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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
—— (5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one 331261-30-4 C12H11NO3S2
(5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— 3,5-dicyclopropylphenol 41381-26-4 C12H14O
3,5-dicyclopropylphenol
—— N,2-bis[(2-hydroxyphenyl)methylideneamino]benzamide 42246-48-0 C21H17N3O3
N,2-bis[(2-hydroxyphenyl)methylideneamino]benzamide
—— 5-amino-7-(2-hydroxy-5-methoxyphenyl)-8-nitro-1,2,3,7-tetrahydroimidazo[1,2-a]pyridine-6-carbonitrile 1446874-51-6 C15H15N5O4
5-amino-7-(2-hydroxy-5-methoxyphenyl)-8-nitro-1,2,3,7-tetrahydroimidazo[1,2-a]pyridine-6-carbonitrile
—— 2,4-Dibromo-6-{[(4-fluorophenyl)imino]methyl}benzenol 329936-44-9 C13H8Br2FNO
2,4-Dibromo-6-{[(4-fluorophenyl)imino]methyl}benzenol
—— 1-(2-Hydroxyphenyl)-2-methyloxiran 62599-37-5 C9H10O2
1-(2-Hydroxyphenyl)-2-methyloxiran
—— 1-(3,5-dibromo-4-hydroxyphenyl)-5-bromouracil 83809-84-1 C10H5Br3N2O3
1-(3,5-dibromo-4-hydroxyphenyl)-5-bromouracil
—— 5-(5-bromo-2-hydroxy-benzylidene)-2-thioxo-thiazolidin-4-one 6318-35-0 C10H6BrNO2S2
5-(5-bromo-2-hydroxy-benzylidene)-2-thioxo-thiazolidin-4-one
—— 5-Hexoxy-2-hydroxybenzaldehyde 291507-16-9 C13H18O3
5-Hexoxy-2-hydroxybenzaldehyde
—— 5,11-di-tert-butyl-17,23,29-trimethyl-31,32,33,34,35-pentahydroxycalix[5]arene 903896-45-7 C46H52O5
5,11-di-tert-butyl-17,23,29-trimethyl-31,32,33,34,35-pentahydroxycalix[5]arene
—— 17,23,29-trimethyl-31,32,33,34,35-pentahydroxycalix[5]arene 903896-48-0 C38H36O5
17,23,29-trimethyl-31,32,33,34,35-pentahydroxycalix[5]arene
—— (2-{[Carboxy-(2-hydroxy-5-methoxy-phenyl)-methyl]-amino}-ethylamino)-(2-hydroxy-5-methoxy-phenyl)-acetic acid 132604-28-5 C20H24N2O8
(2-{[Carboxy-(2-hydroxy-5-methoxy-phenyl)-methyl]-amino}-ethylamino)-(2-hydroxy-5-methoxy-phenyl)-acetic acid
—— N-(3-tert-butyl-5-methoxysalicylidene)phenylene-1,2-diamine 1507512-87-9 C12H19NO2
N-(3-tert-butyl-5-methoxysalicylidene)phenylene-1,2-diamine
—— <i>N</i>,<i>N</i>-dibenzyl-hydrazine; picrate 7626-64-4 C6H3N3O7*C14H16N2
<i>N</i>,<i>N</i>-dibenzyl-hydrazine; picrate
—— N-[2-(4-hydroxyphenyl)ethyl] butanamide 66800-53-1 C12H17NO2
N-[2-(4-hydroxyphenyl)ethyl] butanamide
—— 2-fluoro-4,5-dimethylphenol 709031-97-0 C8H9FO
2-fluoro-4,5-dimethylphenol
—— (5E)-5-(3-Bromo-4-hydroxy-5-methoxybenzylidene)-1,3-thiazolidine-2,4-dione —— C11H8BrNO4S
(5E)-5-(3-Bromo-4-hydroxy-5-methoxybenzylidene)-1,3-thiazolidine-2,4-dione
—— 2-(1-Hydroxy-cyclopentyl)-4-methyl-phenol 130333-15-2 C12H16O2
