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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
—— (2'S,4'R,6'S)-2'-(4'''-hydroxy-3'''-methoxyphenethyl)-6'-(3''''-chloro-4''''-hydroxyphenyl)tetrahydropyran- 4'-yl-3-methoxyphenyl carbamate 1440431-85-5 C28H30ClNO7
(2'S,4'R,6'S)-2'-(4'''-hydroxy-3'''-methoxyphenethyl)-6'-(3''''-chloro-4''''-hydroxyphenyl)tetrahydropyran- 4'-yl-3-methoxyphenyl carbamate
—— 1451930-87-2 C37H38N2O2
—— 2-(1-Dimethylamino-cyclopropyl)-phenol 37520-22-2 C11H15NO
2-(1-Dimethylamino-cyclopropyl)-phenol
—— 2-bromo-4-chloro-6-[(2-propylaminoethylimino)methyl]phenolate 1244781-72-3 C12H16BrClN2O
2-bromo-4-chloro-6-[(2-propylaminoethylimino)methyl]phenolate
—— 5-allylcalix[4]arene 106750-87-2 C31H28O4
5-allylcalix[4]arene
—— 131946-61-7 C16H23NO4
—— 2,2-Dimethyl-butyric acid (1S,2R,5S,6S)-6-[2-(4-methoxy-phenoxy)-ethyl]-5-methyl-2-propyl-cyclohex-3-enylmethyl ester 157117-11-8 C26H40O4
2,2-Dimethyl-butyric acid (1S,2R,5S,6S)-6-[2-(4-methoxy-phenoxy)-ethyl]-5-methyl-2-propyl-cyclohex-3-enylmethyl ester
—— 1338380-86-1 C15H15IO3
—— 5-[(4-hydroxy-3-methoxy-benzylidene)-hydrazino]-pyrazine-2-carboxylic acid (4-hydroxy-3-methoxy-benzylidene)-hydrazide 36805-05-7 C21H20N6O5
5-[(4-hydroxy-3-methoxy-benzylidene)-hydrazino]-pyrazine-2-carboxylic acid (4-hydroxy-3-methoxy-benzylidene)-hydrazide
—— 36361-93-0 C16H20N4O3
—— 62642-24-4 C10H11N3O3S
—— 2-(2-Chloro-2-nitro-ethyl)-3,6-dimethoxy-phenol 117266-60-1 C10H12ClNO5
2-(2-Chloro-2-nitro-ethyl)-3,6-dimethoxy-phenol
—— 1-(2-sec-butylphenyl)-3-(2-hydroxy-4-nitrophenyl)urea 1202526-38-2 C17H19N3O4
1-(2-sec-butylphenyl)-3-(2-hydroxy-4-nitrophenyl)urea
—— N-(4-chlorophenyl)-1-isopropyl-1-methyl-l4-sulfanimine compound with picric acid (1:1) 56158-24-8 C6H3N3O7*C10H14ClNS
N-(4-chlorophenyl)-1-isopropyl-1-methyl-l4-sulfanimine compound with picric acid (1:1)
—— 3-hydroxy-4-(4-hydroxy-phenyl)-1-(3-imidazol-1-yl-propyl)-5-pyridin-4-yl-1,5-dihydro-pyrrol-2-one 1024608-22-7 C21H20N4O3
3-hydroxy-4-(4-hydroxy-phenyl)-1-(3-imidazol-1-yl-propyl)-5-pyridin-4-yl-1,5-dihydro-pyrrol-2-one
—— (5Z)-5-[(5-fluoro-2-hydroxyphenyl)methylidene]-2-[(3S)-3-hydroxypyrrolidin-1-yl]-4,5-dihydro-1,3-thiazol-4-one 1181082-53-0 C14H13FN2O3S
(5Z)-5-[(5-fluoro-2-hydroxyphenyl)methylidene]-2-[(3S)-3-hydroxypyrrolidin-1-yl]-4,5-dihydro-1,3-thiazol-4-one
—— 2-thienyl 2'-hydroxyphenyl ketone oxime 97034-91-8 C11H9NO2S
2-thienyl 2'-hydroxyphenyl ketone oxime
