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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
—— 4-trifluoromethoxy-2-(α-hydroxyethyl)phenol 146575-63-5 C9H9F3O3
4-trifluoromethoxy-2-(α-hydroxyethyl)phenol
—— 2-Chloro-3-(2-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-5-methylcyclohexa-2,5-diene-1,4-dione 180912-30-5 C16H15ClO6
2-Chloro-3-(2-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-5-methylcyclohexa-2,5-diene-1,4-dione
—— 4-Aethoxyresorcinol 55085-14-8 C8H10O3
4-Aethoxyresorcinol
—— α-tert.-Butylaminomethyl-4-hydroxy-3-(1,2-dihydroxyethyl)benzylalkohol 63296-03-7 C14H23NO4
α-tert.-Butylaminomethyl-4-hydroxy-3-(1,2-dihydroxyethyl)benzylalkohol
—— 4-{(2R)-2-[({(2S)-2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl}amino)methyl]-3,4-dihydro-2H-chromen-6-yl}benzoic acid 437764-38-0 C29H33NO6
4-{(2R)-2-[({(2S)-2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl}amino)methyl]-3,4-dihydro-2H-chromen-6-yl}benzoic acid
—— 1-(2-ethoxyethyl)-4-methoxybenzene 174460-92-5 C11H16O2
1-(2-ethoxyethyl)-4-methoxybenzene
—— 4-chloro-6-pentyl-resorcinol 99858-01-2 C11H15ClO2
4-chloro-6-pentyl-resorcinol
—— 2-amino-3,4,5-trimethylphenol 114997-86-3 C9H13NO
2-amino-3,4,5-trimethylphenol
—— 2,15-bis-(4-hydroxy-3-methoxy-phenyl)-1,3,14,16-tetrathia-cyclohexacosane 124120-88-3 C36H56O4S4
2,15-bis-(4-hydroxy-3-methoxy-phenyl)-1,3,14,16-tetrathia-cyclohexacosane
—— (4-ethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid 1265355-04-1 C11H13BO5
(4-ethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid
—— 3-[1-(Pyrid-2-yl-Methyl)4-Piperidinylamino]-1-(4-Hydroxy-Phenoxy)-2-Propanol 252578-07-7 C20H27N3O3
3-[1-(Pyrid-2-yl-Methyl)4-Piperidinylamino]-1-(4-Hydroxy-Phenoxy)-2-Propanol
—— diethyl (hydroxy(2-hydroxy-5-nitrophenyl)methyl)phosphonate 204130-59-6 C11H16NO7P
diethyl (hydroxy(2-hydroxy-5-nitrophenyl)methyl)phosphonate
—— [4-(2-hydroxy(213C)ethyl)phenyl] acetate 208644-96-6 C10H12O3
[4-(2-hydroxy(213C)ethyl)phenyl] acetate
—— [8-13C]-4-hydroxyphenylethanol 208644-95-5 C8H10O2
[8-13C]-4-hydroxyphenylethanol
—— (S)-5-<(3,5-dichloro-2-hydroxy-6-methoxybenzamido)methyl>-1-ethyl-2-pyrrolidone 145351-55-9 C15H18Cl2N2O4
(S)-5-<(3,5-dichloro-2-hydroxy-6-methoxybenzamido)methyl>-1-ethyl-2-pyrrolidone
—— (1E,3E,5E)-1-(4-hydroxy-3,5-dimethoxyphenyl)-6-phenyl-1,3,5-hexatriene 1206103-29-8 C20H20O3
(1E,3E,5E)-1-(4-hydroxy-3,5-dimethoxyphenyl)-6-phenyl-1,3,5-hexatriene
—— 5-{[(3-hydroxy-4-methoxyphenyl)amino]methylene}-2,2-dimethyl-1,3-dioxane-4,6-dione 205448-27-7 C14H15NO6
5-{[(3-hydroxy-4-methoxyphenyl)amino]methylene}-2,2-dimethyl-1,3-dioxane-4,6-dione
—— 4-(4-Hydroxy-2-methyl-phenyl)-butanol-(1) 19143-97-6 C11H16O2
4-(4-Hydroxy-2-methyl-phenyl)-butanol-(1)
