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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
—— 6,6'-(((2-hydroxyethyl)azanediyl)bis(methylene))bis(2-methoxy-4-methylphenol) 1198601-79-4 C20H27NO5
6,6'-(((2-hydroxyethyl)azanediyl)bis(methylene))bis(2-methoxy-4-methylphenol)
—— 1-(4-Benzyloxy-2-hydroxyphenyl)-4-(3',4'-dimethoxyphenoxy)-2-butyn-1-one 56484-59-4 C25H22O6
1-(4-Benzyloxy-2-hydroxyphenyl)-4-(3',4'-dimethoxyphenoxy)-2-butyn-1-one
—— 5,5'-Bis-(1-hydroxy-2,2-dimethyl-propyl)-3,3'-dimethoxy-biphenyl-2,2'-diol 38775-80-3 C24H34O6
5,5'-Bis-(1-hydroxy-2,2-dimethyl-propyl)-3,3'-dimethoxy-biphenyl-2,2'-diol
—— hexyl-[2-(4-hydroxy-phenoxy)-ethyl]-dimethyl-ammonium; bromide 132753-64-1 Br*C16H28NO2
hexyl-[2-(4-hydroxy-phenoxy)-ethyl]-dimethyl-ammonium; bromide
—— 4-<6-Chlor-2,4-dinitro-3-methyl-phenylazo>-2-methyl-phenol 93309-36-5 C14H11ClN4O5
4-<6-Chlor-2,4-dinitro-3-methyl-phenylazo>-2-methyl-phenol
—— 2-(4-Hydroxyphenyl)-5-oxotetrahydrofuran-3-carboxylic acid 1399684-43-5 C11H10O5
2-(4-Hydroxyphenyl)-5-oxotetrahydrofuran-3-carboxylic acid
—— 6-Phenyl-4-<5-iod-2-hydroxy-phenyl>-cyclohexen-(3)-on-(2)-carbonsaeure-(1)-aethylester 102478-61-5 C21H19IO4
6-Phenyl-4-<5-iod-2-hydroxy-phenyl>-cyclohexen-(3)-on-(2)-carbonsaeure-(1)-aethylester
—— 4-(5-(p-tolylamino)-1,3,4-thiadiazol-2-yl)benzene-1,3-diol 117839-96-0 C15H13N3O2S
4-(5-(p-tolylamino)-1,3,4-thiadiazol-2-yl)benzene-1,3-diol
—— 1-(2-bromoethyl)-3-{[2-(4-methoxyphenyl)ethoxy]methyl}benzene 851859-48-8 C18H21BrO2
1-(2-bromoethyl)-3-{[2-(4-methoxyphenyl)ethoxy]methyl}benzene
—— acetovanillone dimethyl ketal 144677-98-5 C11H16O4
acetovanillone dimethyl ketal
—— 4,6-bis-(2-hydroxy-phenyl)-4,5,6,7-tetrahydro-3a<i>H</i>-isoxazolo[4,3-<i>c</i>]pyridin-3-one 132961-19-4 C18H16N2O4
4,6-bis-(2-hydroxy-phenyl)-4,5,6,7-tetrahydro-3a<i>H</i>-isoxazolo[4,3-<i>c</i>]pyridin-3-one
—— 5-(2-hydroxyphenyl)-1,3,4-oxadiazol-(3H)-2-one 89939-35-5 C8H6N2O3
5-(2-hydroxyphenyl)-1,3,4-oxadiazol-(3H)-2-one
—— 5,6-Dihydro-2-o-hydroxyphenyl-4-phenyl-4H-1,3,4-oxadiazin-5-on 28669-15-0 C15H12N2O3
5,6-Dihydro-2-o-hydroxyphenyl-4-phenyl-4H-1,3,4-oxadiazin-5-on
—— 2-heptyl-5-isopentyl-3-methyl-hydroquinone 408310-94-1 C19H32O2
2-heptyl-5-isopentyl-3-methyl-hydroquinone
—— 1186126-06-6 C14H16N2O4
—— 4-Bromo-2-[2-(4-hydroxyphenyl)ethyliminomethyl]phenol 1369431-98-0 C15H14BrNO2
4-Bromo-2-[2-(4-hydroxyphenyl)ethyliminomethyl]phenol
—— 2-hydroxy-3,5-dimethoxy-4-methyl-6-nitrobenzenemethanol 136763-94-5 C10H13NO6
2-hydroxy-3,5-dimethoxy-4-methyl-6-nitrobenzenemethanol
—— <i>N</i>-cyclohexyl-3-hydroxy-mandelamidine; hydrochloride 109495-40-1 C14H20N2O2*ClH