—— 3-hydroxy-5-hydroxymethyl-4-(4-hydroxy-phenyl)-1-(3-imidazol-1-yl-propyl)-1,5-dihydro-pyrrol-2-one 1024608-24-9 C17H19N3O4
3-hydroxy-5-hydroxymethyl-4-(4-hydroxy-phenyl)-1-(3-imidazol-1-yl-propyl)-1,5-dihydro-pyrrol-2-one
—— 6-hydroxy-5-(3,4-dihydroxy-5-nitrophenyl)-2,3-pyrazinedicarbonitrile 134612-57-0 C12H5N5O5
6-hydroxy-5-(3,4-dihydroxy-5-nitrophenyl)-2,3-pyrazinedicarbonitrile
—— tert-butyl N-(4-hydroxybenzenecarboximidoyl)carbamate 76223-52-4 C12H16N2O3
tert-butyl N-(4-hydroxybenzenecarboximidoyl)carbamate
—— 4-Bromo-3-hydroxyphenylboronic acid pinacol ester 2121512-98-7 C12H16BBrO3
4-Bromo-3-hydroxyphenylboronic acid pinacol ester
—— 4-methyl-2-((piperidin-1-ylmethylene)amino)phenol 1334541-37-5 C13H18N2O
4-methyl-2-((piperidin-1-ylmethylene)amino)phenol
—— 26004-95-5 C12H17N3O4
—— 4-Hydroxy-7-[2-[6-[2-(4-phenylmethoxy)phenylethoxy]hexyl]aminoethyl]-1,3-benzothiazol-2(3H)-one hydrochloride 143440-89-5 C30H36N2O4S*ClH
4-Hydroxy-7-[2-[6-[2-(4-phenylmethoxy)phenylethoxy]hexyl]aminoethyl]-1,3-benzothiazol-2(3H)-one hydrochloride
—— 2-methoxy-5-{[(2-piperazin-1-ylethyl)imino]methyl}phenol 1375058-93-7 C14H21N3O2
2-methoxy-5-{[(2-piperazin-1-ylethyl)imino]methyl}phenol
—— N-Carbobenzoxy-homovanillylamin 16010-87-0 C17H19NO4
N-Carbobenzoxy-homovanillylamin
—— 2,4-Dinitro-3,6-di-tert.butyl-phenol 22479-28-3 C14H20N2O5
2,4-Dinitro-3,6-di-tert.butyl-phenol
—— 6-(2-Bromo-4-hydroxy-5-methyl-benzyl)-6-methyl-1,4-dioxa-spiro[4.4]nonan-7-one 170168-29-3 C16H19BrO4
6-(2-Bromo-4-hydroxy-5-methyl-benzyl)-6-methyl-1,4-dioxa-spiro[4.4]nonan-7-one
—— Bis(benzimidazol-2-ylmethyl)(2-hydroxy-5-nitrobenzyl)amine 155797-28-7 C23H20N6O3
Bis(benzimidazol-2-ylmethyl)(2-hydroxy-5-nitrobenzyl)amine
—— 2-(3,4-dihydroxyphenyl)-2-methylcyclopentane-1,3-dione 1262149-43-8 C12H12O4
2-(3,4-dihydroxyphenyl)-2-methylcyclopentane-1,3-dione
—— 1-[5-(4-Hydroxy-3-methoxy-phenyl)-3-(4-{[1-(2-methyl-1H-indol-3-yl)-meth-(E)-ylidene]-amino}-phenyl)-4,5-dihydro-pyrazol-1-yl]-ethanone 114217-22-0 C28H26N4O3
1-[5-(4-Hydroxy-3-methoxy-phenyl)-3-(4-{[1-(2-methyl-1H-indol-3-yl)-meth-(E)-ylidene]-amino}-phenyl)-4,5-dihydro-pyrazol-1-yl]-ethanone
—— Phenol, 4-chloro-2-fluoro-6-(3-pyrrolidinyl)- 1260638-83-2 C10H11ClFNO
Phenol, 4-chloro-2-fluoro-6-(3-pyrrolidinyl)-
—— 4-Bromo-2-[3-(cyclohexylamino)propyliminomethyl]phenol 1357194-06-9 C16H23BrN2O
4-Bromo-2-[3-(cyclohexylamino)propyliminomethyl]phenol
—— dopaminium hydrogen squarate 1256333-23-9 C4H2O4*C8H11NO2
dopaminium hydrogen squarate
