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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
—— 3-chloro-N-[1-(4-hydroxybenzyl)cyclohexyl]propanamide —— C16H22ClNO2
3-chloro-N-[1-(4-hydroxybenzyl)cyclohexyl]propanamide
—— 3-nitro-4-[[(1S)-1-(1H-pyrazol-5-yl)ethyl]amino]phenol —— C11H12N4O3
3-nitro-4-[[(1S)-1-(1H-pyrazol-5-yl)ethyl]amino]phenol
—— 3-[(1R)-1-[[(1R)-1-(1H-pyrazol-5-yl)ethyl]amino]ethyl]phenol —— C13H17N3O
3-[(1R)-1-[[(1R)-1-(1H-pyrazol-5-yl)ethyl]amino]ethyl]phenol
—— 3-[(1R)-1-[[(1S)-1-(1H-pyrazol-5-yl)ethyl]amino]ethyl]phenol —— C13H17N3O
3-[(1R)-1-[[(1S)-1-(1H-pyrazol-5-yl)ethyl]amino]ethyl]phenol
—— 5-[(2-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-cyclohexyl-2-cyclohexylimino-1,3-thiazolidin-4-one —— C23H29BrN2O3S
5-[(2-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-cyclohexyl-2-cyclohexylimino-1,3-thiazolidin-4-one
—— 2-methoxy-5-[[(1R)-1-(1H-pyrazol-5-yl)ethyl]amino]phenol —— C12H15N3O2
2-methoxy-5-[[(1R)-1-(1H-pyrazol-5-yl)ethyl]amino]phenol
—— 2,6-dimethyl-3-[[(1R)-1-(1H-pyrazol-5-yl)ethyl]amino]phenol —— C13H17N3O
2,6-dimethyl-3-[[(1R)-1-(1H-pyrazol-5-yl)ethyl]amino]phenol
—— 4-[(3R)-3-[[(1S)-1-(1H-pyrazol-5-yl)ethyl]amino]butyl]phenol —— C15H21N3O
4-[(3R)-3-[[(1S)-1-(1H-pyrazol-5-yl)ethyl]amino]butyl]phenol
—— 2-methoxy-5-[[(1S)-1-(1H-pyrazol-5-yl)ethyl]amino]phenol —— C12H15N3O2
2-methoxy-5-[[(1S)-1-(1H-pyrazol-5-yl)ethyl]amino]phenol
—— 2,6-dimethyl-3-[[(1S)-1-(1H-pyrazol-5-yl)ethyl]amino]phenol —— C13H17N3O
2,6-dimethyl-3-[[(1S)-1-(1H-pyrazol-5-yl)ethyl]amino]phenol
—— 4-[(3R)-3-[[(1R)-1-(1H-pyrazol-5-yl)ethyl]amino]butyl]phenol —— C15H21N3O
4-[(3R)-3-[[(1R)-1-(1H-pyrazol-5-yl)ethyl]amino]butyl]phenol
—— 2-[(1S)-1-[(4-ethylcyclohexyl)methylamino]ethyl]phenol —— C17H27NO
2-[(1S)-1-[(4-ethylcyclohexyl)methylamino]ethyl]phenol
—— 3-[(1R)-1-[(4-ethylcyclohexyl)methylamino]ethyl]phenol —— C17H27NO
3-[(1R)-1-[(4-ethylcyclohexyl)methylamino]ethyl]phenol
—— 2-[(1R)-1-[(4-ethylcyclohexyl)methylamino]ethyl]phenol —— C17H27NO
2-[(1R)-1-[(4-ethylcyclohexyl)methylamino]ethyl]phenol
—— 3-bromo-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-methoxybenzamide —— C16H15BrN2O4
3-bromo-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-methoxybenzamide
—— 5-(3,3-Dihydroxyprop-1-enyl)-3-methoxybenzene-1,2-diol —— C10H12O5
5-(3,3-Dihydroxyprop-1-enyl)-3-methoxybenzene-1,2-diol
—— 2-amino-4-(3-hydroxyphenyl)-4a,5,6,7-tetrahydro-4H-naphthalene-1,3,3-tricarbonitrile —— C19H16N4O
2-amino-4-(3-hydroxyphenyl)-4a,5,6,7-tetrahydro-4H-naphthalene-1,3,3-tricarbonitrile
—— 2-(4-bromo-2-chlorophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C16H14BrClN2O4
2-(4-bromo-2-chlorophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— 3-chloro-N-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]propane-1-sulfonamide —— C13H20ClNO3S
3-chloro-N-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]propane-1-sulfonamide
—— N-(2-hydroxy-4-nitrophenyl)-2-[4-oxo-2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-thiazolidin-3-yl]acetamide —— C16H11N3O5S3
N-(2-hydroxy-4-nitrophenyl)-2-[4-oxo-2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-thiazolidin-3-yl]acetamide
—— 3-chloro-N-[(1R)-1-(3-hydroxyphenyl)ethyl]propane-1-sulfonamide —— C11H16ClNO3S
3-chloro-N-[(1R)-1-(3-hydroxyphenyl)ethyl]propane-1-sulfonamide
—— 3-chloro-N-[(1R)-1-(2-hydroxyphenyl)ethyl]-N-methylpropane-1-sulfonamide —— C12H18ClNO3S
3-chloro-N-[(1R)-1-(2-hydroxyphenyl)ethyl]-N-methylpropane-1-sulfonamide
—— propan-2-yl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-pentoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C31H36N2O7S
propan-2-yl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-pentoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-chloro-N-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]propane-1-sulfonamide —— C13H20ClNO3S
3-chloro-N-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]propane-1-sulfonamide
—— 3-chloro-N-ethyl-N-[(1R)-1-(3-hydroxyphenyl)ethyl]propane-1-sulfonamide —— C13H20ClNO3S
3-chloro-N-ethyl-N-[(1R)-1-(3-hydroxyphenyl)ethyl]propane-1-sulfonamide
—— prop-2-enyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-phenylmethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C33H30N2O7S
