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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
—— 2-methoxy-5-<4-(3,4,5-trimethoxyphenyl)butyl>phenol 117048-68-7 C20H26O5
2-methoxy-5-<4-(3,4,5-trimethoxyphenyl)butyl>phenol
—— 2-[(4R,5R)-4,5-bis(diphenylphosphanylmethyl)-1,3-dioxolan-2-yl]phenol 171561-26-5 C35H32O3P2
2-[(4R,5R)-4,5-bis(diphenylphosphanylmethyl)-1,3-dioxolan-2-yl]phenol
—— Methyl 5-(3-hydroxy-4-methoxyphenyl)pentanoate 205052-12-6 C13H18O4
Methyl 5-(3-hydroxy-4-methoxyphenyl)pentanoate
—— 4-(3-hydroxy-4-methoxybenzyl)-4,5-dihydro-2(3H)-furanone 140161-07-5 C12H14O4
4-(3-hydroxy-4-methoxybenzyl)-4,5-dihydro-2(3H)-furanone
—— 2-(3-hydroxy-4-methoxyphenyl)-1,3-benzodioxole 137116-72-4 C14H12O4
2-(3-hydroxy-4-methoxyphenyl)-1,3-benzodioxole
—— m,m'-selenodiphenol 98040-20-1 C12H10O2Se
m,m'-selenodiphenol
—— 4-{(4R,5R)-4,5-Bis-[(diphenylphosphanyl)-methyl]-[1,3]dioxolan-2-yl}-phenol 171561-27-6 C35H32O3P2
4-{(4R,5R)-4,5-Bis-[(diphenylphosphanyl)-methyl]-[1,3]dioxolan-2-yl}-phenol
—— 4-((3-hydroxy-4-methoxybenzyl)(4H-1,2,4-triazol-4-yl)amino)benzonitrile 537674-82-1 C17H15N5O2
4-((3-hydroxy-4-methoxybenzyl)(4H-1,2,4-triazol-4-yl)amino)benzonitrile
—— (R)-N-Boc-m-hydroxy-p-methoxyphenyl-Gly 391213-72-2 C14H19NO6
(R)-N-Boc-m-hydroxy-p-methoxyphenyl-Gly
—— 2-(4-Benzyloxy-3,5-dimethyl-phenyl)-ethanol 787571-87-3 C17H20O2
2-(4-Benzyloxy-3,5-dimethyl-phenyl)-ethanol
—— (5E)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one 5556-31-0 C11H8ClNO3S2
(5E)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-Hydroxy-5-methoxy-(2-cyclohexenyl)-benzol 64252-19-3 C13H16O2
2-Hydroxy-5-methoxy-(2-cyclohexenyl)-benzol
—— 5-hydroxy-3-(2-hydroxyphenyl)-5-trifluoromethyl-Δ<sup>2</sup>-isoxazoline 294875-43-7 C10H8F3NO3
5-hydroxy-3-(2-hydroxyphenyl)-5-trifluoromethyl-Δ<sup>2</sup>-isoxazoline
—— 4-nitro-2-((trimethylsilyl)ethynyl)phenol 1188417-61-9 C11H13NO3Si
4-nitro-2-((trimethylsilyl)ethynyl)phenol
—— 4-nitro-2-(thien-2-yl)phenol 373380-63-3 C10H7NO3S
4-nitro-2-(thien-2-yl)phenol
—— 2-[(4-Bromophenyl)methylideneamino]-4-methylphenol 36239-55-1 C14H12BrNO
2-[(4-Bromophenyl)methylideneamino]-4-methylphenol
—— (3-Hydroxy-4-methoxy-2,6-dimethyl-phenyl)-acetic acid ethyl ester 80367-36-8 C13H18O4
(3-Hydroxy-4-methoxy-2,6-dimethyl-phenyl)-acetic acid ethyl ester
—— Parvifloral 21973-34-2 C15H18O3
Parvifloral
—— 6-chloro-2-methyl-3-nitro-phenol 80419-49-4 C7H6ClNO3
6-chloro-2-methyl-3-nitro-phenol
—— N,N'-dimethyl-N,N'-bis(5-methyl-2-hydroxyphenyl)-1,2-diaminoethane 1257328-69-0 C18H24N2O2
N,N'-dimethyl-N,N'-bis(5-methyl-2-hydroxyphenyl)-1,2-diaminoethane
—— disalicylaldimine anthranylamide 42246-48-0 C21H17N3O3
disalicylaldimine anthranylamide
—— 2-tert-butyl-4-methoxy-6-{[(2'-dimethylaminoethyl)methylamino]methyl}phenol 1570188-71-4 C17H30N2O2
2-tert-butyl-4-methoxy-6-{[(2'-dimethylaminoethyl)methylamino]methyl}phenol
—— 2,3,4-Trihydroxybenzylhydrazine,methylate 1246817-07-1 C8H14N2O4
2,3,4-Trihydroxybenzylhydrazine,methylate
—— (E)-6-chloro-3-(3-hydroxy-4-methoxybenzylidene)indolin-2-one 1148119-14-5 C16H12ClNO3
