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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
—— (1S,2R)-2-(4-hydroxyphenyl)cyclopropane-1-carboxylic acid —— C10H10O3
(1S,2R)-2-(4-hydroxyphenyl)cyclopropane-1-carboxylic acid
—— (1R,2S)-2-(3-hydroxyphenyl)cyclopropane-1-carboxylic acid —— C10H10O3
(1R,2S)-2-(3-hydroxyphenyl)cyclopropane-1-carboxylic acid
—— rac-(1R,2R)-2-(3-bromo-4-hydroxy-5-methoxyphenyl)cyclopropane-1-carboxylic acid —— C11H11BrO4
rac-(1R,2R)-2-(3-bromo-4-hydroxy-5-methoxyphenyl)cyclopropane-1-carboxylic acid
—— (6E)-2,4-dibromo-6-[(2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one —— C13H8Br2N2O4
(6E)-2,4-dibromo-6-[(2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one
—— 2-[(5E)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-[2-methoxy-5-(trifluoromethyl)phenyl]acetamide —— C21H16ClF3N2O6S
2-[(5E)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-[2-methoxy-5-(trifluoromethyl)phenyl]acetamide
—— (5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(4-methoxyphenyl)imino-1,3-thiazolidin-4-one —— C18H15BrN2O4S
(5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(4-methoxyphenyl)imino-1,3-thiazolidin-4-one
—— (2E,5E)-5-(3-chloro-4-hydroxybenzylidene)-3-(furan-2-ylmethyl)-2-(phenylimino)-1,3-thiazolidin-4-one —— C21H15ClN2O3S
(2E,5E)-5-(3-chloro-4-hydroxybenzylidene)-3-(furan-2-ylmethyl)-2-(phenylimino)-1,3-thiazolidin-4-one
—— (4Z)-4-[(5-bromo-2-hydroxyanilino)methylidene]-5-methyl-2-phenylpyrazol-3-one —— C17H14BrN3O2
(4Z)-4-[(5-bromo-2-hydroxyanilino)methylidene]-5-methyl-2-phenylpyrazol-3-one
—— (5E)-3-(4-chlorobenzyl)-5-(3,4-dihydroxybenzylidene)-1,3-thiazolidine-2,4-dione —— C17H12ClNO4S
(5E)-3-(4-chlorobenzyl)-5-(3,4-dihydroxybenzylidene)-1,3-thiazolidine-2,4-dione
—— (5E)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-3-[[(2S)-oxolan-2-yl]methyl]-2-phenylimino-1,3-thiazolidin-4-one —— C21H19N3O5S
(5E)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-3-[[(2S)-oxolan-2-yl]methyl]-2-phenylimino-1,3-thiazolidin-4-one
—— 6-tert-butyl-8-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-one —— C16H18N6O3
6-tert-butyl-8-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-one
—— (5E)-5-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(4-methoxyphenyl)imino-1,3-thiazolidin-4-one —— C18H14Br2N2O4S
(5E)-5-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(4-methoxyphenyl)imino-1,3-thiazolidin-4-one
—— (2Z,5E)-5-(3-bromo-2-hydroxy-5-nitrobenzylidene)-2-[(4-ethoxyphenyl)imino]-1,3-thiazolidin-4-one —— C18H14BrN3O5S
(2Z,5E)-5-(3-bromo-2-hydroxy-5-nitrobenzylidene)-2-[(4-ethoxyphenyl)imino]-1,3-thiazolidin-4-one
—— (5E)-5-[(5-Bromo-2-hydroxyphenyl)methylidene]-3-(prop-2-EN-1-YL)-2-sulfanylidene-1,3-thiazolidin-4-one —— C13H10BrNO2S2
(5E)-5-[(5-Bromo-2-hydroxyphenyl)methylidene]-3-(prop-2-EN-1-YL)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-5-[(3-hydroxyphenyl)methylidene]-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one —— C22H16N2O2S
(5E)-5-[(3-hydroxyphenyl)methylidene]-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one
—— (5E)-2-(4-bromophenyl)imino-5-[(5-chloro-2-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C16H10BrClN2O2S
(5E)-2-(4-bromophenyl)imino-5-[(5-chloro-2-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— N-[(Z)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3-(pyrazol-1-ylmethyl)benzamide —— C19H17BrN4O3