—— 4-(1,3-dithiolan-2-yl)benzene-1,2-diol 83521-70-4 C9H10O2S2
4-(1,3-dithiolan-2-yl)benzene-1,2-diol
—— (Z,Z)-5-(3,4-dihydroxybenzylidene)-2-isopropylimino-3-phenyl-thiazolidin-4-one 1228117-20-1 C19H18N2O3S
(Z,Z)-5-(3,4-dihydroxybenzylidene)-2-isopropylimino-3-phenyl-thiazolidin-4-one
—— 4-nitro-2-(thiomorpholin-1-ylmethyl)phenol 887330-74-7 C11H14N2O3S
4-nitro-2-(thiomorpholin-1-ylmethyl)phenol
—— 5,11,17,23-tetrakis[(N,N-dicyclohexylamino)methyl]-25,26,27,28-tetrahydroxycalix[4]arene 1258844-88-0 C80H116N4O4
5,11,17,23-tetrakis[(N,N-dicyclohexylamino)methyl]-25,26,27,28-tetrahydroxycalix[4]arene
—— N-t-butoxycarbonyl-3-hydroxybenzamidine 210962-28-0 C12H16N2O3
N-t-butoxycarbonyl-3-hydroxybenzamidine
—— (E)-2-hydroxy-6-[2-(pyridin-4-yl)ethenyl)nitrobenzene 474744-90-6 C13H10N2O3
(E)-2-hydroxy-6-[2-(pyridin-4-yl)ethenyl)nitrobenzene
—— 4-[[6-Cyclohexyl-5-(methoxymethoxy)pyridin-2-yl]methyl]-2-fluoro-3,5-dimethylphenol 1253220-06-2 C22H28FNO3
4-[[6-Cyclohexyl-5-(methoxymethoxy)pyridin-2-yl]methyl]-2-fluoro-3,5-dimethylphenol
—— 2,4-dichloro-3-hydroxy-5-methoxy-toluene 96682-22-3 C8H8Cl2O2
2,4-dichloro-3-hydroxy-5-methoxy-toluene
—— 5-[[6-[4-Chloro-3-(hydroxymethyl)anilino]pyrimidin-4-yl]amino]-2-methoxyphenol 892414-17-4 C18H17ClN4O3
5-[[6-[4-Chloro-3-(hydroxymethyl)anilino]pyrimidin-4-yl]amino]-2-methoxyphenol
—— 2-Methoxy-4-((E)-(S)-2-pyrrolidin-2-yl-vinyl)-phenol —— C13H17NO2
2-Methoxy-4-((E)-(S)-2-pyrrolidin-2-yl-vinyl)-phenol
—— N-[1-(4-hydroxy-3-methoxyphenyl)ethyl]nonanamide 1391847-96-3 C18H29NO3
N-[1-(4-hydroxy-3-methoxyphenyl)ethyl]nonanamide
—— N-[1-(4-hydroxy-3-methoxyphenyl)ethyl]decanamide 1391847-97-4 C19H31NO3
N-[1-(4-hydroxy-3-methoxyphenyl)ethyl]decanamide
—— (2E,2'E)-1,1'-(5,5'-(piperazine-1,4-diylbis(methylene))bis(4-hydroxy-3-methoxy-5,1-phenylene))bis(3-(pyridin-3-yl)prop-2-en-1-one) 1369787-06-3 C36H36N4O6
(2E,2'E)-1,1'-(5,5'-(piperazine-1,4-diylbis(methylene))bis(4-hydroxy-3-methoxy-5,1-phenylene))bis(3-(pyridin-3-yl)prop-2-en-1-one)
—— (2E,2'E)-1,1'-(5,5'-(piperazine-1,4-diylbis(methylene))bis(4-hydroxy-3-methoxy-5,1-phenylene))bis(3-(pyridin-2-yl)prop-2-en-1-one) 1369787-04-1 C36H36N4O6
(2E,2'E)-1,1'-(5,5'-(piperazine-1,4-diylbis(methylene))bis(4-hydroxy-3-methoxy-5,1-phenylene))bis(3-(pyridin-2-yl)prop-2-en-1-one)
—— (2E,2'E)-1,1'-(5,5'-(Piperazine-1,4-diylbis(methylene))bis(4-hydroxy-3-methoxy-5,1-phenylene))bis(3-(thiophen-2-yl)prop-2-en-1-one) 1369787-30-3 C34H34N2O6S2
(2E,2'E)-1,1'-(5,5'-(Piperazine-1,4-diylbis(methylene))bis(4-hydroxy-3-methoxy-5,1-phenylene))bis(3-(thiophen-2-yl)prop-2-en-1-one)
—— (2E,2'E)-1,1'-(5,5'-(Piperazine-1,4-diylbis(methylene))bis(4-hydroxy-3-methoxy-5,1-phenylene))bis(3-(furan-2-yl)prop-2-en-1-one) 1369787-26-7 C34H34N2O8