—— [(E)-4-[benzyl-[(3,5-dihydroxy-4-methoxyphenyl)methyl]amino]but-2-enyl] methyl carbonate 1374156-38-3 C21H25NO6
[(E)-4-[benzyl-[(3,5-dihydroxy-4-methoxyphenyl)methyl]amino]but-2-enyl] methyl carbonate
—— 5-butyl-3-hydroxy-4-(4-hydroxy-phenyl)-1-(3-imidazol-1-yl-propyl)-1,5-dihydro-pyrrol-2-one 1024608-27-2 C20H25N3O3
5-butyl-3-hydroxy-4-(4-hydroxy-phenyl)-1-(3-imidazol-1-yl-propyl)-1,5-dihydro-pyrrol-2-one
—— 2-(4-hydroxy-benzylidene)-5-methyl-5,6-dihydro-imidazo[2,1-b]thiazol-3-one 30241-81-7 C13H12N2O2S
2-(4-hydroxy-benzylidene)-5-methyl-5,6-dihydro-imidazo[2,1-b]thiazol-3-one
—— 4-[11-(4-chlorophenyl)-7-thia-1,3,4,9,10,12-hexazatricyclo[6.4.0.02,6]dodeca-2,8-dien-5-yl]phenol 128093-29-8 C17H15ClN6OS
4-[11-(4-chlorophenyl)-7-thia-1,3,4,9,10,12-hexazatricyclo[6.4.0.02,6]dodeca-2,8-dien-5-yl]phenol
—— Phenol, 2-[(methyloxidoimino)methyl]- 41105-99-1 C8H9NO2
Phenol, 2-[(methyloxidoimino)methyl]-
—— N-cyclohexyl-N-(4-hydroxybenzyl)methacrylamide 1612841-33-4 C17H23NO2
N-cyclohexyl-N-(4-hydroxybenzyl)methacrylamide
—— diethyl 2-((2E,6E)-8-(2-hydroxyphenyl)-2,6-dimethylocta-2,6-dienyl)-2-(prop-2-ynyl)malonate 1233027-51-4 C26H34O5
diethyl 2-((2E,6E)-8-(2-hydroxyphenyl)-2,6-dimethylocta-2,6-dienyl)-2-(prop-2-ynyl)malonate
—— 3-Hexyl-5-methylamino-3H-imidazole-4-carboxylic acid methylamide; compound with picric acid 117835-30-0 C6H3N3O7*C12H22N4O
3-Hexyl-5-methylamino-3H-imidazole-4-carboxylic acid methylamide; compound with picric acid
—— 4-Benzylsulfanyl-2'-hydroxyisoflavan 209404-37-5 C22H20O2S
4-Benzylsulfanyl-2'-hydroxyisoflavan
—— 4,5-dichloro-3-hydroxy-6-<(1'-methyl-2'-oxocyclohexyl)oxy>-1,2-benzenedicarbonitrile 123674-96-4 C15H12Cl2N2O3
4,5-dichloro-3-hydroxy-6-<(1'-methyl-2'-oxocyclohexyl)oxy>-1,2-benzenedicarbonitrile
—— 2-[(E)-[3-[(E)-(2-hydroxyphenyl)methylideneamino]-1H-1,2,4-triazol-5-yl]iminomethyl]phenol 915022-95-6 C16H13N5O2
2-[(E)-[3-[(E)-(2-hydroxyphenyl)methylideneamino]-1H-1,2,4-triazol-5-yl]iminomethyl]phenol
—— 4-hydroxy-3-methoxy-5-(3-phenylpropylthiomethyl) benzaldehyde 294191-48-3 C17H18O3S
4-hydroxy-3-methoxy-5-(3-phenylpropylthiomethyl) benzaldehyde
—— [4.4]paracyclophan-6-ol 113136-02-0 C20H24O
[4.4]paracyclophan-6-ol
—— 2,6-Di-n-octadecyl-hydrochinon 72319-71-2 C42H78O2
2,6-Di-n-octadecyl-hydrochinon
—— 1050600-89-9 C14H15ClN4O
—— 2-hydroxy-3-methoxybenzaldehyde N-(2,4,6-trichlorophenyl)hydrazone 363600-78-6 C14H11Cl3N2O2
2-hydroxy-3-methoxybenzaldehyde N-(2,4,6-trichlorophenyl)hydrazone