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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-Piperidin-1-yl-pentylsulfanyl)-benzene-1,4-diol; hydrochloride 123192-55-2 C16H25NO2S*ClH
2-(5-Piperidin-1-yl-pentylsulfanyl)-benzene-1,4-diol; hydrochloride
—— 2-ethoxy-3-methoxy-5-methyl-hydroquinone 90927-18-7 C10H14O4
2-ethoxy-3-methoxy-5-methyl-hydroquinone
—— 8,9:13,14-diseco-18-norestrone 81423-34-9 C17H24O2
8,9:13,14-diseco-18-norestrone
—— 4-(5-heptyl-1,3-dioxan-2-yl)phenol 81221-25-2 C17H26O3
4-(5-heptyl-1,3-dioxan-2-yl)phenol
—— 3,5-Dicyan-2,4-dimethyl-phenol 90842-09-4 C10H8N2O
3,5-Dicyan-2,4-dimethyl-phenol
—— (Z)-4-(3,3,3-trifluoroprop-1-en-1-yl)benzene-1,2-diol 1418317-39-1 C9H7F3O2
(Z)-4-(3,3,3-trifluoroprop-1-en-1-yl)benzene-1,2-diol
—— 1223515-70-5 C10H9ClN2OS
—— Co(HASc)2Cl2 140621-98-3 C18H22Cl2CoN6O4
Co(HASc)2Cl2
—— (E)-4-ethyl-N'-(2-hydroxybenzylidene)piperazine-1-carbothiohydrazide 1537866-14-0 C14H20N4OS
(E)-4-ethyl-N'-(2-hydroxybenzylidene)piperazine-1-carbothiohydrazide
—— 1159262-06-2 C35H34O4P2
—— (5R,6R)-5-Benzyl-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-1-[3-(3-methoxy-phenyl)-propionyl]-6-(2-trimethylsilanyl-ethoxymethoxy)-[1,2,4]triazepan-3-one 871905-21-4 C43H55N3O9Si
(5R,6R)-5-Benzyl-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-1-[3-(3-methoxy-phenyl)-propionyl]-6-(2-trimethylsilanyl-ethoxymethoxy)-[1,2,4]triazepan-3-one
—— 2-(4-hydroxy-benzyl)-3,4-dimethyl-1-(3-methyl-but-2-enyl)-piperidin-3-ol 63482-35-9 C19H29NO2
2-(4-hydroxy-benzyl)-3,4-dimethyl-1-(3-methyl-but-2-enyl)-piperidin-3-ol
—— 2-<β-(4'-Hydroxyphenyl)-ethyl>-4,4-dimethyl-Δ1-pyrrolin 78744-76-0 C14H19NO
2-<β-(4'-Hydroxyphenyl)-ethyl>-4,4-dimethyl-Δ1-pyrrolin
—— 3-(2-ethylbutyl)-5-(4-hydroxy-3-methoxy-5-trifluoromethylbenzylidene)thiazolidine-2,4-dione 1372864-89-5 C18H20F3NO4S
3-(2-ethylbutyl)-5-(4-hydroxy-3-methoxy-5-trifluoromethylbenzylidene)thiazolidine-2,4-dione
—— Salicylaldehyd-octadecylthiosemicarbazon 7248-08-0 C26H45N3OS
Salicylaldehyd-octadecylthiosemicarbazon
—— 3-Hydroxy-2,4,6-trimethyl-benzonitrile N-oxide 135778-94-8 C10H11NO2
3-Hydroxy-2,4,6-trimethyl-benzonitrile N-oxide
—— 2-(dodecyl-13-crown-4)phenol 106420-02-4 C28H48O5
2-(dodecyl-13-crown-4)phenol
—— (E)-7-(benzylthio)-1,7-bis(4-hydroxy-3-methoxyphenyl)hept-1-ene-3,5-dione 1118765-51-7 C28H28O6S
(E)-7-(benzylthio)-1,7-bis(4-hydroxy-3-methoxyphenyl)hept-1-ene-3,5-dione
—— 2-Dimethylaminomethyl-5-methoxyhydrochinon 42973-51-3 C10H15NO3
2-Dimethylaminomethyl-5-methoxyhydrochinon
—— (S)-4-isopropyl-2-(2'-hydroxyphenyl)-2-thiazoline 1437326-49-2 C12H15NOS
(S)-4-isopropyl-2-(2'-hydroxyphenyl)-2-thiazoline
—— 4-Allyl-2-chlor-6-methyl-phenol 41389-64-4 C10H11ClO
4-Allyl-2-chlor-6-methyl-phenol
—— 17646-28-5 C14H9FN4O2S
—— cyclotricatechylene-N,N-dimethylformamide 75247-87-9 31C3H7NO*10C21H18O6
cyclotricatechylene-N,N-dimethylformamide
—— N-Jodacetyl-2-(4-hydroxy-3-methoxyphenyl)-ethylamin 53527-15-4 C11H14INO3
N-Jodacetyl-2-(4-hydroxy-3-methoxyphenyl)-ethylamin
—— 5-(3,4-dihydroxybenzylidene)-3-(2-ethylbutyl)thiazolidine-2,4-dione 1372864-80-6 C16H19NO4S
5-(3,4-dihydroxybenzylidene)-3-(2-ethylbutyl)thiazolidine-2,4-dione
—— 4-(3',4'-dihydroxyphenyl)furan-2(5H)-one 7718-81-2 C10H8O4
