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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
—— 1022086-78-7 C16H17NO2
—— 2-(cyclopropylethynyl)phenol 870010-44-9 C11H10O
2-(cyclopropylethynyl)phenol
—— (E)-3-((2,6-dimethylphenylimino)methyl)benzene-1,2-diol 1339943-39-3 C15H15NO2
(E)-3-((2,6-dimethylphenylimino)methyl)benzene-1,2-diol
—— N<sup>1</sup>-4-methylbenzylidene-N<sup>2</sup>-[3-(3-hydroxy-4-methoxyphenyl)-4-(2,5-dihydroxyphenyl)-1,3-thiazol-2-ylidene]hydrazine 1380074-98-5 C24H21N3O4S
N<sup>1</sup>-4-methylbenzylidene-N<sup>2</sup>-[3-(3-hydroxy-4-methoxyphenyl)-4-(2,5-dihydroxyphenyl)-1,3-thiazol-2-ylidene]hydrazine
—— cis-3-m-Hydroxyphenyl-2-aza-4-oxa-decalin 38447-63-1 C14H19NO2
cis-3-m-Hydroxyphenyl-2-aza-4-oxa-decalin
—— Phenol, 3-(1-aminoethyl)-6-chloro-2-fluoro-5-methyl- 1896840-00-8 C9H11ClFNO
Phenol, 3-(1-aminoethyl)-6-chloro-2-fluoro-5-methyl-
—— N,N'-bis(5-fluorosalicylidene)-1,2-phenylenediamine 1190619-37-4 C20H14F2N2O2
N,N'-bis(5-fluorosalicylidene)-1,2-phenylenediamine
—— <i>N</i>'-(4-hydroxy-3-methoxy-benzylidene)-pyrazine-2-carbohydrazonic acid amide 31649-04-4 C13H13N5O2
<i>N</i>'-(4-hydroxy-3-methoxy-benzylidene)-pyrazine-2-carbohydrazonic acid amide
—— 6-[4-(1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)ethylidene)aminophenyl]-4,5-dihydropyridazin-3(2H)one 128995-88-0 C24H21N3O4
6-[4-(1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)ethylidene)aminophenyl]-4,5-dihydropyridazin-3(2H)one
—— tetraaquabis(p-nitrosalicylato)zinc(II) 186966-62-1 C14H16N2O14Zn
tetraaquabis(p-nitrosalicylato)zinc(II)
—— 2-Chloro-6-diethylaminomethyl-4-nitro-phenol 82147-11-3 C11H15ClN2O3
2-Chloro-6-diethylaminomethyl-4-nitro-phenol
—— N'-[(5-chloro-2-hydroxyphenyl)methyl]-N-cyanopropanimidamide 736946-79-5 C11H12ClN3O
N'-[(5-chloro-2-hydroxyphenyl)methyl]-N-cyanopropanimidamide
—— 4-acetoxy-3-bromo-6-methoxy-5-methyl-2-(2,4-pentadienyl)phenol 105104-29-8 C15H17BrO4
4-acetoxy-3-bromo-6-methoxy-5-methyl-2-(2,4-pentadienyl)phenol
—— 2-Amino-3-bromo-5-fluorophenol 1805027-31-9 C6H5BrFNO
2-Amino-3-bromo-5-fluorophenol
—— diethyl(3-hydroxy-4-methoxyphenyl)methylmalonate 361576-50-3 C15H20O6
diethyl(3-hydroxy-4-methoxyphenyl)methylmalonate
—— 4-(Hexadecyliminomethyl)phenol 1246401-83-1 C23H39NO
4-(Hexadecyliminomethyl)phenol
—— 4-(2-Hydroxy-5-nitro-phenyl)-6-(2-methoxy-phenyl)-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester 40188-97-4 C22H21NO7
4-(2-Hydroxy-5-nitro-phenyl)-6-(2-methoxy-phenyl)-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester
—— 2-Chloro-3-(dimethyl-hydrazonomethyl)-phenol 14395-29-0 C9H11ClN2O
2-Chloro-3-(dimethyl-hydrazonomethyl)-phenol
