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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
—— 2,6-Dimethoxy-4-(3-triethylsilylpropyl)phenol 351203-00-4 C17H30O3Si
2,6-Dimethoxy-4-(3-triethylsilylpropyl)phenol
—— 2.4.6.2'.4'.6'-Hexanitro-3.3'-dioxy-azobenzol 134282-24-9 C12H4N8O14
2.4.6.2'.4'.6'-Hexanitro-3.3'-dioxy-azobenzol
—— 4-[4-(5-Piperidin-1-yl-penta-1,3-diynyl)-phenylazo]-phenol 36622-19-2 C22H21N3O
4-[4-(5-Piperidin-1-yl-penta-1,3-diynyl)-phenylazo]-phenol
—— 5-(3,4-dihydroxy-5-methoxyphenyl)-2,2,5-trimethyl-1,3-dioxane-4,6-dione 1026685-66-4 C14H16O7
5-(3,4-dihydroxy-5-methoxyphenyl)-2,2,5-trimethyl-1,3-dioxane-4,6-dione
—— 2-hydroxy-3,5-dinitro-benzoic acid isopropyl ester 52041-11-9 C10H10N2O7
2-hydroxy-3,5-dinitro-benzoic acid isopropyl ester
—— 5-benzyl-3-hydroxy-4-(4-hydroxy-phenyl)-1-(3-imidazol-1-yl-propyl)-1,5-dihydro-pyrrol-2-one 1024608-19-2 C23H23N3O3
5-benzyl-3-hydroxy-4-(4-hydroxy-phenyl)-1-(3-imidazol-1-yl-propyl)-1,5-dihydro-pyrrol-2-one
—— 5-(2-hydroxy-3-methoxy-phenyl)-[1,2]dithiol-3-thione 90920-87-9 C10H8O2S3
5-(2-hydroxy-3-methoxy-phenyl)-[1,2]dithiol-3-thione
—— 3-Ethylsulfanylmethyl-2-hydroxy-6-methyl-cyclohepta-2,4,6-trienone 27168-00-9 C11H14O2S
3-Ethylsulfanylmethyl-2-hydroxy-6-methyl-cyclohepta-2,4,6-trienone
—— 130106-91-1 C15H19N3OS
—— 2-Bromo-4-fluoro-3-(trifluoromethoxy)phenol 1807123-25-6 C7H3BrF4O2
2-Bromo-4-fluoro-3-(trifluoromethoxy)phenol
—— 5-Bromo-2,4-dihydroxybenzaldehyde 2-(4-amino-5-methyl-4H-1,2,4-triazol-3-yl)hydrazone 357158-12-4 C10H11BrN6O2
5-Bromo-2,4-dihydroxybenzaldehyde 2-(4-amino-5-methyl-4H-1,2,4-triazol-3-yl)hydrazone
—— Salicylaldehyd-(2-hydroxy-1-methyl-ethylimin) 3509-49-7 C10H13NO2
Salicylaldehyd-(2-hydroxy-1-methyl-ethylimin)
—— N,N'''-disalicylidene-μ-disulfido-dicarboxamidrazone 130956-36-4 C16H16N6O2S2
N,N'''-disalicylidene-μ-disulfido-dicarboxamidrazone
—— <i>o</i>-phenylenediamine; picrate 78576-95-1 C6H3N3O7*C6H8N2
<i>o</i>-phenylenediamine; picrate
—— 4-(hydrazonomethyl)phenol 52211-82-2 C7H8N2O
4-(hydrazonomethyl)phenol
—— N-(α-Vanillyliden-ethyl)-acetamid 15158-54-0 C12H15NO3
N-(α-Vanillyliden-ethyl)-acetamid
—— p-(2,3,3a,6-tetrahydro-4-methylpyrazolo<3,4-C>pyrazol-3-yl)phenol 76794-85-9 C17H16N4O
p-(2,3,3a,6-tetrahydro-4-methylpyrazolo<3,4-C>pyrazol-3-yl)phenol
