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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
—— 2.5-Dihydroxy-3-methylmercapto-toluol 139553-42-7 C8H10O2S
2.5-Dihydroxy-3-methylmercapto-toluol
—— prop-2-ynyl 5-(3,4-dihydroxyphenethylamino)-5-oxopentanoate 1446429-02-2 C16H19NO5
prop-2-ynyl 5-(3,4-dihydroxyphenethylamino)-5-oxopentanoate
—— 4-(2-pyridylazo)phenol 7687-22-1 C11H9N3O
4-(2-pyridylazo)phenol
—— 4-Chloro-2-(1-hydroxy-1-thiophen-2-ylethyl)phenol 86609-01-0 C12H11ClO2S
4-Chloro-2-(1-hydroxy-1-thiophen-2-ylethyl)phenol
—— tert-Butyl N-[{[(tert-butoxy)carbonyl]imino}({[(4-hydroxyphenyl)methyl]amino}) methyl]carbamate 191097-28-6 C18H27N3O5
tert-Butyl N-[{[(tert-butoxy)carbonyl]imino}({[(4-hydroxyphenyl)methyl]amino}) methyl]carbamate
—— 2-(4-((2,4-diaminopyrimidin-5-yl)methyl)-2,6-dimethoxyphenoxy)-N-(3,4-dihydroxyphenethyl)acetamide 1311968-22-5 C23H27N5O6
2-(4-((2,4-diaminopyrimidin-5-yl)methyl)-2,6-dimethoxyphenoxy)-N-(3,4-dihydroxyphenethyl)acetamide
—— 2-(5-(4-hydroxy-3-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)-N-(4-phenylthiazol-2-yl)acetamide 1277171-25-1 C27H24N4O3S
2-(5-(4-hydroxy-3-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)-N-(4-phenylthiazol-2-yl)acetamide
—— N-β-alanyldopamine 58077-93-3 C11H16N2O3*ClH
N-β-alanyldopamine
—— N1,N3-bis(3-methoxysalicylidene)diethylenetriamine 92449-60-0 C20H25N3O4
N1,N3-bis(3-methoxysalicylidene)diethylenetriamine
—— 7-chloro-5,10-dihydro-4H-thieno[3,2-c][1]benzazepin-4-one 42241-07-6 C8H12N2O2*2ClH
7-chloro-5,10-dihydro-4H-thieno[3,2-c][1]benzazepin-4-one
—— ethyl (Z)-3-((3,4-dihydroxyphenethyl)amino)but-2-enoate 1029376-07-5 C14H19NO4
ethyl (Z)-3-((3,4-dihydroxyphenethyl)amino)but-2-enoate
—— N-eicosanoyl dopamine 565186-20-1 C28H49NO3
N-eicosanoyl dopamine
—— 2-cyano-5-((3,4-dihydroxyphenethyl)amino)-5-oxopentan-2-yl benzodithioate 1146697-76-8 C21H22N2O3S2
2-cyano-5-((3,4-dihydroxyphenethyl)amino)-5-oxopentan-2-yl benzodithioate
—— N-<2-(3,4-dihydroxyphenyl)ethyl>thioacetamide 106787-74-0 C10H13NO2S
N-<2-(3,4-dihydroxyphenyl)ethyl>thioacetamide
—— 2,5-dimethoxy-1,4-benzoquinone anion radical 36376-14-4 C8H8O4
2,5-dimethoxy-1,4-benzoquinone anion radical
—— sulfinylbis[(5-chloro-2,4-dihydroxyphenyl)methanethione] 1298083-50-7 C14H8Cl2O5S3
sulfinylbis[(5-chloro-2,4-dihydroxyphenyl)methanethione]
—— 1-(2',5'-dihydroxyphenyl)-4-methylpyridinium chloride 692776-50-4 C12H12NO2*Cl
1-(2',5'-dihydroxyphenyl)-4-methylpyridinium chloride
—— 2-iodo-4-hydroxy-5-methoxy-benzylamine hydrochloride 872353-77-0 C8H10INO2*ClH
2-iodo-4-hydroxy-5-methoxy-benzylamine hydrochloride
—— prop-2-yn-1-yl-4-((3,4-dihydroxyphenethyl)amino)-4-oxobutanoate 1447848-31-8 C15H17NO5
prop-2-yn-1-yl-4-((3,4-dihydroxyphenethyl)amino)-4-oxobutanoate
—— tert-butyl (2-((tert-butoxycarbonyl)(2-(10-((3,4-dihydroxyphenethyl)amino)-10-oxodecanamido)ethyl)amino)ethyl)(2-((tert-butoxycarbonyl)amino)ethyl)carbamate 1186221-79-3 C39H67N5O10
tert-butyl (2-((tert-butoxycarbonyl)(2-(10-((3,4-dihydroxyphenethyl)amino)-10-oxodecanamido)ethyl)amino)ethyl)(2-((tert-butoxycarbonyl)amino)ethyl)carbamate
—— 7-[3-(tert-butoxycarbonylamino)propyl]-N,N′,N′′-tris[2-(3,4-dihydroxyphenyl)ethyl]adamantane-1,3,5-tricarboxamide 1448150-57-9 C45H58N4O11
7-[3-(tert-butoxycarbonylamino)propyl]-N,N′,N′′-tris[2-(3,4-dihydroxyphenyl)ethyl]adamantane-1,3,5-tricarboxamide
—— 1-[(2-N,N-dimethylpropyldiamino-3,4-dioxocyclobut-1-en-1-yl)]-12-[((2-(3,4-dihydroxyphenethyl)amino)-3,4-dioxocyclobut-1-en-1-yl)]dodecanediamine 1421366-07-5 C33H49N5O6
1-[(2-N,N-dimethylpropyldiamino-3,4-dioxocyclobut-1-en-1-yl)]-12-[((2-(3,4-dihydroxyphenethyl)amino)-3,4-dioxocyclobut-1-en-1-yl)]dodecanediamine
—— 3-((3,4-dihydroxyphenethyl)amino)-4-((3-(N,N-dimethylamino)propyl)amino)cyclobut-3-ene-1,2-dione 1421365-95-8 C17H23N3O4
3-((3,4-dihydroxyphenethyl)amino)-4-((3-(N,N-dimethylamino)propyl)amino)cyclobut-3-ene-1,2-dione
—— 1-((3,4-dihydroxyphenethyl)amino)-2-methyl-1-oxopropan-2-yl isobutyl carbonotrithioate 1314094-48-8 C17H25NO3S3
1-((3,4-dihydroxyphenethyl)amino)-2-methyl-1-oxopropan-2-yl isobutyl carbonotrithioate
—— N-myristoyl dopamine 1107064-73-2 C22H37NO3
N-myristoyl dopamine
—— N,5-di-tert-butyl-2-hydroxy-3-nitrobenzamide 849362-97-6 C15H22N2O4
N,5-di-tert-butyl-2-hydroxy-3-nitrobenzamide
—— 1-(2-(iodo-125I)-4-(2-methoxyethyl)phenoxy)-3-(isopropylamino)propan-2-ol 1251957-60-4 C15H24INO3
1-(2-(iodo-125I)-4-(2-methoxyethyl)phenoxy)-3-(isopropylamino)propan-2-ol
—— 5-bromosalicylidene-(5-nitro-2-hydroxyaniline) 57039-59-5 C13H9BrN2O4
5-bromosalicylidene-(5-nitro-2-hydroxyaniline)
—— 5-S-cysteaminyldopamine dihydrochloride 77504-34-8 C10H16N2O2S*2ClH
5-S-cysteaminyldopamine dihydrochloride
—— 3,5-dichloro-2-hydroxy-6-methyl-benzyl alcohol 118872-28-9 C8H8Cl2O2
3,5-dichloro-2-hydroxy-6-methyl-benzyl alcohol
—— N-(5-methyl-2-hydroxyphenyl)-2-hydroxy-5-chlorobenzaldimine 70693-84-4 C14H12ClNO2
N-(5-methyl-2-hydroxyphenyl)-2-hydroxy-5-chlorobenzaldimine
—— 2-((hexadecylimino)methyl)phenol 16308-55-7 C23H39NO
