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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-(4-chloro-2-fluoro-5-hydroxyphenyl)-3-methyl-3,4,5,6-tetrahydrophthalic acid imide 115313-65-0 C15H13ClFNO3
N-(4-chloro-2-fluoro-5-hydroxyphenyl)-3-methyl-3,4,5,6-tetrahydrophthalic acid imide
—— 2,6-diethyl-4-nitroso-phenol 25054-98-2 C10H13NO2
2,6-diethyl-4-nitroso-phenol
—— N'-(1-(2-hydroxy-4-methoxyphenyl)ethylidene)-2-methoxybenzohydrazide 1234389-89-9 C17H18N2O4
N'-(1-(2-hydroxy-4-methoxyphenyl)ethylidene)-2-methoxybenzohydrazide
—— 4,6-dibromo-2,3-dichloro-phenol 167388-17-2 C6H2Br2Cl2O
4,6-dibromo-2,3-dichloro-phenol
—— PdCl2(o-OHC6H4SCH3)2 110275-28-0 C14H16Cl2O2PdS2
PdCl2(o-OHC6H4SCH3)2
—— 5-(3-hydroxy-phenyl)-pyrazine-2,3-dicarbonitrile 72111-50-3 C12H6N4O
5-(3-hydroxy-phenyl)-pyrazine-2,3-dicarbonitrile
—— N'-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylene]-4,5,6,7-tetrahydro-1H-indazole-3-carbohydrazone 1381840-66-9 C16H17ClN4O3
N'-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylene]-4,5,6,7-tetrahydro-1H-indazole-3-carbohydrazone
—— 2-bromo-4-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 1245635-39-5 C13H18BBrO3
2-bromo-4-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
—— 3-(2,6-Dihydroxy-pyrimidin-4-yl)-2-(2-hydroxy-3-methoxy-phenyl)-thiazolidin-4-one 88351-99-9 C14H13N3O5S
3-(2,6-Dihydroxy-pyrimidin-4-yl)-2-(2-hydroxy-3-methoxy-phenyl)-thiazolidin-4-one
—— 6-(3,5-dibromo-4-hydroxyphenyl)-2,3-dihydro-1,4-diazepinium perchlorate 102536-23-2 C11H10Br2N2O*ClHO4
6-(3,5-dibromo-4-hydroxyphenyl)-2,3-dihydro-1,4-diazepinium perchlorate
—— 2-(1-ethylbut-3-enyl)-4-methoxyphenol 145275-46-3 C13H18O2
2-(1-ethylbut-3-enyl)-4-methoxyphenol
—— (E)-5{(4-hydroxyphenylimino)methyl}benzene-1,2,3-triol 1448846-11-4 C13H11NO4
(E)-5{(4-hydroxyphenylimino)methyl}benzene-1,2,3-triol
—— 607728-29-0 C23H33N7O2
—— (3,5-bis-acetylamino-4-hydroxy-phenyl)-arsonic acid 861293-93-8 C10H13AsN2O6
(3,5-bis-acetylamino-4-hydroxy-phenyl)-arsonic acid
—— 5-[2-(2-hydroxyphenyl)ethyl]-2-cycloocten-1-one 471279-50-2 C16H20O2
5-[2-(2-hydroxyphenyl)ethyl]-2-cycloocten-1-one
—— (2E,4E)-1-(2-hydroxy-4-methoxylphenyl)-4-methyl-5-phenylpenta-2,4-dien-1-one 1649447-95-9 C19H18O3
(2E,4E)-1-(2-hydroxy-4-methoxylphenyl)-4-methyl-5-phenylpenta-2,4-dien-1-one
—— Picric acid; compound with 2-(1-aza-bicyclo[2.2.2]oct-4-yl)-2-methyl-propan-1-ol 40117-86-0 C6H3N3O7*C11H21NO
Picric acid; compound with 2-(1-aza-bicyclo[2.2.2]oct-4-yl)-2-methyl-propan-1-ol
