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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-methoxy-4-{2-(3-methyl-4-nitro-5-isoxazolyl)-1-[(3-methyl-4-nitro-5-isoxazolyl)methyl]ethyl}phenol 1253520-23-8 C18H18N4O8
2-methoxy-4-{2-(3-methyl-4-nitro-5-isoxazolyl)-1-[(3-methyl-4-nitro-5-isoxazolyl)methyl]ethyl}phenol
—— 2-(3-methoxy-4-hydroxyphenyl)-5-(4-methylphenylamino)-1,3,4-thiadiazole 92968-64-4 C16H15N3O2S
2-(3-methoxy-4-hydroxyphenyl)-5-(4-methylphenylamino)-1,3,4-thiadiazole
—— 2-(3-methoxy-4-hydroxyphenyl)-5-(4-methoxyphenylamino)-1,3,4-thiadiazole 1300713-18-1 C16H15N3O3S
2-(3-methoxy-4-hydroxyphenyl)-5-(4-methoxyphenylamino)-1,3,4-thiadiazole
—— (3-fluoro-5-hydroxy-benzyl)-carbamic acid tert-butyl ester 944704-46-5 C12H16FNO3
(3-fluoro-5-hydroxy-benzyl)-carbamic acid tert-butyl ester
—— 5-(4-hydroxy-3-methoxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl acetic acid 120841-37-4 C13H11NO5S2
5-(4-hydroxy-3-methoxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl acetic acid
—— 4,5-dimethyl-3-hydroxy-6-methoxyphthalaldehyde 73861-58-2 C11H12O4
4,5-dimethyl-3-hydroxy-6-methoxyphthalaldehyde
—— 4-[3-(2,4-Dinitro-phenyl)-5-propyl-2,3-dihydro-[1,3,4]oxadiazol-2-yl]-2-methoxy-phenol 85485-36-5 C18H18N4O7
4-[3-(2,4-Dinitro-phenyl)-5-propyl-2,3-dihydro-[1,3,4]oxadiazol-2-yl]-2-methoxy-phenol
—— 5,11,17,23,29,35-hexabromo-37,38,39,40,41,42-hexahydroxycalix[6]arene 171797-88-9 C42H30Br6O6
5,11,17,23,29,35-hexabromo-37,38,39,40,41,42-hexahydroxycalix[6]arene
—— meso-(3-methoxy-4-hydroxyphenyl)dipyrromethane 1262222-41-2 C16H16N2O2
meso-(3-methoxy-4-hydroxyphenyl)dipyrromethane
—— (4-hydroxy-3-methoxybenzylidene)pyrazine-2-carboxylic acid hydrazide 304908-43-8 C13H12N4O3
(4-hydroxy-3-methoxybenzylidene)pyrazine-2-carboxylic acid hydrazide
—— 1,4-bis-(4-hydroxy-phenyl)-butan-2-one 131252-64-7 C16H16O3
1,4-bis-(4-hydroxy-phenyl)-butan-2-one
—— 5-cyano-6-({2-[(4-ethylphenyl)amino]-2-oxoethyl}thio)-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide 896092-99-2 C31H30N4O4S
5-cyano-6-({2-[(4-ethylphenyl)amino]-2-oxoethyl}thio)-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— dimethyl 1,2,3,6-tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-1,3-diphenylpyrimidine-4,5-dicarboxylate 1350895-54-3 C27H26N2O6
dimethyl 1,2,3,6-tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-1,3-diphenylpyrimidine-4,5-dicarboxylate
—— (E)-3-[β-(4-hydroxy-3-methoxyphenyl)-ethenyl]-4,5-dimethyl-1H-pyrazole 1018767-20-8 C14H16N2O2
(E)-3-[β-(4-hydroxy-3-methoxyphenyl)-ethenyl]-4,5-dimethyl-1H-pyrazole
—— 3-((Z)-((Z)-5-(4-hydroxy-3-methoxybenzylidene)-3-methyl-4-oxothiazolidin-2-ylidene)amino)benzoic acid 1448678-45-2 C19H16N2O5S
3-((Z)-((Z)-5-(4-hydroxy-3-methoxybenzylidene)-3-methyl-4-oxothiazolidin-2-ylidene)amino)benzoic acid
—— 2,6-Dicyclohexyl-8-(4-hydroxy-3-methoxy-phenyl)-1,2,4,6,7,8-hexahydro-2,4,6-triaza-s-indacene-3,5-dione 83794-00-7 C28H35N3O4
