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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
—— 6-[(4-Hydroxy-3,5-dimethoxyphenyl)-(pyridin-2-ylamino)methyl]-1,3-benzodioxol-5-ol 191023-11-7 C21H20N2O6
6-[(4-Hydroxy-3,5-dimethoxyphenyl)-(pyridin-2-ylamino)methyl]-1,3-benzodioxol-5-ol
—— 4-(2-ethoxy-2-methoxyethyl)-2,6-dimethylphenol 1097200-10-6 C13H20O3
4-(2-ethoxy-2-methoxyethyl)-2,6-dimethylphenol
—— methyl 2-[(tertbutyldimethylsilyl)oxy]-2-(2-hydroxyphenyl)acetate 435344-65-3 C15H24O4Si
methyl 2-[(tertbutyldimethylsilyl)oxy]-2-(2-hydroxyphenyl)acetate
—— (2E,2'E)-1,1'-(5,5'-(piperazine-1,4-diylbis(methylene))bis(4-hydroxy-3-methoxy-5,1-phenylene))bis(3-(3-methylthiophen-2-yl)prop-2-en-1-one) 1369787-32-5 C36H38N2O6S2
(2E,2'E)-1,1'-(5,5'-(piperazine-1,4-diylbis(methylene))bis(4-hydroxy-3-methoxy-5,1-phenylene))bis(3-(3-methylthiophen-2-yl)prop-2-en-1-one)
—— methyl (6-fluoro-2-hydroxy-3-nitrophenyl)acetate 361336-91-6 C9H8FNO5
methyl (6-fluoro-2-hydroxy-3-nitrophenyl)acetate
—— 5-Chloropyrimidine-2,4,6-triamine; 2,4,6-trinitrophenol 7464-07-5 C10H9ClN8O7
5-Chloropyrimidine-2,4,6-triamine; 2,4,6-trinitrophenol
—— 2-Morpholinomethyl-hydrochinon 6452-80-8 C11H15NO3
2-Morpholinomethyl-hydrochinon
—— (R*,S*)-2,2'-(dithiobis{1-[(2-aminoethyl)methylamino]-2,1-ethanediyl})bis(phenol) 183113-68-0 C22H34N4O2S2
(R*,S*)-2,2'-(dithiobis{1-[(2-aminoethyl)methylamino]-2,1-ethanediyl})bis(phenol)
—— N-(5-hydroxypentyl)-N-[1-(2-hydroxyphenyl)ethyl]amine 651304-80-2 C13H21NO2
N-(5-hydroxypentyl)-N-[1-(2-hydroxyphenyl)ethyl]amine
—— 3-hydroxymethyl-4-methoxy-6-(2-propenyl)phenol 359844-06-7 C11H14O3
3-hydroxymethyl-4-methoxy-6-(2-propenyl)phenol
—— 4-(5,6-dibromohexyl)phenol 109493-06-3 C12H16Br2O
4-(5,6-dibromohexyl)phenol
—— hydroquinone; compound with diethylamine 34376-20-0 C4H11N*2C6H6O2
hydroquinone; compound with diethylamine
—— Copper;2-(3-hydroxypropyliminomethyl)phenol 14843-54-0 C20H26CuN2O4
Copper;2-(3-hydroxypropyliminomethyl)phenol
—— Copper;2-(2-hydroxyethyliminomethyl)phenol 13987-24-1 C18H22CuN2O4
Copper;2-(2-hydroxyethyliminomethyl)phenol
—— 4-[3-(2,2-diethoxyethoxy)prop-1-ynyl]phenol 1254984-91-2 C15H20O4
4-[3-(2,2-diethoxyethoxy)prop-1-ynyl]phenol
—— Cobalt;2-methoxy-6-(phenyliminomethyl)phenol 18449-03-1 C28H26CoN2O4
Cobalt;2-methoxy-6-(phenyliminomethyl)phenol
—— 2-[(1-Hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)iminomethyl]phenol;ZINC —— C32H48N4O4Zn
