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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
—— (4R)-1-(3,5-dihydroxyphenyl)-4-hydroxypentan-2-one 1347706-73-3 C11H14O4
(4R)-1-(3,5-dihydroxyphenyl)-4-hydroxypentan-2-one
—— (S)-N-(2-hydroxy-3-methoxybenzylidene)-1-phenylethylamine 1204611-64-2 C16H17NO2
(S)-N-(2-hydroxy-3-methoxybenzylidene)-1-phenylethylamine
—— N,N'-bis[2-{(salicylidenimine)amino}ethyl]piperazine 80744-39-4 C22H28N4O2
N,N'-bis[2-{(salicylidenimine)amino}ethyl]piperazine
—— 3-Oleylcatechol 7573-09-3 C24H40O2
3-Oleylcatechol
—— 4-(4,6-bis-octylsulfanyl-[1,3,5]triazin-2-ylamino)-2-methyl-phenol 989-57-1 C26H42N4OS2
4-(4,6-bis-octylsulfanyl-[1,3,5]triazin-2-ylamino)-2-methyl-phenol
—— [3-(2,4-dioxo-thiazolidin-3-yl)-2-nitro-phenyl]-mercury(1+); acetate 73219-74-6 C11H8HgN2O6S
[3-(2,4-dioxo-thiazolidin-3-yl)-2-nitro-phenyl]-mercury(1+); acetate
—— 1-{2-[(2-hydroxy-benzylidene)-hydrazono]-4-methyl-3-phenyl-2,3-dihydrothiazol-5-yl}-ethanone 1136238-75-9 C19H17N3O2S
1-{2-[(2-hydroxy-benzylidene)-hydrazono]-4-methyl-3-phenyl-2,3-dihydrothiazol-5-yl}-ethanone
—— 6-Methoxy-4-methyl-2-(2-hydroxy-α-methyl-benzylidenhydrazino)-pyrimidin 92296-31-6 C14H16N4O2
6-Methoxy-4-methyl-2-(2-hydroxy-α-methyl-benzylidenhydrazino)-pyrimidin
—— 1-acetyl-3-[(5-hydroxy-2,4-dimethoxy-3-methylphenyl)methyl]piperazine-2,5-dione 127103-52-0 C16H20N2O6
1-acetyl-3-[(5-hydroxy-2,4-dimethoxy-3-methylphenyl)methyl]piperazine-2,5-dione
—— 3-(4-hydroxy-3,5-dimethoxyphenyl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione 1215294-02-2 C20H16N2O5
3-(4-hydroxy-3,5-dimethoxyphenyl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione
—— 6,6'-dimethoxy-3,3'-(piperazine-1,4-diyldiimino-dimethyl)-bis-phenol 21323-29-5 C20H24N4O4
6,6'-dimethoxy-3,3'-(piperazine-1,4-diyldiimino-dimethyl)-bis-phenol
—— 41377-94-0 C16H13BrN4O4S
—— 2,4-Dihydroxy-5-methoxyphenylglycol 2964-10-5 C9H12O5
2,4-Dihydroxy-5-methoxyphenylglycol
—— 17646-24-1 C14H9FN4OS
—— 5-Brommethyl-o-vanillin 2973-70-8 C9H9BrO3
5-Brommethyl-o-vanillin
—— 5-Methoxy-4-tert.-butyloxy-2-tert.-butyl-phenol 21243-79-8 C15H24O3
5-Methoxy-4-tert.-butyloxy-2-tert.-butyl-phenol
—— 4-Cyclohex-2-enyl-2-methyl-phenol 40141-06-8 C13H16O
4-Cyclohex-2-enyl-2-methyl-phenol
—— 1-Ethyl-1,2,3,6-Tetrahydro-5-(2-hydroxyphenyl)-pyridin 30455-71-1 C13H17NO
