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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-[2-(3-Trimethylsilylphenyl)ethynyl]phenol 1426919-95-0 C17H18OSi
4-[2-(3-Trimethylsilylphenyl)ethynyl]phenol
—— tert-butyl (4-bromo-2-hydroxybenzyl)(2-hydroxyethyl)carbamate 1445903-00-3 C14H20BrNO4
tert-butyl (4-bromo-2-hydroxybenzyl)(2-hydroxyethyl)carbamate
—— 3-(4-hydroxy-3,5-dimethyl-phenyl)-1-(5-methyl-4-phenyl-thiophen-2-yl)-propan-1-one 917873-23-5 C22H22O2S
3-(4-hydroxy-3,5-dimethyl-phenyl)-1-(5-methyl-4-phenyl-thiophen-2-yl)-propan-1-one
—— 2-(1-Pentylheptyl)-phenol 17404-55-6 C18H30O
2-(1-Pentylheptyl)-phenol
—— 2-(2-hydroxy-phenyl)-isoxazolo[2,3-<i>a</i>]pyridinylium; bromide 61395-19-5 Br*C13H10NO2
2-(2-hydroxy-phenyl)-isoxazolo[2,3-<i>a</i>]pyridinylium; bromide
—— 2-(5-decyl)phenol 17404-51-2 C16H26O
2-(5-decyl)phenol
—— 2-(1-Hydroxyprop-2-ynyl)-4-methylphenol 1384475-76-6 C10H10O2
2-(1-Hydroxyprop-2-ynyl)-4-methylphenol
—— 2-(4-hydroxyphenyl)-4-methylcyclohex-3-en-1-one 137359-74-1 C13H14O2
2-(4-hydroxyphenyl)-4-methylcyclohex-3-en-1-one
—— (S)-(+)-1-(3,4-dihydroxyphenyl)ethane-1,2-diol 55254-51-8 C8H10O4
(S)-(+)-1-(3,4-dihydroxyphenyl)ethane-1,2-diol
—— 2-[(4-Hydroxy-3-nitrophenyl)methylidene]propanedinitrile 90947-89-0 C10H5N3O3
2-[(4-Hydroxy-3-nitrophenyl)methylidene]propanedinitrile
—— N-Bnezyldopamine 37491-72-8 C15H17NO2
N-Bnezyldopamine
—— β-(2,4-dihydroxybenzoyl)acrylic acid 34857-11-9 C10H8O5
β-(2,4-dihydroxybenzoyl)acrylic acid
—— 4-(2-pyridylazo)resorcinol 1141-59-9 C11H9N3O2
4-(2-pyridylazo)resorcinol
—— 2,6-Dimethyl-4-((5-(3-pyridinyl)-2H-tetrazol-2-yl)methyl)phenol 104186-22-3 C15H15N5O
2,6-Dimethyl-4-((5-(3-pyridinyl)-2H-tetrazol-2-yl)methyl)phenol
—— 4-[(5-Benzyltetrazol-1-yl)methyl]-2,6-dimethylphenol 104065-32-9 C17H18N4O
4-[(5-Benzyltetrazol-1-yl)methyl]-2,6-dimethylphenol
—— dibenzo[d,f][1,3]dioxepin-1,1'-diol 189299-65-8 C13H10O4
dibenzo[d,f][1,3]dioxepin-1,1'-diol
—— N-[(E)-furan-2-ylmethylideneamino]-4-hydroxy-3-methoxybenzamide 1415691-87-0 C13H12N2O4
N-[(E)-furan-2-ylmethylideneamino]-4-hydroxy-3-methoxybenzamide
—— phenol; hydrazinium-phenolate 108668-86-6 2C6H6O*H4N2
phenol; hydrazinium-phenolate
—— 2,8,14,20-Tetrakis(4-hydroxybutyl)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 174510-99-7 C44H56O12
2,8,14,20-Tetrakis(4-hydroxybutyl)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
—— ethyl (2Z)-5-amino-6-cyano-7-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methylidene]-3-oxo-7H-[1,3]thiazolo[3,2-a]pyridine-8-carboxylate 5678-53-5 C24H19N3O5S
ethyl (2Z)-5-amino-6-cyano-7-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methylidene]-3-oxo-7H-[1,3]thiazolo[3,2-a]pyridine-8-carboxylate
—— (5Z)-5-{[5-(2-hydroxy-5-nitrophenyl)furan-2-yl]methylidene}-2-thioxoimidazolidin-4-one 5731-62-4 C14H9N3O5S
(5Z)-5-{[5-(2-hydroxy-5-nitrophenyl)furan-2-yl]methylidene}-2-thioxoimidazolidin-4-one
—— <1-14C>-Phenol 22167-43-7 C6H6O
<1-14C>-Phenol
—— 4-(morpholinomethyl)benzene-1,3-diol 94564-78-0 C11H15NO3
4-(morpholinomethyl)benzene-1,3-diol
—— (5Z)-5-(4-hydroxybenzylidene)-3-(2-methoxyethyl)-2-thioxo-1,3-thiazolidin-4-one 5879-70-9 C13H13NO3S2
(5Z)-5-(4-hydroxybenzylidene)-3-(2-methoxyethyl)-2-thioxo-1,3-thiazolidin-4-one
—— (5E)-1-(4-chlorophenyl)-5-(4-hydroxy-3-methoxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione 5174-75-4 C18H13ClN2O5
(5E)-1-(4-chlorophenyl)-5-(4-hydroxy-3-methoxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
—— E-5-(2-hydroxyphenylmethylene)-4-oxo-2-thioxo-1,3-thiazolidine 81154-11-2 C10H7NO2S2
E-5-(2-hydroxyphenylmethylene)-4-oxo-2-thioxo-1,3-thiazolidine
—— 4,5-dimethoxy-2-(2-tert-butyldimethylsiloxyethyl)benzaldehyde 406215-63-2 C17H28O4Si
4,5-dimethoxy-2-(2-tert-butyldimethylsiloxyethyl)benzaldehyde
