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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-(2-Chloroallyl)-4-methoxyphenol 53299-62-0 C10H11ClO2
2-(2-Chloroallyl)-4-methoxyphenol
—— N,N'-bis(2-hydroxyacetophenone)-o-phenylenediamine 133345-51-4 C22H20N2O2
N,N'-bis(2-hydroxyacetophenone)-o-phenylenediamine
—— <2-Brom-4-hydroxy-5-methoxy-phenyl>-essigsaeure-methylester 90841-70-6 C10H11BrO4
<2-Brom-4-hydroxy-5-methoxy-phenyl>-essigsaeure-methylester
—— C-undecylcavitandtetrol 169219-14-1 C76H112O12
C-undecylcavitandtetrol
—— 7-[(4-Hydroxyphenyl)methylidene]-4'-methylspiro[2,4-dihydro-[1,3]thiazolo[3,2-b][1,2,4,5]tetrazine-3,1'-cyclohexane]-6-one 112919-58-1 C17H20N4O2S
7-[(4-Hydroxyphenyl)methylidene]-4'-methylspiro[2,4-dihydro-[1,3]thiazolo[3,2-b][1,2,4,5]tetrazine-3,1'-cyclohexane]-6-one
—— 2-[(triisopropylsilyl)ethynyl]phenol 1062451-35-7 C17H26OSi
2-[(triisopropylsilyl)ethynyl]phenol
—— 2,2'-ditelluridediyldiphenol 1235774-36-3 C12H10O2Te2
2,2'-ditelluridediyldiphenol
—— 2,3,5-trichloro-4-methyl-phenol 608-91-3 C7H5Cl3O
2,3,5-trichloro-4-methyl-phenol
—— (E)-9-(2-hydroxyphenyl)non-3-en-8-yn-2-one 1356471-32-3 C15H16O2
(E)-9-(2-hydroxyphenyl)non-3-en-8-yn-2-one
—— thiazolidine-2,4-dione-2-vanillylidenehydrazone 118836-83-2 C11H11N3O3S
thiazolidine-2,4-dione-2-vanillylidenehydrazone
—— Z-4-(heptadec-8'-enyl)benzene-1,2-diol 122850-26-4 C23H38O2
Z-4-(heptadec-8'-enyl)benzene-1,2-diol
—— 5-((Z)-4-hydroxy-3-methoxybenzylidene)-2-thioxo-4-thiazolidinone 99972-65-3 C11H9NO3S2
5-((Z)-4-hydroxy-3-methoxybenzylidene)-2-thioxo-4-thiazolidinone
—— (Z,Z)-4-(heptadeca-8',11'-dienyl)benzene-1,2-diol 105419-12-3 C23H36O2
(Z,Z)-4-(heptadeca-8',11'-dienyl)benzene-1,2-diol
—— 6-ethyl-4-amino-2,3-dimethyl-phenol 708258-12-2 C10H15NO
6-ethyl-4-amino-2,3-dimethyl-phenol
—— 2,5-Bis-<bis-(2-hydroxy-aethyl)aminomethyl>-hydrochinon 114510-02-0 C16H28N2O6
2,5-Bis-<bis-(2-hydroxy-aethyl)aminomethyl>-hydrochinon
—— methyl p-hydroxybenzenesulfinate 125927-95-9 C7H8O3S
methyl p-hydroxybenzenesulfinate
—— E-4-(heptadec-8'-enyl)benzene-1,2-diol 122850-27-5 C23H38O2
E-4-(heptadec-8'-enyl)benzene-1,2-diol
—— 2-Methoxy-3,4,5,6-tetramethylphenol 74725-16-9 C11H16O2
2-Methoxy-3,4,5,6-tetramethylphenol
—— 4-methoxyphenyl-E-(3-hydroxy-5-methoxy)-styryl ether 960069-06-1 C16H16O4
4-methoxyphenyl-E-(3-hydroxy-5-methoxy)-styryl ether
—— 2,6-Bis-(morpholinomethyl)-4-methoxyphenol 21594-93-4 C17H26N2O4
2,6-Bis-(morpholinomethyl)-4-methoxyphenol
—— 1-(2,5-dihydroxy-phenyl)-ethanone thiosemicarbazone 102872-09-3 C9H11N3O2S
1-(2,5-dihydroxy-phenyl)-ethanone thiosemicarbazone
—— tert-Butyl 3-(4-hydroxy-2-methylphenyl)propanoate 591777-17-2 C14H20O3
tert-Butyl 3-(4-hydroxy-2-methylphenyl)propanoate
—— 4-(Furan-2-yl)-3-(1-hydroxybut-3-ynyl)phenol 1361252-48-3 C14H12O3
4-(Furan-2-yl)-3-(1-hydroxybut-3-ynyl)phenol
—— 3,5-Dimethoxy-2-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenol 190973-16-1 C14H19NO3
3,5-Dimethoxy-2-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenol
—— (3E,5E)-3,5-bis(4-hydroxy-3-methoxybenzylidene)-1-methylpiperidin-4-one 861968-02-7 C22H23NO5
(3E,5E)-3,5-bis(4-hydroxy-3-methoxybenzylidene)-1-methylpiperidin-4-one
—— N-[3-(dimethylamino)propyl]-3-(2-hydroxyphenyl)propanamide 287199-24-0 C14H22N2O2
N-[3-(dimethylamino)propyl]-3-(2-hydroxyphenyl)propanamide
—— N-methyl-2-(2-hydroxy-5-methoxy-4-(pentylthio)phenyl)-3-methylbutylamine 129658-15-7 C18H31NO2S
N-methyl-2-(2-hydroxy-5-methoxy-4-(pentylthio)phenyl)-3-methylbutylamine
—— methyl (3,6-dihydroxy-2-formyl-5-methoxyphenyl)thioacetate 80427-83-4 C11H12O6S
methyl (3,6-dihydroxy-2-formyl-5-methoxyphenyl)thioacetate