N-[(Z)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3-(pyrazol-1-ylmethyl)benzamide
—— (2S)-2-amino-4-[4-(2-methoxyethyl)phenoxy]butanenitrile —— C13H18N2O2
(2S)-2-amino-4-[4-(2-methoxyethyl)phenoxy]butanenitrile
—— (2R)-2-amino-4-[4-(2-methoxyethyl)phenoxy]butanenitrile —— C13H18N2O2
(2R)-2-amino-4-[4-(2-methoxyethyl)phenoxy]butanenitrile
—— (2S)-2-(ethylamino)-4-[4-(2-methoxyethyl)phenoxy]butanenitrile —— C15H22N2O2
(2S)-2-(ethylamino)-4-[4-(2-methoxyethyl)phenoxy]butanenitrile
—— (2R)-2-(ethylamino)-4-[4-(2-methoxyethyl)phenoxy]butanenitrile —— C15H22N2O2
(2R)-2-(ethylamino)-4-[4-(2-methoxyethyl)phenoxy]butanenitrile
—— (3E)-3-[7-(2-hydroxy-3-methoxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione —— C18H19NO5S
(3E)-3-[7-(2-hydroxy-3-methoxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione
—— (2E)-2-[(Z)-(2-bromo-5-hydroxyphenyl)methylidenehydrazinylidene]-1,3-thiazolidin-4-one —— C10H8BrN3O2S
(2E)-2-[(Z)-(2-bromo-5-hydroxyphenyl)methylidenehydrazinylidene]-1,3-thiazolidin-4-one
—— (7E)-7-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-8-oxonaphthalene-1,6-disulfonic acid —— C16H10N4O12S2
(7E)-7-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-8-oxonaphthalene-1,6-disulfonic acid
—— (4E)-3-hydroxy-4-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]cyclohexa-2,5-dien-1-one —— C12H8N4O7
(4E)-3-hydroxy-4-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]cyclohexa-2,5-dien-1-one
—— sodium;(6Z)-4-amino-6-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-5-oxonaphthalene-1-sulfonate —— C16H10N5NaO9S
sodium;(6Z)-4-amino-6-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-5-oxonaphthalene-1-sulfonate
—— (6Z)-3-(diethylamino)-6-[(2-hydroxy-5-nitrophenyl)hydrazinylidene]cyclohexa-2,4-dien-1-one —— C16H18N4O4
(6Z)-3-(diethylamino)-6-[(2-hydroxy-5-nitrophenyl)hydrazinylidene]cyclohexa-2,4-dien-1-one
—— (6Z)-6-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-4-methylcyclohexa-2,4-dien-1-one —— C13H10N4O6
(6Z)-6-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-4-methylcyclohexa-2,4-dien-1-one
—— (1E)-1-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]naphthalen-2-one —— C16H10N4O6
(1E)-1-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]naphthalen-2-one
—— 2-Hydroxy-4-{1-[(4-hydroxyphenyl)methyl]pyrrol-2-yl}-4-oxobut-2-enoic acid —— C15H13NO5
2-Hydroxy-4-{1-[(4-hydroxyphenyl)methyl]pyrrol-2-yl}-4-oxobut-2-enoic acid
—— 26,30-dihydroxy-3,15,22,34-tetrazaheptacyclo[34.2.2.217,20.14,8.110,14.123,27.129,33]hexatetraconta-1,3,5,8(46),10(45),12,14,16,18,20,23(42),24,26,29,31,33(41),35,37,39,43-icosaene-7,11-dione —— C42H32N4O4
26,30-dihydroxy-3,15,22,34-tetrazaheptacyclo[34.2.2.217,20.14,8.110,14.123,27.129,33]hexatetraconta-1,3,5,8(46),10(45),12,14,16,18,20,23(42),24,26,29,31,33(41),35,37,39,43-icosaene-7,11-dione
—— (9Z,13Z,28Z,32Z)-19,23-dihydroxy-40,43-dioxa-8,15,27,34-tetrazaheptacyclo[33.3.1.13,7.110,13.116,20.122,26.129,32]tetratetraconta-1(39),3(44),5,7,9,11,13,16(42),17,19,22,24,26(41),28,30,32,34,36-octadecaene-4,38-dione —— C38H28N4O6
(9Z,13Z,28Z,32Z)-19,23-dihydroxy-40,43-dioxa-8,15,27,34-tetrazaheptacyclo[33.3.1.13,7.110,13.116,20.122,26.129,32]tetratetraconta-1(39),3(44),5,7,9,11,13,16(42),17,19,22,24,26(41),28,30,32,34,36-octadecaene-4,38-dione