2,6-Dicyclohexyl-8-(4-hydroxy-3-methoxy-phenyl)-1,2,4,6,7,8-hexahydro-2,4,6-triaza-s-indacene-3,5-dione
—— α-<3-Methoxy-4-hydroxy-benzyl>-butyrolacton 91497-43-7 C12H14O4
α-<3-Methoxy-4-hydroxy-benzyl>-butyrolacton
—— 7-cyano-6-[(4-hydroxy-3-methoxybenzylidene)amino]-N-phenyl-2,3-dihydro-1H-pyrrolizine-5-carboxamide 1214879-97-6 C23H20N4O3
7-cyano-6-[(4-hydroxy-3-methoxybenzylidene)amino]-N-phenyl-2,3-dihydro-1H-pyrrolizine-5-carboxamide
—— 10-gingerol 1212158-11-6 C21H34O4
10-gingerol
—— 1-(1-(4-hydroxy-3-methoxybenzyl)-1H-indol-3-yl)-N,N,N-trimethylmethanaminiumiodide 1458694-16-0 C20H25N2O2*I
1-(1-(4-hydroxy-3-methoxybenzyl)-1H-indol-3-yl)-N,N,N-trimethylmethanaminiumiodide
—— 1-cyclopropyl-3-(4-hydroxyphenyl)propan-1-one 66422-86-4 C12H14O2
1-cyclopropyl-3-(4-hydroxyphenyl)propan-1-one
—— diethyl 1,2,3,6-tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-1,3-diphenylpyrimidine-4,5-dicarboxylate 1350895-31-6 C29H30N2O6
diethyl 1,2,3,6-tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-1,3-diphenylpyrimidine-4,5-dicarboxylate
—— 3-(3-chloro-4-hydroxy-5-methoxybenzoyl)-1,1-dioxo-1,2-dihydro-3H-1,3-benzothiazole 1285573-11-6 C15H12ClNO5S
3-(3-chloro-4-hydroxy-5-methoxybenzoyl)-1,1-dioxo-1,2-dihydro-3H-1,3-benzothiazole
—— dimethyl (4R-5R)-2-(2-hydroxyphenyl)-1,3-dioxolane-4,5-dicarboxylate 486998-80-5 C13H14O7
dimethyl (4R-5R)-2-(2-hydroxyphenyl)-1,3-dioxolane-4,5-dicarboxylate
—— 1-Carbamoyl-1-ethoxy-2-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)phenyl]ethane 251976-97-3 C20H25NO6S
1-Carbamoyl-1-ethoxy-2-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)phenyl]ethane
—— diisopropyl 2-(2-hydroxyphenyl)-1,3-dioxolane-4,5-dicarboxylate 1351353-30-4 C17H22O7
diisopropyl 2-(2-hydroxyphenyl)-1,3-dioxolane-4,5-dicarboxylate
—— Sodium hydrogen methylarsonate 2-methyl-4,6-dinitrophenolate (2/1/1) 51202-32-5 C8H9AsN2Na2O8
Sodium hydrogen methylarsonate 2-methyl-4,6-dinitrophenolate (2/1/1)
—— 4-(3-(7-chloro-6-fluoro-4-nitrobenzo[d]thiazol-2-ylamino)-1-(7-chloro-6-fluorobenzo[d]thiazol-2-yl)-4,5-dihydro-1Hpyrazol-5-yl)-2-methoxyphenol 1367374-97-7 C24H14Cl2F2N6O4S2
4-(3-(7-chloro-6-fluoro-4-nitrobenzo[d]thiazol-2-ylamino)-1-(7-chloro-6-fluorobenzo[d]thiazol-2-yl)-4,5-dihydro-1Hpyrazol-5-yl)-2-methoxyphenol
—— 4-(3-(7-chloro-6-fluoro-5-nitrobenzo[d]thiazol-2-ylamino)-1-(7-chloro-6-fluorobenzo[d]thiazol-2-yl)-4,5-dihydro-1Hpyrazol-5-yl)-2-methoxyphenol 1367374-91-1 C24H14Cl2F2N6O4S2
4-(3-(7-chloro-6-fluoro-5-nitrobenzo[d]thiazol-2-ylamino)-1-(7-chloro-6-fluorobenzo[d]thiazol-2-yl)-4,5-dihydro-1Hpyrazol-5-yl)-2-methoxyphenol
—— 4-(1-(7-chloro-6-fluorobenzo[d]thiazol-2-yl)-3-(7-chloro-6-fluorobenzo[d]thiazol-2-ylamino)-4,5-dihydro-1H-pyrazol-5-yl)-2-methoxyphenol 1311166-21-8 C24H15Cl2F2N5O2S2