2-[(1-Hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)iminomethyl]phenol;ZINC
—— 2-[[2-(2,3-Dimethoxyphenyl)-3-[(2-hydroxy-3-methoxyphenyl)methyl]-1,3-diazinan-1-yl]methyl]-6-methoxyphenol 5740-57-8 C28H34N2O6
2-[[2-(2,3-Dimethoxyphenyl)-3-[(2-hydroxy-3-methoxyphenyl)methyl]-1,3-diazinan-1-yl]methyl]-6-methoxyphenol
—— 4,4'-(1,3-Dimethylcyclobutane-1,3-diyl)diphenol 3788-29-2 C18H20O2
4,4'-(1,3-Dimethylcyclobutane-1,3-diyl)diphenol
—— 2-bromo-N-[4-[2,6-diamino-5-(4-chlorophenyl)pyrimidin-4-yl]butyl]acetamide; 2,4,6-trinitrophenol 20535-93-7 C22H22BrClN8O8
2-bromo-N-[4-[2,6-diamino-5-(4-chlorophenyl)pyrimidin-4-yl]butyl]acetamide; 2,4,6-trinitrophenol
—— 4-[3-(diethylamino)propyl]-2,6-dimethoxyphenol 99878-73-6 C15H25NO3
4-[3-(diethylamino)propyl]-2,6-dimethoxyphenol
—— Phenol, 2-methoxy-6-[[(4-methyl-2-pyridinyl)imino]methyl]- 106052-58-8 C14H14N2O2
Phenol, 2-methoxy-6-[[(4-methyl-2-pyridinyl)imino]methyl]-
—— 2-chloro-3-hydroxy-6-nitro-4-propenyltoluene 88062-29-7 C10H10ClNO3
2-chloro-3-hydroxy-6-nitro-4-propenyltoluene
—— 2-(Benzyliminomethyl)phenol;copper 14655-06-2 C28H26CuN2O2
2-(Benzyliminomethyl)phenol;copper
—— 5-amino-4-chloro-2-(2,3-dihydroxy-phenyl)-2<i>H</i>-pyridazin-3-one 50512-54-4 C10H8ClN3O3
5-amino-4-chloro-2-(2,3-dihydroxy-phenyl)-2<i>H</i>-pyridazin-3-one
—— 2-bromo-4-fluoro-5-methoxyphenol 1185836-63-8 C7H6BrFO2
2-bromo-4-fluoro-5-methoxyphenol
—— 2,5-bis(4-fluoro-3-hydroxyphenyl)thiophene 1430419-24-1 C16H10F2O2S
2,5-bis(4-fluoro-3-hydroxyphenyl)thiophene
—— 4-[(2,5-Dimethylphenyl)iminomethyl]benzene-1,2-diol 5375-10-0 C15H15NO2
4-[(2,5-Dimethylphenyl)iminomethyl]benzene-1,2-diol
—— 2-Fluoro-4-hydroxy-5-methoxyphenyl glycol 141523-14-0 C9H11FO4
2-Fluoro-4-hydroxy-5-methoxyphenyl glycol
—— 5-fluoronorepinephrine 71144-41-7 C8H10FNO3
5-fluoronorepinephrine
—— 2-(1-Hydroxybut-3-ynyl)-4-nitrophenol 1262961-94-3 C10H9NO4
2-(1-Hydroxybut-3-ynyl)-4-nitrophenol
—— 2-[(4-chlorophenylimino)methyl]-4-nitrophenol 5280-15-9 C13H9ClN2O3
2-[(4-chlorophenylimino)methyl]-4-nitrophenol
—— 2,6-Dicyan-hydrochinon 4655-71-4 C8H4N2O2
2,6-Dicyan-hydrochinon
—— [rac]-2-ethoxy-3-(4-hydroxy-3-methoxy-phenyl)-propionic acid ethyl ester 343870-75-7 C14H20O5
[rac]-2-ethoxy-3-(4-hydroxy-3-methoxy-phenyl)-propionic acid ethyl ester
—— (5E)-5-(5-bromo-2-hydroxy-3-methoxybenzylidene)-3-methyl-2-thioxo-1,3-thiazolidin-4-one 326019-49-2 C12H10BrNO3S2
(5E)-5-(5-bromo-2-hydroxy-3-methoxybenzylidene)-3-methyl-2-thioxo-1,3-thiazolidin-4-one