—— (9Z,34Z)-20,24-dihydroxy-8,16,28,36,42,45-hexazaheptacyclo[35.3.1.13,7.110,14.117,21.123,27.130,34]hexatetraconta-1(41),3(46),5,7,9,11,13,15,17(44),18,20,23,25,27(43),28,30,32,34,36,38-icosaene-4,40-dione —— C40H30N6O4
(9Z,34Z)-20,24-dihydroxy-8,16,28,36,42,45-hexazaheptacyclo[35.3.1.13,7.110,14.117,21.123,27.130,34]hexatetraconta-1(41),3(46),5,7,9,11,13,15,17(44),18,20,23,25,27(43),28,30,32,34,36,38-icosaene-4,40-dione
—— 2-hydroxy-4-nitro-N'-[(4-oxocyclohexa-2,5-dien-1-ylidene)methyl]benzohydrazide —— C14H11N3O5
2-hydroxy-4-nitro-N'-[(4-oxocyclohexa-2,5-dien-1-ylidene)methyl]benzohydrazide
—— 2-methoxy-6-[(E)-2-(1-methyl-2H-pyridin-2-yl)ethenyl]phenol —— C15H17NO2
2-methoxy-6-[(E)-2-(1-methyl-2H-pyridin-2-yl)ethenyl]phenol
—— N-[(1Z)-4,4-dicyano-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)buta-1,3-dien-2-yl]benzamide —— C20H15N3O4
N-[(1Z)-4,4-dicyano-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)buta-1,3-dien-2-yl]benzamide
—— 4-[(Z)-2-(methylamino)-1-phenylmethoxyethenyl]benzene-1,2-diol —— C16H17NO3
4-[(Z)-2-(methylamino)-1-phenylmethoxyethenyl]benzene-1,2-diol
—— 3-[(8E,11E)-pentadeca-8,11-dienyl]benzene-1,2-diol;3-[(8E,11E)-pentadeca-8,11,14-trienyl]benzene-1,2-diol;3-[(E)-pentadec-8-enyl]benzene-1,2-diol —— C63H96O6
3-[(8E,11E)-pentadeca-8,11-dienyl]benzene-1,2-diol;3-[(8E,11E)-pentadeca-8,11,14-trienyl]benzene-1,2-diol;3-[(E)-pentadec-8-enyl]benzene-1,2-diol
—— (3Z)-5-ethyl-3-[(2-hydroxy-5-nitrophenyl)methylidene]thiophen-2-one —— C13H11NO4S
(3Z)-5-ethyl-3-[(2-hydroxy-5-nitrophenyl)methylidene]thiophen-2-one
—— (3Z)-3-[(5-chloro-2-hydroxyphenyl)methylidene]-5-phenylthiophen-2-one —— C17H11ClO2S
(3Z)-3-[(5-chloro-2-hydroxyphenyl)methylidene]-5-phenylthiophen-2-one
—— 4-[(E)-2-(1-methyl-2H-pyridin-2-yl)ethenyl]benzene-1,2-diol —— C14H15NO2
4-[(E)-2-(1-methyl-2H-pyridin-2-yl)ethenyl]benzene-1,2-diol
—— 4-[(E)-2-(5-ethyl-1-methyl-2H-pyridin-2-yl)ethenyl]benzene-1,2-diol —— C16H19NO2
4-[(E)-2-(5-ethyl-1-methyl-2H-pyridin-2-yl)ethenyl]benzene-1,2-diol
—— 2-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]guanidine —— C9H12N4O
2-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]guanidine
—— (5E)-5-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-6-oxonaphthalene-2-sulfonic acid —— C16H10N4O9S
(5E)-5-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-6-oxonaphthalene-2-sulfonic acid
—— [(1R)-1-(5-methyl-1,3,4-oxadiazol-2-yl)ethyl] 2-(3-hydroxyphenyl)acetate —— C13H14N2O4
[(1R)-1-(5-methyl-1,3,4-oxadiazol-2-yl)ethyl] 2-(3-hydroxyphenyl)acetate
—— 2-methoxy-4-[(E)-2-(1-methyl-2H-pyridin-2-yl)ethenyl]phenol —— C15H17NO2
2-methoxy-4-[(E)-2-(1-methyl-2H-pyridin-2-yl)ethenyl]phenol
—— 2,3,5-trichloro-6-[(2Z)-2-[5-(2,4,5-trichloro-3,6-dihydroxyphenyl)-3H-1,3-thiazol-2-ylidene]-3H-1,3-thiazol-5-yl]cyclohexa-2,5-diene-1,4-dione —— C18H6Cl6N2O4S2
2,3,5-trichloro-6-[(2Z)-2-[5-(2,4,5-trichloro-3,6-dihydroxyphenyl)-3H-1,3-thiazol-2-ylidene]-3H-1,3-thiazol-5-yl]cyclohexa-2,5-diene-1,4-dione
—— (Z)-3-chloro-4-(3'-chloro-4'-hydroxyphenyl)-5-(4 —— C17H10Cl2O4
(Z)-3-chloro-4-(3'-chloro-4'-hydroxyphenyl)-5-(4
—— 3,5-dimethoxy-4-hydroxy benzylidene)-N-ethyl piperidone —— C29H33NO7
3,5-dimethoxy-4-hydroxy benzylidene)-N-ethyl piperidone
—— (Z)-3-bromo-4-(3-chloro-4-hydroxyphenyl)-5-[1-(4-hydroxyphenyl)methylidene]-2(5H)-furanone —— C17H10BrClO4
(Z)-3-bromo-4-(3-chloro-4-hydroxyphenyl)-5-[1-(4-hydroxyphenyl)methylidene]-2(5H)-furanone