—— 4-Hydroxy-3-methoxy-benzoic acid N'-[(N'-benzoyl-N-methyl-hydrazino)-imino-methyl]-hydrazide 34687-52-0 C17H19N5O4
4-Hydroxy-3-methoxy-benzoic acid N'-[(N'-benzoyl-N-methyl-hydrazino)-imino-methyl]-hydrazide
—— Thioacetic acid S-[1-(4-hydroxy-phenyl)-2-nitro-ethyl] ester 34188-56-2 C10H11NO4S
Thioacetic acid S-[1-(4-hydroxy-phenyl)-2-nitro-ethyl] ester
—— 4-Bromo-6-[(4-bromoanilino)methylidene]-2-iodocyclohexa-2,4-dien-1-one 649560-29-2 C13H8Br2INO
4-Bromo-6-[(4-bromoanilino)methylidene]-2-iodocyclohexa-2,4-dien-1-one
—— 3-[3-(2-tert-Butylamino-1-hydroxy-ethyl)-5-hydroxy-phenoxy]-propane-1,2-diol 63437-36-5 C15H25NO5
3-[3-(2-tert-Butylamino-1-hydroxy-ethyl)-5-hydroxy-phenoxy]-propane-1,2-diol
—— 2-[(Z)-2-chloro-2-nitroethenyl]-3,6-dimethoxyphenol 117672-27-2 C10H10ClNO5
2-[(Z)-2-chloro-2-nitroethenyl]-3,6-dimethoxyphenol
—— β-(3-Methoxy-4-hydroxyphenyl)ethylamide of 3'-bromo-4'-benzyloxyphenylacetic acid 16589-79-0 C24H24BrNO4
β-(3-Methoxy-4-hydroxyphenyl)ethylamide of 3'-bromo-4'-benzyloxyphenylacetic acid
—— [3-(3,4-dimethoxyphenyl)-4,4-dimethyl-4,5-dihydropyrazol-1-yl]-(3-hydroxy-4-methoxyphenyl)methanone 1417707-04-0 C21H24N2O5
[3-(3,4-dimethoxyphenyl)-4,4-dimethyl-4,5-dihydropyrazol-1-yl]-(3-hydroxy-4-methoxyphenyl)methanone
—— [3-butyl-5-[1-(3-chloro-4-hydroxy-phenylamino)-meth-(E,Z)-ylidene]-4-oxo-thiazolidin-2(E,Z)-ylidene]-cyanoacetic acid ethyl ester 851646-67-8 C19H20ClN3O4S
[3-butyl-5-[1-(3-chloro-4-hydroxy-phenylamino)-meth-(E,Z)-ylidene]-4-oxo-thiazolidin-2(E,Z)-ylidene]-cyanoacetic acid ethyl ester
—— 2-(1-isopropylthio-2-propenyl)-4-methylphenol 124313-20-8 C13H18OS
2-(1-isopropylthio-2-propenyl)-4-methylphenol
—— 9,10-dibutyltriptycene-2,3,6,7,12,13-hexaol 1207429-32-0 C28H30O6
9,10-dibutyltriptycene-2,3,6,7,12,13-hexaol
—— 6,8-di-O-benzyl-5-deoxy-5-(2,4-dinitrophenylamino)-1,2-O-isopropylidene-7-O-methylsulfonyl-3-O-methylthiomethyl-β-L-erythro-L-talooctofuranose-(1,4) 109748-27-8 C34H41N3O13S2
6,8-di-O-benzyl-5-deoxy-5-(2,4-dinitrophenylamino)-1,2-O-isopropylidene-7-O-methylsulfonyl-3-O-methylthiomethyl-β-L-erythro-L-talooctofuranose-(1,4)
—— Allyl-furan-2-ylmethyl-m-tolyl-amine; compound with picric acid 95124-51-9 C6H3N3O7*C15H17NO
Allyl-furan-2-ylmethyl-m-tolyl-amine; compound with picric acid
—— bis(3-dodecyloxy-5-hydroxyphenyl)ethyne 1159587-66-2 C38H58O4
bis(3-dodecyloxy-5-hydroxyphenyl)ethyne
—— 4-[(3-hydroxyphenyl)-(3-methyl-1-phenyl-5-sulfanylidene-4H-pyrazol-4-yl)methyl]-5-methyl-2-phenyl-4H-pyrazol-3-one 96128-58-4 C27H24N4O2S
4-[(3-hydroxyphenyl)-(3-methyl-1-phenyl-5-sulfanylidene-4H-pyrazol-4-yl)methyl]-5-methyl-2-phenyl-4H-pyrazol-3-one
—— 3-tert. butyl-5-nitro-6-methyl-N-(4'-methyl-5'-nitropyrid-2'-yl)salicylamide 57187-69-6 C18H20N4O6
