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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
—— 4-(2',3'-dihydroxyphenyl)-3,4-dihydrofuro[3,4-b]pyridine-2,5-(1H,7H)-dione 1356120-83-6 C13H11NO5
4-(2',3'-dihydroxyphenyl)-3,4-dihydrofuro[3,4-b]pyridine-2,5-(1H,7H)-dione
—— (Z)-4-methoxy-2-[(3-methyl )-3-pentenyl]phenol 1383253-11-9 C13H18O2
(Z)-4-methoxy-2-[(3-methyl )-3-pentenyl]phenol
—— cyclo-(4-iodo-L-phenylalanyl)-3-hydroxy-4-O-methyl-L-tyrosine 152429-84-0 C19H19IN2O4
cyclo-(4-iodo-L-phenylalanyl)-3-hydroxy-4-O-methyl-L-tyrosine
—— tert-butyl allyl(3-hydroxyphenethyl)carbamate 1446309-98-3 C16H23NO3
tert-butyl allyl(3-hydroxyphenethyl)carbamate
—— 144284-41-3 2C6H3N3O7*C16H21N5S
—— methyl (2R,3R)-1-[4-(2-hydroxy-5-methylphenyl)-1,3-thiazol-2-yl]-2-methylpyrrolidine-3-carboxylate 1423070-88-5 C17H20N2O3S
methyl (2R,3R)-1-[4-(2-hydroxy-5-methylphenyl)-1,3-thiazol-2-yl]-2-methylpyrrolidine-3-carboxylate
—— 3,4,6-Trichloro-5-hydroxy-1,2-benzenedicarbonitrile 30757-51-8 C8HCl3N2O
3,4,6-Trichloro-5-hydroxy-1,2-benzenedicarbonitrile
—— 4-(2-(4-nitrophenylhydrazono))-1-(6-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-3-methyl-1H-pyrazol-5(4H)-one 1456804-33-3 C20H15N9O6S
4-(2-(4-nitrophenylhydrazono))-1-(6-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-3-methyl-1H-pyrazol-5(4H)-one
—— 3-Nitro-salicylsaeure-dodecylamid 94432-08-3 C19H30N2O4
3-Nitro-salicylsaeure-dodecylamid
—— (5Z)-5-[(4-fluoro-2-hydroxyphenyl)methylidene]-2-[(2R)-4-(2-hydroxyethyl)-2-methylpiperazin-1-yl]-4,5-dihydro-1,3-thiazol-4-one 1181082-73-4 C17H20FN3O3S
(5Z)-5-[(4-fluoro-2-hydroxyphenyl)methylidene]-2-[(2R)-4-(2-hydroxyethyl)-2-methylpiperazin-1-yl]-4,5-dihydro-1,3-thiazol-4-one
—— (2,5-Dihydroxy-phenyl)-dimethyl-sulfonium 45867-10-5 C8H11O2S
(2,5-Dihydroxy-phenyl)-dimethyl-sulfonium
—— (R)-2-[4-(4-benzyl-piperazin-1-yl)-piperidin-1-yl]-1-(4-hydroxy-3-methoxy-5-methyl-benzyl)-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate 930603-95-5 C42H54N6O6
(R)-2-[4-(4-benzyl-piperazin-1-yl)-piperidin-1-yl]-1-(4-hydroxy-3-methoxy-5-methyl-benzyl)-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate
—— <2-Hydroxy-Benzyliden>-<5-Methyl-3-isoxazolylcarbonyl>-hydrazin 99989-35-2 C12H11N3O3
<2-Hydroxy-Benzyliden>-<5-Methyl-3-isoxazolylcarbonyl>-hydrazin
—— 162716-22-5 C44H54HgO2S2
