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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
—— (3E,5E)-3,5-bis(4-hydroxybenzylidene)-tetrahydropyran-4-one 1268636-56-1 C19H16O4
(3E,5E)-3,5-bis(4-hydroxybenzylidene)-tetrahydropyran-4-one
—— 1-(3-hydroxy-4-methoxybenzyl)-3-methylthiourea 1400799-56-5 C10H14N2O2S
1-(3-hydroxy-4-methoxybenzyl)-3-methylthiourea
—— N-(3-Hydroxy-4-methoxybenzyl)-formamid 42973-74-0 C9H11NO3
N-(3-Hydroxy-4-methoxybenzyl)-formamid
—— 5-(2-hydroxy-5-chloro-anilino)-3<i>H</i>-[1,3,4]thiadiazole-2-thione 73310-98-2 C8H6ClN3OS2
5-(2-hydroxy-5-chloro-anilino)-3<i>H</i>-[1,3,4]thiadiazole-2-thione
—— decanoic acid [4-oxo-2-(2-hydroxyphenyl)-thiazolidin-3-yl]amide 1316243-30-7 C19H28N2O3S
decanoic acid [4-oxo-2-(2-hydroxyphenyl)-thiazolidin-3-yl]amide
—— o-allenyl phenol 53487-43-7 C9H8O
o-allenyl phenol
—— 4-(4-hydroxy-2-methyl-phenyl)-thiosemicarbazide 68372-11-2 C8H11N3OS
4-(4-hydroxy-2-methyl-phenyl)-thiosemicarbazide
—— 1-(2-hydroxyphenyl)-6-phenylhexane 167145-24-6 C18H22O
1-(2-hydroxyphenyl)-6-phenylhexane
—— 15-Hydroxy<10>paracyclophan-12,13-dicarbonsaeure-dimethylester 91590-49-7 C20H28O5
15-Hydroxy<10>paracyclophan-12,13-dicarbonsaeure-dimethylester
—— (1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid 1265355-16-5 C10H11BO5
(1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid
—— 2,3,5,6-tetrakis-chloromethyl-hydroquinone 858219-16-6 C10H10Cl4O2
2,3,5,6-tetrakis-chloromethyl-hydroquinone
—— 2,3,5,6-tetrakishydroxymethylbenzene-1,4-diol 42934-02-1 C10H14O6
2,3,5,6-tetrakishydroxymethylbenzene-1,4-diol
—— N-(5-Chlor-salicyliden)-2-amino-propan 42551-71-3 C10H12ClNO
N-(5-Chlor-salicyliden)-2-amino-propan
—— 2-(4-Hydroxyphenyl)-3-(1-oxo-1lambda~5~-pyridin-2-yl)-1,3-thiazolidin-4-one 87780-45-8 C14H12N2O3S
2-(4-Hydroxyphenyl)-3-(1-oxo-1lambda~5~-pyridin-2-yl)-1,3-thiazolidin-4-one
—— 2-(2-Hydroxyphenyl)-3-(1-oxo-1lambda~5~-pyridin-2-yl)-1,3-thiazolidin-4-one 87780-44-7 C14H12N2O3S
2-(2-Hydroxyphenyl)-3-(1-oxo-1lambda~5~-pyridin-2-yl)-1,3-thiazolidin-4-one
—— 2-(4-hydroxy-2,3-dimethylphenyl)acetic acid 21453-51-0 C10H12O3
2-(4-hydroxy-2,3-dimethylphenyl)acetic acid
—— 2-butyl-5-methylresorcinol 41395-25-9 C11H16O2
2-butyl-5-methylresorcinol
—— 2-(2-hydroxyphenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-1-oxyl 626206-32-4 C13H17N2O2
2-(2-hydroxyphenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-1-oxyl
