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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-[(E)-[(E)-1-(2-hydroxyphenyl)ethylidenehydrazinylidene]methyl]phenol 143628-73-3 C15H14N2O2
2-[(E)-[(E)-1-(2-hydroxyphenyl)ethylidenehydrazinylidene]methyl]phenol
—— 2-(2-amino-6-phenyl-6H-1,3-thiazin-4-yl)-4-methylphenol 75793-92-9 C17H16N2OS
2-(2-amino-6-phenyl-6H-1,3-thiazin-4-yl)-4-methylphenol
—— Ethyl 4-hydroxy-3-(2-methyl-4-thiazolyl)benzeneacetate 91920-67-1 C14H15NO3S
Ethyl 4-hydroxy-3-(2-methyl-4-thiazolyl)benzeneacetate
—— 4-Fluoro-2-[(2-propynoxyimino)methyl]phenol 103743-19-7 C10H8FNO2
4-Fluoro-2-[(2-propynoxyimino)methyl]phenol
—— ethyl 2-(4-hydroxy-3-methoxy-5-methylphenyl)acetate 765302-61-2 C12H16O4
ethyl 2-(4-hydroxy-3-methoxy-5-methylphenyl)acetate
—— N-(4'-benzyloxy-3'-methoxyphenylethyl)-2-(2-bromo-5-hydroxy-4-methoxyphenyl)acetamide 892805-32-2 C25H26BrNO5
N-(4'-benzyloxy-3'-methoxyphenylethyl)-2-(2-bromo-5-hydroxy-4-methoxyphenyl)acetamide
—— tert-butyl (4R)-4-[(R)-(2,6-dihydroxy-4-pentadecylphenyl)-hydroxymethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 116079-45-9 C32H55NO6
tert-butyl (4R)-4-[(R)-(2,6-dihydroxy-4-pentadecylphenyl)-hydroxymethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
—— 6-(1,2-Dimethylbutyl)-2,4-dinitrophenol 19165-90-3 C12H16N2O5
6-(1,2-Dimethylbutyl)-2,4-dinitrophenol
—— N-<3,5-Dinitro-2-hydroxy-benzyliden>-p-phenetidin 4487-69-8 C15H13N3O6
N-<3,5-Dinitro-2-hydroxy-benzyliden>-p-phenetidin
—— (E)-methyl 3-(3-chloro-4-hydroxyphenyl)-2-(hydroxyimino)propanoate 1314789-34-8 C10H10ClNO4
(E)-methyl 3-(3-chloro-4-hydroxyphenyl)-2-(hydroxyimino)propanoate
—— 4-(1-methyl-1-p-xylylcyclobutane-3-yl)-2-(2-hydroxy-5-bromobenzolidenehydrazino)thiazole 588710-16-1 C23H24BrN3OS
4-(1-methyl-1-p-xylylcyclobutane-3-yl)-2-(2-hydroxy-5-bromobenzolidenehydrazino)thiazole
—— (E)-2-(3-azido-3-methylbut-1-en-1-yl)-4-methoxyphenol 1429629-10-6 C12H15N3O2
(E)-2-(3-azido-3-methylbut-1-en-1-yl)-4-methoxyphenol
—— S-[2-benzyl-3-[(3,4-dihydroxyphenyl)methylamino]-3-oxopropyl] ethanethioate 122410-25-7 C19H21NO4S
S-[2-benzyl-3-[(3,4-dihydroxyphenyl)methylamino]-3-oxopropyl] ethanethioate
—— 2,3,5,6-tetraamino-hydroquinone 22811-73-0 C6H10N4O2
2,3,5,6-tetraamino-hydroquinone
—— 5,11,17-trimethyl-23-[8-(25,26,27,28-tetrahydroxy-11,17,23-trimethyl-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl)octyl]pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol 124028-44-0 C70H74O8