—— (E)-4'-hydroxy-3'-methoxyacetophenone O-4-nitrobenzyl oxime 1072708-72-5 C16H16N2O5
(E)-4'-hydroxy-3'-methoxyacetophenone O-4-nitrobenzyl oxime
—— Methyl 3-(4-hydroxyphenyl)-5-isoxazoleacetate 478336-93-5 C12H11NO4
Methyl 3-(4-hydroxyphenyl)-5-isoxazoleacetate
—— 3-(2-furyl)-1-{5-[3-(2-furyl)-2-propenoyl]-2,4-dihydroxyphenyl}-2-propen-1-one 124469-49-4 C20H14O4S2
3-(2-furyl)-1-{5-[3-(2-furyl)-2-propenoyl]-2,4-dihydroxyphenyl}-2-propen-1-one
—— 6-methyl-2-(3-chloro-2-propenyl)phenol 102117-79-3 C10H11ClO
6-methyl-2-(3-chloro-2-propenyl)phenol
—— 1-(benzyloxy)-2-methoxy-4-(2-octyloxyethyl)benzene 1327337-42-7 C24H34O3
1-(benzyloxy)-2-methoxy-4-(2-octyloxyethyl)benzene
—— peonolphenylhydrazone 7397-15-1 C15H16N2O2
peonolphenylhydrazone
—— 2-(2,3,6,7-tetrahydro-[1,4]thiazepin-5-yl)-phenol 53244-72-7 C11H13NOS
2-(2,3,6,7-tetrahydro-[1,4]thiazepin-5-yl)-phenol
—— 2-[5-(2-methoxy-phenyl)-1-phenyl-4,5-dihydro-1<i>H</i>-pyrazol-3-yl]-4-nitro-phenol 40189-12-6 C22H19N3O4
2-[5-(2-methoxy-phenyl)-1-phenyl-4,5-dihydro-1<i>H</i>-pyrazol-3-yl]-4-nitro-phenol
—— 2-(Bis-methylsulfanyl-methyl)-4,6-dinitro-phenol 6842-33-7 C9H10N2O5S2
2-(Bis-methylsulfanyl-methyl)-4,6-dinitro-phenol
—— 2-Methoxy-5-methyl-4-thiocyanato-phenol 600134-69-8 C9H9NO2S
2-Methoxy-5-methyl-4-thiocyanato-phenol
—— 2,2'-Sulfanediylbis{N'-[(E)-(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]propanehydrazide} 6940-64-3 C20H20N6O8S
2,2'-Sulfanediylbis{N'-[(E)-(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]propanehydrazide}
—— 3-Chloro-2,4,6-trifluoro-5-nitrophenol 113512-58-6 C6HClF3NO3
3-Chloro-2,4,6-trifluoro-5-nitrophenol
—— 2-methyl-5-(2-pyridinio)isoxazolidinium dipicrate 132326-43-3 2C6H3N3O7*C9H12N2O
2-methyl-5-(2-pyridinio)isoxazolidinium dipicrate
—— 6-methyl-4-(3-chloro-2-propenyl)phenol 102117-80-6 C10H11ClO
6-methyl-4-(3-chloro-2-propenyl)phenol
—— 1-Propanone,3-(3-ethyl-4-hydroxy-5-methylphenyl)-1-[4,5,6,7-tetrahydro-5,5-dimethyl-3-(trifluoromethyl)benzo[c]thien-1-yl]- 910641-19-9 C23H27F3O2S
1-Propanone,3-(3-ethyl-4-hydroxy-5-methylphenyl)-1-[4,5,6,7-tetrahydro-5,5-dimethyl-3-(trifluoromethyl)benzo[c]thien-1-yl]-
—— 2-Methoxy-4-{[(E)-5-pyridin-4-yl-[1,3,4]oxadiazol-2-ylimino]-methyl}-phenol 117616-45-2 C15H12N4O3
2-Methoxy-4-{[(E)-5-pyridin-4-yl-[1,3,4]oxadiazol-2-ylimino]-methyl}-phenol
—— (E)-but-2-enedioic acid;4-[3-[6-[[3-(3,4-dihydroxyphenoxy)-2-hydroxypropyl]amino]hexylamino]-2-hydroxypropoxy]benzene-1,2-diol 62950-81-6 C4H4O4*C24H36N2O8
(E)-but-2-enedioic acid;4-[3-[6-[[3-(3,4-dihydroxyphenoxy)-2-hydroxypropyl]amino]hexylamino]-2-hydroxypropoxy]benzene-1,2-diol