(E)-6-chloro-3-(3-hydroxy-4-methoxybenzylidene)indolin-2-one
—— 2-(2-hydroxy-phenyl)-3-hydroxy-1,3-azaphosphorinane-3-oxide 1075800-08-6 C10H14NO3P
2-(2-hydroxy-phenyl)-3-hydroxy-1,3-azaphosphorinane-3-oxide
—— 2,6-bis-(4-hydroxy-3-methoxy-<i>trans</i>-styryl)-pyridine 114863-90-0 C23H21NO4
2,6-bis-(4-hydroxy-3-methoxy-<i>trans</i>-styryl)-pyridine
—— 3,5-dimethoxy-[4-(13)C]phenol 1256603-03-8 C8H10O3
3,5-dimethoxy-[4-(13)C]phenol
—— [2-(13)C]phloroglucinol 1256603-01-6 C6H6O3
[2-(13)C]phloroglucinol
—— [2-13C]resorcinol 85940-98-3 C6H6O2
[2-13C]resorcinol
—— <methyl-14C>-metacresol 65135-15-1 C7H8O
<methyl-14C>-metacresol
—— 3-[8-(4-Hydroxyphenyl)pentadecyl]phenol 96712-09-3 C27H40O2
3-[8-(4-Hydroxyphenyl)pentadecyl]phenol
—— cardbisphenol 113494-64-7 C27H40O2
cardbisphenol
—— 2,6-Dichlorovanillin 108545-01-3 C8H6Cl2O3
2,6-Dichlorovanillin
—— 3-(2-hydroxy-phenyl)-6-phenyl-furo[3,2-b]furan-2,5-dione 487-33-2 C18H10O5
3-(2-hydroxy-phenyl)-6-phenyl-furo[3,2-b]furan-2,5-dione
—— 2-amino-4,6-bis-(3-hydroxy-4-methoxyphenyl)-5-nitrocyclohex-2-ene-1,3,3-tricarbonitrile 1228031-37-5 C23H19N5O6
2-amino-4,6-bis-(3-hydroxy-4-methoxyphenyl)-5-nitrocyclohex-2-ene-1,3,3-tricarbonitrile
—— 4-Chlor-2-aethyl-6-aethylphenol 53346-76-2 C10H13ClO
4-Chlor-2-aethyl-6-aethylphenol
—— Calcium;2-dodecylphenol;formaldehyde;methanamine;sulfane;dihydroxide —— C20H41CaNO4S
Calcium;2-dodecylphenol;formaldehyde;methanamine;sulfane;dihydroxide
—— 2,5,6-Trifluor-4-nitroresorcinol 31438-88-7 C6H2F3NO4
2,5,6-Trifluor-4-nitroresorcinol
—— Ethyl 4-cyano-5-propan-2-ylsulfanyl-3-(3,4,5-trihydroxyphenyl)thiophene-2-carboxylate 1426384-42-0 C17H17NO5S2
Ethyl 4-cyano-5-propan-2-ylsulfanyl-3-(3,4,5-trihydroxyphenyl)thiophene-2-carboxylate
—— (2-hydroxyphenyl)bis(4-methyl-pyrazolyl)methane 1401660-69-2 C15H16N4O
(2-hydroxyphenyl)bis(4-methyl-pyrazolyl)methane
—— 3-bromo-4-hydroxy-N,N-dimethyl-5-nitrobenzenesulfonamide 61712-36-5 C8H9BrN2O5S
3-bromo-4-hydroxy-N,N-dimethyl-5-nitrobenzenesulfonamide
—— N-(3-chlorophenyl)-3-(3-hydroxy-4-methoxy-phenyl)-propanamide 1613391-33-5 C16H16ClNO3
N-(3-chlorophenyl)-3-(3-hydroxy-4-methoxy-phenyl)-propanamide
—— (5R)-5-hexyl-3-(4-hydroxyphenyl)-1,3-oxazolidin-2-one 136719-36-3 C15H21NO3
(5R)-5-hexyl-3-(4-hydroxyphenyl)-1,3-oxazolidin-2-one
—— (2R,4R)-2-(4-hydroxyphenyl)-4-decanolide 134282-60-3 C16H22O3
(2R,4R)-2-(4-hydroxyphenyl)-4-decanolide
—— 2-Nitro-4-piperidin-1-ylsulfonylphenol 1097090-32-8 C11H14N2O5S
2-Nitro-4-piperidin-1-ylsulfonylphenol
—— 2-<(α-Methyl-benzyl)-aminomethyl>-hydrochinon 94026-89-8 C15H17NO2
2-<(α-Methyl-benzyl)-aminomethyl>-hydrochinon
—— 4,5-dihydro-2-(3-hydroxyphenyl)-4(R)-phenyloxazole 174770-67-3 C15H13NO2
4,5-dihydro-2-(3-hydroxyphenyl)-4(R)-phenyloxazole
—— 2-sec-Butylaminomethyl-hydrochinon 91340-13-5 C11H17NO2
2-sec-Butylaminomethyl-hydrochinon
—— 2-Isopropylaminomethyl-hydrochinon 91252-14-1 C10H15NO2
2-Isopropylaminomethyl-hydrochinon
—— 2-fluoro-5-hydroxy-4-methylphenol 205448-40-4 C7H7FO2
2-fluoro-5-hydroxy-4-methylphenol