—— 2-[(2-Hydroxy-3-methylphenyl)methylideneamino]-4,5-dimethylphenol 5483-30-7 C16H17NO2
2-[(2-Hydroxy-3-methylphenyl)methylideneamino]-4,5-dimethylphenol
—— 5,11,17,23-Tetrakis(4-hydroxybutoxymethyl)-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 1274936-98-9 C64H96O16
5,11,17,23-Tetrakis(4-hydroxybutoxymethyl)-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
—— 4-[(1S)-1-hydroxypropyl]-2-methoxyphenol 1192364-47-8 C10H14O3
4-[(1S)-1-hydroxypropyl]-2-methoxyphenol
—— 1-(furan-2-ylmethyl)-1-(4-hydroxybenzyl)-3,3-dimethyl urea 1350123-02-2 C15H18N2O3
1-(furan-2-ylmethyl)-1-(4-hydroxybenzyl)-3,3-dimethyl urea
—— 2,3-dibromo-6-hydroxy-5-methoxybenzaldehyde 20035-42-1 C8H6Br2O3
2,3-dibromo-6-hydroxy-5-methoxybenzaldehyde
—— 4,6-dinitrosalicylic acid 65841-03-4 C7H4N2O7
4,6-dinitrosalicylic acid
—— 2,3,6-Trimethyl-4-nitroso-phenol 38104-97-1 C9H11NO2
2,3,6-Trimethyl-4-nitroso-phenol
—— 4-chloro-2-[3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-5-yl]phenol 637321-20-1 C16H15ClN2O
4-chloro-2-[3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-5-yl]phenol
—— 3-[5-(2-hydroxy-benzylidene)-4-oxo-2-thioxo-thiazolidin-3-yl]-propionic acid 7025-21-0 C13H11NO4S2
3-[5-(2-hydroxy-benzylidene)-4-oxo-2-thioxo-thiazolidin-3-yl]-propionic acid
—— 2-methoxy-6-[4-[(3-nitroanilino)methyl]-3-(N-phenylanilino)-4,5-dihydro-1,2-oxazol-5-yl]phenol 1179820-95-1 C29H26N4O5
2-methoxy-6-[4-[(3-nitroanilino)methyl]-3-(N-phenylanilino)-4,5-dihydro-1,2-oxazol-5-yl]phenol
—— 2-methoxy-6-[4-[(2-nitroanilino)methyl]-3-(N-phenylanilino)-4,5-dihydro-1,2-oxazol-5-yl]phenol 1179820-96-2 C29H26N4O5
2-methoxy-6-[4-[(2-nitroanilino)methyl]-3-(N-phenylanilino)-4,5-dihydro-1,2-oxazol-5-yl]phenol
—— 2-acetyl-3-(4-hydroxy-3-methoxyphenyl)-N-phenyl-5-propan-2-yl-3,4-dihydropyrazole-4-carboxamide 1239420-74-6 C22H25N3O4
2-acetyl-3-(4-hydroxy-3-methoxyphenyl)-N-phenyl-5-propan-2-yl-3,4-dihydropyrazole-4-carboxamide
—— 2-(Benzenesulfonyl)-3-(5-bromo-2-hydroxy-3-methoxyphenyl)prop-2-enenitrile 691375-72-1 C16H12BrNO4S
2-(Benzenesulfonyl)-3-(5-bromo-2-hydroxy-3-methoxyphenyl)prop-2-enenitrile
—— 2-(Benzenesulfonyl)-3-(2-hydroxy-3-methoxyphenyl)prop-2-enenitrile 691375-85-6 C16H13NO4S
2-(Benzenesulfonyl)-3-(2-hydroxy-3-methoxyphenyl)prop-2-enenitrile
—— 3-benzyl-2-(4-hydroxybenzyl)sulfonylamino-5-(4-hydroxyphenyl)pyrazine 1238832-33-1 C24H21N3O4S
3-benzyl-2-(4-hydroxybenzyl)sulfonylamino-5-(4-hydroxyphenyl)pyrazine