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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-[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
—— 5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylphenol 1369414-58-3 C14H24O2Si
5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylphenol
—— N-<β-(3.4-Dihydroxyphenyl)-ethyl>-cyclohexancarboxamid 42600-76-0 C15H21NO3
N-<β-(3.4-Dihydroxyphenyl)-ethyl>-cyclohexancarboxamid
—— 3-(2-Ethylphenyl)-2-(2-ethylphenyl)imino-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one 354545-04-3 C26H24N2O2S
3-(2-Ethylphenyl)-2-(2-ethylphenyl)imino-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (R<sub>S</sub>)-1-(2-hydroxy-4,6-dimethoxy-3-methylphenyl)-2-(p-tolylsulfinyl)ethanol 249931-47-3 C18H22O5S
(R<sub>S</sub>)-1-(2-hydroxy-4,6-dimethoxy-3-methylphenyl)-2-(p-tolylsulfinyl)ethanol
—— 5-<1-(hydroxy)-1-(4-hydroxyphenyl)methyl>-3-thiophenesulfonamide 155954-67-9 C11H11NO4S2
5-<1-(hydroxy)-1-(4-hydroxyphenyl)methyl>-3-thiophenesulfonamide
—— 3-nitrosalicylaldehyde oxime 17580-64-2 C7H6N2O4
3-nitrosalicylaldehyde oxime
—— 4-[(3,5-dibromo-4-hydroxyphenyl)methyl]-6-methyl-2-(methylamino)-3-(phenylmethoxymethyl)-7,8-dihydro-4H-imidazo[4,5-d]azepin-5-one 1509904-00-0 C24H26Br2N4O3
4-[(3,5-dibromo-4-hydroxyphenyl)methyl]-6-methyl-2-(methylamino)-3-(phenylmethoxymethyl)-7,8-dihydro-4H-imidazo[4,5-d]azepin-5-one
—— 4-methyl-2-(tetrahydrofuran-2-yl)phenol 80810-53-3 C11H14O2
4-methyl-2-(tetrahydrofuran-2-yl)phenol
—— 2,6-dimethyl-4-(octadecylthiomethyl)phenol 1258429-69-4 C27H48OS
2,6-dimethyl-4-(octadecylthiomethyl)phenol
—— 5,11-diallylcalix[4]arene 181635-69-8 C34H32O4
5,11-diallylcalix[4]arene
—— 3-methoxy-2-hydroxy-5-chlorotoluene 86232-26-0 C8H9ClO2
3-methoxy-2-hydroxy-5-chlorotoluene
—— 3-Hydroxy-2,6-dinitro-5-(2-nitro-phenylsulfanyl)-benzoic acid 81384-32-9 C13H7N3O9S
3-Hydroxy-2,6-dinitro-5-(2-nitro-phenylsulfanyl)-benzoic acid
—— 6,8-dihydroxy-9H-benzo [e]pyrrolo[2,1-b][1,3]oxazin-9-one 288839-59-8 C11H7NO4
6,8-dihydroxy-9H-benzo [e]pyrrolo[2,1-b][1,3]oxazin-9-one
—— 6-hydroxy-3-methoxy-5-propylanthranilamide 138224-09-6 C11H16N2O3
6-hydroxy-3-methoxy-5-propylanthranilamide
—— 7-allyl-6,8-dihydroxy-9H-benzo [e]pyrrolo[2,1-b][1,3]oxazin-9-one 288839-62-3 C14H11NO4
7-allyl-6,8-dihydroxy-9H-benzo [e]pyrrolo[2,1-b][1,3]oxazin-9-one
—— 1,4,5,8,9,12,13,16-octahydroxytetra-o-phenylene 511303-95-0 C24H16O8
1,4,5,8,9,12,13,16-octahydroxytetra-o-phenylene
—— 2,3-diethynyl 5,6-dimethylhydroquinone 198124-89-9 C12H10O2
2,3-diethynyl 5,6-dimethylhydroquinone
—— 2,3-Dimethyl-5,6-bis(2-trimethylsilylethynyl)benzene-1,4-diol 198124-88-8 C18H26O2Si2
2,3-Dimethyl-5,6-bis(2-trimethylsilylethynyl)benzene-1,4-diol
—— 4-morpholin-4-ylmethyl-benzene-1,2,3-triol 41273-92-1 C11H15NO4
4-morpholin-4-ylmethyl-benzene-1,2,3-triol
—— 4-(7-carboxy-1,1-dimethyl-3-oxaheptyl )-5-(3-hydroxyphenyl)-3,3-dimethyl-2,3-dihydrofuran 594859-80-0 C21H30O5
4-(7-carboxy-1,1-dimethyl-3-oxaheptyl )-5-(3-hydroxyphenyl)-3,3-dimethyl-2,3-dihydrofuran