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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
—— (5Z)-5-[(3-fluoro-2-hydroxyphenyl)methylidene]-2-(4-methylpiperazin-1-yl)-4,5-dihydro-1,3-thiazol-4-one 1181081-53-7 C15H16FN3O2S
(5Z)-5-[(3-fluoro-2-hydroxyphenyl)methylidene]-2-(4-methylpiperazin-1-yl)-4,5-dihydro-1,3-thiazol-4-one
—— 4-Methoxy-6-[[2-(3,5,6-trichloropyridin-2-yl)hydrazinyl]methylidene]cyclohexa-2,4-dien-1-one 5610-25-3 C13H10Cl3N3O2
4-Methoxy-6-[[2-(3,5,6-trichloropyridin-2-yl)hydrazinyl]methylidene]cyclohexa-2,4-dien-1-one
—— 4-Nitro-benzoic acid [1-(2,4,6-trihydroxy-phenyl)-meth-(E)-ylidene]-hydrazide 26683-29-4 C14H11N3O6
4-Nitro-benzoic acid [1-(2,4,6-trihydroxy-phenyl)-meth-(E)-ylidene]-hydrazide
—— 5-(2-aminopyrimidin-4-ylamino)-2-chlorophenol 933045-99-9 C10H9ClN4O
5-(2-aminopyrimidin-4-ylamino)-2-chlorophenol
—— N,N'-bis{2-[(2-ethylimino)methyl]phenol}piperazine 78186-31-9 C22H28N4O2
N,N'-bis{2-[(2-ethylimino)methyl]phenol}piperazine
—— methyl 3-(2-hydroxy-4-nitrophenyl)-3-(3-methoxy-3-oxopropyl)sulfanylpropanoate 114106-46-6 C14H17NO7S
methyl 3-(2-hydroxy-4-nitrophenyl)-3-(3-methoxy-3-oxopropyl)sulfanylpropanoate
—— 1-(2-Phenylaethoxy)-2-(3-hydroxyphenyl)-propan 70120-23-9 C17H20O2
1-(2-Phenylaethoxy)-2-(3-hydroxyphenyl)-propan
—— 3-(2-Amino-1-hydroxypropan-2-yl)phenol hydrochloride 1803603-59-9 C9H14ClNO2
3-(2-Amino-1-hydroxypropan-2-yl)phenol hydrochloride
—— Phenol, 2-(difluoromethyl)-3,6-difluoro- 1261477-77-3 C7H4F4O
Phenol, 2-(difluoromethyl)-3,6-difluoro-
—— nitrosoimino-di-acetic acid bis-salicylidenehydrazide 110335-57-4 C18H18N6O5
nitrosoimino-di-acetic acid bis-salicylidenehydrazide
—— 2-Fluor-3-(3,4-dihydroxy-phenyl)-propionsaeure-methylester 22179-95-9 C10H11FO4
2-Fluor-3-(3,4-dihydroxy-phenyl)-propionsaeure-methylester
—— 5-(3-bromo-2-hydroxy-5-methylphenyl)-3-phenylisoxazole 140885-86-5 C16H12BrNO2
5-(3-bromo-2-hydroxy-5-methylphenyl)-3-phenylisoxazole
—— methyl 4-(2',3'-dihydroxyphenyl)-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate 1356120-68-7 C15H14ClNO5
methyl 4-(2',3'-dihydroxyphenyl)-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate
—— N,N'-Bis-(2-hydroxy-5-methoxy-phenyl)-malonamide 25798-53-2 C17H18N2O6
N,N'-Bis-(2-hydroxy-5-methoxy-phenyl)-malonamide
—— ((E)-2-Cyclooct-1-enyl)-phenol 72471-06-8 C14H18O
((E)-2-Cyclooct-1-enyl)-phenol
—— 4-(3-chloro-4-hydroxyphenyl)-5-(2-cyclohexylacetyl)-6-ethyl-3,4-dihydropyrimidin-2(1H)-one 1224684-00-7 C20H25ClN2O3
4-(3-chloro-4-hydroxyphenyl)-5-(2-cyclohexylacetyl)-6-ethyl-3,4-dihydropyrimidin-2(1H)-one
—— 4-Bromo-2-ethynylphenol 2228319-60-4 C8H5BrO
4-Bromo-2-ethynylphenol
—— 1050599-67-1 C13H12ClFN4O
—— 5,5'-bis-octadecylcarbamoyloxy-2,2'-(6-methoxy-[1,3,5]triazine-2,4-diyl)-bis-phenol 4686-56-0 C54H87N5O7
5,5'-bis-octadecylcarbamoyloxy-2,2'-(6-methoxy-[1,3,5]triazine-2,4-diyl)-bis-phenol
—— (E)-2-(3'-methyloct-2'-en-6'-ynyl)-4-methylphenol 1163722-45-9 C16H20O
(E)-2-(3'-methyloct-2'-en-6'-ynyl)-4-methylphenol
—— 4-iodo-2-(3'-methyl-2'-butenyl)-6-(3''-methyl-2''-butenyl)phenol 364358-95-2 C16H21IO
4-iodo-2-(3'-methyl-2'-butenyl)-6-(3''-methyl-2''-butenyl)phenol
—— diisobutyl (((2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)amino)(2-hydroxy-3,5-diiodophenyl)methyl)phosphonate 1225188-61-3 C19H26I2N3O6P
diisobutyl (((2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)amino)(2-hydroxy-3,5-diiodophenyl)methyl)phosphonate