<i>N</i>-cyclohexyl-3-hydroxy-mandelamidine; hydrochloride
—— diethyl (E)-2-(4-(2-hydroxy-5-methoxyphenyl)-2-methylbut-2-enyl)-2-(prop-2-ynyl)malonate 1233027-46-7 C22H28O6
diethyl (E)-2-(4-(2-hydroxy-5-methoxyphenyl)-2-methylbut-2-enyl)-2-(prop-2-ynyl)malonate
—— 2-(4-Chloro-2,6-dimethyl-phenoxy)-N-[2-(4-hydroxy-phenyl)-ethyl]-acetamide 63294-23-5 C18H20ClNO3
2-(4-Chloro-2,6-dimethyl-phenoxy)-N-[2-(4-hydroxy-phenyl)-ethyl]-acetamide
—— 910638-65-2 C21H27NO3S
—— 5-Difluoromethyl-3-(2-hydroxy-5-methyl-phenyl)-4,5-dihydro-isoxazol-5-ol 511528-90-8 C11H11F2NO3
5-Difluoromethyl-3-(2-hydroxy-5-methyl-phenyl)-4,5-dihydro-isoxazol-5-ol
—— 4-ethoxy-2,3-dimethylphenol 1216256-55-1 C10H14O2
4-ethoxy-2,3-dimethylphenol
—— α,ω-decanediyldiammonium dipicrate 80056-70-8 2C6H3N3O7*C10H24N2
α,ω-decanediyldiammonium dipicrate
—— 2,6-dibromo-3,5-dimethyl-4-(3-methylenepent-4-yn-1-yl)phenol 1245947-86-7 C14H14Br2O
2,6-dibromo-3,5-dimethyl-4-(3-methylenepent-4-yn-1-yl)phenol
—— (5S)-3-acetyl-1-(4-bromophenyl)-5-[(4-hydroxyphenyl)methyl]-2,5-dihydro-1,2,4-triazin-6-one 139456-00-1 C18H16BrN3O3
(5S)-3-acetyl-1-(4-bromophenyl)-5-[(4-hydroxyphenyl)methyl]-2,5-dihydro-1,2,4-triazin-6-one
—— diisopropyl ((5-bromo-2-hydroxyphenyl)(hydroxy)methyl)phosphonate 33472-10-5 C13H20BrO5P
diisopropyl ((5-bromo-2-hydroxyphenyl)(hydroxy)methyl)phosphonate
—— 25,26,27,28-tetrahydroxy-5,11,17,23-tetrakis(propyldimethylsilyl)calix[4]arene 1092456-10-4 C48H72O4Si4
25,26,27,28-tetrahydroxy-5,11,17,23-tetrakis(propyldimethylsilyl)calix[4]arene
—— cis,cis-1,3,5-tris[(2,3-dihydroxybenzylidene)aminomethyl]cyclohexane 881842-12-2 C30H33N3O6
cis,cis-1,3,5-tris[(2,3-dihydroxybenzylidene)aminomethyl]cyclohexane
—— tributyl-(2,5-dihydroxy-phenyl)-phosphonium betaine 58877-86-4 C18H31O2P
tributyl-(2,5-dihydroxy-phenyl)-phosphonium betaine
—— 2,3,5-tribromo-4-methyl-6-nitrophenol 105590-20-3 C7H4Br3NO3
2,3,5-tribromo-4-methyl-6-nitrophenol
—— (E)-1-Cyano-2-(4-hydroxy-3-methoxy-phenyl)-ethenesulfonic acid amide 41827-48-9 C10H10N2O4S
(E)-1-Cyano-2-(4-hydroxy-3-methoxy-phenyl)-ethenesulfonic acid amide
—— 5-[(2-Cyclohexylimino-4-cyclopropyl-1,3-thiazol-3-yl)iminomethyl]benzene-1,2,4-triol 1459803-35-0 C19H23N3O3S
5-[(2-Cyclohexylimino-4-cyclopropyl-1,3-thiazol-3-yl)iminomethyl]benzene-1,2,4-triol
—— 3,3',3'',3'''-(((2,4,6,8-tetraethyl-14,16,34,36,54,56,74,76-octahydroxy-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-15,35,55,75-tetrayl)tetrakis(methylene))tetrakis(ethylazanediyl))tetrakis(2,2-dimethylpropanal) 1239171-45-9 C68H100N4O12