prop-2-enyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-phenylmethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-methylpropyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-[3-methoxy-4-(3-methylbutoxy)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C32H38N2O7S
2-methylpropyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-[3-methoxy-4-(3-methylbutoxy)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N-ethyl-N-[(1S)-1-(3-hydroxyphenyl)ethyl]-3-oxobutanamide —— C14H19NO3
N-ethyl-N-[(1S)-1-(3-hydroxyphenyl)ethyl]-3-oxobutanamide
—— propan-2-yl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-phenylmethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C33H32N2O7S
propan-2-yl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-phenylmethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— prop-2-enyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-[3-methoxy-4-(3-methylbutoxy)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C31H34N2O7S
prop-2-enyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-[3-methoxy-4-(3-methylbutoxy)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C28H28N2O7S
ethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-methylpropyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C30H32N2O7S
2-methylpropyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— prop-2-enyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H28N2O7S
prop-2-enyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— methyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H26N2O7S
methyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-methoxyethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H30N2O8S
2-methoxyethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— propan-2-yl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H30N2O7S
propan-2-yl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— benzyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C33H30N2O7S
benzyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N-[(1R)-1-(2-hydroxyphenyl)ethyl]-N-methyl-3-oxobutanamide —— C13H17NO3
N-[(1R)-1-(2-hydroxyphenyl)ethyl]-N-methyl-3-oxobutanamide
—— benzyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-[3-methoxy-4-(3-methylbutoxy)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C35H36N2O7S
benzyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-[3-methoxy-4-(3-methylbutoxy)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-pentoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C30H34N2O7S
ethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-pentoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— benzyl 5-(4-butoxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C34H34N2O7S
benzyl 5-(4-butoxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— benzyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-pentoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C35H36N2O7S
benzyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-pentoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (E)-4-[[(1R)-1-(2-hydroxyphenyl)ethyl]-methylamino]-4-oxobut-2-enoic acid —— C13H15NO4
(E)-4-[[(1R)-1-(2-hydroxyphenyl)ethyl]-methylamino]-4-oxobut-2-enoic acid
—— 4-[[(1S)-1-(2-hydroxyphenyl)ethyl]-methylamino]-4-oxobutanoic acid —— C13H17NO4
4-[[(1S)-1-(2-hydroxyphenyl)ethyl]-methylamino]-4-oxobutanoic acid
—— 4-[ethyl-[(1S)-1-(3-hydroxyphenyl)ethyl]amino]-4-oxobutanoic acid —— C14H19NO4
4-[ethyl-[(1S)-1-(3-hydroxyphenyl)ethyl]amino]-4-oxobutanoic acid
—— 4-[[(1R)-1-(2-hydroxyphenyl)ethyl]-methylamino]-4-oxobutanoic acid —— C13H17NO4
4-[[(1R)-1-(2-hydroxyphenyl)ethyl]-methylamino]-4-oxobutanoic acid
—— 4-[ethyl-[(1R)-1-(3-hydroxyphenyl)ethyl]amino]-4-oxobutanoic acid —— C14H19NO4
4-[ethyl-[(1R)-1-(3-hydroxyphenyl)ethyl]amino]-4-oxobutanoic acid
—— ethyl 5-(4-butoxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H32N2O7S
ethyl 5-(4-butoxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (1S,2S)-2-[[(1S)-1-(2-hydroxyphenyl)ethyl]-methylcarbamoyl]cyclopropane-1-carboxylic acid —— C14H17NO4
(1S,2S)-2-[[(1S)-1-(2-hydroxyphenyl)ethyl]-methylcarbamoyl]cyclopropane-1-carboxylic acid
—— 5-[[(1S)-1-(2-hydroxyphenyl)ethyl]-methylamino]-5-oxopentanoic acid —— C14H19NO4
5-[[(1S)-1-(2-hydroxyphenyl)ethyl]-methylamino]-5-oxopentanoic acid