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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-(3,5-diiodo-4-methoxyphenyl)ethanol 1246457-11-3 C9H10I2O2
2-(3,5-diiodo-4-methoxyphenyl)ethanol
—— (S)-2-(1-hydroxy-2-nitroethyl)phenol 1268725-89-8 C8H9NO4
(S)-2-(1-hydroxy-2-nitroethyl)phenol
—— 2-Hydroxy-3,5,6-trimethyl-hydrochinon 69690-66-0 C9H12O3
2-Hydroxy-3,5,6-trimethyl-hydrochinon
—— 36024-86-9 C16H17NO
—— 1,4-dimethoxy-2,5-dimethoxymethyloxy-6-hydroxybenzene 99621-84-8 C12H18O7
1,4-dimethoxy-2,5-dimethoxymethyloxy-6-hydroxybenzene
—— (2S,3R)-2,4,4-Trimethyl-2-phenyl-3,4-dihydro-2H-pyrrole-3-carboxylic acid ethyl ester; compound with picric acid 117103-25-0 C6H3N3O7*C16H21NO2
(2S,3R)-2,4,4-Trimethyl-2-phenyl-3,4-dihydro-2H-pyrrole-3-carboxylic acid ethyl ester; compound with picric acid
—— (E)-3-(benzo[b]thiophen-2-yl)-2-(4-hydroxy-3,5-dimethoxyphenyl)acrylonitrile 1453269-74-3 C19H15NO3S
(E)-3-(benzo[b]thiophen-2-yl)-2-(4-hydroxy-3,5-dimethoxyphenyl)acrylonitrile
—— cyano-acetic acid-(2,4-dihydroxy-6-methyl-benzylidenehydrazide) 21236-20-4 C11H11N3O3
cyano-acetic acid-(2,4-dihydroxy-6-methyl-benzylidenehydrazide)
—— 2-(2-Hydroxy-3,5-dinitro-phenyl-hydrazono)-3-methylimino-buttersaeureaethylester 5507-07-3 C13H15N5O7
2-(2-Hydroxy-3,5-dinitro-phenyl-hydrazono)-3-methylimino-buttersaeureaethylester
—— salicylaldehyde-(5-iodo-[2]pyridylimine) 91493-11-7 C12H9IN2O
salicylaldehyde-(5-iodo-[2]pyridylimine)
—— 2-Hydroxy-5-nitro-α-iodo-acetanilid 26958-88-3 C8H7IN2O4
2-Hydroxy-5-nitro-α-iodo-acetanilid
—— 5-bromo-3-chloro-2,4-dinitro-phenol 858855-19-3 C6H2BrClN2O5
5-bromo-3-chloro-2,4-dinitro-phenol
—— 2-diphenyltelluronio-4-hydroxyphenolate 116043-18-6 C18H14O2Te
2-diphenyltelluronio-4-hydroxyphenolate
—— 2,3,5,6-tetrachloro-4-(p-methylbenzyloxy)phenol 75141-90-1 C14H10Cl4O2
2,3,5,6-tetrachloro-4-(p-methylbenzyloxy)phenol
—— 2,5-dihydroxyphenyl 1-piperidinedithioate 596814-96-9 C12H15NO2S2
2,5-dihydroxyphenyl 1-piperidinedithioate
—— 4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-2-hydroxy-1-methyl-but-3-enyl)-5-methyl-phenol 914086-81-0 C18H30O3Si
4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-2-hydroxy-1-methyl-but-3-enyl)-5-methyl-phenol
—— N-<5-(2,2-dicyanoethenyl)salicyloyl>dicyclohexylurea 138851-35-1 C24H28N4O3
N-<5-(2,2-dicyanoethenyl)salicyloyl>dicyclohexylurea
—— 2-(4-Nitro-2-hydroxy-phenylhydrazono)-3-methylbuttersaeure 19169-15-4 C11H13N3O5
2-(4-Nitro-2-hydroxy-phenylhydrazono)-3-methylbuttersaeure
—— 4-(3-Propoxypropyl)benzene-1,2-diol 1012310-04-1 C12H18O3
4-(3-Propoxypropyl)benzene-1,2-diol
—— (+)-4-(4-butoxy-5,5,5-trifluoropentyl)phenol 137616-18-3 C15H21F3O2
(+)-4-(4-butoxy-5,5,5-trifluoropentyl)phenol
—— 3-(4-hydroxy-2-methyl-phenylimino)-3H-[1,2,4]-thiadiazolo[4,3-a]-pyridine 148257-30-1 C13H11N3OS
3-(4-hydroxy-2-methyl-phenylimino)-3H-[1,2,4]-thiadiazolo[4,3-a]-pyridine
—— 2,6-Dichloro-3-(hydroxy-methoxy-methyl)-4,5-dimethyl-phenol 111811-70-2 C10H12Cl2O3
2,6-Dichloro-3-(hydroxy-methoxy-methyl)-4,5-dimethyl-phenol
—— 2-(1-hydroxy-3-methyl-butyl)phenol 193687-89-7 C11H16O2
2-(1-hydroxy-3-methyl-butyl)phenol
—— 2,4-dibromo-6-[1,2,4]triazolo[3,4-b][1,3,4]oxadiazol-6-yl-phenol 75821-18-0 C9H4Br2N4O2
2,4-dibromo-6-[1,2,4]triazolo[3,4-b][1,3,4]oxadiazol-6-yl-phenol
—— 3-Amino-2-hydroxy-5-nitrobenzonitrile 1058704-80-5 C7H5N3O3
3-Amino-2-hydroxy-5-nitrobenzonitrile
—— 3-(2-(2-hydroxy-4-nitrophenyl)hydrazineylidene)pentane-2,4-dione compound with ethane-1,2-diamine (1:1) 1262976-54-4 C2H8N2*C11H11N3O5