—— N-[(E)-1-(5-chlorothiophen-2-yl)ethylideneamino]-4-hydroxy-3-methoxybenzamide —— C14H13ClN2O3S
N-[(E)-1-(5-chlorothiophen-2-yl)ethylideneamino]-4-hydroxy-3-methoxybenzamide
—— ethyl (2Z)-2-[(4-hydroxy-3-iodo-5-methoxyphenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate 5649-32-1 C25H23IN2O6S
ethyl (2Z)-2-[(4-hydroxy-3-iodo-5-methoxyphenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5Z)-5-[(2-hydroxyphenyl)methylidene]-2-(4-methylpiperidin-1-yl)-1,3-thiazol-4-one 5956-25-2 C16H18N2O2S
(5Z)-5-[(2-hydroxyphenyl)methylidene]-2-(4-methylpiperidin-1-yl)-1,3-thiazol-4-one
—— (5Z)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-1-(3-methylphenyl)-1,3-diazinane-2,4,6-trione 5974-41-4 C19H15ClN2O5
(5Z)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-1-(3-methylphenyl)-1,3-diazinane-2,4,6-trione
—— (5E)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-3-(3,4-dimethylphenyl)-6-hydroxypyrimidine-2,4(3H,5H)-dione 6019-75-6 C20H17ClN2O5
(5E)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-3-(3,4-dimethylphenyl)-6-hydroxypyrimidine-2,4(3H,5H)-dione
—— N'-[(E)-(3-hydroxyphenyl)methylidene]-2-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)acetohydrazide —— C13H14N4O3
N'-[(E)-(3-hydroxyphenyl)methylidene]-2-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)acetohydrazide
—— 2,3-dimethyl-4-thiocyanatophenol 6186-84-1 C9H9NOS
2,3-dimethyl-4-thiocyanatophenol
—— (5E)-1-(4-fluorophenyl)-5-(4-hydroxy-3-iodo-5-methoxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione 5960-00-9 C18H12FIN2O5
(5E)-1-(4-fluorophenyl)-5-(4-hydroxy-3-iodo-5-methoxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
—— 2-Hydroxy-4-nitrobenzenesulfonamide 1261863-13-1 C6H6N2O5S
2-Hydroxy-4-nitrobenzenesulfonamide
—— 2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy]ethylamine 118797-50-5 C14H23NO2
2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy]ethylamine
—— 2,3-dimethyl-4-nitro-6-(2-propenyl)phenol 182010-87-3 C11H13NO3
2,3-dimethyl-4-nitro-6-(2-propenyl)phenol
—— 4-bromo-2,3-dimethyl-6-(2-propenyl)phenol 182010-84-0 C11H13BrO
4-bromo-2,3-dimethyl-6-(2-propenyl)phenol
—— 4-(2-hydroxy-3,4-dimethyl-phenyl)-butyric acid 855223-27-7 C12H16O3
4-(2-hydroxy-3,4-dimethyl-phenyl)-butyric acid
—— 4-Allyl-2,3-dimethyl-phenol 3727-18-2 C11H14O
4-Allyl-2,3-dimethyl-phenol
—— 5-Allyl-2,3-dimethylphenol 40793-87-1 C11H14O
5-Allyl-2,3-dimethylphenol
—— methyl (4Z)-1-ethyl-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxopyrrole-3-carboxylate 5955-40-8 C17H19NO5
methyl (4Z)-1-ethyl-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxopyrrole-3-carboxylate
—— 4,6-diiodo-2,3-dimethyl-phenol 17938-68-0 C8H8I2O
4,6-diiodo-2,3-dimethyl-phenol
—— bis(5-tert-butyl-2-furyl)(2-hydroxy-5-nitrophenyl)methane 1313199-65-3 C23H27NO5
bis(5-tert-butyl-2-furyl)(2-hydroxy-5-nitrophenyl)methane
—— 3-Methyl-4,6-di-t-butyl-2-nitrophenol 3114-65-6 C15H23NO3
3-Methyl-4,6-di-t-butyl-2-nitrophenol
—— (5E)-1-(4-fluorophenyl)-5-(4-hydroxy-3-methoxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione 5963-82-6 C18H13FN2O5
(5E)-1-(4-fluorophenyl)-5-(4-hydroxy-3-methoxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
—— N-[(E)-(2-chlorophenyl)methylideneamino]-3,4,5-trihydroxybenzamide 329047-62-3 C14H11ClN2O4
N-[(E)-(2-chlorophenyl)methylideneamino]-3,4,5-trihydroxybenzamide
—— (5E)-1-(4-bromo-3-methylphenyl)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-1,3-diazinane-2,4,6-trione 6063-89-4 C19H14BrClN2O5
(5E)-1-(4-bromo-3-methylphenyl)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-1,3-diazinane-2,4,6-trione
—— methyl (4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-(pyridin-3-ylmethyl)pyrrole-3-carboxylate 6132-61-2 C21H20N2O5
methyl (4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-(pyridin-3-ylmethyl)pyrrole-3-carboxylate