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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
—— (Z)-1-(2-chloro-3,4,5-trimethoxyphenyl)-3-(3-hydroxy-4-methoxyphenylamino)prop-2-en-1-one 1379535-65-5 C19H20ClNO6
(Z)-1-(2-chloro-3,4,5-trimethoxyphenyl)-3-(3-hydroxy-4-methoxyphenylamino)prop-2-en-1-one
—— 5-[[6-[[5-chloro-2-[(6-hydroxyhexyl)oxy]phenyl]amino]-4-pyrimidinyl]amino]-2-methoxy-phenol 892413-82-0 C23H27ClN4O4
5-[[6-[[5-chloro-2-[(6-hydroxyhexyl)oxy]phenyl]amino]-4-pyrimidinyl]amino]-2-methoxy-phenol
—— 2-methoxy-5-(thiazol-2-ylamino)phenol 933045-58-0 C10H10N2O2S
2-methoxy-5-(thiazol-2-ylamino)phenol
—— 5-(dimethylamino)-2-methoxyphenol 189191-61-5 C9H13NO2
5-(dimethylamino)-2-methoxyphenol
—— 5-amino-2-methoxy-phenol; hydrochloride 35589-31-2 C7H9NO2*ClH
5-amino-2-methoxy-phenol; hydrochloride
—— N-[3-[4-(2-hydroxyethyl)phenoxy]-3-phenylpropyl]-N-methyl-2-propylpentanamide 1615654-17-5 C26H37NO3
N-[3-[4-(2-hydroxyethyl)phenoxy]-3-phenylpropyl]-N-methyl-2-propylpentanamide
—— N-[(4-hydroxyphenyl)methylideneamino]dodecanamide 303088-02-0 C19H30N2O2
N-[(4-hydroxyphenyl)methylideneamino]dodecanamide
—— 3-fluoro-4-nitroso-phenol 2369-07-5 C6H4FNO2
3-fluoro-4-nitroso-phenol
—— 3-Hydroxy-p-anisaldehyde (p-bromophenyl)hydrazone 27246-76-0 C14H13BrN2O2
3-Hydroxy-p-anisaldehyde (p-bromophenyl)hydrazone
—— 4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 1562342-07-7 C13H19BO4
4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
—— (4R)-2-(4-hydroxy-3,5-dimethoxyphenyl)thiazolidine-4-carboxylic acid 1014082-11-1 C12H15NO5S
(4R)-2-(4-hydroxy-3,5-dimethoxyphenyl)thiazolidine-4-carboxylic acid
—— (Z)-3-(5-phenylpent-3-en-1-ynyl)phenol 1450991-09-9 C17H14O
(Z)-3-(5-phenylpent-3-en-1-ynyl)phenol
—— 4-octadecyl-resorcinol 21093-23-2 C24H42O2
4-octadecyl-resorcinol
—— (E)-3-(5-phenylpent-3-en-1-ynyl)phenol 1450991-15-7 C17H14O
(E)-3-(5-phenylpent-3-en-1-ynyl)phenol
—— Methyl-(4-hydroxy-3-octadecyl-phenyl)-aether 35175-57-6 C25H44O2
Methyl-(4-hydroxy-3-octadecyl-phenyl)-aether
—— methyl N-[(2-hydroxyphenyl)methylideneamino]-N-methylcarbamodithioate 128643-95-8 C10H12N2OS2
methyl N-[(2-hydroxyphenyl)methylideneamino]-N-methylcarbamodithioate
—— methyl 2-hydroxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate 307300-47-6 C13H14O3
methyl 2-hydroxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate
—— 1-(tert-Butyldiphenylsiloxy)-2-cyclopropylidene-2-(2-hydroxy-4-methylphenyl)ethane 154698-97-2 C28H32O2Si
1-(tert-Butyldiphenylsiloxy)-2-cyclopropylidene-2-(2-hydroxy-4-methylphenyl)ethane
—— 2-Bromo-3-[(dimethylamino)methyl]-6-methoxyphenol 100200-96-2 C10H14BrNO2
2-Bromo-3-[(dimethylamino)methyl]-6-methoxyphenol
—— 4-(5-((2,4-difluorobenzyl)thio)-1,3,4-oxadiazol-2-yl)-2-methoxyphenol 1391739-52-8 C16H12F2N2O3S
4-(5-((2,4-difluorobenzyl)thio)-1,3,4-oxadiazol-2-yl)-2-methoxyphenol
—— N-(5-hydroxypentyl)-2-hydroxy-1-methoxy-4-aminobenzene 195534-24-8 C12H19NO3
N-(5-hydroxypentyl)-2-hydroxy-1-methoxy-4-aminobenzene
—— 3,4-dibromo-pyrocatechol 170473-59-3 C6H4Br2O2
3,4-dibromo-pyrocatechol
—— 5-(cyclopropyl(3-hydroxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione 1142223-02-6 C16H18O5
5-(cyclopropyl(3-hydroxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione
—— 4-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Henicosafluorodecyl)phenol 165182-88-7 C16H5F21O
4-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Henicosafluorodecyl)phenol
—— methyl 2-(5-chloro-2-hydroxyphenyl)acetate 441356-47-4 C9H9ClO3
methyl 2-(5-chloro-2-hydroxyphenyl)acetate
—— trans 4-(3-hydroxy-4-methoxyphenyl)but-3-enoic acid 98799-44-1 C11H12O4
