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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-(2-hydroxy-4-nitrophenyl)-2-(3-methylphenoxy)acetamide —— C15H14N2O5
N-(2-hydroxy-4-nitrophenyl)-2-(3-methylphenoxy)acetamide
—— 4-[[(2-hydroxy-5-methoxy-3-prop-2-enylphenyl)methyl-methylamino]methyl]-N-methylbenzamide —— C21H26N2O3
4-[[(2-hydroxy-5-methoxy-3-prop-2-enylphenyl)methyl-methylamino]methyl]-N-methylbenzamide
—— (1R,2S,3S,4R)-3-[2-(3,4-dihydroxyphenyl)ethylcarbamoyl]bicyclo[2.2.1]hept-5-ene-2-carboxylic acid —— C17H19NO5
(1R,2S,3S,4R)-3-[2-(3,4-dihydroxyphenyl)ethylcarbamoyl]bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
—— (1R,2S,3R,4R)-3-[2-(3,4-dihydroxyphenyl)ethylcarbamoyl]bicyclo[2.2.1]hept-5-ene-2-carboxylic acid —— C17H19NO5
(1R,2S,3R,4R)-3-[2-(3,4-dihydroxyphenyl)ethylcarbamoyl]bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
—— (2R)-N-(2-hydroxy-4-nitrophenyl)oxolane-2-carboxamide —— C11H12N2O5
(2R)-N-(2-hydroxy-4-nitrophenyl)oxolane-2-carboxamide
—— (1R,3S,5S,8S,9S,13S,14S)-8-hydroxy-14-(3-hydroxy-4,5-dimethoxyphenyl)-4,10-dioxa-15,16-dithia-11,18-diazapentacyclo[11.3.2.01,11.03,5.03,9]octadec-6-ene-12,17-dione —— C20H20N2O8S2
(1R,3S,5S,8S,9S,13S,14S)-8-hydroxy-14-(3-hydroxy-4,5-dimethoxyphenyl)-4,10-dioxa-15,16-dithia-11,18-diazapentacyclo[11.3.2.01,11.03,5.03,9]octadec-6-ene-12,17-dione
—— (1R,3S,5S,8S,9S,13S,14R)-8-hydroxy-14-(3-hydroxy-4,5-dimethoxyphenyl)-4,10-dioxa-15,16-dithia-11,18-diazapentacyclo[11.3.2.01,11.03,5.03,9]octadec-6-ene-12,17-dione —— C20H20N2O8S2
(1R,3S,5S,8S,9S,13S,14R)-8-hydroxy-14-(3-hydroxy-4,5-dimethoxyphenyl)-4,10-dioxa-15,16-dithia-11,18-diazapentacyclo[11.3.2.01,11.03,5.03,9]octadec-6-ene-12,17-dione
—— (1R,3S,5S,8S,9S,13R,14S)-8-hydroxy-14-(3-hydroxy-4,5-dimethoxyphenyl)-4,10-dioxa-15,16-dithia-11,18-diazapentacyclo[11.3.2.01,11.03,5.03,9]octadec-6-ene-12,17-dione —— C20H20N2O8S2
(1R,3S,5S,8S,9S,13R,14S)-8-hydroxy-14-(3-hydroxy-4,5-dimethoxyphenyl)-4,10-dioxa-15,16-dithia-11,18-diazapentacyclo[11.3.2.01,11.03,5.03,9]octadec-6-ene-12,17-dione
—— (1R,3S,5S,8S,9S,13R,14R)-8-hydroxy-14-(3-hydroxy-4,5-dimethoxyphenyl)-4,10-dioxa-15,16-dithia-11,18-diazapentacyclo[11.3.2.01,11.03,5.03,9]octadec-6-ene-12,17-dione —— C20H20N2O8S2
(1R,3S,5S,8S,9S,13R,14R)-8-hydroxy-14-(3-hydroxy-4,5-dimethoxyphenyl)-4,10-dioxa-15,16-dithia-11,18-diazapentacyclo[11.3.2.01,11.03,5.03,9]octadec-6-ene-12,17-dione
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(3,4-dimethylphenoxy)acetamide —— C18H19BrN2O4
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(3,4-dimethylphenoxy)acetamide
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2,5-dimethylphenoxy)acetamide —— C18H19BrN2O4
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2,5-dimethylphenoxy)acetamide
—— 4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[(3-methoxyphenoxy)methyl]-1H-1,2,4-triazole-5-thione —— C18H18N4O4S
4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[(3-methoxyphenoxy)methyl]-1H-1,2,4-triazole-5-thione
—— 4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1,2,4-triazolidine-3,5-dithione —— C10H10N4O2S2
4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1,2,4-triazolidine-3,5-dithione
—— 3-(2-cyclohexylethyl)-4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione —— C18H24N4O2S
3-(2-cyclohexylethyl)-4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione
—— 2-[[4-[(3-Fluoro-4-methoxyphenyl)methyl]piperazin-1-yl]methyl]-4-methoxy-6-prop-2-enylphenol —— C23H29FN2O3
2-[[4-[(3-Fluoro-4-methoxyphenyl)methyl]piperazin-1-yl]methyl]-4-methoxy-6-prop-2-enylphenol