3-(2-(2-hydroxy-4-nitrophenyl)hydrazineylidene)pentane-2,4-dione compound with ethane-1,2-diamine (1:1)
—— 5,5'-(2,5,8,11-tetraazadodeca-1,11-diene-1,12-diyl)bis(4-hydroxy-2-methoxybenzenesulfonate) 118807-98-0 C22H28N4O10S2
5,5'-(2,5,8,11-tetraazadodeca-1,11-diene-1,12-diyl)bis(4-hydroxy-2-methoxybenzenesulfonate)
—— 1-(2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl)-4-hydroxybenzene 651035-56-2 C12H14O4
1-(2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl)-4-hydroxybenzene
—— 1-(4-Hydroxy-3-methoxy-benzyl)-3-propyl-urea 50992-85-3 C12H18N2O3
1-(4-Hydroxy-3-methoxy-benzyl)-3-propyl-urea
—— β-(4-Hydroxy-2,3,5,6-tetrabromphenoxy)ethylbromid 31406-90-3 C8H5Br5O2
β-(4-Hydroxy-2,3,5,6-tetrabromphenoxy)ethylbromid
—— 4-(5-Diethylamino-penta-1,3-diynyl)-2-methyl-phenol 33834-10-5 C16H19NO
4-(5-Diethylamino-penta-1,3-diynyl)-2-methyl-phenol
—— N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]-2-(2-methyl-1,3-thiazol-4-yl)acetamide 5705-26-0 C14H15N3O3S
N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]-2-(2-methyl-1,3-thiazol-4-yl)acetamide
—— 3,3'-Tetradecamethylenbis(5-methoxyphenol) 50637-32-6 C28H42O4
3,3'-Tetradecamethylenbis(5-methoxyphenol)
—— 1,5-p-xylylene-bridged tert-butylcalix[8]arene 507488-87-1 C96H118O8
1,5-p-xylylene-bridged tert-butylcalix[8]arene
—— 3-chlorophen-2,4,6-d3-ol 124286-02-8 C6H5ClO
3-chlorophen-2,4,6-d3-ol
—— 4-Hydroxy-8-(2,3,5,6-tetrachloro-4-hydroxy-phenoxy)-bicyclo[3.3.1]nona-2,6-dien-9-one 127223-01-2 C15H10Cl4O4
4-Hydroxy-8-(2,3,5,6-tetrachloro-4-hydroxy-phenoxy)-bicyclo[3.3.1]nona-2,6-dien-9-one
—— 4-heptafluoroisopropyl-2-methoxyphenol 353273-05-9 C10H7F7O2
4-heptafluoroisopropyl-2-methoxyphenol
—— 1398573-40-4 C24H38BrNO4
—— Adamantan-1-yl-(4-adamantan-1-yl-1H-imidazol-2-yl)-methanone; compound with picric acid 33813-37-5 C6H3N3O7*C24H32N2O
Adamantan-1-yl-(4-adamantan-1-yl-1H-imidazol-2-yl)-methanone; compound with picric acid
—— 4-(2,2-dibromovinyl)-2-chlorophenol 1159343-17-5 C8H5Br2ClO
4-(2,2-dibromovinyl)-2-chlorophenol
—— 2,4-dibromo-6-[(Z)-2-chloro-2-nitroethenyl]phenol 117672-20-5 C8H4Br2ClNO3
2,4-dibromo-6-[(Z)-2-chloro-2-nitroethenyl]phenol
—— 4-Ethylsulfanyl-3-nitro-phenol 774-23-2 C8H9NO3S
4-Ethylsulfanyl-3-nitro-phenol
—— 15,35,55,75,95,115,135,155-octa-tert-butyl-1,3,5,7,9,11,13,15(1,3)-octabenzenacyclohexadecaphan-12,32,52,72,92,112,132,152-octaol compound with 2,2,6,6-tetramethylpiperidin-4-amine (1:1) 138847-23-1 C9H20N2*2C88H112O8
15,35,55,75,95,115,135,155-octa-tert-butyl-1,3,5,7,9,11,13,15(1,3)-octabenzenacyclohexadecaphan-12,32,52,72,92,112,132,152-octaol compound with 2,2,6,6-tetramethylpiperidin-4-amine (1:1)
—— 1082287-39-5 C18H16N6O6
—— isovaleric acid salicylidenehydrazide 100253-74-5 C12H16N2O2
isovaleric acid salicylidenehydrazide
—— S-benzyl-β-N-((2-hydroxy-3-methoxyphenyl)-methylene)-dithiocarbazate 122504-33-0 C16H16N2O2S2
S-benzyl-β-N-((2-hydroxy-3-methoxyphenyl)-methylene)-dithiocarbazate
—— 2-[1-(2-aminopropylimino)ethyl]phenol 1636124-63-4 C11H16N2O
2-[1-(2-aminopropylimino)ethyl]phenol
—— 2,2',2''-[1,2,4]triazine-3,5,6-triyl-tris-phenol 105092-08-8 C21H15N3O3
2,2',2''-[1,2,4]triazine-3,5,6-triyl-tris-phenol
—— Phenylsulfanyl-acetic acid [1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-hydrazide 152489-31-1 C16H16N2O3S
Phenylsulfanyl-acetic acid [1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-hydrazide
—— 2,4-Dihydroxy-6-methoxy-trimesinaldehyd 34374-87-3 C10H8O6
2,4-Dihydroxy-6-methoxy-trimesinaldehyd