4-(1-(7-chloro-6-fluorobenzo[d]thiazol-2-yl)-3-(7-chloro-6-fluorobenzo[d]thiazol-2-ylamino)-4,5-dihydro-1H-pyrazol-5-yl)-2-methoxyphenol
—— 2,2-dimethyl-propionic acid 4-[2-{3-[2-chloro-4-(6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenoxy]-propoxy}-ethyl]-phenyl ester 890042-64-5 C26H31ClN2O5
2,2-dimethyl-propionic acid 4-[2-{3-[2-chloro-4-(6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenoxy]-propoxy}-ethyl]-phenyl ester
—— 3,4,6-trichloroguaiacol 60712-44-9 C7H5Cl3O2
3,4,6-trichloroguaiacol
—— 6-vinyleugenol 1607447-04-0 C12H14O2
6-vinyleugenol
—— diisopropyl (4R-5R)-2-(2-hydroxyphenyl)-1,3-dioxolane-4,5-dicarboxylate 1351353-26-8 C17H22O7
diisopropyl (4R-5R)-2-(2-hydroxyphenyl)-1,3-dioxolane-4,5-dicarboxylate
—— (E)-1,4-(2-hydroxy-3-methoxybenzaldehyde)-2-ene 1208220-60-3 C20H20O6
(E)-1,4-(2-hydroxy-3-methoxybenzaldehyde)-2-ene
—— 5-(3-chloro-4,5-dihydroxyphenyl)pentanoic acid 116314-10-4 C11H13ClO4
5-(3-chloro-4,5-dihydroxyphenyl)pentanoic acid
—— 2-bromo-3-chloro-5-methoxy-1,4-dihydroxybenzene 1365030-40-5 C7H6BrClO3
2-bromo-3-chloro-5-methoxy-1,4-dihydroxybenzene
—— 4-(adamantan-1-ylaminomethyl)-2-methoxyphenol 1019579-47-5 C18H25NO2
4-(adamantan-1-ylaminomethyl)-2-methoxyphenol
—— 2,5-dibromo-4-(10-bromodecyloxy)phenol 174215-82-8 C16H23Br3O2
2,5-dibromo-4-(10-bromodecyloxy)phenol
—— 2-methoxy-6-((E)-3-(trimethylsilyl)allyl)phenol 1075184-42-7 C13H20O2Si
2-methoxy-6-((E)-3-(trimethylsilyl)allyl)phenol
—— 4-(adamantan-1-ylaminomethyl)benzene-1,2-diol 1019629-77-6 C17H23NO2
4-(adamantan-1-ylaminomethyl)benzene-1,2-diol
—— 2',4'-Dihydroxyacetophenone oxime 850925-13-2 C8H9NO3
2',4'-Dihydroxyacetophenone oxime
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-1-methyl-3-(3-carbamoylphenyl)propylamine hydrochloride —— C19H24N2O3*ClH
N-[2-(3,4-dihydroxyphenyl)ethyl]-1-methyl-3-(3-carbamoylphenyl)propylamine hydrochloride
—— 4-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(3-hydroxy-4-methyl-pent-1-ynyl)-6-methoxy-phenol 343309-54-6 C20H32O4Si
4-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(3-hydroxy-4-methyl-pent-1-ynyl)-6-methoxy-phenol
—— 2,6-Dimethyl-4-<3-(pyrrol-1-yl)propyl>phenol 125437-44-7 C15H19NO
2,6-Dimethyl-4-<3-(pyrrol-1-yl)propyl>phenol
—— 2-isothiazol-4-yl-phenol 25392-16-9 C9H7NOS
2-isothiazol-4-yl-phenol
—— 3-ethyl-4-o-hydroxybenzylidenamino-4,5-dihydro-1,2,4-triazol-5-one 137182-48-0 C11H12N4O2
3-ethyl-4-o-hydroxybenzylidenamino-4,5-dihydro-1,2,4-triazol-5-one
—— 4-bromo-2-((6-methylpyridin-2-ylimino)methyl)phenol 307326-14-3 C13H11BrN2O
4-bromo-2-((6-methylpyridin-2-ylimino)methyl)phenol
—— Phenol, 2-chloro-4-ethenyl-6-methoxy- 112602-32-1 C9H9ClO2
Phenol, 2-chloro-4-ethenyl-6-methoxy-
—— 3-(3-amino-4-chloro-6-fluoro-2-hydroxyphenyl)-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione 289883-11-0 C11H10ClFN4O3S
3-(3-amino-4-chloro-6-fluoro-2-hydroxyphenyl)-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione