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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
—— Dimethyl 16,40-dihydroxy-12,20,36,44-tetrathianonacyclo[44.2.2.27,10.222,25.231,34.12,6.114,18.126,30.138,42]hexaconta-1(48),2(60),3,5,7(59),8,10(58),14(57),15,17,22(56),23,25(55),26,28,30(54),31,33,38,40,42(51),46,49,52-tetracosaene-54,60-dicarboxylate 177798-49-1 C60H52O6S4
Dimethyl 16,40-dihydroxy-12,20,36,44-tetrathianonacyclo[44.2.2.27,10.222,25.231,34.12,6.114,18.126,30.138,42]hexaconta-1(48),2(60),3,5,7(59),8,10(58),14(57),15,17,22(56),23,25(55),26,28,30(54),31,33,38,40,42(51),46,49,52-tetracosaene-54,60-dicarboxylate
—— 5,6-dibromo-2-methylphenol 77339-21-0 C7H6Br2O
5,6-dibromo-2-methylphenol
—— 4-(4-Methyl-4,5-dihydro-1H-pyrazol-3-yl)-phenol 123716-82-5 C10H12N2O
4-(4-Methyl-4,5-dihydro-1H-pyrazol-3-yl)-phenol
—— (6R)-N-(2-hydroxy-5-methylphenyl)-4-methoxy-6-phenyl-3,4-didehydropiperidin-2-one 910471-00-0 C19H19NO3
(6R)-N-(2-hydroxy-5-methylphenyl)-4-methoxy-6-phenyl-3,4-didehydropiperidin-2-one
—— (R)-fornicin A 908588-41-0 C16H18O4
(R)-fornicin A
—— 5-fluoro-3-hydroxy-2-methylbenzonitrile 1591829-03-6 C8H6FNO
5-fluoro-3-hydroxy-2-methylbenzonitrile
—— 2-{[(2-furanylmethyl)amino]methyl}-6-(methoxy)phenol 827328-42-7 C13H15NO3
2-{[(2-furanylmethyl)amino]methyl}-6-(methoxy)phenol
—— 9-(3-bromo-4-hydroxy-5-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione 329211-33-8 C24H27BrO5
9-(3-bromo-4-hydroxy-5-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
—— 9-(3,5-dibromo-4-hydroxyphenyl)-3,3,6,6-tetramethyl-4,5,7,9-tetrahydro-2H-xanthene-1,8-dione 5626-17-5 C23H24Br2O4
9-(3,5-dibromo-4-hydroxyphenyl)-3,3,6,6-tetramethyl-4,5,7,9-tetrahydro-2H-xanthene-1,8-dione
—— 4-[(1S,3aR,7aS)-1,3,3a,4,5,7a-hexahydro-3,3,6-trimethylisobenzofuran-1-yl]-2-methoxyphenol 1260153-11-4 C18H24O3
4-[(1S,3aR,7aS)-1,3,3a,4,5,7a-hexahydro-3,3,6-trimethylisobenzofuran-1-yl]-2-methoxyphenol
—— 4-[(1R,3aR,7aS)-1,3,3a,4,5,7a-hexahydro-3,3,6-trimethylisobenzofuran-1-yl]-2-methoxyphenol 1260153-18-1 C18H24O3
4-[(1R,3aR,7aS)-1,3,3a,4,5,7a-hexahydro-3,3,6-trimethylisobenzofuran-1-yl]-2-methoxyphenol
—— 4-[(3αR,7αS)-1,3,3α,4,5,7α-hexahydro-3,3,6-trimethylisobenzofuran-1-yl]-2-methoxyphenol 1352734-67-8 C18H24O3
4-[(3αR,7αS)-1,3,3α,4,5,7α-hexahydro-3,3,6-trimethylisobenzofuran-1-yl]-2-methoxyphenol
—— 4-(4,5-di-p-tolyl-1H-imidazol-2-yl)phenol 24777-16-0 C23H20N2O
4-(4,5-di-p-tolyl-1H-imidazol-2-yl)phenol
—— 3-azido-2,4,6-trinitrophenol 1613311-04-8 C6H2N6O7
3-azido-2,4,6-trinitrophenol
—— [(R)-2-hydroxy-1-(4-hydroxy-2-methyl-phenyl)ethyl]carbamic acid tert-butyl ester 1286280-58-7 C14H21NO4
[(R)-2-hydroxy-1-(4-hydroxy-2-methyl-phenyl)ethyl]carbamic acid tert-butyl ester
—— 2-[[4-[(4-Ethoxyphenyl)methyl]piperazin-1-yl]methyl]-4-methoxyphenol 6117-65-3 C21H28N2O3
2-[[4-[(4-Ethoxyphenyl)methyl]piperazin-1-yl]methyl]-4-methoxyphenol
—— 6-Hydroxymethyl-2,3-dimethoxy-phenol 219918-14-6 C9H12O4
6-Hydroxymethyl-2,3-dimethoxy-phenol
—— (Z)-5-(3-Bromo-2-hydroxy-5-methoxybenzylidene)-2-thioxothiazolidin-4-one —— C11H8BrNO3S2
(Z)-5-(3-Bromo-2-hydroxy-5-methoxybenzylidene)-2-thioxothiazolidin-4-one
—— 4-(2-cyanoethyl)-2,6-dimethylphenol 58471-30-0 C11H13NO
4-(2-cyanoethyl)-2,6-dimethylphenol
—— 4-But-2-enyl-o-kresol 7572-85-2 C11H14O
4-But-2-enyl-o-kresol
—— (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