3,3',3'',3'''-(((2,4,6,8-tetraethyl-14,16,34,36,54,56,74,76-octahydroxy-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-15,35,55,75-tetrayl)tetrakis(methylene))tetrakis(ethylazanediyl))tetrakis(2,2-dimethylpropanal)
—— methyl 2-chloro-3-[4-[2-(4-methoxyphenyl)ethoxy]phenyl]propanoate 85003-16-3 C19H21ClO4
methyl 2-chloro-3-[4-[2-(4-methoxyphenyl)ethoxy]phenyl]propanoate
—— (R)-(+)-3-<4-<2-(cyclopropylmethoxy)ethyl>phenoxy>-1,2-propanodiol acetonide 108008-05-5 C18H26O4
(R)-(+)-3-<4-<2-(cyclopropylmethoxy)ethyl>phenoxy>-1,2-propanodiol acetonide
—— 3-(4-chloro-phenyl)-2-(2-hydroxy-5-methyl-phenyl)-2-methyl-thiazolidin-4-one 59271-92-0 C17H16ClNO2S
3-(4-chloro-phenyl)-2-(2-hydroxy-5-methyl-phenyl)-2-methyl-thiazolidin-4-one
—— 2-Hydroxythiobenzoyl-(2,6-dimethylmorpholin) 57954-40-2 C13H17NO2S
2-Hydroxythiobenzoyl-(2,6-dimethylmorpholin)
—— 3-(2,4-dihydroxybenzyl)-4-hydroxy-N-propylbutanamide 1515405-81-8 C14H21NO4
3-(2,4-dihydroxybenzyl)-4-hydroxy-N-propylbutanamide
—— 129275-75-8 C20H12HgN2O4S4
—— (2-Brom-4,5-methylendioxy-phenyl)-essigsaeure-(3-hydroxy-4-methoxy-benzyliden)-hydrazid 14502-07-9 C17H15BrN2O5
(2-Brom-4,5-methylendioxy-phenyl)-essigsaeure-(3-hydroxy-4-methoxy-benzyliden)-hydrazid
—— 5-Nitro-4-hydroxy-isophthalsaeure-dipentylester 93902-20-6 C18H25NO7
5-Nitro-4-hydroxy-isophthalsaeure-dipentylester
—— 3,4-dihydroxy-benzaldehyde-(3-chloro-2,4,6-trinitro-phenylhydrazone) 108798-53-4 C13H8ClN5O8
3,4-dihydroxy-benzaldehyde-(3-chloro-2,4,6-trinitro-phenylhydrazone)
—— 5-nitro-2-(4-nitro-benzenesulfonyl)-phenol 855419-70-4 C12H8N2O7S
5-nitro-2-(4-nitro-benzenesulfonyl)-phenol
—— [1-(benzo[d][1,3]dioxol-5-yl)-1H-tetrazol-5-yl](3-hydroxy-4-methoxyphenyl)methanone 1268445-72-2 C16H12N4O5
[1-(benzo[d][1,3]dioxol-5-yl)-1H-tetrazol-5-yl](3-hydroxy-4-methoxyphenyl)methanone
—— 3<i>exo</i>-acetoxy-7<i>exo</i>,9-dimethyl-9-aza-bicyclo[3.3.1]nonane; picrate 109156-50-5 C6H3N3O7*C12H21NO2
3<i>exo</i>-acetoxy-7<i>exo</i>,9-dimethyl-9-aza-bicyclo[3.3.1]nonane; picrate
—— (monochloro)oxozirconium(IV) 2,4-dinitrophenoxide 1129549-10-5 C6H3N2O5*Cl*OZr
(monochloro)oxozirconium(IV) 2,4-dinitrophenoxide
—— N-[(3-bromo-5-chloro-2-hydroxyphenyl)methylideneamino]-3-methoxy-2-methylbenzamide 1235562-95-4 C16H14BrClN2O3
N-[(3-bromo-5-chloro-2-hydroxyphenyl)methylideneamino]-3-methoxy-2-methylbenzamide
—— thiazolidine-2,4-dion-2-(5-ethyl-2,4-dihydroxy-benzylidenehydrazone) 108676-44-4 C12H13N3O3S
thiazolidine-2,4-dion-2-(5-ethyl-2,4-dihydroxy-benzylidenehydrazone)
—— o-Hydroxy-N-(3,3,4-trimethylthietan-2-ylidene)aniline 204649-42-3 C12H15NOS
o-Hydroxy-N-(3,3,4-trimethylthietan-2-ylidene)aniline