trans 4-(3-hydroxy-4-methoxyphenyl)but-3-enoic acid
—— 5-(2-Hydroxy-3-methoxy-phenyl)-valeriansaeure 54131-06-5 C12H16O4
5-(2-Hydroxy-3-methoxy-phenyl)-valeriansaeure
—— 2,2,2-trifluoro-N-<(2,3,5-trichloro-6-hydroxyphenyl)methyl>acetamide 81440-72-4 C9H5Cl3F3NO2
2,2,2-trifluoro-N-<(2,3,5-trichloro-6-hydroxyphenyl)methyl>acetamide
—— (3R)-6,7-bis(hydroxymethyl)-3-(4-hydroxyphenyl)-5-methyl-1H,3H-pyrrolo[1,2-c]thiazole 1609535-73-0 C15H17NO3S
(3R)-6,7-bis(hydroxymethyl)-3-(4-hydroxyphenyl)-5-methyl-1H,3H-pyrrolo[1,2-c]thiazole
—— (+)-1-(4-Hydroxyphenoxy)-3-isopropyl-amino-2-propanol 58165-85-8 C12H19NO3
(+)-1-(4-Hydroxyphenoxy)-3-isopropyl-amino-2-propanol
—— 2-(4-phenylbutyl)phenyl 124211-67-2 C17H20O
2-(4-phenylbutyl)phenyl
—— 4-(2-aminopropoxy)-3-(hydroxymethyl)-5-methylphenol 1237512-73-0 C11H17NO3
4-(2-aminopropoxy)-3-(hydroxymethyl)-5-methylphenol
—— (S)-2-(2-hydroxy-4-methoxyphenylamino)-thiazoline-5,5-dimethyl-4-carboxylic acid 1334386-02-5 C13H16N2O4S
(S)-2-(2-hydroxy-4-methoxyphenylamino)-thiazoline-5,5-dimethyl-4-carboxylic acid
—— 4-[[6-[2-[2-[6-[(3,4-Dihydroxyphenyl)methylamino]hexylamino]ethyldisulfanyl]ethylamino]hexylamino]methyl]benzene-1,2-diol 75575-17-6 C30H50N4O4S2
4-[[6-[2-[2-[6-[(3,4-Dihydroxyphenyl)methylamino]hexylamino]ethyldisulfanyl]ethylamino]hexylamino]methyl]benzene-1,2-diol
—— 2-(thiophen-3-ylmethyl)phenol 109106-67-4 C11H10OS
2-(thiophen-3-ylmethyl)phenol
—— 2-Cyclopent-3-enylmethyl-3,4-difluoro-phenol 248275-64-1 C12H12F2O
2-Cyclopent-3-enylmethyl-3,4-difluoro-phenol
—— 4-hydroxy-3-methoxy-α-nitro-<i>cis</i>-cinnamonitrile 58046-27-8 C10H8N2O4
4-hydroxy-3-methoxy-α-nitro-<i>cis</i>-cinnamonitrile
—— methyl 3-cyano-3-(4-hydroxy-2-methoxyphenyl)propanoate 1356600-84-4 C12H13NO4
methyl 3-cyano-3-(4-hydroxy-2-methoxyphenyl)propanoate
—— (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one 1216936-80-9 C19H17NO4
(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one
—— Diethyl 2-[(4-hydroxy-3-methoxyanilino)methylidene]propanedioate 104007-05-8 C15H19NO6
Diethyl 2-[(4-hydroxy-3-methoxyanilino)methylidene]propanedioate
—— (E)-1-(2-hydroxy-3,4-dimethoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one 1216936-78-5 C19H17NO4
(E)-1-(2-hydroxy-3,4-dimethoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one
—— 2,5-di(1-propynyl)-1,4-benzenediol 1331730-62-1 C12H10O2
2,5-di(1-propynyl)-1,4-benzenediol
—— (E)-1-(2-hydroxy-3,4,6-trimethoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one 1216936-79-6 C20H19NO5
(E)-1-(2-hydroxy-3,4,6-trimethoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one
—— 1-(2-ethyl-6,8-dimethylimidazo[1,2-b]pyridazin-3-yl)-1-(4-hydroxyphenyl)methanol 143258-65-5 C17H19N3O2
1-(2-ethyl-6,8-dimethylimidazo[1,2-b]pyridazin-3-yl)-1-(4-hydroxyphenyl)methanol
—— N,N′,N′′-tris(3,4-dihydroxybenzylidene)adamantane-1,3,5-tripropaneamine 1448150-60-4 C40H49N3O6
N,N′,N′′-tris(3,4-dihydroxybenzylidene)adamantane-1,3,5-tripropaneamine
—— 4-(6-methoxy-2,3-dihydrobenzo[1,4]oxathiin-2-yl)benzene-1,2-diol 1616377-38-8 C15H14O4S
4-(6-methoxy-2,3-dihydrobenzo[1,4]oxathiin-2-yl)benzene-1,2-diol
—— 3,7-diaza-5,5-dimethyl-2,8-bis(2'-hydroxyphenyl)nonane 187960-80-1 C21H30N2O2
3,7-diaza-5,5-dimethyl-2,8-bis(2'-hydroxyphenyl)nonane
—— 2-(2-hydroxyphenyl)-2-methylcyclobutanone 121004-50-0 C11H12O2
2-(2-hydroxyphenyl)-2-methylcyclobutanone
—— acetamino-5-methoxyresorcinol 460048-04-8 C9H11NO4
acetamino-5-methoxyresorcinol
—— (3Z)-6-chloro-3-[(3-hydroxy-4-methoxyphenyl)methylidene]thiochromen-4-one 135521-95-8 C17H13ClO3S
(3Z)-6-chloro-3-[(3-hydroxy-4-methoxyphenyl)methylidene]thiochromen-4-one