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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
—— 1-cyclopropyl-1-[(1R)-1-cyclopropylethyl]-3-[(3-fluoro-4-hydroxyphenyl)methyl]urea —— C16H21FN2O2
1-cyclopropyl-1-[(1R)-1-cyclopropylethyl]-3-[(3-fluoro-4-hydroxyphenyl)methyl]urea
—— 1-cyclopropyl-1-[(1S)-1-cyclopropylethyl]-3-[(3-fluoro-4-hydroxyphenyl)methyl]urea —— C16H21FN2O2
1-cyclopropyl-1-[(1S)-1-cyclopropylethyl]-3-[(3-fluoro-4-hydroxyphenyl)methyl]urea
—— (3R)-N-[2-(3,4-dihydroxyphenyl)ethyl]-3-phenylbutanamide —— C18H21NO3
(3R)-N-[2-(3,4-dihydroxyphenyl)ethyl]-3-phenylbutanamide
—— (2E)-5-amino-7-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methylidene]-3-oxo-7H-[1,3]thiazolo[3,2-a]pyridine-6,8-dicarbonitrile —— C22H14N4O3S
(2E)-5-amino-7-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methylidene]-3-oxo-7H-[1,3]thiazolo[3,2-a]pyridine-6,8-dicarbonitrile
—— 6-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-4-methylcyclohexa-2,4-dien-1-one —— C13H10N4O6
6-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-4-methylcyclohexa-2,4-dien-1-one
—— diethyl (5S,6S,7R)-7-(2-hydroxy-5-nitrophenyl)-2-oxo-3,5,6,7-tetrahydrothiopyrano[2,3-d][1,3]thiazole-5,6-dicarboxylate —— C18H18N2O8S2
diethyl (5S,6S,7R)-7-(2-hydroxy-5-nitrophenyl)-2-oxo-3,5,6,7-tetrahydrothiopyrano[2,3-d][1,3]thiazole-5,6-dicarboxylate
—— (2Z)-2-[(2-hydroxy-5-nitrophenyl)hydrazinylidene]-3-oxobutanamide —— C10H10N4O5
(2Z)-2-[(2-hydroxy-5-nitrophenyl)hydrazinylidene]-3-oxobutanamide
—— [Amino-(4-hydroxy-3-methoxyphenyl)methylidene]azanium —— C8H11N2O2+
[Amino-(4-hydroxy-3-methoxyphenyl)methylidene]azanium
—— [1-amino-2-(2-hydroxy-3-methoxyphenyl)ethylidene]azanium —— C9H13N2O2+
[1-amino-2-(2-hydroxy-3-methoxyphenyl)ethylidene]azanium
—— [Amino-[2-[amino(azaniumylidene)methyl]-3,6-dihydroxyphenyl]methylidene]azanium —— C8H12N4O2+2
[Amino-[2-[amino(azaniumylidene)methyl]-3,6-dihydroxyphenyl]methylidene]azanium
—— (1S,2R)-N-[(2-hydroxyphenyl)methyl]-2-nitrocyclopropane-1-carboxamide —— C11H12N2O4
(1S,2R)-N-[(2-hydroxyphenyl)methyl]-2-nitrocyclopropane-1-carboxamide
—— (1R,2S)-N-[(2-hydroxyphenyl)methyl]-2-nitrocyclopropane-1-carboxamide —— C11H12N2O4
(1R,2S)-N-[(2-hydroxyphenyl)methyl]-2-nitrocyclopropane-1-carboxamide
—— (1S,2S)-N-[(2-hydroxyphenyl)methyl]-2-nitrocyclopropane-1-carboxamide —— C11H12N2O4
(1S,2S)-N-[(2-hydroxyphenyl)methyl]-2-nitrocyclopropane-1-carboxamide
—— (3Z)-3-[(4-hydroxyphenyl)methylidene]-5-phenylfuran-2-one —— C17H12O3
(3Z)-3-[(4-hydroxyphenyl)methylidene]-5-phenylfuran-2-one
—— (1R,2R)-N-[(2-hydroxyphenyl)methyl]-2-nitrocyclopropane-1-carboxamide —— C11H12N2O4
(1R,2R)-N-[(2-hydroxyphenyl)methyl]-2-nitrocyclopropane-1-carboxamide
—— (2Z)-2-[3-(2,5-dihydroxyphenyl)-1-hydroxypropylidene]cyclopentan-1-one —— C14H16O4
(2Z)-2-[3-(2,5-dihydroxyphenyl)-1-hydroxypropylidene]cyclopentan-1-one
—— 2-[[(1S,2R,4aS,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl]benzene-1,4-diol —— C21H30O2
2-[[(1S,2R,4aS,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl]benzene-1,4-diol