5,11,17-trimethyl-23-[8-(25,26,27,28-tetrahydroxy-11,17,23-trimethyl-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl)octyl]pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol
—— 3-[(1R,2R)-2-(2-hydroxy-benzylideneamino)-cyclohexyl]-1-isopropyl-4-phenyl-3H-imidazol-1-ium bromide 1094598-52-3 Br*C25H30N3O
3-[(1R,2R)-2-(2-hydroxy-benzylideneamino)-cyclohexyl]-1-isopropyl-4-phenyl-3H-imidazol-1-ium bromide
—— 2-Brom-1-(2-hydroxy-4-methoxy-phenyl)-propan-1,3-dion 7295-31-0 C10H9BrO4
2-Brom-1-(2-hydroxy-4-methoxy-phenyl)-propan-1,3-dion
—— S-methyl-β-N(2-hydroxy-5-methylphenyl)methylenedithiocarbazate 147951-58-4 C10H12N2OS2
S-methyl-β-N(2-hydroxy-5-methylphenyl)methylenedithiocarbazate
—— 5-(2-hydroxy-5-methylphenyl)-3-isoxazolecarboxylic acid 164171-53-3 C11H9NO4
5-(2-hydroxy-5-methylphenyl)-3-isoxazolecarboxylic acid
—— 2-Methyl-6-(propan-2-yliminomethyl)phenol 117364-91-7 C11H15NO
2-Methyl-6-(propan-2-yliminomethyl)phenol
—— 2-[1-(2-Hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-pent-4-enoic acid ethyl ester 110189-70-3 C15H18O4
2-[1-(2-Hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-pent-4-enoic acid ethyl ester
—— 2-Nitro-4-(p-Chlorphenylsulfonyl)-phenol 42800-26-0 C12H8ClNO5S
2-Nitro-4-(p-Chlorphenylsulfonyl)-phenol
—— (R)-1-(tert-butyl)-7-hydroxy-2,3-dihydro-1H-phosphindole 1-oxide 1477517-30-8 C12H17O2P
(R)-1-(tert-butyl)-7-hydroxy-2,3-dihydro-1H-phosphindole 1-oxide
—— 2-[2-(2,3-difluoro-4-hydroxy-phenyl)-6-hydroxy-4-methyl-3H-inden-1-yl]-furan-3-carbonitrile 1019985-42-2 C21H13F2NO3
2-[2-(2,3-difluoro-4-hydroxy-phenyl)-6-hydroxy-4-methyl-3H-inden-1-yl]-furan-3-carbonitrile
—— 4-chloro-2-[(2-ethylaminoethylimino)methyl]phenol 188907-02-0 C11H15ClN2O
4-chloro-2-[(2-ethylaminoethylimino)methyl]phenol
—— 4-(2-Hydroxy-3-isopropylamino-propoxy)-2-hydroxymethyl-phenol 76167-06-1 C13H21NO4
4-(2-Hydroxy-3-isopropylamino-propoxy)-2-hydroxymethyl-phenol
—— ethyl [(4-chloro-3-hydroxybenzyl)thio]acetate 672931-42-9 C11H13ClO3S
ethyl [(4-chloro-3-hydroxybenzyl)thio]acetate
—— 3-(benzyloxy)-2-[4-(2-hydroxyethyl)-2-iodophenoxy]propan-1-ol 686780-28-9 C18H21IO4
3-(benzyloxy)-2-[4-(2-hydroxyethyl)-2-iodophenoxy]propan-1-ol
—— 1177388-23-6 C25H30O2S
—— 2-(3-hydroxyphenyl)-1,1-diisopropyl-2-methoxyethene 172024-42-9 C15H22O2
2-(3-hydroxyphenyl)-1,1-diisopropyl-2-methoxyethene
—— 2-[(4-Hydroxy-3-methoxyphenyl)methylidene]cyclohexan-1-one 193208-97-8 C14H16O3
2-[(4-Hydroxy-3-methoxyphenyl)methylidene]cyclohexan-1-one
—— 2-tert-butyl-2-(5-tert-butyl-2-hydroxyphenylthio)-1,3,2-benzoxathiaphosphole 77065-46-4 C20H25O2PS2
2-tert-butyl-2-(5-tert-butyl-2-hydroxyphenylthio)-1,3,2-benzoxathiaphosphole
—— Picric acid; compound with 2-phenyl-4,5-dihydro-3H-pyrrole-3-carboxylic acid ethyl ester 117103-10-3 C6H3N3O7*C13H15NO2
Picric acid; compound with 2-phenyl-4,5-dihydro-3H-pyrrole-3-carboxylic acid ethyl ester
—— 5-(1H-indol-3-yl)-4-isopropyl-2-methoxyphenol 1613299-20-9 C18H19NO2
5-(1H-indol-3-yl)-4-isopropyl-2-methoxyphenol
—— 2,6-Dihydroxy-4-methyl-isophthaldialdehyd-dioxim 10209-58-2 C9H10N2O4
2,6-Dihydroxy-4-methyl-isophthaldialdehyd-dioxim
—— 1-(tert-butyl)-7-hydroxy-2,3-dihydro-1H-phosphindole 1-oxide 1477517-29-5 C12H17O2P
1-(tert-butyl)-7-hydroxy-2,3-dihydro-1H-phosphindole 1-oxide
—— (2R,3R)-2-formylamino-3-(4-hydroxyphenyl)-1,3-propanediol 129413-12-3 C10H13NO4
(2R,3R)-2-formylamino-3-(4-hydroxyphenyl)-1,3-propanediol
—— 4-Chloro-phenol; compound with piperazine 93017-67-5 C4H10N2*C6H5ClO
4-Chloro-phenol; compound with piperazine
—— 4-{[1-(2-Ethyl-pyridin-4-yl)-meth-(Z)-ylidene]-hydrazonomethyl}-2-methoxy-phenol 19736-21-1 C16H17N3O2
4-{[1-(2-Ethyl-pyridin-4-yl)-meth-(Z)-ylidene]-hydrazonomethyl}-2-methoxy-phenol
—— N-(3-(1-pyrrolyl)propyl)salicylaldimine 172922-28-0 C14H16N2O
N-(3-(1-pyrrolyl)propyl)salicylaldimine
—— 2-ethoxy-6-methoxy-4-methylphenol 1574215-75-0 C10H14O3
2-ethoxy-6-methoxy-4-methylphenol
—— 1-(4-(iodomethyl)-1,3-dithiolan-2-ylidene)pyrrolidin-1-ium iodide 1160429-27-5 C8H13INS2*I
1-(4-(iodomethyl)-1,3-dithiolan-2-ylidene)pyrrolidin-1-ium iodide
—— 2-[1'-(4'-(2''-pyridyl)-2'-thiabutyl)]-4-methoxyphenol 956252-25-8 C15H17NO2S
2-[1'-(4'-(2''-pyridyl)-2'-thiabutyl)]-4-methoxyphenol
—— (2-butoxyethyl)-4-methoxybenzene 54829-49-1 C13H20O2
(2-butoxyethyl)-4-methoxybenzene
—— 4-Dodecylsulfanyl-3-nitro-phenol 798-99-2 C18H29NO3S
4-Dodecylsulfanyl-3-nitro-phenol
—— 1-(3',4'-dihydroxyphenyl)-3-methylbut-2-en-1-one 97911-29-0 C11H12O3
1-(3',4'-dihydroxyphenyl)-3-methylbut-2-en-1-one
—— 1384118-57-3 C24H32LaN7O6
—— 1374852-58-0 C21H18N2O2
—— 2,3,6-trimethyl-4-[(4-aminophenyldimethylsilyl)methylthio]phenol 1230388-48-3 C18H25NOSSi
2,3,6-trimethyl-4-[(4-aminophenyldimethylsilyl)methylthio]phenol
—— (E)-2-(1-ethyl-5-methylhex-2-enyl)phenol 87512-61-6 C15H22O
(E)-2-(1-ethyl-5-methylhex-2-enyl)phenol