—— (E)-1-(2,4-difluorobenzyl)-5-((2,4-difluorobenzylimino)(2-hydroxy-4-methoxyphenyl)methyl)pyridin-2(1H)-one 1201816-89-8 C27H20F4N2O3
(E)-1-(2,4-difluorobenzyl)-5-((2,4-difluorobenzylimino)(2-hydroxy-4-methoxyphenyl)methyl)pyridin-2(1H)-one
—— 3,3'-(4,6-Dihydroxy-5-methyl-1,3-phenylene)dipropanenitrile 88421-70-9 C13H14N2O2
3,3'-(4,6-Dihydroxy-5-methyl-1,3-phenylene)dipropanenitrile
—— 2-[(3-hydroxy-4,4,5,5-tetramethylimidazoline)-2-yl]phenol 899419-40-0 C13H18N2O2
2-[(3-hydroxy-4,4,5,5-tetramethylimidazoline)-2-yl]phenol
—— 2-methoxy-4-[(2R,4R,5R,6S)-2,5,6-trimethyl-1,3-dioxan-4-yl]phenol 88536-83-8 C14H20O4
2-methoxy-4-[(2R,4R,5R,6S)-2,5,6-trimethyl-1,3-dioxan-4-yl]phenol
—— 2-methoxy-4-[(2R,4R,5R,6R)-2,5,6-trimethyl-1,3-dioxan-4-yl]phenol 88536-83-8 C14H20O4
2-methoxy-4-[(2R,4R,5R,6R)-2,5,6-trimethyl-1,3-dioxan-4-yl]phenol
—— Diethyl 3,3'-(4,6-dihydroxy-5-nitro-1,3-phenylene)dipropanoate 88421-75-4 C16H21NO8
Diethyl 3,3'-(4,6-dihydroxy-5-nitro-1,3-phenylene)dipropanoate
—— 3,3',3''-[2-(2-Cyanoethoxy)-4,6-dihydroxybenzene-1,3,5-triyl]tripropanenitrile 88421-74-3 C18H18N4O3
3,3',3''-[2-(2-Cyanoethoxy)-4,6-dihydroxybenzene-1,3,5-triyl]tripropanenitrile
—— 3,3'-(4,6-Dihydroxy-1,3-phenylene)dipropanenitrile 88421-69-6 C12H12N2O2
3,3'-(4,6-Dihydroxy-1,3-phenylene)dipropanenitrile
—— 3,3',3''-(2,4-Dihydroxybenzene-1,3,5-triyl)tripropanenitrile 88421-72-1 C15H15N3O2
3,3',3''-(2,4-Dihydroxybenzene-1,3,5-triyl)tripropanenitrile
—— 2-(2-Hydroxy-5-methoxyphenylazo)-1-methylbenzimidazole 65446-33-5 C15H14N4O2
2-(2-Hydroxy-5-methoxyphenylazo)-1-methylbenzimidazole
—— 3-[4-(morpholin-4-yl)pyrido[3',2':4,5]furo[3,2-d]pyrimidin-2-yl]-5-nitrophenol 1509919-73-6 C19H15N5O5
3-[4-(morpholin-4-yl)pyrido[3',2':4,5]furo[3,2-d]pyrimidin-2-yl]-5-nitrophenol
—— 3,3'-(4,6-Dihydroxy-5-nitro-1,3-phenylene)dipropanenitrile 88421-71-0 C12H11N3O4
3,3'-(4,6-Dihydroxy-5-nitro-1,3-phenylene)dipropanenitrile
—— ethyl (2Z,5E)-2-hydroxy-4-oxo-6-phenylhexa-2,5-dienoate 1203610-94-9 C12H11NO4
ethyl (2Z,5E)-2-hydroxy-4-oxo-6-phenylhexa-2,5-dienoate
—— 6<(dimethylamino)methyl>-2-methoxy-4-methylphenol 123752-64-7 C11H17NO2
6<(dimethylamino)methyl>-2-methoxy-4-methylphenol
—— 3-(((tert-butyldimethylsilyl)oxy)methyl)phenol 96013-78-4 C13H22O2Si
3-(((tert-butyldimethylsilyl)oxy)methyl)phenol
—— 5-[(5-bromo-2-hydroxyphenyl)methylideneamino]-1H-pyrimidine-2,4-dione 42485-30-3 C11H8BrN3O3
5-[(5-bromo-2-hydroxyphenyl)methylideneamino]-1H-pyrimidine-2,4-dione