—— 6-[2-[3,4-di(phenylmethoxy)phenyl]ethoxy]hexanoic acid 178486-12-9 C28H32O5
6-[2-[3,4-di(phenylmethoxy)phenyl]ethoxy]hexanoic acid
—— 4-hydroxy-3,5-dimethoxydihydrocinnamide 88865-58-1 C11H15NO4
4-hydroxy-3,5-dimethoxydihydrocinnamide
—— salicylaldehyde nitroaminoguanizone 67082-03-5 C8H9N5O3
salicylaldehyde nitroaminoguanizone
—— methyl 2-((4S,5S)-1-(4-hydroxyphenyl)-4-methyl-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-5-yl)acetate 1610371-48-6 C14H15F3N2O3
methyl 2-((4S,5S)-1-(4-hydroxyphenyl)-4-methyl-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-5-yl)acetate
—— N-<2-(3,4-dihydroxyphenyl)ethyl>imidazoline hydrochloride salt 96826-03-8 C11H14N2O2*ClH
N-<2-(3,4-dihydroxyphenyl)ethyl>imidazoline hydrochloride salt
—— methyl (3S)-3-(4-hydroxyphenyl)hexanoate 1073545-27-3 C13H18O3
methyl (3S)-3-(4-hydroxyphenyl)hexanoate
—— N-[(2,4-dihydroxyphenyl)methylideneamino]-2-diphenylphosphorylacetamide 135689-10-0 C21H19N2O4P
N-[(2,4-dihydroxyphenyl)methylideneamino]-2-diphenylphosphorylacetamide
—— 4-(2-hydroxybenzylideneamino)-5-mercapto-3-ethyl-4H-1,2,4-triazole 119153-17-2 C11H12N4OS
4-(2-hydroxybenzylideneamino)-5-mercapto-3-ethyl-4H-1,2,4-triazole
—— 2-methoxy-5-{2-[2-(3-methoxyphenyl)ethylamino]ethyl}phenol 1395084-76-0 C18H23NO3
2-methoxy-5-{2-[2-(3-methoxyphenyl)ethylamino]ethyl}phenol
—— (α'R,2S)-2-(5'-Hydroxy-2'-methoxy-α'-methylbenzyloxy)propanal 162285-90-7 C12H16O4
(α'R,2S)-2-(5'-Hydroxy-2'-methoxy-α'-methylbenzyloxy)propanal
—— (α'S,2S)-2-(5'-Hydroxy-2'-methoxy-α'-methylbenzyloxy)propanal 162285-89-4 C12H16O4
(α'S,2S)-2-(5'-Hydroxy-2'-methoxy-α'-methylbenzyloxy)propanal
—— Hydrochinon, Ameisensaeure 50673-37-5 CH2O2*C6H6O2
Hydrochinon, Ameisensaeure
—— 2-Octyl-4,6-dinitrophenol 4467-92-9 C14H20N2O5
2-Octyl-4,6-dinitrophenol
—— 2-(2,3-epoxy-3-methylbutyl)-4-methoxyphenol 144705-45-3 C12H16O3
2-(2,3-epoxy-3-methylbutyl)-4-methoxyphenol
—— 2-(1,3-dioxolan-2-ylmethyl)-4-methoxyphenol 141989-04-0 C11H14O4
2-(1,3-dioxolan-2-ylmethyl)-4-methoxyphenol
—— Tetraethyl (2-hydroxy-5-methoxy-1,3-phenylene)bis(phosphonate) 91633-10-2 C15H26O8P2
Tetraethyl (2-hydroxy-5-methoxy-1,3-phenylene)bis(phosphonate)
—— (E)-1-(3',4'-dihydroxyphenyl)but-2-en-1-one 97911-35-8 C10H10O3
(E)-1-(3',4'-dihydroxyphenyl)but-2-en-1-one
—— 5,11,17,23-Tetrakis(2-hydroxyethoxymethyl)-2,8,14,20-tetrakis(2-methylpropyl)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 1274936-99-0 C56H80O16
5,11,17,23-Tetrakis(2-hydroxyethoxymethyl)-2,8,14,20-tetrakis(2-methylpropyl)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
—— 2,8,14,20-Tetrakis(2-methylpropyl)-5,11,17,23-tetrakis(2-propoxyethoxymethyl)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 1274937-07-3 C68H104O16
2,8,14,20-Tetrakis(2-methylpropyl)-5,11,17,23-tetrakis(2-propoxyethoxymethyl)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
—— 5,11,17,23-Tetrakis(2-butoxyethoxymethyl)-2,8,14,20-tetrakis(2-methylpropyl)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 1274937-08-4 C72H112O16
5,11,17,23-Tetrakis(2-butoxyethoxymethyl)-2,8,14,20-tetrakis(2-methylpropyl)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
—— ethyl 4-(4-hydroxy-3-methoxyphenyl)-6-methyl-1,3-bis(morpholin-4-ylmethyl)-2-oxo-4H-pyrimidine-5-carboxylate 1190370-91-2 C25H36N4O7
ethyl 4-(4-hydroxy-3-methoxyphenyl)-6-methyl-1,3-bis(morpholin-4-ylmethyl)-2-oxo-4H-pyrimidine-5-carboxylate
—— 2,8,14,20-Tetrakis(2-methylpropyl)-5,11,17,23-tetrakis(prop-2-ynoxymethyl)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 1094618-95-7 C60H72O12
2,8,14,20-Tetrakis(2-methylpropyl)-5,11,17,23-tetrakis(prop-2-ynoxymethyl)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