—— 1-(2-Hydroxy-4-methoxyphenyl)-3-(2-methyl-4-thiazolyl)propenone 80378-03-6 C14H13NO3S
1-(2-Hydroxy-4-methoxyphenyl)-3-(2-methyl-4-thiazolyl)propenone
—— 4-Chlor-2-aethyl-6-n-butylphenol 53346-78-4 C12H17ClO
4-Chlor-2-aethyl-6-n-butylphenol
—— 5-(5-bromo-2-hydroxybenzylidene)-2-imino-3-(pyridin-2-yl)thiazolidin-4-one 1200830-59-6 C15H10BrN3O2S
5-(5-bromo-2-hydroxybenzylidene)-2-imino-3-(pyridin-2-yl)thiazolidin-4-one
—— 4,6-diethyl-5-methyl-resorcinol 856335-14-3 C11H16O2
4,6-diethyl-5-methyl-resorcinol
—— 2-((2-(piperazin-1-yl)ethylimino)methyl)phenol 93968-73-1 C13H19N3O
2-((2-(piperazin-1-yl)ethylimino)methyl)phenol
—— (1S,2R)-1-Azidocarbonyl-2-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid methyl ester 117942-48-0 C12H11N3O4
(1S,2R)-1-Azidocarbonyl-2-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid methyl ester
—— (E)-N'-[1-(2-hydroxy-4-methoxyphenyl)ethyliden]isonicotinoyl-hydrazide 1262304-90-4 C15H15N3O3
(E)-N'-[1-(2-hydroxy-4-methoxyphenyl)ethyliden]isonicotinoyl-hydrazide
—— 4-(Azidomethyl)benzene-1,3-diol 1557925-76-4 C7H7N3O2
4-(Azidomethyl)benzene-1,3-diol
—— [5-[1-(3-chloro-4-hydroxy-5-methyl-phenylamino)-meth-(E,Z)-ylidene]-3-ethyl-4-oxo-thiazolidin-2(E,Z)-ylidene]-cyanoacetic acid ethyl ester 851646-66-7 C18H18ClN3O4S
[5-[1-(3-chloro-4-hydroxy-5-methyl-phenylamino)-meth-(E,Z)-ylidene]-3-ethyl-4-oxo-thiazolidin-2(E,Z)-ylidene]-cyanoacetic acid ethyl ester
—— (S)-2-(tert-butyldimethylsiloxy)-2-[3,4,5-tris(hydroxy)phenyl]ethylamine 1258852-44-6 C14H25NO4Si
(S)-2-(tert-butyldimethylsiloxy)-2-[3,4,5-tris(hydroxy)phenyl]ethylamine
—— 84775-04-2 C8H11NO2*C12H30N6*4H
—— 4-(tricyclo[4.3.1.1<sup>3,8</sup>]undec-1-ylaminomethyl)benzene-1,3-diol 1443121-73-0 C18H25NO2
4-(tricyclo[4.3.1.1<sup>3,8</sup>]undec-1-ylaminomethyl)benzene-1,3-diol
—— N-(2-hydroxyacetophenonyl)-2-iminoethylpyridine 105516-43-6 C15H16N2O
N-(2-hydroxyacetophenonyl)-2-iminoethylpyridine
—— t-butyl N-[4-hydroxybutyl-1-(4-hydroxyphenyl)]-N-methylcarbamate 444646-45-1 C16H25NO4
t-butyl N-[4-hydroxybutyl-1-(4-hydroxyphenyl)]-N-methylcarbamate
—— N<sup>1</sup>-4-chlorobenzylidene-N<sup>2</sup>-[3-(4-hydroxy-3-methoxyphenyl)-4-(2,5-dihydroxyphenyl)-1,3-thiazol-2-ylidene]hydrazine 1380075-04-6 C23H18ClN3O4S
N<sup>1</sup>-4-chlorobenzylidene-N<sup>2</sup>-[3-(4-hydroxy-3-methoxyphenyl)-4-(2,5-dihydroxyphenyl)-1,3-thiazol-2-ylidene]hydrazine
—— 2'-Hydroxy-5'-methylbenzaldehyd-5-chlor-2-methylanil 34800-98-1 C15H14ClNO
2'-Hydroxy-5'-methylbenzaldehyd-5-chlor-2-methylanil