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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-[1-[2-[3-(4-(2-Isobutoxy-ethyl)phenoxy)-2-hydroxypropylamino]ethyl]benzimidazol-5-yl]-3(2H)-pyridazinone 133177-66-9 C28H35N5O4
6-[1-[2-[3-(4-(2-Isobutoxy-ethyl)phenoxy)-2-hydroxypropylamino]ethyl]benzimidazol-5-yl]-3(2H)-pyridazinone
—— 6-[1-[3-[3-(4-(2-Isobutoxy-ethyl)phenoxy)-2-hydroxypropylamino]propyl]-2-methyl-benzimidazol-5-yl]-4,5-dihydro-3(2H)-pyridazinone 133155-04-1 C30H41N5O4
6-[1-[3-[3-(4-(2-Isobutoxy-ethyl)phenoxy)-2-hydroxypropylamino]propyl]-2-methyl-benzimidazol-5-yl]-4,5-dihydro-3(2H)-pyridazinone
—— 2-(oct-1-ynyl)phenol 99209-63-9 C14H18O
2-(oct-1-ynyl)phenol
—— 3-(3,4-dihydroxyphenyl)-N-adamantyl-propaneamide 125789-39-1 C19H25NO3
3-(3,4-dihydroxyphenyl)-N-adamantyl-propaneamide
—— 3-(dithiophen-2-ylmethyl)phenol 1227746-83-9 C15H12OS2
3-(dithiophen-2-ylmethyl)phenol
—— 2-sulfanilyl-phloroglucinol 105456-65-3 C12H11NO5S
2-sulfanilyl-phloroglucinol
—— diethyl α-formyl (4-hydroxy-3-methoxy-5-methylbenzyl)phosphonate 407584-04-7 C14H21O6P
diethyl α-formyl (4-hydroxy-3-methoxy-5-methylbenzyl)phosphonate
—— N-methylpyrrolidinium picrate 6012-25-5 C5H11N*C6H3N3O7
N-methylpyrrolidinium picrate
—— diethyl α-(4-hydroxy-3-methoxy-5-methylphenyl)-β-[N-(2-benzothiazolyl)-amino]-ethylphosphonate 407583-72-6 C21H27N2O5PS
diethyl α-(4-hydroxy-3-methoxy-5-methylphenyl)-β-[N-(2-benzothiazolyl)-amino]-ethylphosphonate
—— 4-chloro-3-methoxy-2-(phenylethynyl)phenol 137394-93-5 C15H11ClO2
4-chloro-3-methoxy-2-(phenylethynyl)phenol
—— 6,6′-dimethoxy-2,2′-[4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]-diphenol 1312014-52-0 C24H24N2O4
6,6′-dimethoxy-2,2′-[4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]-diphenol
—— 2-(benzothiazol-2-yliminomethyl)-4-nitrophenol 17750-71-9 C14H9N3O3S
2-(benzothiazol-2-yliminomethyl)-4-nitrophenol
—— 2'-Hydroxy-N-methylisobutyrthioanilid 85937-55-9 C11H15NOS
2'-Hydroxy-N-methylisobutyrthioanilid
—— 3-bromo-2,6-dimethoxy-4-(methoxymethyl)phenol 137898-25-0 C10H13BrO4
3-bromo-2,6-dimethoxy-4-(methoxymethyl)phenol
—— 3-(diethylamino)-4-methylphenol 6265-08-3 C11H17NO
3-(diethylamino)-4-methylphenol
—— 5-chlorosalicylaldehyde azine 903635-16-5 C14H11ClN2O2
5-chlorosalicylaldehyde azine
—— (S)-(-)-3-<4-<2-(cyclopropylmethoxy)ethyl>phenoxy>-1-(isopropylamino)-2-propanol maleate 93221-49-9 C4H4O4*C18H29NO3
(S)-(-)-3-<4-<2-(cyclopropylmethoxy)ethyl>phenoxy>-1-(isopropylamino)-2-propanol maleate
—— 3-((2-hydroxy-3-methoxybenzylidene)amino)benzoic acid 196617-28-4 C15H13NO4
3-((2-hydroxy-3-methoxybenzylidene)amino)benzoic acid
—— 4-(1,3-dioxolan-2-yl)-2,6-bis(trimethylsilyl)phenol 1276113-18-8 C15H26O3Si2
4-(1,3-dioxolan-2-yl)-2,6-bis(trimethylsilyl)phenol
—— 2,6-diiodo-5-methoxy-3-(methoxymethoxy)phenol 140410-36-2 C9H10I2O4
2,6-diiodo-5-methoxy-3-(methoxymethoxy)phenol
—— 2-iodo-5-methoxy-3-(methoxymethoxy)phenol 140410-32-8 C9H11IO4
2-iodo-5-methoxy-3-(methoxymethoxy)phenol
—— 4-[2-[4-[4-[2,5-Dihexyl-4-[2-(4-hydroxyphenyl)ethynyl]phenyl]buta-1,3-diynyl]-2,5-dihexylphenyl]ethynyl]phenol 312624-95-6 C56H66O2
4-[2-[4-[4-[2,5-Dihexyl-4-[2-(4-hydroxyphenyl)ethynyl]phenyl]buta-1,3-diynyl]-2,5-dihexylphenyl]ethynyl]phenol
—— 4-butylguaiacol 59832-96-1 C11H16O2
4-butylguaiacol
—— 14,19-Dioxa-1,11-diazatricyclo[9.5.5.14,8]docosa-4(22),5,7-trien-22-ol 144316-90-5 C18H28N2O3