—— Isopropylmalonsaeure-di-(salicyliden)-hydrazid 26878-68-2 C20H22N4O4
Isopropylmalonsaeure-di-(salicyliden)-hydrazid
—— 5-(4-hydroxy-3,5-dimethylphenyl)-3H-1,2-dithiole-3-thione 1023740-35-3 C11H10OS3
5-(4-hydroxy-3,5-dimethylphenyl)-3H-1,2-dithiole-3-thione
—— 2-amino-6-chlorophenol hydrochloride 126892-07-7 C6H6ClNO*ClH
2-amino-6-chlorophenol hydrochloride
—— N,N-(2,6-pyridinediyldimethylidyne)bis(2-hydroxy-4-nitrobenzenamine) 1429408-81-0 C19H13N5O6
N,N-(2,6-pyridinediyldimethylidyne)bis(2-hydroxy-4-nitrobenzenamine)
—— (2Z,4E,6E)-4-amino-6-((4-hydroxyphenyl)imino)hexa-2,4-dienoic acid 145005-84-1 C12H12N2O3
(2Z,4E,6E)-4-amino-6-((4-hydroxyphenyl)imino)hexa-2,4-dienoic acid
—— [1-(2-Hydroxy-4-methoxyphenyl)ethylideneamino]urea 116235-60-0 C10H13N3O3
[1-(2-Hydroxy-4-methoxyphenyl)ethylideneamino]urea
—— 2-(3-Hydroxy-2,5-diiodophenyl)acetonitrile 1806349-73-4 C8H5I2NO
2-(3-Hydroxy-2,5-diiodophenyl)acetonitrile
—— tert-butyl 4-(5-cyclopentyl-4-hydroxy-2-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate 1233531-18-4 C21H28N2O5
tert-butyl 4-(5-cyclopentyl-4-hydroxy-2-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate
—— 1419172-36-3 C21H20O6S2
—— 2-heptyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 1542755-53-2 C19H31BO3
2-heptyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
—— N,N'-bis[(4S<sub>p</sub>,13R<sub>p</sub>)-13-phenyl-4-[2.2]paracyclophanyl]-1,2-ethylenediamine 1029694-13-0 C46H44N2
N,N'-bis[(4S<sub>p</sub>,13R<sub>p</sub>)-13-phenyl-4-[2.2]paracyclophanyl]-1,2-ethylenediamine
—— 5-tert-butyl-11,17,23,29-tetramethyl-31,32,33,34,35-pentahydroxycalix[5]arene 78666-06-5 C43H46O5
5-tert-butyl-11,17,23,29-tetramethyl-31,32,33,34,35-pentahydroxycalix[5]arene
—— 3-(4-hydroxy-benzylidene)-5,6,7,8-tetrahydro-benzo[<i>d</i>]imidazo[2,1-<i>b</i>]thiazol-2-one 63751-35-9 C16H14N2O2S
3-(4-hydroxy-benzylidene)-5,6,7,8-tetrahydro-benzo[<i>d</i>]imidazo[2,1-<i>b</i>]thiazol-2-one
—— 3-methyl-benzo[<i>b</i>]selenophen-5-ol 60814-04-2 C9H8OSe
3-methyl-benzo[<i>b</i>]selenophen-5-ol
—— 2,4-Bis[[tert-butyl(dimethyl)silyl]oxymethyl]phenol 1057086-63-1 C20H38O3Si2
2,4-Bis[[tert-butyl(dimethyl)silyl]oxymethyl]phenol
—— 4,5-Dihydroxy-4,5-bis-<2,4-dihydroxy-phenyl>-octan-1,8-disaeure-dimethylester 14328-05-3 C22H26O10