—— 3-Hydroxy-4-methoxyphenethylamin-<sup>3</sup>H 110781-82-3 C9H13NO2
3-Hydroxy-4-methoxyphenethylamin-<sup>3</sup>H
—— 2-<5'-(p-methoxyphenyloxy)-2'-cyclopentenyl>-p-methoxyphenol 106550-33-8 C19H20O4
2-<5'-(p-methoxyphenyloxy)-2'-cyclopentenyl>-p-methoxyphenol
—— 3-(2-Hydroxy-ethylamino)-5-methoxy-2,6-dimethyl-phenol 112009-67-3 C11H17NO3
3-(2-Hydroxy-ethylamino)-5-methoxy-2,6-dimethyl-phenol
—— 4-(5-chloro-5-nitro-[1,3]dioxan-2-yl)-phenol 119750-04-8 C10H10ClNO5
4-(5-chloro-5-nitro-[1,3]dioxan-2-yl)-phenol
—— (R)-2-((2-hydroxy-1-phenylethylimino)methyl)-4-nitrophenol 875294-56-7 C15H14N2O4
(R)-2-((2-hydroxy-1-phenylethylimino)methyl)-4-nitrophenol
—— 2,6-Dinitro-phenol; compound with piperidine 82571-87-7 C5H11N*C6H4N2O5
2,6-Dinitro-phenol; compound with piperidine
—— 2-(3,4-dihydroxyphenyl)[1-13C]ethylamine 70034-81-0 C8H11NO2
2-(3,4-dihydroxyphenyl)[1-13C]ethylamine
—— 90317-02-5 C30H34CuN2O6*O4S
—— N-(3,4-dihydroxybenzyl)oleamide 5099-98-9 C25H41NO3
N-(3,4-dihydroxybenzyl)oleamide
—— N-[(4-chlorophenyl)methyl]-3-(3,4-dihydroxyphenyl)propanamide 1609176-86-4 C16H16ClNO3
N-[(4-chlorophenyl)methyl]-3-(3,4-dihydroxyphenyl)propanamide
—— 5,17-dichloro-4,6,11,16,18,23-hexamethyl-25,26,27,28-tetrahydroxycalix<4>arene 137695-97-7 C34H34Cl2O4
5,17-dichloro-4,6,11,16,18,23-hexamethyl-25,26,27,28-tetrahydroxycalix<4>arene
—— Benzenepropanal, 4-chloro-3-hydroxy- 1261821-64-0 C9H9ClO2
Benzenepropanal, 4-chloro-3-hydroxy-
—— 2-Fluor-3-(3,4-dihydroxy-phenyl)-propionsaeure-hydrazid 22179-97-1 C9H11FN2O3
2-Fluor-3-(3,4-dihydroxy-phenyl)-propionsaeure-hydrazid
—— 1-(2'-hydroxy-3',4',6'-trimethoxyphenyl)-3-(1-indol-3-yl)-prop-2-en-1-one 33268-80-3 C20H19NO5
1-(2'-hydroxy-3',4',6'-trimethoxyphenyl)-3-(1-indol-3-yl)-prop-2-en-1-one
—— o-vanilline thiocarbohydrazone 166899-44-1 C17H18N4O4S
o-vanilline thiocarbohydrazone
—— 37124-61-1 C19H17ClN2O4
—— 35516-08-6 C15H25N3O2
—— 2-Hydroxy-5-<2.4-dihydroxy-phenyl>-benzochinon-(1.4) 93353-52-7 C12H8O5
2-Hydroxy-5-<2.4-dihydroxy-phenyl>-benzochinon-(1.4)
—— 17α-ethinyl-3-methoxy-10,17-dihydroxy-9,10-secoestra-1,3,5(10)-trien-9-one 104150-57-4 C21H26O4
17α-ethinyl-3-methoxy-10,17-dihydroxy-9,10-secoestra-1,3,5(10)-trien-9-one
—— 4-fluoro-2,3,5,6-tetramethylphenol 300395-10-2 C10H13FO
4-fluoro-2,3,5,6-tetramethylphenol
—— 2-[(2-cyclooctyl-6-methylphenylimino)methyl]phenol 1072934-07-6 C22H27NO
2-[(2-cyclooctyl-6-methylphenylimino)methyl]phenol
—— amentol 1'-methyl ether 111455-63-1 C28H40O5
amentol 1'-methyl ether
—— 3-amino-4-[(4-hydroxyphenyl)methylene]-1H-pyrazol-5(4H)-one 1267391-77-4 C10H9N3O2
3-amino-4-[(4-hydroxyphenyl)methylene]-1H-pyrazol-5(4H)-one
—— 4-(3,4-Dicyano-2,5-dihydroxy-phenyl)-cyclohexanecarboxylic acid methyl ester 179617-84-6 C16H16N2O4
4-(3,4-Dicyano-2,5-dihydroxy-phenyl)-cyclohexanecarboxylic acid methyl ester
—— 4-(3-chloro-4-hydroxyphenyl)-6-ethyl-5-(3-phenylpropanoyl)-3,4-dihydropyrimidin-2(1H)-one 1224683-85-5 C21H21ClN2O3
4-(3-chloro-4-hydroxyphenyl)-6-ethyl-5-(3-phenylpropanoyl)-3,4-dihydropyrimidin-2(1H)-one
—— 4-(2-ethyl-hexyl)-resorcinol 83671-26-5 C14H22O2
4-(2-ethyl-hexyl)-resorcinol
—— 33851-98-8 C12H19N3O
—— 2-[2-[2-[2-[(2-Hydroxy-5-methylphenyl)methylideneamino]ethylamino]ethylamino]ethyliminomethyl]-4-methylphenol 1277164-44-9 C22H30N4O2
2-[2-[2-[2-[(2-Hydroxy-5-methylphenyl)methylideneamino]ethylamino]ethylamino]ethyliminomethyl]-4-methylphenol