hydroxy-4-methoxyphenyl)methylidene]-2-(2-methoxyphenoxy)acetohydrazide —— C17H18N2O5
N'-[(E)-(3-Hydroxy-4-methoxyphenyl)methylidene]-2-(2-methoxyphenoxy)acetohydrazide
—— N'-[(E)-(3-Hydroxy-4-nitrophenyl)methylidene]-2-[(4-methylphenyl)amino]acetohydrazide —— C16H16N4O4
N'-[(E)-(3-Hydroxy-4-nitrophenyl)methylidene]-2-[(4-methylphenyl)amino]acetohydrazide
—— N'-[(E)-(4-cyanophenyl)methylidene]-2-hydroxy-5-nitrobenzohydrazide —— C15H10N4O4
N'-[(E)-(4-cyanophenyl)methylidene]-2-hydroxy-5-nitrobenzohydrazide
—— N'-[(E)-(3-Hydroxy-4-methoxyphenyl)methylidene]-2-(4-methylphenoxy)acetohydrazide —— C17H18N2O4
N'-[(E)-(3-Hydroxy-4-methoxyphenyl)methylidene]-2-(4-methylphenoxy)acetohydrazide
—— N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-methylphenoxy)acetamide —— C17H18N2O4
N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-methylphenoxy)acetamide
—— 3-[(2E)-2-(3-tert-butyl-6-oxocyclohexa-2,4-dien-1-ylidene)hydrazinyl]-2-hydroxy-5-nitrobenzenesulfonic acid —— C16H17N3O7S
3-[(2E)-2-(3-tert-butyl-6-oxocyclohexa-2,4-dien-1-ylidene)hydrazinyl]-2-hydroxy-5-nitrobenzenesulfonic acid
—— 3-{[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]amino}-8-methoxy-1H-pyrimido[5,4-b]indole-2,4(3H,5H)-dione —— C19H16N4O5
3-{[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]amino}-8-methoxy-1H-pyrimido[5,4-b]indole-2,4(3H,5H)-dione
—— 2-amino-4-ethyl-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1,3-thiazole-5-carboxamide —— C14H16N4O3S
2-amino-4-ethyl-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1,3-thiazole-5-carboxamide
—— (2Z,5Z)-5-benzylidene-2-[(E)-benzylidenehydrazinylidene]-3-(4-hydroxyphenyl)-1,3-thiazolidin-4-one —— C23H17N3O2S
(2Z,5Z)-5-benzylidene-2-[(E)-benzylidenehydrazinylidene]-3-(4-hydroxyphenyl)-1,3-thiazolidin-4-one
—— 2,6-dibromo-4-(3-phenyl-2,5-dihydro-1,2,4-oxadiazol-5-yl)phenol;N,N-diethylethanamine —— C20H25Br2N3O2
2,6-dibromo-4-(3-phenyl-2,5-dihydro-1,2,4-oxadiazol-5-yl)phenol;N,N-diethylethanamine
—— ethyl (2E,5R)-5-(2,4-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-(2,4-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
—— 7-bromo-3,3-bis(4-hydroxy-3-methoxyphenyl)-5-methyl-1H-indol-2-one —— C23H20BrNO5
7-bromo-3,3-bis(4-hydroxy-3-methoxyphenyl)-5-methyl-1H-indol-2-one
—— 3,3-bis(4-hydroxy-3-methoxyphenyl)-7-methyl-5-nitro-1H-indol-2-one —— C23H20N2O7
3,3-bis(4-hydroxy-3-methoxyphenyl)-7-methyl-5-nitro-1H-indol-2-one
—— ethyl (2E,5R)-2-[(5-bromo-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H17BrN2O4S2
ethyl (2E,5R)-2-[(5-bromo-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5R)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3,4-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H25BrN2O7S
ethyl (2E,5R)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3,4-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5S)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3,4-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H25BrN2O7S
ethyl (2E,5S)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3,4-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5R)-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,5R)-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
—— ethyl (2E,5R)-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,5R)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-(4-ethoxyphenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C17H18N2O6
2-(4-ethoxyphenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-2-(3-methylphenoxy)acetamide —— C16H16N2O5
N-[(2-hydroxy-5-nitrophenyl)methyl]-2-(3-methylphenoxy)acetamide
—— 3-(4-chlorophenyl)sulfonyl-N-[(2-hydroxy-5-nitrophenyl)methyl]propanamide —— C16H15ClN2O6S
3-(4-chlorophenyl)sulfonyl-N-[(2-hydroxy-5-nitrophenyl)methyl]propanamide
—— 3-(1,3-benzothiazol-2-yl)-N-[(2-hydroxy-5-nitrophenyl)methyl]propanamide —— C17H15N3O4S
