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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
—— trans-4,5-bis(2-hydroxy-5-bromophenyl)-2-methyl-1,3-dioxolane 124483-15-4 C16H14Br2O4
trans-4,5-bis(2-hydroxy-5-bromophenyl)-2-methyl-1,3-dioxolane
—— 2-(2-(4-hydroxybenzylidene)hydrazinyl)thiazol-4(5H)-one 155225-30-2 C10H9N3O2S
2-(2-(4-hydroxybenzylidene)hydrazinyl)thiazol-4(5H)-one
—— 5-(4-Hydroxy-3-nitro-phenyl)-thiazolidine-2,4-dione 201802-04-2 C9H6N2O5S
5-(4-Hydroxy-3-nitro-phenyl)-thiazolidine-2,4-dione
—— Monomethylether von 2-C-Methylgrevillol 66284-55-7 C21H36O2
Monomethylether von 2-C-Methylgrevillol
—— N-(5-methoxy-2-hydroxybenzylidene)pyridine-2-amine 73446-99-8 C13H12N2O2
N-(5-methoxy-2-hydroxybenzylidene)pyridine-2-amine
—— 5-Chloro-2-hydroxy-3-nitro-benzoic acid [1-phenyl-meth-(Z)-ylidene]-hydrazide 5198-32-3 C14H10ClN3O4
5-Chloro-2-hydroxy-3-nitro-benzoic acid [1-phenyl-meth-(Z)-ylidene]-hydrazide
—— Acetic acid 2-{formyl-[2-(2,4,6-tribromo-3-hydroxy-phenyl)-ethyl]-amino}-1-methyl-ethyl ester 293756-97-5 C14H16Br3NO4
Acetic acid 2-{formyl-[2-(2,4,6-tribromo-3-hydroxy-phenyl)-ethyl]-amino}-1-methyl-ethyl ester
—— 3-(4-Hydroxy-3-methyl-phenyl)-butyronitrile 18782-18-8 C11H13NO
3-(4-Hydroxy-3-methyl-phenyl)-butyronitrile
—— 6-[(2-Hydroxy-3-methoxyphenyl)methyl]-1,4,8,11-tetrazacyclotetradecane-5,7-dione 188925-61-3 C18H28N4O4
6-[(2-Hydroxy-3-methoxyphenyl)methyl]-1,4,8,11-tetrazacyclotetradecane-5,7-dione
—— 5-(5-methyl-[1,3,4]oxadiazol-2-yl)-3-nitro-benzene-1,2-diol 923288-14-6 C9H7N3O5
5-(5-methyl-[1,3,4]oxadiazol-2-yl)-3-nitro-benzene-1,2-diol
—— 2-Acetonyl-3-methoxy-5-methyl-phenol 96418-47-2 C11H14O3
2-Acetonyl-3-methoxy-5-methyl-phenol
—— (+)-trans-(S,S)-[2-(2-cyclopropylmethyloxy-5-hydroxyphenyl)cyclopropyl]methylamine hydrochloride 1245559-94-7 C14H19NO2*ClH
(+)-trans-(S,S)-[2-(2-cyclopropylmethyloxy-5-hydroxyphenyl)cyclopropyl]methylamine hydrochloride
—— N-(2-Hydroxy-aethyl)-N-(4-hydroxy-benzyl)-dichloracetamid 4185-17-5 C11H13Cl2NO3
N-(2-Hydroxy-aethyl)-N-(4-hydroxy-benzyl)-dichloracetamid
—— 5-<5-Chlor-2-hydroxy-4-methyl-phenyl>-valeriansaeure 4654-13-1 C12H15ClO3
5-<5-Chlor-2-hydroxy-4-methyl-phenyl>-valeriansaeure
—— 2-Brom-4-sec-pentyl-m-cresol 2502-72-9 C12H17BrO
2-Brom-4-sec-pentyl-m-cresol
—— N,N'-bis-(2-hydroxy-3,5-dimethyl-benzyl)-N-methyl-urea 102167-33-9 C20H26N2O3