—— 5-[(4-hydroxy-3-methoxyphenyl)methylideneamino]-1H-pyrimidine-2,4-dione 273745-81-6 C12H11N3O4
5-[(4-hydroxy-3-methoxyphenyl)methylideneamino]-1H-pyrimidine-2,4-dione
—— 5-[(5-chloro-2-hydroxyphenyl)methylideneamino]-1H-pyrimidine-2,4-dione 273745-71-4 C11H8ClN3O3
5-[(5-chloro-2-hydroxyphenyl)methylideneamino]-1H-pyrimidine-2,4-dione
—— 5-pentadec-8'-enyl resorcinol 500-68-5 C21H34O2
5-pentadec-8'-enyl resorcinol
—— 6,6'-Dimethyl-2,2'-[1,3-diazinane-1,3-diylbis(methylene)]diphenol 1133150-08-9 C20H26N2O2
6,6'-Dimethyl-2,2'-[1,3-diazinane-1,3-diylbis(methylene)]diphenol
—— N-[3-(2-hydroxyphenyl)prop-2-ynyl]propanamide 211803-65-5 C12H13NO2
N-[3-(2-hydroxyphenyl)prop-2-ynyl]propanamide
—— 3-bromo-4-fluoro-2-nitrophenol 1374772-55-0 C6H3BrFNO3
3-bromo-4-fluoro-2-nitrophenol
—— 2,4-Dimethoxy-6-(2-methyloctan-2-yl)phenol 89244-02-0 C17H28O3
2,4-Dimethoxy-6-(2-methyloctan-2-yl)phenol
—— 1-hydroxy-2-((bis(tert-butoxycarbonyl)amino))methylbenzene 1214728-75-2 C17H25NO5
1-hydroxy-2-((bis(tert-butoxycarbonyl)amino))methylbenzene
—— 1-[2-{5-(4-hydroxy-3-methoxyphenyl)(2E, 4E)-2, 4-pentadienoylamino}ethyl]-4-(3-indolyl)piperidine 124956-25-8 C27H31N3O3
1-[2-{5-(4-hydroxy-3-methoxyphenyl)(2E, 4E)-2, 4-pentadienoylamino}ethyl]-4-(3-indolyl)piperidine
—— 3,5-bis(mercaptomethyl)-2,4,6-trimethyl-phenol 115006-90-1 C11H16OS2
3,5-bis(mercaptomethyl)-2,4,6-trimethyl-phenol
—— (2E,4E)-5-(3,5-dimethoxy-4-hydroxyphenyl)-N-(2-(4-(1H-indol-3-yl)piperidin-1-yl)ethyl)-2,4-pentadienamide 124956-36-1 C28H33N3O4
(2E,4E)-5-(3,5-dimethoxy-4-hydroxyphenyl)-N-(2-(4-(1H-indol-3-yl)piperidin-1-yl)ethyl)-2,4-pentadienamide
—— 4(R)-4-((4-(2-methoxyethyl)phenoxy)methyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 935547-68-5 C20H31NO5
4(R)-4-((4-(2-methoxyethyl)phenoxy)methyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
—— 1-(2-hydroxy-3-nitrophenyl)-3-mesitylthiourea 851886-82-3 C16H17N3O3S
1-(2-hydroxy-3-nitrophenyl)-3-mesitylthiourea
—— [2-hydroxy-2-(4-hydroxyphenyl)propyl][(methylethyl)sulfonyl]amine 305447-70-5 C12H19NO4S
[2-hydroxy-2-(4-hydroxyphenyl)propyl][(methylethyl)sulfonyl]amine
—— 4-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenol 1134111-40-2 C12H15NO3S
4-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenol
—— 1,1'-pentamethylenebis[2,5-dimethoxy-4-hydroxy-3,6-bis(methoxymethoxy)benzene] 99622-20-5 C29H44O14
1,1'-pentamethylenebis[2,5-dimethoxy-4-hydroxy-3,6-bis(methoxymethoxy)benzene]