3-(1,3-benzothiazol-2-yl)-N-[(2-hydroxy-5-nitrophenyl)methyl]propanamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-1-benzofuran-2-carboxamide —— C16H12N2O5
N-[(2-hydroxy-5-nitrophenyl)methyl]-1-benzofuran-2-carboxamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-2-(4-methoxyphenyl)acetamide —— C16H16N2O5
N-[(2-hydroxy-5-nitrophenyl)methyl]-2-(4-methoxyphenyl)acetamide
—— 2-(2,3-dihydro-1H-inden-5-yloxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C18H18N2O5
2-(2,3-dihydro-1H-inden-5-yloxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— 2-(2,4-dichlorophenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C15H12Cl2N2O4
2-(2,4-dichlorophenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-2-(1H-indol-3-yl)acetamide —— C17H15N3O4
N-[(2-hydroxy-5-nitrophenyl)methyl]-2-(1H-indol-3-yl)acetamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-2-[2-methoxy-4-[(E)-prop-1-enyl]phenoxy]acetamide —— C19H20N2O6
N-[(2-hydroxy-5-nitrophenyl)methyl]-2-[2-methoxy-4-[(E)-prop-1-enyl]phenoxy]acetamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-3-(4-methylphenoxy)propanamide —— C17H18N2O5
N-[(2-hydroxy-5-nitrophenyl)methyl]-3-(4-methylphenoxy)propanamide
—— 2-[(4-fluorophenyl)sulfonyl-methylamino]-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C16H16FN3O6S
2-[(4-fluorophenyl)sulfonyl-methylamino]-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-2,5-dimethyl-1-propan-2-ylpyrrole-3-carboxamide —— C17H21N3O4
N-[(2-hydroxy-5-nitrophenyl)methyl]-2,5-dimethyl-1-propan-2-ylpyrrole-3-carboxamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-3-(4-methylphenyl)sulfonylpropanamide —— C17H18N2O6S
N-[(2-hydroxy-5-nitrophenyl)methyl]-3-(4-methylphenyl)sulfonylpropanamide
—— 2-[2-(4-chloroanilino)-2-oxoethyl]sulfanyl-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C17H16ClN3O5S
2-[2-(4-chloroanilino)-2-oxoethyl]sulfanyl-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— 2-(2,6-dimethylphenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C17H18N2O5
2-(2,6-dimethylphenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]cyclopropanecarboxamide —— C11H12N2O4
N-[(2-hydroxy-5-nitrophenyl)methyl]cyclopropanecarboxamide
—— 2-(4-tert-butylphenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C19H22N2O5
2-(4-tert-butylphenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— 2-(3,5-dimethylphenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C17H18N2O5
2-(3,5-dimethylphenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— (E)-3-(5-bromothiophen-2-yl)-N-[(2-hydroxy-5-nitrophenyl)methyl]prop-2-enamide —— C14H11BrN2O4S
(E)-3-(5-bromothiophen-2-yl)-N-[(2-hydroxy-5-nitrophenyl)methyl]prop-2-enamide
—— 2,5-dichloro-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide —— C15H12Cl2N2O3
2,5-dichloro-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide
—— ethyl (2E,5R)-5-(2-bromo-4,5-dimethoxyphenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H22BrN3O8S
ethyl (2E,5R)-5-(2-bromo-4,5-dimethoxyphenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5S)-5-(4-fluorophenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide —— C27H19FN4O5S
(5S)-5-(4-fluorophenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
—— methyl (2R)-2-(3-chloro-4-methylanilino)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate —— C19H19ClF3NO5
methyl (2R)-2-(3-chloro-4-methylanilino)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate
—— ethyl (2Z,5S)-2-[[2-[2-(benzylamino)-2-oxoethoxy]phenyl]methylidene]-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C33H31N3O7S
ethyl (2Z,5S)-2-[[2-[2-(benzylamino)-2-oxoethoxy]phenyl]methylidene]-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-(3-Bromo-4-hydroxy-5-methoxybenzylidene)-3-(2-methylphenyl)-2-[(2-methylphenyl)imino]-1,3-thiazolidin-4-one —— C25H21BrN2O3S
5-(3-Bromo-4-hydroxy-5-methoxybenzylidene)-3-(2-methylphenyl)-2-[(2-methylphenyl)imino]-1,3-thiazolidin-4-one