1-Ethyl-1,2,3,6-Tetrahydro-5-(2-hydroxyphenyl)-pyridin
—— 4-<(Methylthiomethyl)thio>-m-kresol 37708-42-2 C9H12OS2
4-<(Methylthiomethyl)thio>-m-kresol
—— 2-(1-Methylpropoxy)-4,6-dinitrophenol 70491-12-2 C10H12N2O6
2-(1-Methylpropoxy)-4,6-dinitrophenol
—— 3,4,5-Trimethoxy-6-brom-salicylaldehyd 65162-37-0 C10H11BrO5
3,4,5-Trimethoxy-6-brom-salicylaldehyd
—— 3-<5'-Amino-4'-(3'',4'',5''-trihydroxyphenyl)pyrazol-1'-yl>-5,6-diphenyl-1,2,4-triazine 118509-04-9 C24H18N6O3
3-<5'-Amino-4'-(3'',4'',5''-trihydroxyphenyl)pyrazol-1'-yl>-5,6-diphenyl-1,2,4-triazine
—— 5-(3-Furanyl)-2-hydroxy-3-methoxybenzaldehyde 1093118-63-8 C12H10O4
5-(3-Furanyl)-2-hydroxy-3-methoxybenzaldehyde
—— 4,6-di[(1E)-N-(2-hydroxy-4-methylphenyl)ethanimidoyl]benzene-1,3-diol 1403748-52-6 C24H24N2O4
4,6-di[(1E)-N-(2-hydroxy-4-methylphenyl)ethanimidoyl]benzene-1,3-diol
—— 4-(2-((3-hydroxy-4-methoxyphenethyl)amino)ethyl)-2-methoxyphenol hydrochloride 75608-44-5 C18H23NO4*ClH
4-(2-((3-hydroxy-4-methoxyphenethyl)amino)ethyl)-2-methoxyphenol hydrochloride
—— 2-(2'-hydroxy-5'-nitrophenyl)-5-tert-butyl-1,3-dithiane 152821-31-3 C14H19NO3S2
2-(2'-hydroxy-5'-nitrophenyl)-5-tert-butyl-1,3-dithiane
—— 4-bromo-2-{[6-(3-chloro-4-fluoro-phenylamino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]-hydrazonomethyl}-6-methoxy-phenol 851661-46-6 C18H12BrClFN7O3
4-bromo-2-{[6-(3-chloro-4-fluoro-phenylamino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]-hydrazonomethyl}-6-methoxy-phenol
—— 5-{[2-(3,4-Dichloro-phenyl)-2-hydroxy-ethylamino]-methyl}-2-methoxy-phenol 34047-51-3 C16H17Cl2NO3
5-{[2-(3,4-Dichloro-phenyl)-2-hydroxy-ethylamino]-methyl}-2-methoxy-phenol
—— tris(2-hydroxyethyl)ammonium 2-nitrophenolate 57695-36-0 C6H5NO3*C6H15NO3
tris(2-hydroxyethyl)ammonium 2-nitrophenolate
—— 2-{(E)-((1S)-2-hydroxy-1-phenylethylimino)methyl}phenol 113866-46-9 C15H15NO2
2-{(E)-((1S)-2-hydroxy-1-phenylethylimino)methyl}phenol
—— bis[2-((2-hydroxy-3-methoxybenzyl)amino)ethyl]amine 316135-34-9 C20H29N3O4
bis[2-((2-hydroxy-3-methoxybenzyl)amino)ethyl]amine
—— tris-O,O',O''-((S)-[2.2]paracyclophan-4-yl) borate 1114975-10-8 C48H45BO3
tris-O,O',O''-((S)-[2.2]paracyclophan-4-yl) borate
—— 2-methyl-4-triisopropylsilanyloxy-phenol 1001208-14-5 C16H28O2Si
2-methyl-4-triisopropylsilanyloxy-phenol
—— 5,5',5''-trihexyl-4,4',4''-[1,3,5]triazine-2,4,6-triyl-tris-benzene-1,3-diol 107385-09-1 C39H51N3O6
5,5',5''-trihexyl-4,4',4''-[1,3,5]triazine-2,4,6-triyl-tris-benzene-1,3-diol
—— 2,4-dinitro-5-(N,N-diethylamino)phenol-4-N<sup>15</sup> 136833-41-5 C10H13N3O5
2,4-dinitro-5-(N,N-diethylamino)phenol-4-N<sup>15</sup>
—— N'-(2-hydroxy-5-methylphenyl)-N,N-bis(2-methylpropyl)methanimidamide 1323158-80-0 C16H26N2O
N'-(2-hydroxy-5-methylphenyl)-N,N-bis(2-methylpropyl)methanimidamide
—— 4-benzo[1,3]dioxol-5-yl-1-(3-hydroxy-4-methoxy-benzyl)-piperidine-2,6-dione 111065-42-0 C20H19NO6
4-benzo[1,3]dioxol-5-yl-1-(3-hydroxy-4-methoxy-benzyl)-piperidine-2,6-dione
—— 2-[1-(5-Vinyl-pyridin-2-yl)-ethyl]-phenol 41603-22-9 C15H15NO
2-[1-(5-Vinyl-pyridin-2-yl)-ethyl]-phenol
—— 4-(2-Hydroxy-4-methylpent-4-en-2-yl)phenol 939969-36-5 C12H16O2
4-(2-Hydroxy-4-methylpent-4-en-2-yl)phenol
—— 4-Fluor-2-sec-pentyl-phenol 443-11-8 C11H15FO
4-Fluor-2-sec-pentyl-phenol
—— 3-(2-Brom-4-methoxy-5-hydroxy-phenyl)-propionsaeureaethylester 25437-82-5 C12H15BrO4
3-(2-Brom-4-methoxy-5-hydroxy-phenyl)-propionsaeureaethylester
—— α-Methyl-α-(2-hydroxy-5-methylphenyl)-2-furanmethanol 89177-77-5 C13H14O3
α-Methyl-α-(2-hydroxy-5-methylphenyl)-2-furanmethanol
—— (S)-3-((R)-2-allylhexanoyl)-4-(4-hydroxybenzyl)oxazolidin-2-one 1010683-85-8 C19H25NO4
(S)-3-((R)-2-allylhexanoyl)-4-(4-hydroxybenzyl)oxazolidin-2-one
—— Thiophosphoric acid S-(5-chloro-2-hydroxy-phenyl) ester O,O'-dimethyl ester 3586-49-0 C8H10ClO4PS
Thiophosphoric acid S-(5-chloro-2-hydroxy-phenyl) ester O,O'-dimethyl ester
—— 1-benzo[1,3]dioxol-5-ylmethyl-4-(3,4,5-trimethoxy-benzoyl)-piperazine 94917-37-0 C21H24N2O6
1-benzo[1,3]dioxol-5-ylmethyl-4-(3,4,5-trimethoxy-benzoyl)-piperazine
—— 2,5,6-Trihydroxy-1,3-dimethyl-4-aethyl-benzol 90926-34-4 C10H14O3
2,5,6-Trihydroxy-1,3-dimethyl-4-aethyl-benzol
—— 2-(3-chloro-4-(4-methoxybenzyloxy)phenyl)ethanol 1147391-90-9 C16H17ClO3
2-(3-chloro-4-(4-methoxybenzyloxy)phenyl)ethanol
—— 5-(2-hydroxy-5-methoxyphenyl)-2(5H)-furanone 1397289-82-5 C11H10O4
5-(2-hydroxy-5-methoxyphenyl)-2(5H)-furanone
—— N-(5-acetamido-2-hydroxyphenyl)-2-nitro-4-trifluoromethyl aniline 141798-45-0 C15H12F3N3O4
N-(5-acetamido-2-hydroxyphenyl)-2-nitro-4-trifluoromethyl aniline
—— N-(2-hydroxybenzylidene)aniline hydrochloride 53451-71-1 C13H11NO*ClH
N-(2-hydroxybenzylidene)aniline hydrochloride