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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
—— N-[(2R)-butan-2-yl]-3-(2-hydroxyphenyl)propanamide —— C13H19NO2
N-[(2R)-butan-2-yl]-3-(2-hydroxyphenyl)propanamide
—— 6-[(R)-(4-hydroxy-3,5-dimethoxyphenyl)-(pyridin-2-ylamino)methyl]-1,3-benzodioxol-5-ol —— C21H20N2O6
6-[(R)-(4-hydroxy-3,5-dimethoxyphenyl)-(pyridin-2-ylamino)methyl]-1,3-benzodioxol-5-ol
—— 6-[(S)-(2-hydroxy-3-methoxyphenyl)-morpholin-4-ylmethyl]-1,3-benzodioxol-5-ol —— C19H21NO6
6-[(S)-(2-hydroxy-3-methoxyphenyl)-morpholin-4-ylmethyl]-1,3-benzodioxol-5-ol
—— 6-[(S)-(2-hydroxy-3-methoxyphenyl)-morpholin-4-ium-4-ylmethyl]-1,3-benzodioxol-5-ol —— C19H22NO6+
6-[(S)-(2-hydroxy-3-methoxyphenyl)-morpholin-4-ium-4-ylmethyl]-1,3-benzodioxol-5-ol
—— 6-[(R)-(4-hydroxy-3,5-dimethoxyphenyl)-(pyridin-1-ium-2-ylamino)methyl]-1,3-benzodioxol-5-ol —— C21H21N2O6+
6-[(R)-(4-hydroxy-3,5-dimethoxyphenyl)-(pyridin-1-ium-2-ylamino)methyl]-1,3-benzodioxol-5-ol
—— 6-[(S)-(2-hydroxy-3-methoxyphenyl)-(pyrimidin-2-ylamino)methyl]-1,3-benzodioxol-5-ol —— C19H17N3O5
6-[(S)-(2-hydroxy-3-methoxyphenyl)-(pyrimidin-2-ylamino)methyl]-1,3-benzodioxol-5-ol
—— 4-bromo-2-[(2S,6R)-4-(4-ethylphenyl)-2-pyridin-3-yl-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C23H22BrN3O
4-bromo-2-[(2S,6R)-4-(4-ethylphenyl)-2-pyridin-3-yl-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— (5Z)-5-(2-hydroxybenzylidene)-3-(prop-2-en-1-yl)-2-thioxo-1,3-thiazolidin-4-one —— C13H11NO2S2
(5Z)-5-(2-hydroxybenzylidene)-3-(prop-2-en-1-yl)-2-thioxo-1,3-thiazolidin-4-one
—— (4R)-4-(2-hydroxy-5-nitrophenyl)-6-methyl-N-phenyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide —— C18H16N4O4S
(4R)-4-(2-hydroxy-5-nitrophenyl)-6-methyl-N-phenyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide
—— 2,4-Dibromo-6-[di(morpholin-4-ium-4-yl)methyl]phenol —— C15H22Br2N2O3+2
2,4-Dibromo-6-[di(morpholin-4-ium-4-yl)methyl]phenol
—— (4Z)-2-(2,4-dichlorophenyl)-4-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-oxazol-5-one —— C16H8Cl2N2O5
(4Z)-2-(2,4-dichlorophenyl)-4-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-oxazol-5-one
—— (4Z)-2-cyclohexyl-4-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-oxazol-5-one —— C16H16N2O5
(4Z)-2-cyclohexyl-4-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-oxazol-5-one
—— (4R)-5-acetyl-4-(3-hydroxy-4-methoxyphenyl)-6-methyl-3,4-dihydro-1H-pyrimidin-2-one —— C14H16N2O4
(4R)-5-acetyl-4-(3-hydroxy-4-methoxyphenyl)-6-methyl-3,4-dihydro-1H-pyrimidin-2-one
—— (4S)-5-acetyl-4-(3-hydroxy-4-methoxyphenyl)-6-methyl-3,4-dihydro-1H-pyrimidin-2-one —— C14H16N2O4
(4S)-5-acetyl-4-(3-hydroxy-4-methoxyphenyl)-6-methyl-3,4-dihydro-1H-pyrimidin-2-one
—— (2E)-2,5-bis[(4-hydroxy-3-methoxyphenyl)methylidene]cyclopentan-1-one —— C21H20O5
(2E)-2,5-bis[(4-hydroxy-3-methoxyphenyl)methylidene]cyclopentan-1-one
—— (2R)-2-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-2-phenylacetate —— C19H14NO5S2-
(2R)-2-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-2-phenylacetate
—— (2S)-2-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-2-phenylacetate —— C19H14NO5S2-
(2S)-2-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-2-phenylacetate
—— 2-(2-Hydroxy-3-methoxyphenyl)-5-methyl-7-propyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one —— C19H28N2O3+2
2-(2-Hydroxy-3-methoxyphenyl)-5-methyl-7-propyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one
—— (5-Formyl-2-hydroxy-3-methoxyphenyl)methyl-dimethylazanium —— C11H16NO3+
(5-Formyl-2-hydroxy-3-methoxyphenyl)methyl-dimethylazanium
—— [5-(2,2-Dicyanoethenyl)-2-hydroxy-3-methoxyphenyl]methyl-dimethylazanium —— C14H16N3O2+
[5-(2,2-Dicyanoethenyl)-2-hydroxy-3-methoxyphenyl]methyl-dimethylazanium
—— 2-[(6S)-6,12-dihydrobenzimidazolo[1,2-c]quinazolin-6-yl]-4-nitrophenol —— C20H14N4O3
2-[(6S)-6,12-dihydrobenzimidazolo[1,2-c]quinazolin-6-yl]-4-nitrophenol
—— 2-[(2S,6S)-4-(4-bromophenyl)-2-thiophen-2-yl-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C21H19BrN2O2S
2-[(2S,6S)-4-(4-bromophenyl)-2-thiophen-2-yl-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— 2-[(2S,6S)-4-(4-bromophenyl)-2-thiophen-3-yl-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol —— C20H16BrClN2OS
2-[(2S,6S)-4-(4-bromophenyl)-2-thiophen-3-yl-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(morpholin-4-ium-4-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H19N2O4S2+
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(morpholin-4-ium-4-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-[(2R,6R)-4-(4-bromophenyl)-2-thiophen-2-yl-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C21H19BrN2O2S
2-[(2R,6R)-4-(4-bromophenyl)-2-thiophen-2-yl-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— 2-[(2R,6S)-4-(4-bromophenyl)-2-thiophen-2-yl-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C21H19BrN2O2S
2-[(2R,6S)-4-(4-bromophenyl)-2-thiophen-2-yl-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— (2S)-2-[4-(2-methoxyethyl)phenoxy]propanamide —— C12H17NO3
(2S)-2-[4-(2-methoxyethyl)phenoxy]propanamide
—— 2-[(4aR,6R,6aR,10bS)-2,3,4,4a,6,6a,7,8,9,10b-decahydro-1H-benzo[c]chromen-6-yl]phenol —— C19H24O2
2-[(4aR,6R,6aR,10bS)-2,3,4,4a,6,6a,7,8,9,10b-decahydro-1H-benzo[c]chromen-6-yl]phenol
—— 2-[(1R,2R,5S)-4,4,8-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol —— C17H22O2
2-[(1R,2R,5S)-4,4,8-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol
—— [(1S,3R)-3-methylcyclohexyl] (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C20H26N2O5
[(1S,3R)-3-methylcyclohexyl] (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— (5Z)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C11H8BrNO2S2
(5Z)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— 4-[[4-[(4-Fluorophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol —— C20H27FN2O3+2
4-[[4-[(4-Fluorophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol
—— 2,6-Dimethoxy-4-[[4-[(4-methylsulfanylphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol —— C21H30N2O3S+2
2,6-Dimethoxy-4-[[4-[(4-methylsulfanylphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol
—— 2-(5-Bromo-2-hydroxyphenyl)-5,7-dipropyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one —— C20H29BrN2O2+2
2-(5-Bromo-2-hydroxyphenyl)-5,7-dipropyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-phenyl-3-[(Z)-(3,5,5-trimethylcyclohex-3-en-1-ylidene)amino]imidazol-4-one —— C26H27N3O3
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-phenyl-3-[(Z)-(3,5,5-trimethylcyclohex-3-en-1-ylidene)amino]imidazol-4-one
—— 2-chloro-6-methoxy-4-[(E)-2-nitroprop-1-enyl]phenol —— C10H10ClNO4
2-chloro-6-methoxy-4-[(E)-2-nitroprop-1-enyl]phenol
—— 2-amino-4-(hydroxymethyl)-6-methoxyphenol —— C8H11NO3
2-amino-4-(hydroxymethyl)-6-methoxyphenol
—— (1S)-1-chloro-1-(3-chloro-4-hydroxy-5-methoxyphenyl)butan-2-one —— C11H12Cl2O3
(1S)-1-chloro-1-(3-chloro-4-hydroxy-5-methoxyphenyl)butan-2-one
—— 2-chloro-4-[(2R)-2-chloropropyl]-6-methoxyphenol —— C10H12Cl2O2
2-chloro-4-[(2R)-2-chloropropyl]-6-methoxyphenol
—— (1R)-1-chloro-1-(3-chloro-4-hydroxy-5-methoxyphenyl)propan-2-one —— C10H10Cl2O3
(1R)-1-chloro-1-(3-chloro-4-hydroxy-5-methoxyphenyl)propan-2-one
—— 2-Chloro-4-(2-hydrazinyl-4-methyl-1,3-thiazol-5-yl)-6-methoxyphenol —— C11H12ClN3O2S
2-Chloro-4-(2-hydrazinyl-4-methyl-1,3-thiazol-5-yl)-6-methoxyphenol
—— 2-chloro-4-[(2S)-2-chloropropyl]-6-methoxyphenol —— C10H12Cl2O2
2-chloro-4-[(2S)-2-chloropropyl]-6-methoxyphenol
—— (5Z)-2-(4-bromophenyl)imino-5-[(5-chloro-2-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C16H10BrClN2O2S
(5Z)-2-(4-bromophenyl)imino-5-[(5-chloro-2-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 2-Amino-4-(3-chloropropyl)-6-methoxyphenol —— C10H14ClNO2
2-Amino-4-(3-chloropropyl)-6-methoxyphenol
—— (1R)-1-chloro-1-(3-chloro-4-hydroxy-5-methoxyphenyl)butan-2-one —— C11H12Cl2O3
(1R)-1-chloro-1-(3-chloro-4-hydroxy-5-methoxyphenyl)butan-2-one
—— 2-chloro-4-[(2R)-2-hydroxybutyl]-6-methoxyphenol —— C11H15ClO3
2-chloro-4-[(2R)-2-hydroxybutyl]-6-methoxyphenol
—— 2-chloro-4-[(2R)-2-chlorobutyl]-6-methoxyphenol —— C11H14Cl2O2
2-chloro-4-[(2R)-2-chlorobutyl]-6-methoxyphenol
—— (5Z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-2-(3-methylphenyl)imino-1,3-thiazolidin-4-one —— C17H13BrN2O2S
(5Z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-2-(3-methylphenyl)imino-1,3-thiazolidin-4-one
—— (2S)-2-(4-hydroxy-3-methoxyphenyl)-6-(3-methylanilino)-4-oxo-2,3-dihydro-1,3-thiazine-5-carbonitrile —— C19H17N3O3S
(2S)-2-(4-hydroxy-3-methoxyphenyl)-6-(3-methylanilino)-4-oxo-2,3-dihydro-1,3-thiazine-5-carbonitrile
—— (2R)-2-(2-hydroxy-3-methoxyphenyl)-6-(3-methoxyanilino)-4-oxo-2,3-dihydro-1,3-thiazine-5-carbonitrile —— C19H17N3O4S
(2R)-2-(2-hydroxy-3-methoxyphenyl)-6-(3-methoxyanilino)-4-oxo-2,3-dihydro-1,3-thiazine-5-carbonitrile