N,N'-bis-(2-hydroxy-3,5-dimethyl-benzyl)-N-methyl-urea
—— 4-<4-Hydroxy-phenyl>-1,3-dithiol-2-thion 15919-31-0 C9H6OS3
4-<4-Hydroxy-phenyl>-1,3-dithiol-2-thion
—— 5-Methoxy-3,4-bis-(3-methyl-but-2-enyloxy)-benzene-1,2-dicarbaldehyde 84018-95-1 C19H24O5
5-Methoxy-3,4-bis-(3-methyl-but-2-enyloxy)-benzene-1,2-dicarbaldehyde
—— 5-salicylidene-thiazolidine-2,4-dione-2-furfurylidenehydrazone 108272-30-6 C15H11N3O3S
5-salicylidene-thiazolidine-2,4-dione-2-furfurylidenehydrazone
—— 2-(1,3-benzothiazol-2-ylsulfanyl)-N'-[(E)-(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]acetohydrazide 302950-64-7 C17H14BrN3O3S2
2-(1,3-benzothiazol-2-ylsulfanyl)-N'-[(E)-(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]acetohydrazide
—— 4-chloro-5-(3-methoxyphenylsulfonyl)-1,2-benzenediol 105847-31-2 C13H11ClO5S
4-chloro-5-(3-methoxyphenylsulfonyl)-1,2-benzenediol
—— 2,6-Dinitro-4-(1-butylhexyl)-phenol 6465-66-3 C16H24N2O5
2,6-Dinitro-4-(1-butylhexyl)-phenol
—— N-<3-(2-hydroxy-3-methoxyphenyl)propyl>-6-bromobenzamide 119873-39-1 C17H18BrNO3
N-<3-(2-hydroxy-3-methoxyphenyl)propyl>-6-bromobenzamide
—— 2-{[(E)-3-Amino-[1,2,4]triazol-4-ylimino]-methyl}-3,5-dimethoxy-phenol 103409-09-2 C11H13N5O3
2-{[(E)-3-Amino-[1,2,4]triazol-4-ylimino]-methyl}-3,5-dimethoxy-phenol
—— S-octylisothiourea picrate 92724-61-3 C6H3N3O7*C9H20N2S
S-octylisothiourea picrate
—— 2-[(2-isopropylaminoethylimino)methyl]-5-methoxy phenol 1313435-65-2 C13H20N2O2
2-[(2-isopropylaminoethylimino)methyl]-5-methoxy phenol
—— 4,6-bis(diethylaminomethyl)-2-nitrophenol 127396-48-9 C16H27N3O3
4,6-bis(diethylaminomethyl)-2-nitrophenol
—— N-[(E)-(4-hydroxy-3-methoxyphenyl)methylideneamino]-2-pyridin-2-ylsulfanylacetamide 326000-60-6 C15H15N3O3S
N-[(E)-(4-hydroxy-3-methoxyphenyl)methylideneamino]-2-pyridin-2-ylsulfanylacetamide
—— 2-[[2-[[(2-Hydroxyphenyl)methylideneamino]methyl]-3-pyridin-2-ylpropyl]iminomethyl]phenol 219510-15-3 C23H23N3O2
2-[[2-[[(2-Hydroxyphenyl)methylideneamino]methyl]-3-pyridin-2-ylpropyl]iminomethyl]phenol
—— 2-[[2-[1-(2-Hydroxyphenyl)ethylideneamino]phenyl]iminomethyl]-5-methoxyphenol 1265833-48-4 C22H20N2O3
2-[[2-[1-(2-Hydroxyphenyl)ethylideneamino]phenyl]iminomethyl]-5-methoxyphenol
—— (E)-N'-[1-(2-hydroxy-5-nitrophenyl)ethyliden]isonicotinoyl-hydrazide 1262304-91-5 C14H12N4O4
(E)-N'-[1-(2-hydroxy-5-nitrophenyl)ethyliden]isonicotinoyl-hydrazide