2-(1-Hydroxy-cyclopentyl)-4-methyl-phenol
—— 5-(1-cyclohexylethyl) resorcinol 26685-18-7 C14H20O2
5-(1-cyclohexylethyl) resorcinol
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one 58215-51-3 C12H10BrNO3S2
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-(2-Hydroxymethyl-5-methyl-1-cyclohexenyl)-5-n-pentyl-resorcin 67795-22-6 C19H28O3
2-(2-Hydroxymethyl-5-methyl-1-cyclohexenyl)-5-n-pentyl-resorcin
—— 5-(1-methyl-hexyl)-benzene-1,3-diol 22168-68-9 C13H20O2
5-(1-methyl-hexyl)-benzene-1,3-diol
—— 3,4,5-trihydroxy-benzoic acid isopropylidenehydrazide 99068-92-5 C10H12N2O4
3,4,5-trihydroxy-benzoic acid isopropylidenehydrazide
—— (E)-3,4,5-trihydroxy-N'-(2-hydroxybenzylidene)benzohydrazide 25054-55-1 C14H12N2O5
(E)-3,4,5-trihydroxy-N'-(2-hydroxybenzylidene)benzohydrazide
—— 5-(2-hydroxy-5-nitrophenyl)-2,3-dihydro-1,4-diazepine-7-carboxylic acid 90380-30-6 C12H11N3O5
5-(2-hydroxy-5-nitrophenyl)-2,3-dihydro-1,4-diazepine-7-carboxylic acid
—— 5-[(5-Bromo-2-hydroxyphenyl)methylidene]-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one 313470-10-9 C12H10BrNO2S2
5-[(5-Bromo-2-hydroxyphenyl)methylidene]-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5-Benzyltetrazol-2-yl)methyl 2-(4-hydroxyphenyl)acetate 1350837-09-0 C17H16N4O3
(5-Benzyltetrazol-2-yl)methyl 2-(4-hydroxyphenyl)acetate
—— 3-(2-phenyl-oxazolidin-5-yl)-phenol 57614-96-7 C15H15NO2
3-(2-phenyl-oxazolidin-5-yl)-phenol
—— 2-tert-Butyl-4-isopropyl-6-methoxy-phenol 33837-80-8 C14H22O2
2-tert-Butyl-4-isopropyl-6-methoxy-phenol
—— 1-{4-[2-(6-Hydrazino-pyridazin-3-yloxy)-ethyl]-phenoxy}-3-isopropylamino-propan-2-ol 1027995-84-1 C18H27N5O3
1-{4-[2-(6-Hydrazino-pyridazin-3-yloxy)-ethyl]-phenoxy}-3-isopropylamino-propan-2-ol
—— 1-{4-[2-(6-Chloro-pyridazin-3-yloxy)-ethyl]-phenoxy}-3-isopropylamino-propan-2-ol 81488-57-5 C18H24ClN3O3
1-{4-[2-(6-Chloro-pyridazin-3-yloxy)-ethyl]-phenoxy}-3-isopropylamino-propan-2-ol
—— (5Z)-3-cyclohexyl-5-[(3,4-dihydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one 327054-63-7 C16H17NO3S2
(5Z)-3-cyclohexyl-5-[(3,4-dihydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-(2-(3-hydroxybenzylidene)hydrazinyl)thiazol-4(5H)-one 333776-51-5 C10H9N3O2S
2-(2-(3-hydroxybenzylidene)hydrazinyl)thiazol-4(5H)-one
—— 3-((Z)-((Z)-5-(4-hydroxy-3-methoxybenzylidene)-3-ethyl-4-oxothiazolidin-2-ylidene)amino)benzoic acid 1448678-46-3 C20H18N2O5S
3-((Z)-((Z)-5-(4-hydroxy-3-methoxybenzylidene)-3-ethyl-4-oxothiazolidin-2-ylidene)amino)benzoic acid
—— Phenol, 2-bromo-6-[[(2-bromophenyl)imino]methyl]-4-chloro- 414899-38-0 C13H8Br2ClNO