3-tert. butyl-5-nitro-6-methyl-N-(4'-methyl-5'-nitropyrid-2'-yl)salicylamide
—— 4,4-Bis-(4-hydroxy-3,5-dimethyl-phenyl)-butyric acid methyl ester 13605-01-1 C21H26O4
4,4-Bis-(4-hydroxy-3,5-dimethyl-phenyl)-butyric acid methyl ester
—— 2-(9-Chloro-4,4,5,5,6,6,7,7,8,8,9,9-dodecafluoro-2-iodo-nonyl)-4-methoxy-phenol 272125-03-8 C16H12ClF12IO2
2-(9-Chloro-4,4,5,5,6,6,7,7,8,8,9,9-dodecafluoro-2-iodo-nonyl)-4-methoxy-phenol
—— 4-ferrocenyl-2-nitrophenol 868762-22-5 C16H13FeNO3
4-ferrocenyl-2-nitrophenol
—— 4-(benzyloxy)-2-hydroxy-3-methoxybenzaldehyde 1616877-70-3 C15H14O4
4-(benzyloxy)-2-hydroxy-3-methoxybenzaldehyde
—— 2-(1-Hydroxy-4-methylcyclohexyl)phenol 1243356-17-3 C13H18O2
2-(1-Hydroxy-4-methylcyclohexyl)phenol
—— 4-{[6-(4-fluoro-phenylamino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]-hydrazonomethyl}-benzene-1,3-diol 851661-08-0 C17H12FN7O3
4-{[6-(4-fluoro-phenylamino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]-hydrazonomethyl}-benzene-1,3-diol
—— 2-[2,4-Dihydroxy-5-(1-propenyl)phenyl]-4,6-bis-(2,4-dimethylphenyl)-s-triazine 176843-70-2 C28H27N3O2
2-[2,4-Dihydroxy-5-(1-propenyl)phenyl]-4,6-bis-(2,4-dimethylphenyl)-s-triazine
—— 2-hydroxy-3-nitrobenzaldehyde-N-(3-methoxy-2-pyrazinyl)hydrazone 378780-64-4 C12H11N5O4
2-hydroxy-3-nitrobenzaldehyde-N-(3-methoxy-2-pyrazinyl)hydrazone
—— 6-Hydroxy-2,3,4-trimethyl-N-phenyl-thiobenzamide 120951-66-8 C16H17NOS
6-Hydroxy-2,3,4-trimethyl-N-phenyl-thiobenzamide
—— (-)-(R)-3-(6-dimethylaminomethyl-cyclohex-1-enyl)-phenol hydrochloride 197145-28-1 C15H21NO*ClH
(-)-(R)-3-(6-dimethylaminomethyl-cyclohex-1-enyl)-phenol hydrochloride
—— dimethyl traversate 102607-65-8 C20H20O8
dimethyl traversate
—— 2-Chloro-3-(β-methylamino-β-methyl-α-ethoxycarbonyl)vinyl-5-methylhydroquinone 129247-33-2 C14H18ClNO4
2-Chloro-3-(β-methylamino-β-methyl-α-ethoxycarbonyl)vinyl-5-methylhydroquinone
—— [3-butyl-5-[1-(4-hydroxy-3-methyl-phenylamino)-meth-(E,Z)-ylidene]-4-oxo-thiazolidin-2(E,Z)-ylidene]-cyanoacetic acid ethyl ester 851646-68-9 C20H23N3O4S
[3-butyl-5-[1-(4-hydroxy-3-methyl-phenylamino)-meth-(E,Z)-ylidene]-4-oxo-thiazolidin-2(E,Z)-ylidene]-cyanoacetic acid ethyl ester
—— m-Hydroxybutyrylacetanilid 59661-89-1 C12H15NO3
m-Hydroxybutyrylacetanilid
—— 2-chloro-4-[(E)-4-methyl-2-nitropent-1-enyl]phenol 1035694-93-9 C12H14ClNO3
2-chloro-4-[(E)-4-methyl-2-nitropent-1-enyl]phenol
—— 4-[(E)-(2-hydroxy-3-methoxyphenyl)methylideneamino]-3-(5-methyl-1H-pyrazol-3-yl)-1H-1,2,4-triazole-5-thione 1189315-55-6 C14H14N6O2S
4-[(E)-(2-hydroxy-3-methoxyphenyl)methylideneamino]-3-(5-methyl-1H-pyrazol-3-yl)-1H-1,2,4-triazole-5-thione
—— 2-<2-hydroxy-1-(isopropylthio)ethyl>-4-methoxyphenol 111437-45-7 C12H18O3S
2-<2-hydroxy-1-(isopropylthio)ethyl>-4-methoxyphenol