—— (2R,3S,5R)-5-(Diethoxy-phosphoryl)-4,4-dimethyl-2-phenyl-pyrrolidine-3-carboxylic acid ethyl ester; compound with picric acid 117083-37-1 C6H3N3O7*C19H30NO5P
(2R,3S,5R)-5-(Diethoxy-phosphoryl)-4,4-dimethyl-2-phenyl-pyrrolidine-3-carboxylic acid ethyl ester; compound with picric acid
—— 2-Hepta-1,6-diynylphenol 1197157-94-0 C13H12O
2-Hepta-1,6-diynylphenol
—— 81421-01-4 C18H17CoIN4O4
—— 4-bromo-2-hydroxy-5-methoxy-3-methylbenzaldehyde 1332271-10-9 C9H9BrO3
4-bromo-2-hydroxy-5-methoxy-3-methylbenzaldehyde
—— 151366-16-4 C76H86Co2N8
—— Benzoesaeure-(3azo1)-naphthol-(2)-<2,4-dinitro-phenylester> 96170-30-8 C23H14N4O7
Benzoesaeure-(3azo1)-naphthol-(2)-<2,4-dinitro-phenylester>
—— 5-Brom-o-vanillal-anilin 7396-67-0 C14H12BrNO2
5-Brom-o-vanillal-anilin
—— (5Z)-5-[(4-fluoro-2-hydroxyphenyl)methylidene]-2-[(3R)-3-(pyrrolidin-1-yl)pyrrolidin-1-yl]-4,5-dihydro-1,3-thiazol-4-one 1181082-83-6 C18H20FN3O2S
(5Z)-5-[(4-fluoro-2-hydroxyphenyl)methylidene]-2-[(3R)-3-(pyrrolidin-1-yl)pyrrolidin-1-yl]-4,5-dihydro-1,3-thiazol-4-one
—— 4-(4-hydroxyphenyl)butyl N-(1-adamantyl)carbamate 1004305-41-2 C21H29NO3
4-(4-hydroxyphenyl)butyl N-(1-adamantyl)carbamate
—— {2-[2-(4-Hydroxy-phenyl)-ethyl]-[1,3]dioxolan-2-yl}-acetonitrile 93559-09-2 C13H15NO3
{2-[2-(4-Hydroxy-phenyl)-ethyl]-[1,3]dioxolan-2-yl}-acetonitrile
—— 75366-22-2 C6H3N3O7*C8H11N*C40H80N4O8
—— 1469921-86-5 C52H72O10
—— 4,5-bis(phenylethynyl)benzene-1,2-diol 509146-56-9 C22H14O2
4,5-bis(phenylethynyl)benzene-1,2-diol
—— diethyl ((R)-(2-hydroxyphenyl)(((R)-1-phenylethyl)amino)methyl)phosphonate 1537890-28-0 C19H26NO4P
diethyl ((R)-(2-hydroxyphenyl)(((R)-1-phenylethyl)amino)methyl)phosphonate
—— N-(2-Hydroxy-3-methyl-5-methylsulfanyl-benzyl)-acrylamide 13579-37-8 C12H15NO2S
N-(2-Hydroxy-3-methyl-5-methylsulfanyl-benzyl)-acrylamide
—— 1340478-98-9 C18H30O2Si
—— 10-(2,5-dihydroxy-phenyl)-decanoic acid ethyl ester 146803-76-1 C18H28O4
10-(2,5-dihydroxy-phenyl)-decanoic acid ethyl ester
—— 129529-30-2 C12H19O4P
—— 2,4-dihydroxy-5-isopentyl-benzaldehyde 100257-37-2 C12H16O3
2,4-dihydroxy-5-isopentyl-benzaldehyde
—— 1473394-63-6 C10H10ClO3P
—— acetic acid-(4-hydroxy-3-methyl-5-nitro-anilide) 84498-49-7 C9H10N2O4
acetic acid-(4-hydroxy-3-methyl-5-nitro-anilide)
—— (R)-4'-benzyl-3,4-dihydroxytolazoline 85612-45-9 C17H18N2O2*ClH
(R)-4'-benzyl-3,4-dihydroxytolazoline