Phenol, 2-bromo-6-[[(2-bromophenyl)imino]methyl]-4-chloro-
—— 1-(3-hydroxy-4-methoxybenzylidene)-4-(4-tolyl)thiosemicarbazide 316131-26-7 C16H17N3O2S
1-(3-hydroxy-4-methoxybenzylidene)-4-(4-tolyl)thiosemicarbazide
—— 3-[(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid —— C14H13NO5S2
3-[(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid
—— 2-methoxy-6-[5-(4-methoxy-phenyl)-3,4-dihydro-2<i>H</i>-pyrazol-3-yl]-phenol 58721-64-5 C17H18N2O3
2-methoxy-6-[5-(4-methoxy-phenyl)-3,4-dihydro-2<i>H</i>-pyrazol-3-yl]-phenol
—— (Z)-3-(4-chlorophenyl)-5-(4-hydroxy-3-methoxybenzylidene)-2-thioxothiazolidin-4-one 1198159-41-9 C17H12ClNO3S2
(Z)-3-(4-chlorophenyl)-5-(4-hydroxy-3-methoxybenzylidene)-2-thioxothiazolidin-4-one
—— 4-(5-Chloro-2-hydroxy-phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyridine-3-carbonitrile 79250-17-2 C13H11ClN2O2
4-(5-Chloro-2-hydroxy-phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyridine-3-carbonitrile
—— 2-(4-hydroxy-3-methoxyphenyl)-3-(2-piperazin-1-ylethyl)-1,3-thiazolidin-4-one 1375059-00-9 C16H23N3O3S
2-(4-hydroxy-3-methoxyphenyl)-3-(2-piperazin-1-ylethyl)-1,3-thiazolidin-4-one
—— 2-(4-hydroxyphenyl)-3-(2-piperazin-1-ylethyl)-1,3-thiazolidin-4-one 1375058-99-3 C15H21N3O2S
2-(4-hydroxyphenyl)-3-(2-piperazin-1-ylethyl)-1,3-thiazolidin-4-one
—— 2-(3-hydroxy-4-methoxyphenyl)-3-(2-piperazin-1-ylethyl)-1,3-thiazolidin-4-one 1375058-96-0 C16H23N3O3S
2-(3-hydroxy-4-methoxyphenyl)-3-(2-piperazin-1-ylethyl)-1,3-thiazolidin-4-one
—— 2-(3-hydroxyphenyl)-3-(2-piperazin-1-ylethyl)-1,3-thiazolidin-4-one 1375058-98-2 C15H21N3O2S
2-(3-hydroxyphenyl)-3-(2-piperazin-1-ylethyl)-1,3-thiazolidin-4-one
—— 2-methoxy-4-[(2-piperazin-1-ylethylimino)methyl]phenol 1352004-93-3 C14H21N3O2
2-methoxy-4-[(2-piperazin-1-ylethylimino)methyl]phenol
—— (E)-4-fluoro-2-((2-(piperazin-1-yl)ethylimino)methyl)phenol 1246463-53-5 C13H18FN3O
(E)-4-fluoro-2-((2-(piperazin-1-yl)ethylimino)methyl)phenol
—— 2-(Pyridyl-2-amino)-4-(5-fluoro-2-hydroxy-phenyl)-thiazole 3833-85-0 C14H10FN3OS
2-(Pyridyl-2-amino)-4-(5-fluoro-2-hydroxy-phenyl)-thiazole
—— 2-(7-Furan-2-yl-2,3-dihydro-1H-[1,4]diazepin-5-yl)-4-methyl-phenol 99698-72-3 C16H16N2O2
2-(7-Furan-2-yl-2,3-dihydro-1H-[1,4]diazepin-5-yl)-4-methyl-phenol
—— 4-Chloro-2-(7-furan-2-yl-2,3-dihydro-1H-[1,4]diazepin-5-yl)-phenol 99698-73-4 C15H13ClN2O2
4-Chloro-2-(7-furan-2-yl-2,3-dihydro-1H-[1,4]diazepin-5-yl)-phenol
—— 5-Benzyliden-3-<salicylidenamino>-rhodanin 1438-25-1 C17H12N2O2S2
5-Benzyliden-3-<salicylidenamino>-rhodanin