—— N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-methoxy-4-(3-methylbutoxy)benzamide —— C21H26N2O5
N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-methoxy-4-(3-methylbutoxy)benzamide
—— 5,11,23-tris[(2S)-butan-2-yl]-17-[(2R)-butan-2-yl]pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol —— C44H56O4
5,11,23-tris[(2S)-butan-2-yl]-17-[(2R)-butan-2-yl]pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol
—— 5,11-bis[(2R)-butan-2-yl]-17,23-bis[(2S)-butan-2-yl]pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol —— C44H56O4
5,11-bis[(2R)-butan-2-yl]-17,23-bis[(2S)-butan-2-yl]pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol
—— 2-[(1R,2R,4R)-2-bicyclo[2.2.1]heptanyl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide —— C17H23NO3
2-[(1R,2R,4R)-2-bicyclo[2.2.1]heptanyl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide
—— 2-[(1R,2S,4R)-2-bicyclo[2.2.1]heptanyl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide —— C17H23NO3
2-[(1R,2S,4R)-2-bicyclo[2.2.1]heptanyl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide
—— (5Z)-2-(3H-1,3-benzothiazol-2-ylidenemethyl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C19H14N2O3S2
(5Z)-2-(3H-1,3-benzothiazol-2-ylidenemethyl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— (5Z)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-piperidin-1-yl-1,3-thiazol-4-one —— C15H15N3O4S
(5Z)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-piperidin-1-yl-1,3-thiazol-4-one
—— (5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-piperidin-1-yl-1,3-thiazol-4-one —— C17H20N2O4S
(5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-piperidin-1-yl-1,3-thiazol-4-one
—— 5-[[(3R)-3-(2-hydroxyethyl)-4-(1-propan-2-ylpiperidin-4-yl)piperazin-1-yl]methyl]-2-methoxyphenol —— C22H37N3O3
5-[[(3R)-3-(2-hydroxyethyl)-4-(1-propan-2-ylpiperidin-4-yl)piperazin-1-yl]methyl]-2-methoxyphenol
—— 5-chloro-4-[[(3R)-3-(2-hydroxyethyl)-4-(1-propan-2-ylpiperidin-4-yl)piperazin-1-yl]methyl]-2-methoxyphenol —— C22H36ClN3O3
5-chloro-4-[[(3R)-3-(2-hydroxyethyl)-4-(1-propan-2-ylpiperidin-4-yl)piperazin-1-yl]methyl]-2-methoxyphenol
—— 1-(3-Bromophenyl)-3-[(2-hydroxy-5-nitrophenyl)methyl]thiourea —— C14H12BrN3O3S
1-(3-Bromophenyl)-3-[(2-hydroxy-5-nitrophenyl)methyl]thiourea
—— 1-(3-bromophenyl)-3-(2-hydroxy-5-nitrophenyl)thiourea —— C13H10BrN3O3S
1-(3-bromophenyl)-3-(2-hydroxy-5-nitrophenyl)thiourea
—— 5-chloro-4-[[(3R)-3-(2-hydroxyethyl)-4-propan-2-ylpiperazin-1-yl]methyl]-2-methoxyphenol —— C17H27ClN2O3
5-chloro-4-[[(3R)-3-(2-hydroxyethyl)-4-propan-2-ylpiperazin-1-yl]methyl]-2-methoxyphenol
—— 4-[[(3R)-3-(2-hydroxyethyl)-4-(1-propan-2-ylpiperidin-4-yl)piperazin-1-yl]methyl]-3-methoxyphenol —— C22H37N3O3
4-[[(3R)-3-(2-hydroxyethyl)-4-(1-propan-2-ylpiperidin-4-yl)piperazin-1-yl]methyl]-3-methoxyphenol
—— 4-hydroxy-N-[(E)-(3-methyl-1,3-benzothiazol-2-ylidene)amino]-3-nitrobenzenesulfonamide —— C14H12N4O5S2
4-hydroxy-N-[(E)-(3-methyl-1,3-benzothiazol-2-ylidene)amino]-3-nitrobenzenesulfonamide
—— 4-[(3R)-3-[[(1R,2S,3S)-2,3-dimethylcyclohexyl]amino]butyl]phenol —— C18H29NO
4-[(3R)-3-[[(1R,2S,3S)-2,3-dimethylcyclohexyl]amino]butyl]phenol
—— 4-[(3S)-3-[[(1S,2S,3S)-2,3-dimethylcyclohexyl]amino]butyl]phenol —— C18H29NO
4-[(3S)-3-[[(1S,2S,3S)-2,3-dimethylcyclohexyl]amino]butyl]phenol
—— 3-[(Z)-[[3-chloro-5-(trifluoromethyl)pyridin-2-yl]hydrazinylidene]methyl]phenol —— C13H9ClF3N3O
3-[(Z)-[[3-chloro-5-(trifluoromethyl)pyridin-2-yl]hydrazinylidene]methyl]phenol
—— 2-[[(3R)-3-(2-hydroxyethyl)-4-[(2-methylphenyl)methyl]piperazin-1-yl]methyl]-5-methoxyphenol —— C22H30N2O3
2-[[(3R)-3-(2-hydroxyethyl)-4-[(2-methylphenyl)methyl]piperazin-1-yl]methyl]-5-methoxyphenol
—— (2E,5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-(2-oxo-2-pyridin-4-ylethylidene)-1,3-thiazolidin-4-one —— C18H14N2O4S
(2E,5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-(2-oxo-2-pyridin-4-ylethylidene)-1,3-thiazolidin-4-one
—— (2E,5Z)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-(2-oxo-2-pyridin-4-ylethylidene)-1,3-thiazolidin-4-one —— C17H11N3O5S
(2E,5Z)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-(2-oxo-2-pyridin-4-ylethylidene)-1,3-thiazolidin-4-one
—— (2E,5E)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-(2-oxo-2-pyridin-4-ylethylidene)-1,3-thiazolidin-4-one —— C17H11N3O5S
(2E,5E)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-(2-oxo-2-pyridin-4-ylethylidene)-1,3-thiazolidin-4-one
—— (2E,5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-(2-oxo-2-pyridin-4-ylethylidene)-1,3-thiazolidin-4-one —— C18H14N2O4S
(2E,5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-(2-oxo-2-pyridin-4-ylethylidene)-1,3-thiazolidin-4-one
—— (2Z,5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-(2-oxo-2-pyridin-4-ylethylidene)-1,3-thiazolidin-4-one —— C18H14N2O4S
(2Z,5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-(2-oxo-2-pyridin-4-ylethylidene)-1,3-thiazolidin-4-one
—— (2E,5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-(2-oxo-2-pyridin-4-ylethylidene)-1,3-thiazolidin-4-one —— C18H14N2O4S
(2E,5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-(2-oxo-2-pyridin-4-ylethylidene)-1,3-thiazolidin-4-one
—— (2Z,5E)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-(2-oxo-2-pyridin-4-ylethylidene)-1,3-thiazolidin-4-one —— C17H11N3O5S
(2Z,5E)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-(2-oxo-2-pyridin-4-ylethylidene)-1,3-thiazolidin-4-one
—— (2E,5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-(2-oxo-2-pyridin-4-ylethylidene)-1,3-thiazolidin-4-one —— C18H14N2O4S
(2E,5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-(2-oxo-2-pyridin-4-ylethylidene)-1,3-thiazolidin-4-one
—— 4-[[(3R)-4-[(2-ethoxyphenyl)methyl]-3-(2-hydroxyethyl)piperazin-1-yl]methyl]-2-methoxyphenol —— C23H32N2O4
4-[[(3R)-4-[(2-ethoxyphenyl)methyl]-3-(2-hydroxyethyl)piperazin-1-yl]methyl]-2-methoxyphenol
—— (2Z,5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-(2-oxo-2-pyridin-4-ylethylidene)-1,3-thiazolidin-4-one —— C18H14N2O4S
(2Z,5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-(2-oxo-2-pyridin-4-ylethylidene)-1,3-thiazolidin-4-one
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-4-ethoxybenzamide —— C17H17BrN2O4
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-4-ethoxybenzamide
—— 2-[[(3R)-3-(2-hydroxyethyl)-4-(2-methylpropyl)piperazin-1-yl]methyl]-5-methoxyphenol —— C18H30N2O3
2-[[(3R)-3-(2-hydroxyethyl)-4-(2-methylpropyl)piperazin-1-yl]methyl]-5-methoxyphenol
—— 4-[[(3R)-3-(2-hydroxyethyl)-4-(2-methylpropyl)piperazin-1-yl]methyl]-2,6-dimethoxyphenol —— C19H32N2O4
4-[[(3R)-3-(2-hydroxyethyl)-4-(2-methylpropyl)piperazin-1-yl]methyl]-2,6-dimethoxyphenol
—— 2-[[(3R)-3-(2-hydroxyethyl)-4-(2-methylpropyl)piperazin-1-yl]methyl]-6-methoxyphenol —— C18H30N2O3
2-[[(3R)-3-(2-hydroxyethyl)-4-(2-methylpropyl)piperazin-1-yl]methyl]-6-methoxyphenol
—— 2-[[(3R)-4-[(2-fluoro-4-methoxyphenyl)methyl]-3-(2-hydroxyethyl)piperazin-1-yl]methyl]-6-methoxyphenol —— C22H29FN2O4
2-[[(3R)-4-[(2-fluoro-4-methoxyphenyl)methyl]-3-(2-hydroxyethyl)piperazin-1-yl]methyl]-6-methoxyphenol
—— 4-[[(3R)-3-(2-hydroxyethyl)-4-[(2-methylphenyl)methyl]piperazin-1-yl]methyl]-2,6-dimethoxyphenol —— C23H32N2O4
4-[[(3R)-3-(2-hydroxyethyl)-4-[(2-methylphenyl)methyl]piperazin-1-yl]methyl]-2,6-dimethoxyphenol