—— 4-(5-methyl-1(3)<i>H</i>-imidazol-4-ylmethyl)-phenol 15142-93-5 C11H12N2O
4-(5-methyl-1(3)<i>H</i>-imidazol-4-ylmethyl)-phenol
—— (5Z)-5-[(2-hydroxyphenyl)methylidene]-2-(4-methyl-1,4-diazepan-1-yl)-4,5-dihydro-1,3-thiazol-4-one 1181081-49-1 C16H19N3O2S
(5Z)-5-[(2-hydroxyphenyl)methylidene]-2-(4-methyl-1,4-diazepan-1-yl)-4,5-dihydro-1,3-thiazol-4-one
—— (R)-(4-hydroxy-3-nitrophenyl)(3-(4-methoxyphenoxy)pyrrolidin-1-yl)methanone 1204419-02-2 C18H18N2O6
(R)-(4-hydroxy-3-nitrophenyl)(3-(4-methoxyphenoxy)pyrrolidin-1-yl)methanone
—— 2-[(Z)-(3R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-1,3-dimethyl-6-triethylsilanyl-hex-1-en-5-ynyl]-benzo[1,3,2]dioxaborole 646520-47-0 C26H43BO3Si2
2-[(Z)-(3R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-1,3-dimethyl-6-triethylsilanyl-hex-1-en-5-ynyl]-benzo[1,3,2]dioxaborole
—— 2-bromo-3,4-dimethyl-6-nitro-phenol 854663-52-8 C8H8BrNO3
2-bromo-3,4-dimethyl-6-nitro-phenol
—— 2,6-dimethyl-4-(6-phenyl-1,2,5-oxadiazolo[3,4-b]pyrazin-5-yl)phenol 1351707-61-3 C18H14N4O2
2,6-dimethyl-4-(6-phenyl-1,2,5-oxadiazolo[3,4-b]pyrazin-5-yl)phenol
—— 2-[dideuterio(phenyl)methyl]phenol 1021878-00-1 C13H12O
2-[dideuterio(phenyl)methyl]phenol
—— 2-(Chloracetylamido-methyl)-4-ethoxyphenol 30115-59-4 C11H14ClNO3
2-(Chloracetylamido-methyl)-4-ethoxyphenol
—— 4-(1-Propylbutyl)-2,6-dinitrophenol*Cyclohexylamin 17572-32-6 C6H13N*C13H18N2O5
4-(1-Propylbutyl)-2,6-dinitrophenol*Cyclohexylamin
—— 3-(6,7-dichlorobenzo[d]thiazol-2-yl)-5-(4-hydroxy-3-methoxybenzylidene)-2-phenyl-3,5-dihydro-4H-imidazol-4-one 1252043-02-9 C24H15Cl2N3O3S
3-(6,7-dichlorobenzo[d]thiazol-2-yl)-5-(4-hydroxy-3-methoxybenzylidene)-2-phenyl-3,5-dihydro-4H-imidazol-4-one
—— 2-(1,3-benzothiazol-2-ylsulfanyl)-N'-[(E)-(4-hydroxy-3,5-dimethoxyphenyl)methylidene]acetohydrazide 303107-48-4 C18H17N3O4S2
2-(1,3-benzothiazol-2-ylsulfanyl)-N'-[(E)-(4-hydroxy-3,5-dimethoxyphenyl)methylidene]acetohydrazide
—— 4-(4,5-Dihydro-1H-imidazol-2-ylmethoxy)-phenol 1096703-17-1 C10H12N2O2
4-(4,5-Dihydro-1H-imidazol-2-ylmethoxy)-phenol
—— 2-Benzylidenamino-1-(3-hydroxy-phenyl)-aethan-1-ol 25283-28-7 C15H15NO2
2-Benzylidenamino-1-(3-hydroxy-phenyl)-aethan-1-ol
—— 4-hydroxy-3-(4-hydroxybutyl)-1-(3-methoxyphenyl)-[1,8]-naphthyridin-2(1H)-one 99220-18-5 C19H20N2O4
4-hydroxy-3-(4-hydroxybutyl)-1-(3-methoxyphenyl)-[1,8]-naphthyridin-2(1H)-one