—— 4-[(1S)-1-hydroxy-2-(methylamino)ethyl]-2-methylphenol —— C10H15NO2
4-[(1S)-1-hydroxy-2-(methylamino)ethyl]-2-methylphenol
—— Tris(diethylamino)-(2-hydroxyphenyl)phosphanium —— C18H35N3OP+
Tris(diethylamino)-(2-hydroxyphenyl)phosphanium
—— (2-Hydroxy-5-methylphenyl)-dimethylsulfanium —— C9H13OS+
(2-Hydroxy-5-methylphenyl)-dimethylsulfanium
—— 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]-2-methylphenol —— C10H15NO2
4-[(1R)-1-hydroxy-2-(methylamino)ethyl]-2-methylphenol
—— (2S)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-(5-methylthiophen-2-yl)propanamide —— C17H21NO3S
(2S)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-(5-methylthiophen-2-yl)propanamide
—— (3R)-N-[(1R)-1-(3-hydroxyphenyl)ethyl]-N,3,4-trimethylpentanamide —— C16H25NO2
(3R)-N-[(1R)-1-(3-hydroxyphenyl)ethyl]-N,3,4-trimethylpentanamide
—— (3R)-N-[(1S)-1-(3-hydroxyphenyl)ethyl]-N,3,4-trimethylpentanamide —— C16H25NO2
(3R)-N-[(1S)-1-(3-hydroxyphenyl)ethyl]-N,3,4-trimethylpentanamide
—— (3S)-N-[(1S)-1-(3-hydroxyphenyl)ethyl]-N,3,4-trimethylpentanamide —— C16H25NO2
(3S)-N-[(1S)-1-(3-hydroxyphenyl)ethyl]-N,3,4-trimethylpentanamide
—— (2R)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-(5-methylthiophen-2-yl)propanamide —— C17H21NO3S
(2R)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-(5-methylthiophen-2-yl)propanamide
—— (3S)-N-[(1R)-1-(3-hydroxyphenyl)ethyl]-N,3,4-trimethylpentanamide —— C16H25NO2
(3S)-N-[(1R)-1-(3-hydroxyphenyl)ethyl]-N,3,4-trimethylpentanamide
—— 2,5-bis[(2S)-2-ethylhexyl]benzene-1,4-diol —— C22H38O2
2,5-bis[(2S)-2-ethylhexyl]benzene-1,4-diol
—— 5-[(2R)-2-ethylhexyl]-2-[(2S)-2-ethylhexyl]benzene-1,4-diol —— C22H38O2
5-[(2R)-2-ethylhexyl]-2-[(2S)-2-ethylhexyl]benzene-1,4-diol
—— 2,5-bis[(2R)-2-ethylhexyl]benzene-1,4-diol —— C22H38O2
2,5-bis[(2R)-2-ethylhexyl]benzene-1,4-diol
—— 2-{[(5Z)-5-(2-bromo-4-hydroxy-5-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]methyl}benzonitrile —— C19H13BrN2O4S
2-{[(5Z)-5-(2-bromo-4-hydroxy-5-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]methyl}benzonitrile
—— (Z)-N'-(4-hydroxy-3-methoxybenzylidene)-2-(benzo[d]oxazol-2-ylthio)acetohydrazide —— C17H15N3O4S
(Z)-N'-(4-hydroxy-3-methoxybenzylidene)-2-(benzo[d]oxazol-2-ylthio)acetohydrazide
—— 1-hydroxy-2-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]guanidine —— C9H12N4O3
1-hydroxy-2-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]guanidine
—— (5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-[6-[(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C28H28N2O6S4
(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-[6-[(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexyl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— [amino(oxoniumylidene)methyl]-[(Z)-(3-methoxy-2-oxoniophenyl)methylideneamino]azanide;cobalt(2+);hydroxide —— C9H13CoN3O4+2
[amino(oxoniumylidene)methyl]-[(Z)-(3-methoxy-2-oxoniophenyl)methylideneamino]azanide;cobalt(2+);hydroxide
—— 1-(cyclopropylmethyl)-1-[(4-hydroxyphenyl)methyl]-3-[(1S)-1-(5-methylfuran-2-yl)ethyl]urea —— C19H24N2O3
1-(cyclopropylmethyl)-1-[(4-hydroxyphenyl)methyl]-3-[(1S)-1-(5-methylfuran-2-yl)ethyl]urea
—— 1-(cyclopropylmethyl)-1-[(4-hydroxyphenyl)methyl]-3-[(1R)-1-(5-methylfuran-2-yl)ethyl]urea —— C19H24N2O3
1-(cyclopropylmethyl)-1-[(4-hydroxyphenyl)methyl]-3-[(1R)-1-(5-methylfuran-2-yl)ethyl]urea
—— N-[(Z)-1-(benzotriazol-1-yl)propan-2-ylideneamino]-4-hydroxy-3-methoxybenzamide —— C17H17N5O3
N-[(Z)-1-(benzotriazol-1-yl)propan-2-ylideneamino]-4-hydroxy-3-methoxybenzamide
—— (5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-3-[(4-methoxyphenyl)methyl]-2-phenylimino-1,3-thiazolidin-4-one —— C26H24N2O5S
(5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-3-[(4-methoxyphenyl)methyl]-2-phenylimino-1,3-thiazolidin-4-one
—— (5Z)-5-benzylidene-2-(4-hydroxyphenyl)imino-3-prop-2-enyl-1,3-thiazolidin-4-one —— C19H16N2O2S
(5Z)-5-benzylidene-2-(4-hydroxyphenyl)imino-3-prop-2-enyl-1,3-thiazolidin-4-one
—— (5Z)-3-cyclopentyl-5-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one —— C22H20Br2N2O3S
(5Z)-3-cyclopentyl-5-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one
—— 2-(1,3-benzoxazol-2-ylsulfanyl)-N-[(Z)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C17H14BrN3O4S
2-(1,3-benzoxazol-2-ylsulfanyl)-N-[(Z)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— (E)-2-cyano-3-[5-(2-hydroxy-5-nitrophenyl)furan-2-yl]prop-2-enamide —— C14H9N3O5
(E)-2-cyano-3-[5-(2-hydroxy-5-nitrophenyl)furan-2-yl]prop-2-enamide
—— 2-(3-Bromo-2-hydroxy-5-nitrobenzylidene)benzo[b]thiophen-3(2H)-one —— C15H8BrNO4S
2-(3-Bromo-2-hydroxy-5-nitrobenzylidene)benzo[b]thiophen-3(2H)-one
—— N-[(2S)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]-6-methyl-1-propan-2-ylpyrazolo[3,4-b]pyridine-5-carboxamide —— C22H28N4O4
N-[(2S)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]-6-methyl-1-propan-2-ylpyrazolo[3,4-b]pyridine-5-carboxamide
—— N-[(2R)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]-6-methyl-1-propan-2-ylpyrazolo[3,4-b]pyridine-5-carboxamide —— C22H28N4O4
N-[(2R)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]-6-methyl-1-propan-2-ylpyrazolo[3,4-b]pyridine-5-carboxamide
—— 2-chloro-N-[(5E)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-4-methylbenzamide —— C20H17ClN2O5S2
2-chloro-N-[(5E)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-4-methylbenzamide
—— N-[2-(4-hydroxyphenyl)ethyl]-4-[(5Z)-4-oxo-5-(thiophen-2-ylmethylidene)-2-thioxo-1,3-thiazolidin-3-yl]butanamide —— C20H20N2O3S3
N-[2-(4-hydroxyphenyl)ethyl]-4-[(5Z)-4-oxo-5-(thiophen-2-ylmethylidene)-2-thioxo-1,3-thiazolidin-3-yl]butanamide
—— (2R)-2-(2-chloro-4-fluorophenoxy)-N-[(2R)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]propanamide —— C20H23ClFNO5
(2R)-2-(2-chloro-4-fluorophenoxy)-N-[(2R)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]propanamide
—— (2S)-2-(2-chloro-4-fluorophenoxy)-N-[(2S)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]propanamide —— C20H23ClFNO5
(2S)-2-(2-chloro-4-fluorophenoxy)-N-[(2S)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]propanamide