—— 4-{[(E)-1,3-Dimethyl-butylimino]-methyl}-phenol 30121-94-9 C13H19NO
4-{[(E)-1,3-Dimethyl-butylimino]-methyl}-phenol
—— 6-amino-2,4-dibromo-3-methoxy-phenol 857628-40-1 C7H7Br2NO2
6-amino-2,4-dibromo-3-methoxy-phenol
—— 1346751-50-5 C24H18Cl2N4O7
—— (+/-)-8,9:13,14-diseco-18-norestradiol 76976-64-2 C17H26O2
(+/-)-8,9:13,14-diseco-18-norestradiol
—— 4-[1-(amino-3-methylbutyl)cyclobutyl]phenol 1010817-76-1 C15H23NO
4-[1-(amino-3-methylbutyl)cyclobutyl]phenol
—— 4-[(5-Methylfuran-2-yl)methyl]phenol 66124-08-1 C12H12O2
4-[(5-Methylfuran-2-yl)methyl]phenol
—— Sodium;3-hydroxybenzenesulfinate 932377-15-6 C6H5O3S*Na
Sodium;3-hydroxybenzenesulfinate
—— 4,4'-(piperazine-1,4-diyldiimino-dimethyl)-bis-benzene-1,3-diol 21323-28-4 C18H20N4O4
4,4'-(piperazine-1,4-diyldiimino-dimethyl)-bis-benzene-1,3-diol
—— 2-(3-Hydroxypent-1-yn-3-yl)phenol 1384475-77-7 C11H12O2
2-(3-Hydroxypent-1-yn-3-yl)phenol
—— 1205125-04-7 C16H23N9O
—— 5-(4-hydroxy-phenyl)-3-pyrrolidinomethyl-3<i>H</i>-[1,3,4]oxadiazol-2-one 108800-25-5 C13H15N3O3
5-(4-hydroxy-phenyl)-3-pyrrolidinomethyl-3<i>H</i>-[1,3,4]oxadiazol-2-one
—— N,N'-bis(2-hydroxybenzylidene)-1,1-diaminooctane 123431-66-3 C22H28N2O2
N,N'-bis(2-hydroxybenzylidene)-1,1-diaminooctane
—— 3-Methoxy-4-hydroxy-benzoesaeure-<bis-(2-hydroxy-aethyl)-amid> 5942-23-4 C12H17NO5
3-Methoxy-4-hydroxy-benzoesaeure-<bis-(2-hydroxy-aethyl)-amid>
—— 4-((2-((2-hydroxy-5-methoxybenzylidene)amino)ethyl)amino)pent-3-en-2-one 89376-45-4 C15H20N2O3
4-((2-((2-hydroxy-5-methoxybenzylidene)amino)ethyl)amino)pent-3-en-2-one
—— (3S)-(-)-8-<(1S,4R)-camphanoyloxy>-3,4-dihydro-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one 172588-08-8 C26H26O8
(3S)-(-)-8-<(1S,4R)-camphanoyloxy>-3,4-dihydro-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one
—— 4-Hydroxy-3methoxybenzaldehyde-4-methylthiosemicarbazone 4275-89-2 C10H13N3O2S
4-Hydroxy-3methoxybenzaldehyde-4-methylthiosemicarbazone
—— (4-amino-2-hydroxy-5-nitro-phenyl)-arsonic acid 861789-22-2 C6H7AsN2O6
(4-amino-2-hydroxy-5-nitro-phenyl)-arsonic acid
—— 3,4-dihydroxy-tri-<i>N</i>-methyl-anilinium; hydrogencarbonate 117862-06-3 CHO3*C9H14NO2
3,4-dihydroxy-tri-<i>N</i>-methyl-anilinium; hydrogencarbonate
—— N-(2-Hydroxy-aethyl)-N-(2-hydroxy-benzyl)-dichloracetamid 4380-21-6 C11H13Cl2NO3
N-(2-Hydroxy-aethyl)-N-(2-hydroxy-benzyl)-dichloracetamid