4,5-Dihydroxy-4,5-bis-<2,4-dihydroxy-phenyl>-octan-1,8-disaeure-dimethylester
—— 6-(4-bromo-3-hydroxyphenyl)-2,3-dihydro-1,4-diazepinium perchlorate 102536-29-8 C11H11BrN2O*ClHO4
6-(4-bromo-3-hydroxyphenyl)-2,3-dihydro-1,4-diazepinium perchlorate
—— 3-Salicyliden-2,4-tetrahydrofurandion 342625-39-2 C11H8O4
3-Salicyliden-2,4-tetrahydrofurandion
—— 4-(adamantan-1-ylaminomethyl)benzene-1,2,3-triol 1443121-45-6 C17H23NO3
4-(adamantan-1-ylaminomethyl)benzene-1,2,3-triol
—— 3-Methyl-2-[trans-6-(m-hydroxyphenyl)-3-hexenyl]-2-cyclopentenone 53214-77-0 C18H22O2
3-Methyl-2-[trans-6-(m-hydroxyphenyl)-3-hexenyl]-2-cyclopentenone
—— 5-imino-4-[(2'-amino-4'-hydroxy-5'-methyl)phenyl]imino-3-methyl-1-(β-hydroxyethyl)pyrazoline 197433-71-9 C13H17N5O2
5-imino-4-[(2'-amino-4'-hydroxy-5'-methyl)phenyl]imino-3-methyl-1-(β-hydroxyethyl)pyrazoline
—— 1336808-63-9 C9H7Br3O2
—— 2-Formamido-6-methoxyphenol 51029-17-5 C8H9NO3
2-Formamido-6-methoxyphenol
—— Thioschwefligesaeure-bis-(6-hydroxy-4-methyl-benzylester) 53055-33-7 C16H18O4S2
Thioschwefligesaeure-bis-(6-hydroxy-4-methyl-benzylester)
—— 1-cyclohexyl-2-(2-hydroxy-3-methylphenyl)propan-1-one 1607446-87-6 C16H22O2
1-cyclohexyl-2-(2-hydroxy-3-methylphenyl)propan-1-one
—— {Fe(II)-(gallacetophenone phenylhydrazone)2(water)2} 125920-89-0 C28H30FeN4O8
{Fe(II)-(gallacetophenone phenylhydrazone)2(water)2}
—— 2-hydroxy-5-methoxyphenyl(2,2'-bis-3-methylindolyl)methane 1393904-92-1 C26H24N2O2
2-hydroxy-5-methoxyphenyl(2,2'-bis-3-methylindolyl)methane
—— methyl 3-(3-chloro-2-hydroxyphenyl)-3-(3-methoxy-3-oxopropyl)sulfanylpropanoate 114106-29-5 C14H17ClO5S
methyl 3-(3-chloro-2-hydroxyphenyl)-3-(3-methoxy-3-oxopropyl)sulfanylpropanoate
—— 103375-95-7 C6H3N3O7*C12H16N2S
—— 4,5-dichloro-3-hydroxy-6-(2-methylallyloxy)phthalonitrile 1449251-49-3 C12H8Cl2N2O2
4,5-dichloro-3-hydroxy-6-(2-methylallyloxy)phthalonitrile
—— 5-(1,2-dihydroxy-ethyl)-3-hydroxy-4-(4-hydroxy-phenyl)-1-(3-imidazol-1-yl-propyl)-1,5-dihydro-pyrrol-2-one 1024608-02-3 C18H21N3O5
5-(1,2-dihydroxy-ethyl)-3-hydroxy-4-(4-hydroxy-phenyl)-1-(3-imidazol-1-yl-propyl)-1,5-dihydro-pyrrol-2-one
—— α-(3-Hydroxy-4-nitrobenzylthio)-essigsaeure 50434-04-3 C9H9NO5S
α-(3-Hydroxy-4-nitrobenzylthio)-essigsaeure
—— <i>N</i>-ethyl-aniline; picrate 14953-20-9 C6H3N3O7*C8H11N
<i>N</i>-ethyl-aniline; picrate