2-((hexadecylimino)methyl)phenol
—— 202145-92-4 C34H58N4O8
—— S-methyl-β-N-(2-hydroxyphenylethylene)dithiocarbazate 42204-02-4 C10H12N2OS2
S-methyl-β-N-(2-hydroxyphenylethylene)dithiocarbazate
—— (S)-N1-{3-[4-(3-Amino-propylamino)-butylamino]-propyl}-2-[2-(2,4-dihydroxy-phenyl)-acetylamino]-succinamide; hydrochloride 113954-21-5 C22H38N6O5*ClH
(S)-N1-{3-[4-(3-Amino-propylamino)-butylamino]-propyl}-2-[2-(2,4-dihydroxy-phenyl)-acetylamino]-succinamide; hydrochloride
—— e bond and ligand) 67777-63-3 C11H13NO3
e bond and ligand)
—— 2-(4-hydroxy-3-methoxyphenyl)-N-(3-(4-(2-(4-hydroxy-3-methoxyphenyl)acetamido)butylamino)propyl)acetamide trifluoroacetic acid salt 1416971-76-0 C2HF3O2*C25H35N3O6
2-(4-hydroxy-3-methoxyphenyl)-N-(3-(4-(2-(4-hydroxy-3-methoxyphenyl)acetamido)butylamino)propyl)acetamide trifluoroacetic acid salt
—— (o-hydroxyphenyl)phenylphosphineoxide 85599-05-9 C12H11O2P
(o-hydroxyphenyl)phenylphosphineoxide
—— 5,5'-dithiobis(salicylaldehyde-2-hydroxyacetophenoneazine) 107321-91-5 C30H26N4O4S2
5,5'-dithiobis(salicylaldehyde-2-hydroxyacetophenoneazine)
—— 3-(4,5-dibromo-3-hydroxyphenyl)-2-thioxo-1,3-thiazolidin-4-one 76187-11-6 C9H5Br2NO2S2
3-(4,5-dibromo-3-hydroxyphenyl)-2-thioxo-1,3-thiazolidin-4-one
—— 2-bromo-3-methoxy-6-vinylphenol 1358063-31-6 C9H9BrO2
2-bromo-3-methoxy-6-vinylphenol
—— (E)-4-(pyridin-4-yldiazenyl)phenol 253333-13-0 C11H9N3O
(E)-4-(pyridin-4-yldiazenyl)phenol
—— (S)-3-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propanoic acid (S)-3-aminopiperidine salt 1460202-50-9 C5H12N2*C15H14O5
(S)-3-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propanoic acid (S)-3-aminopiperidine salt
—— 2-Bromo-6-methoxy-3-((E)-2-phenylsulfanyl-vinyl)-phenol 871951-77-8 C15H13BrO2S
2-Bromo-6-methoxy-3-((E)-2-phenylsulfanyl-vinyl)-phenol
—— (4-hydroxybenzaldehyde)dithiocarbazate 118718-22-2 C15H14N2OS2
(4-hydroxybenzaldehyde)dithiocarbazate
—— 2-methyl-5-methylsulfanyl-hydroquinone 859497-13-5 C8H10O2S
2-methyl-5-methylsulfanyl-hydroquinone
—— 2-isopropoxy-3-methoxy-6-iodophenol 905751-80-6 C10H13IO3
2-isopropoxy-3-methoxy-6-iodophenol
—— 3-methyl-4-trimethylsilanyl-phenol 17876-96-9 C10H16OSi
3-methyl-4-trimethylsilanyl-phenol
—— 2-(((3-((4-((3-aminopropyl)amino)butyl)amino)propyl)imino)methyl)phenol 1533410-82-0 C17H30N4O
2-(((3-((4-((3-aminopropyl)amino)butyl)amino)propyl)imino)methyl)phenol
—— N,N'-bis(5-bromo-3-methoxysalicylidene)propylene-1,3-diamine 263350-93-2 C19H20Br2N2O4
N,N'-bis(5-bromo-3-methoxysalicylidene)propylene-1,3-diamine