4-(3',4'-dihydroxyphenyl)furan-2(5H)-one
—— 1,2-bis(benzyloxy)-4-(2′-hexadecyloxyethyl)benzene 1436383-09-3 C38H54O3
1,2-bis(benzyloxy)-4-(2′-hexadecyloxyethyl)benzene
—— 2,5-Dimethoxy-3-formyl-hydrochinon 34603-02-6 C9H10O5
2,5-Dimethoxy-3-formyl-hydrochinon
—— phenol; compound with butanone 13624-47-0 C4H8O*C6H6O
phenol; compound with butanone
—— [(3-Hydroxy-benzimidoyl)-aminooxy]-acetic acid ethyl ester 63409-74-5 C11H14N2O4
[(3-Hydroxy-benzimidoyl)-aminooxy]-acetic acid ethyl ester
—— (3-amino-5-chloro-4-hydroxy-phenyl)-arsonic acid 861788-80-9 C6H7AsClNO4
(3-amino-5-chloro-4-hydroxy-phenyl)-arsonic acid
—— 3-iodo-5-thiophen-3-ylphenol 1123157-89-0 C10H7IOS
3-iodo-5-thiophen-3-ylphenol
—— 2-Methoxy-4-[(4-methyl-5-phenylazo-thiazol-2-yl)-hydrazonomethyl]-phenol 121876-71-9 C18H17N5O2S
2-Methoxy-4-[(4-methyl-5-phenylazo-thiazol-2-yl)-hydrazonomethyl]-phenol
—— 2-methoxy-4-[5-(3-methyl-1,4-dioxoquinoxalin-2-yl)-3,4-dihydro-2H-pyrazol-3-yl]phenol 1301603-62-2 C19H18N4O4
2-methoxy-4-[5-(3-methyl-1,4-dioxoquinoxalin-2-yl)-3,4-dihydro-2H-pyrazol-3-yl]phenol
—— (E)-3-[2-(benzothiazol-2-ylsulfanyl)vinyl]-5-methoxyphenol 1042717-52-1 C16H13NO2S2
(E)-3-[2-(benzothiazol-2-ylsulfanyl)vinyl]-5-methoxyphenol
—— 1-Carbaethoxy-4-<3-methoxy-2-hydroxybenzyl>-piperazin 28533-21-3 C15H22N2O4
1-Carbaethoxy-4-<3-methoxy-2-hydroxybenzyl>-piperazin
—— 6-(2,5-dihydroxy-phenyl)-4,5-dihydro-2<i>H</i>-pyridazin-3-one 39499-68-8 C10H10N2O3
6-(2,5-dihydroxy-phenyl)-4,5-dihydro-2<i>H</i>-pyridazin-3-one
—— 2-iodo-4-nitro-6-(perfluoroethyl)phenol 1132942-98-3 C8H3F5INO3
2-iodo-4-nitro-6-(perfluoroethyl)phenol
—— 2-Dimethylamino-4-nitro-5-chlorphenol 56024-96-5 C8H9ClN2O3
2-Dimethylamino-4-nitro-5-chlorphenol
—— 1-(2,5-Dihydroxy-phenyl)-tetrahydro-thiophenium; bromide 92277-97-9 Br*C10H13O2S
1-(2,5-Dihydroxy-phenyl)-tetrahydro-thiophenium; bromide
—— 2-Amino-4(5)-(2-hydroxyethyl)imidazol-Pikrat 60246-09-5 C5H9N3O*C6H3N3O7
2-Amino-4(5)-(2-hydroxyethyl)imidazol-Pikrat
—— 2-(4-hydroxy-3-methoxy-benzylidene)-6-nitro-benzo[4,5]imidazo[2,1-<i>b</i>]thiazol-3-one 65183-26-8 C17H11N3O5S
2-(4-hydroxy-3-methoxy-benzylidene)-6-nitro-benzo[4,5]imidazo[2,1-<i>b</i>]thiazol-3-one
—— 5-[(4-(5-cyclohexylthien)-3-yl)phenyl]-5-methyl-3,4-dihydroxy-2(5H)-furanone 1098478-99-9 C21H22O4S
5-[(4-(5-cyclohexylthien)-3-yl)phenyl]-5-methyl-3,4-dihydroxy-2(5H)-furanone
—— hydroquinone; compound with hydrogen sulfide 14342-92-8 3C6H6O2*H2S
hydroquinone; compound with hydrogen sulfide
—— 3,9-dihydroxy-6,7-dihydro-5 H-dibenzo[a,c]cycloheptene 1314519-08-8 C15H14O2
3,9-dihydroxy-6,7-dihydro-5 H-dibenzo[a,c]cycloheptene
—— (1Z)-1-(2,4-dihydroxyphenyl)ethanone oxime 111364-29-5 C8H9NO3
(1Z)-1-(2,4-dihydroxyphenyl)ethanone oxime
—— 2-chloro-4-(phenylethynyl)phenol 1161837-56-4 C14H9ClO
2-chloro-4-(phenylethynyl)phenol
—— 4-((2-(4-fluoro-phenyl)hydrazono)methyl)benzene-1,3-diol 391272-60-9 C13H11FN2O2
4-((2-(4-fluoro-phenyl)hydrazono)methyl)benzene-1,3-diol
—— 4-bromo-3,5-dimethoxy-2,6-dimethylphenol 1080023-53-5 C10H13BrO3
4-bromo-3,5-dimethoxy-2,6-dimethylphenol
—— 2-Hydroxy-3-methoxy-5-(5-methyl-2-thienyl)benzaldehyde 1093118-45-6 C13H12O3S
2-Hydroxy-3-methoxy-5-(5-methyl-2-thienyl)benzaldehyde