(2E,2'E)-1,1'-(5,5'-(Piperazine-1,4-diylbis(methylene))bis(4-hydroxy-3-methoxy-5,1-phenylene))bis(3-(furan-2-yl)prop-2-en-1-one)
—— 2-[[4-(4-Hydroxy-3-methoxyphenyl)-1,3-thiazol-2-yl]amino]-2-oxoacetic acid 74604-72-1 C12H10N2O5S
2-[[4-(4-Hydroxy-3-methoxyphenyl)-1,3-thiazol-2-yl]amino]-2-oxoacetic acid
—— (R)-Norruspolin 132340-25-1 C13H17NO2
(R)-Norruspolin
—— SPH3MA 103392-24-1 C10H13N3O3
SPH3MA
—— 2-Amino-4-(4-hydroxy-3-methoxy-phenyl)-thiophene-3-carboxylic acid ethyl ester 914202-60-1 C14H15NO4S
2-Amino-4-(4-hydroxy-3-methoxy-phenyl)-thiophene-3-carboxylic acid ethyl ester
—— (R)-N-((R)-1-(4-hydroxy-3-methoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide 1021491-08-6 C13H21NO3S
(R)-N-((R)-1-(4-hydroxy-3-methoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide
—— 2-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,3-dioxolane 1046799-63-6 C11H14O4
2-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,3-dioxolane
—— Phosphonic acid, (6-(4-hydroxyphenoxy)hexyl)-, diethyl ester 89210-98-0 C16H27O5P
Phosphonic acid, (6-(4-hydroxyphenoxy)hexyl)-, diethyl ester
—— 3-(2,2-dimethoxypropyl)-2-fluoro-4-nitrophenol 1210828-40-2 C11H14FNO5
3-(2,2-dimethoxypropyl)-2-fluoro-4-nitrophenol
—— 1-(3-hydroxy-5-methoxy-4-methylphenyl)-2-methoxymethoxypropane 886989-20-4 C13H20O4
1-(3-hydroxy-5-methoxy-4-methylphenyl)-2-methoxymethoxypropane
—— 2-hydroxy-6-(2-hydroxypropyl)-4-methoxy-3-methylbenzaldehyde 886989-18-0 C12H16O4
2-hydroxy-6-(2-hydroxypropyl)-4-methoxy-3-methylbenzaldehyde
—— 1-(3-hydroxy-5-methoxy-4-methylphenyl)-2-propanol 886989-19-1 C11H16O3
1-(3-hydroxy-5-methoxy-4-methylphenyl)-2-propanol
—— ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-5-(4-methylsulfanylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate 5824-50-0 C24H20BrN3O6S2
ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-5-(4-methylsulfanylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-(3-hydroxyphenyl)pentene 28749-99-7 C11H14O
5-(3-hydroxyphenyl)pentene
—— 5,11,17,23-Tetrakis(but-3-ynoxymethyl)-2,8,14,20-tetrakis(2-methylpropyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol 1094618-96-8 C64H80O12
5,11,17,23-Tetrakis(but-3-ynoxymethyl)-2,8,14,20-tetrakis(2-methylpropyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol
—— α-(3-hydroxyphenyl)propionic acid ethyl ester 88975-43-3 C11H14O3
α-(3-hydroxyphenyl)propionic acid ethyl ester
—— 5,11,17,23-Tetrakis(but-3-enoxymethyl)-2,8,14,20-tetrakis(2-methylpropyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol 1094618-92-4 C64H88O12
5,11,17,23-Tetrakis(but-3-enoxymethyl)-2,8,14,20-tetrakis(2-methylpropyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol