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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
—— (2R)-N-(1,3-benzodioxol-5-yl)-2-[[2-(4,6-dimethylpyrimidin-2-yl)sulfanylacetyl]-[(4-methoxyphenyl)methyl]amino]-2-(4-hydroxy-3-methoxyphenyl)acetamide —— C32H32N4O7S
(2R)-N-(1,3-benzodioxol-5-yl)-2-[[2-(4,6-dimethylpyrimidin-2-yl)sulfanylacetyl]-[(4-methoxyphenyl)methyl]amino]-2-(4-hydroxy-3-methoxyphenyl)acetamide
—— (2R)-N-(1,3-benzodioxol-5-yl)-2-[[2-(4,6-dimethylpyrimidin-2-yl)sulfanylacetyl]-[(2-methylphenyl)methyl]amino]-2-(4-hydroxy-3-methoxyphenyl)acetamide —— C32H32N4O6S
(2R)-N-(1,3-benzodioxol-5-yl)-2-[[2-(4,6-dimethylpyrimidin-2-yl)sulfanylacetyl]-[(2-methylphenyl)methyl]amino]-2-(4-hydroxy-3-methoxyphenyl)acetamide
—— (2S)-N-(1,3-benzodioxol-5-yl)-2-[[2-(4,6-dimethylpyrimidin-2-yl)sulfanylacetyl]-[(2-methylphenyl)methyl]amino]-2-(4-hydroxy-3-methoxyphenyl)acetamide —— C32H32N4O6S
(2S)-N-(1,3-benzodioxol-5-yl)-2-[[2-(4,6-dimethylpyrimidin-2-yl)sulfanylacetyl]-[(2-methylphenyl)methyl]amino]-2-(4-hydroxy-3-methoxyphenyl)acetamide
—— (2S)-N-(1,3-benzodioxol-5-yl)-2-[[2-(4,6-dimethylpyrimidin-2-yl)sulfanylacetyl]-[(4-methoxyphenyl)methyl]amino]-2-(4-hydroxy-3-methoxyphenyl)acetamide —— C32H32N4O7S
(2S)-N-(1,3-benzodioxol-5-yl)-2-[[2-(4,6-dimethylpyrimidin-2-yl)sulfanylacetyl]-[(4-methoxyphenyl)methyl]amino]-2-(4-hydroxy-3-methoxyphenyl)acetamide
—— (5E)-3-tert-butyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H17NO3S2
(5E)-3-tert-butyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-3-(4-ethylphenyl)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C20H19NO4S2
(5E)-3-(4-ethylphenyl)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-3-(furan-2-ylmethyl)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H15NO5S2
(5Z)-3-(furan-2-ylmethyl)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 11-[(5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]undecanoic acid —— C23H31NO6S2
11-[(5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]undecanoic acid
—— (Z)-2-(5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)ethanesulfonic acid —— C14H15NO7S3
(Z)-2-(5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)ethanesulfonic acid
—— 2-[(5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]ethanesulfonic acid —— C12H11NO6S3
2-[(5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]ethanesulfonic acid
—— 11-[(5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]undecanoic acid —— C21H27NO5S2
11-[(5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]undecanoic acid
—— (5Z)-3-tert-butyl-5-[(4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C14H15NO2S2
(5Z)-3-tert-butyl-5-[(4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-3-(4-ethylphenyl)-5-[(4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15NO2S2
(5Z)-3-(4-ethylphenyl)-5-[(4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-3-(4-ethylphenyl)-5-[(2-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15NO2S2
(5E)-3-(4-ethylphenyl)-5-[(2-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-5-(3,4-dihydroxybenzylidene)-3-[2-(4-methoxyphenyl)ethyl]-2-thioxo-1,3-thiazolidin-4-one —— C19H17NO4S2
(5E)-5-(3,4-dihydroxybenzylidene)-3-[2-(4-methoxyphenyl)ethyl]-2-thioxo-1,3-thiazolidin-4-one
—— (5Z)-3-(4-butylphenyl)-5-[(4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C20H19NO2S2
(5Z)-3-(4-butylphenyl)-5-[(4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-3-(furan-2-ylmethyl)-5-[(3-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H11NO3S2
(5Z)-3-(furan-2-ylmethyl)-5-[(3-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-[(5Z)-5-[(3-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]ethanesulfonic acid —— C12H11NO5S3
2-[(5Z)-5-[(3-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]ethanesulfonic acid
—— 2-[(5Z)-5-[(4-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]ethanesulfonic acid —— C12H11NO5S3
2-[(5Z)-5-[(4-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]ethanesulfonic acid
—— (E)-N-(1,3-benzodioxol-5-ylmethyl)-N-[(1S)-2-(cyclohexylamino)-2-oxo-1-pyridin-4-ylethyl]-4-(2-hydroxy-4-methoxyphenyl)-4-oxobut-2-enamide —— C32H33N3O7
(E)-N-(1,3-benzodioxol-5-ylmethyl)-N-[(1S)-2-(cyclohexylamino)-2-oxo-1-pyridin-4-ylethyl]-4-(2-hydroxy-4-methoxyphenyl)-4-oxobut-2-enamide
—— (9aR)-7-[[(9aR)-6-hydroxy-8-oxo-3,4,9,9a-tetrahydro-2H-pyrimido[2,1-b][1,3]thiazin-7-yl]-(4-hydroxyphenyl)methyl]-6-hydroxy-3,4,9,9a-tetrahydro-2H-pyrimido[2,1-b][1,3]thiazin-8-one —— C21H24N4O5S2
(9aR)-7-[[(9aR)-6-hydroxy-8-oxo-3,4,9,9a-tetrahydro-2H-pyrimido[2,1-b][1,3]thiazin-7-yl]-(4-hydroxyphenyl)methyl]-6-hydroxy-3,4,9,9a-tetrahydro-2H-pyrimido[2,1-b][1,3]thiazin-8-one
—— (4R)-1-(4,6-dimethylpyrimidin-2-yl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C21H23N5O4
(4R)-1-(4,6-dimethylpyrimidin-2-yl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (2S)-2-hydroxy-2-(2-hydroxyphenyl)propanoic acid —— C9H10O4
(2S)-2-hydroxy-2-(2-hydroxyphenyl)propanoic acid
—— N-[(Z)-(3-hydroxyphenyl)methylideneamino]-2-pyridin-1-ium-1-ylacetamide —— C14H14N3O2+
N-[(Z)-(3-hydroxyphenyl)methylideneamino]-2-pyridin-1-ium-1-ylacetamide
—— (6E)-6-[(2-hydroxy-4-nitroanilino)methylidene]-4-nitrocyclohexa-2,4-dien-1-one —— C13H9N3O6
(6E)-6-[(2-hydroxy-4-nitroanilino)methylidene]-4-nitrocyclohexa-2,4-dien-1-one
—— (2S)-2-(5-bromo-2-hydroxy-3-methoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C17H17BrN2O3S
(2S)-2-(5-bromo-2-hydroxy-3-methoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2R)-2-(5-bromo-2-hydroxy-3-methoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C17H17BrN2O3S
(2R)-2-(5-bromo-2-hydroxy-3-methoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— 5-[(4R)-2-amino-1,4-dihydro-[1,3,5]triazino[1,2-a]benzimidazol-4-yl]-2-methoxyphenol —— C16H15N5O2
5-[(4R)-2-amino-1,4-dihydro-[1,3,5]triazino[1,2-a]benzimidazol-4-yl]-2-methoxyphenol
—— N-(2-hydroxy-5-nitrophenyl)-6-[(5Z)-4-oxo-2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-thiazolidin-3-yl]hexanamide —— C20H19N3O5S3
N-(2-hydroxy-5-nitrophenyl)-6-[(5Z)-4-oxo-2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-thiazolidin-3-yl]hexanamide
—— 4-amino-5-N-benzyl-5-N-[(1R)-2-(cyclohexylamino)-1-(4-hydroxy-3-methoxyphenyl)-2-oxoethyl]-1,2-thiazole-3,5-dicarboxamide —— C27H31N5O5S
4-amino-5-N-benzyl-5-N-[(1R)-2-(cyclohexylamino)-1-(4-hydroxy-3-methoxyphenyl)-2-oxoethyl]-1,2-thiazole-3,5-dicarboxamide
—— 4-amino-5-N-benzyl-5-N-[(1S)-2-(cyclohexylamino)-1-(4-hydroxy-3-methoxyphenyl)-2-oxoethyl]-1,2-thiazole-3,5-dicarboxamide —— C27H31N5O5S
4-amino-5-N-benzyl-5-N-[(1S)-2-(cyclohexylamino)-1-(4-hydroxy-3-methoxyphenyl)-2-oxoethyl]-1,2-thiazole-3,5-dicarboxamide
—— (4R)-1-(1,3-benzothiazol-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C21H18N4O3S
(4R)-1-(1,3-benzothiazol-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— 4-[(E)-pentadec-8-enyl]benzene-1,3-diol —— C21H34O2
4-[(E)-pentadec-8-enyl]benzene-1,3-diol
—— methyl 2-[[(2S)-5-cyano-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1,3-thiazin-6-yl]sulfanyl]acetate —— C14H12N2O4S2
methyl 2-[[(2S)-5-cyano-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1,3-thiazin-6-yl]sulfanyl]acetate
—— methyl 2-[[(2S)-5-cyano-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-2,3-dihydro-1,3-thiazin-6-yl]sulfanyl]acetate —— C15H14N2O5S2
methyl 2-[[(2S)-5-cyano-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-2,3-dihydro-1,3-thiazin-6-yl]sulfanyl]acetate
—— (5Z)-3-ethyl-2-(4-ethylphenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C21H22N2O3S
(5Z)-3-ethyl-2-(4-ethylphenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (3Z)-3-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-6-chloro-1H-indol-2-one —— C16H11BrClNO3
(3Z)-3-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-6-chloro-1H-indol-2-one
—— [(1S)-1-amino-2-(3,4-dihydroxyphenyl)ethyl]phosphonic acid —— C8H12NO5P
[(1S)-1-amino-2-(3,4-dihydroxyphenyl)ethyl]phosphonic acid
—— 6-[(S)-(4-hydroxy-3,5-dimethoxyphenyl)-(pyrimidin-2-ylamino)methyl]-1,3-benzodioxol-5-ol —— C20H19N3O6
6-[(S)-(4-hydroxy-3,5-dimethoxyphenyl)-(pyrimidin-2-ylamino)methyl]-1,3-benzodioxol-5-ol
—— 6-[(R)-(4,5-dihydropyrimidin-2-ylamino)-(2-hydroxy-3-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol —— C19H19N3O5
6-[(R)-(4,5-dihydropyrimidin-2-ylamino)-(2-hydroxy-3-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol
—— (2R,5E)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-2-(4-ethylanilino)-1,3-thiazolidin-4-one —— C19H19ClN2O3S
(2R,5E)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-2-(4-ethylanilino)-1,3-thiazolidin-4-one
—— (3R,3aR)-3-(4-hydroxy-3-methoxyphenyl)-2-phenyl-3a,6-dihydro-3H-pyrazolo[3,4-d][1,3]thiazol-5-one —— C17H15N3O3S
(3R,3aR)-3-(4-hydroxy-3-methoxyphenyl)-2-phenyl-3a,6-dihydro-3H-pyrazolo[3,4-d][1,3]thiazol-5-one
—— (2S)-2-[1,3-benzodioxol-5-yl-[2-(benzotriazol-1-yl)acetyl]amino]-N-tert-butyl-2-(3-hydroxy-4-methoxyphenyl)acetamide —— C28H29N5O6
(2S)-2-[1,3-benzodioxol-5-yl-[2-(benzotriazol-1-yl)acetyl]amino]-N-tert-butyl-2-(3-hydroxy-4-methoxyphenyl)acetamide
—— 2-fluoro-5-[(1S)-1-hydroxy-2-(methylamino)ethyl]phenol —— C9H12FNO2
2-fluoro-5-[(1S)-1-hydroxy-2-(methylamino)ethyl]phenol
—— 2-fluoro-3-[(1S)-1-hydroxy-2-(methylamino)ethyl]phenol —— C9H12FNO2
2-fluoro-3-[(1S)-1-hydroxy-2-(methylamino)ethyl]phenol
—— ethyl (2R,3S)-3-(2-hydroxyphenyl)oxirane-2-carboxylate —— C11H12O4
ethyl (2R,3S)-3-(2-hydroxyphenyl)oxirane-2-carboxylate
—— (Z)-11-bromo-N-[(4-hydroxy-3-methoxyphenyl)methyl]undec-10-enamide —— C19H28BrNO3
(Z)-11-bromo-N-[(4-hydroxy-3-methoxyphenyl)methyl]undec-10-enamide
—— 3-[(3S,8S)-3,8-ditert-butyldodecyl]phenol —— C26H46O
3-[(3S,8S)-3,8-ditert-butyldodecyl]phenol
—— 4-[(4R)-octan-4-yl]phenol —— C14H22O
4-[(4R)-octan-4-yl]phenol
—— 1-amino-3-[(E)-[1-(3-hydroxy-4-methoxyphenyl)-2-[(3S)-3-hydroxy-2-oxo-1H-indol-3-yl]ethylidene]amino]urea —— C18H19N5O5
1-amino-3-[(E)-[1-(3-hydroxy-4-methoxyphenyl)-2-[(3S)-3-hydroxy-2-oxo-1H-indol-3-yl]ethylidene]amino]urea