14,19-Dioxa-1,11-diazatricyclo[9.5.5.14,8]docosa-4(22),5,7-trien-22-ol
—— 14,17,22,25-Tetraoxa-1,11-diazatricyclo[9.8.8.14,8]octacosa-4(28),5,7-trien-28-ol 144588-02-3 C22H36N2O5
14,17,22,25-Tetraoxa-1,11-diazatricyclo[9.8.8.14,8]octacosa-4(28),5,7-trien-28-ol
—— 4,7,20-Trioxa-1,10-diazatricyclo[8.7.5.112,16]tricosa-12,14,16(23)-trien-23-ol 157717-71-0 C18H28N2O4
4,7,20-Trioxa-1,10-diazatricyclo[8.7.5.112,16]tricosa-12,14,16(23)-trien-23-ol
—— 4-hydroxy-2'-hydroxysalicylanil 1761-59-7 C13H11NO3
4-hydroxy-2'-hydroxysalicylanil
—— 2-(2-hydroxyphenyl)-1,2-benzisoselenazol-3(2H)-one 81744-03-8 C13H9NO2Se
2-(2-hydroxyphenyl)-1,2-benzisoselenazol-3(2H)-one
—— 2,6-bis(2-hydroxyphenyliminomethyl)pyridine 1823-48-9 C19H15N3O2
2,6-bis(2-hydroxyphenyliminomethyl)pyridine
—— 2-(pyrrol-2-ylidenemethylamino)phenol 922511-40-8 C11H10N2O
2-(pyrrol-2-ylidenemethylamino)phenol
—— 2-Cyclopentyl-5-methyl-phenol 35293-57-3 C12H16O
2-Cyclopentyl-5-methyl-phenol
—— 4-Cyclopentyl-o-kresol 1791-42-0 C12H16O
4-Cyclopentyl-o-kresol
—— t-butyl N-(2-hydroxyphenyl)sulphinamoylacetate 95778-73-7 C12H17NO4S
t-butyl N-(2-hydroxyphenyl)sulphinamoylacetate
—— 2-chloro-4-cyclopentylphenol 13081-30-6 C11H13ClO
2-chloro-4-cyclopentylphenol
—— 2-Nitrosobenzene-1,3-diol 66266-79-3 C6H5NO3
2-Nitrosobenzene-1,3-diol
—— 4-hydroxy-2-methyl-5-nitro(N,N-dimethyl)benzenesulfonamide 473477-12-2 C9H12N2O5S
4-hydroxy-2-methyl-5-nitro(N,N-dimethyl)benzenesulfonamide
—— 4-Bromo-2-cyclohex-2-enyl-phenol 173537-19-4 C12H13BrO
4-Bromo-2-cyclohex-2-enyl-phenol
—— 5,11,17,23-Tetramethyl-2,8,14,20-tetra(nonyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol 168405-78-5 C68H104O8
5,11,17,23-Tetramethyl-2,8,14,20-tetra(nonyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol
—— 2,5-dihydroxyphenyl-phenyl phosphinic acid 2,6-dimethyl-phenyl ester 880871-30-7 C20H19O4P
2,5-dihydroxyphenyl-phenyl phosphinic acid 2,6-dimethyl-phenyl ester
—— 2-amino-4-(4-hydroxyphenyl)thiiophene-3-carbonitrile 173026-49-8 C11H8N2OS
2-amino-4-(4-hydroxyphenyl)thiiophene-3-carbonitrile
—— N-(2-nitrophenylsulfenyl)-β-(3-hydroxy-4-methoxyphenyl)ethylamine 1620818-54-3 C15H16N2O4S
N-(2-nitrophenylsulfenyl)-β-(3-hydroxy-4-methoxyphenyl)ethylamine
—— 3-Methoxy-4-hydroxy-5-brom-hydrozimtsaeuremethylester 58335-57-2 C11H13BrO4
3-Methoxy-4-hydroxy-5-brom-hydrozimtsaeuremethylester
—— 3-bromo-4-isopropyloxy-5-methoxyphenol 905811-33-8 C10H13BrO3
3-bromo-4-isopropyloxy-5-methoxyphenol
—— 3-bromo-4-hydroxy-5-methoxy-mandelonitrile 54246-09-2 C9H8BrNO3
3-bromo-4-hydroxy-5-methoxy-mandelonitrile
—— 3,5-dihydroxyisobutenylbenzene 88464-60-2 C10H12O2
3,5-dihydroxyisobutenylbenzene
—— 4-Benzyloxy-2-bromo-6-methoxyphenol 255826-40-5 C14H13BrO3
4-Benzyloxy-2-bromo-6-methoxyphenol
—— 5-bromo-3-methoxy-4-(methoxymethoxy)phenol 133099-83-9 C9H11BrO4
5-bromo-3-methoxy-4-(methoxymethoxy)phenol
—— 3-bromo-4-{[(tert-butyl)(dimethyl)silyl]oxy}-5-methoxyphenol 255826-38-1 C13H21BrO3Si
3-bromo-4-{[(tert-butyl)(dimethyl)silyl]oxy}-5-methoxyphenol
—— 4-chloro-2-(1-hydroxy-2-methyl-propyl)-5-methoxy-phenol 1106538-44-6 C11H15ClO3
4-chloro-2-(1-hydroxy-2-methyl-propyl)-5-methoxy-phenol
—— 4-hydroxy-3-methoxy-5-(3',7'-dimethyl-7'-hydroxy-6'-phenylselenyl-2'-octenyl)benzyl alcohol 474970-81-5 C24H32O4Se
4-hydroxy-3-methoxy-5-(3',7'-dimethyl-7'-hydroxy-6'-phenylselenyl-2'-octenyl)benzyl alcohol