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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
—— 1-[6-(2-chloro-5-hydroxyphenoxy)hexyl]imidazole 134789-61-0 C15H19ClN2O2
1-[6-(2-chloro-5-hydroxyphenoxy)hexyl]imidazole
—— 2-[2-(2-{2-[2-(2,5-Dimethoxy-benzyloxy)-ethoxy]-ethoxy}-ethoxy)-ethoxymethyl]-benzene-1,4-diol 139520-93-7 C24H34O9
2-[2-(2-{2-[2-(2,5-Dimethoxy-benzyloxy)-ethoxy]-ethoxy}-ethoxy)-ethoxymethyl]-benzene-1,4-diol
—— (5R)-3-(3-fluoro-4-hydroxy-phenyl)-5-(4-methyl-[1,2,3]triazol-1-ylmethyl)-oxazolidin-2-one 926279-45-0 C13H13FN4O3
(5R)-3-(3-fluoro-4-hydroxy-phenyl)-5-(4-methyl-[1,2,3]triazol-1-ylmethyl)-oxazolidin-2-one
—— 478400-49-6 C27H29NO3
—— 6-[(2-Amino-4,5-dimethylanilino)methylidene]-2-methoxycyclohexa-2,4-dien-1-one 112750-10-4 C16H18N2O2
6-[(2-Amino-4,5-dimethylanilino)methylidene]-2-methoxycyclohexa-2,4-dien-1-one
—— 5-chloro-2-hydroxy-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 133296-84-1 C16H11Cl2N3O2S
5-chloro-2-hydroxy-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone
—— (3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)phenyl]-4-formyl-3-methylpyrrolidine-2,2-dicarboxylate 1455451-90-7 C27H33NO6
(3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)phenyl]-4-formyl-3-methylpyrrolidine-2,2-dicarboxylate
—— 4-Chloro-2-[3-(4-fluoro-phenoxy)-propyl]-6-methyl-phenol 110723-69-8 C16H16ClFO2
4-Chloro-2-[3-(4-fluoro-phenoxy)-propyl]-6-methyl-phenol
—— 2-{3,4-bis-[2-(3,4-didodecyloxyphenyl)ethoxy]phenyl}ethanol 1352994-12-7 C72H122O7
2-{3,4-bis-[2-(3,4-didodecyloxyphenyl)ethoxy]phenyl}ethanol
—— 72109-67-2 C34H35BrO4
—— 71146-98-0 C19H24O4
—— (5R)-3-(3-fluoro-4-hydroxy-phenyl)-5-(isoxazol-3-yloxymethyl)-oxazolidin-2-one 926279-55-2 C13H11FN2O5
(5R)-3-(3-fluoro-4-hydroxy-phenyl)-5-(isoxazol-3-yloxymethyl)-oxazolidin-2-one
—— 5-(2-hydroxy-3-methylphenyl)-3-phenylisoxazole 140885-85-4 C16H13NO2
5-(2-hydroxy-3-methylphenyl)-3-phenylisoxazole
—— 3-(3,5-difluoro-4-hydroxy-phenyl)-3a-hydroxy-1-oxo-1,3a,4,5,6,6a-hexahydro-pentalene-2-carbonitrile 1104634-42-5 C15H11F2NO3
3-(3,5-difluoro-4-hydroxy-phenyl)-3a-hydroxy-1-oxo-1,3a,4,5,6,6a-hexahydro-pentalene-2-carbonitrile
—— 2-[[(2S)-2-[(2-hydroxyphenyl)methylideneamino]-2-phenylethyl]iminomethyl]phenol 41013-31-4 C22H20N2O2
2-[[(2S)-2-[(2-hydroxyphenyl)methylideneamino]-2-phenylethyl]iminomethyl]phenol
—— (Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-imino-1-methylimidazolidin-4-one 1393445-18-5 C13H15N3O4
(Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-imino-1-methylimidazolidin-4-one
—— 1190880-30-8 C22H17ClN4O2
—— 4-[8,8,9,9,10,10-Hexafluoro-14-(4-hydroxyphenyl)-1,2-dimethyl-3,15-dithiatetracyclo[10.3.0.02,6.07,11]pentadeca-4,6,11,13-tetraen-4-yl]phenol 606142-38-5 C27H18F6O2S2
4-[8,8,9,9,10,10-Hexafluoro-14-(4-hydroxyphenyl)-1,2-dimethyl-3,15-dithiatetracyclo[10.3.0.02,6.07,11]pentadeca-4,6,11,13-tetraen-4-yl]phenol
—— [6-(3-Hydroxy-4-methoxy-phenyl)-2-oxo-hexyl]-phosphonic acid diethyl ester 205052-15-9 C17H27O6P
[6-(3-Hydroxy-4-methoxy-phenyl)-2-oxo-hexyl]-phosphonic acid diethyl ester
—— 1-Ethyl-3-(4-hydroxy-3-methoxy-benzyl)-urea 50992-84-2 C11H16N2O3
1-Ethyl-3-(4-hydroxy-3-methoxy-benzyl)-urea
—— (S)-3-(2-hydroxy-4-methoxybenzylideneamino)-4-isopropyl-2-oxazolidone 1187455-37-3 C14H18N2O4
(S)-3-(2-hydroxy-4-methoxybenzylideneamino)-4-isopropyl-2-oxazolidone
—— ethylene-bis(thioglycolic acid-salicylidene-hydrazide) 16042-79-8 C20H22N4O4S2
ethylene-bis(thioglycolic acid-salicylidene-hydrazide)
—— 2-tert-butyl-6-[[(1R,2R,4R,5R)-5-[(3-tert-butyl-2-hydroxy-5-methoxyphenyl)methylideneamino]-2-bicyclo[2.2.2]octanyl]iminomethyl]-4-methoxyphenol 1620152-17-1 C32H44N2O4
2-tert-butyl-6-[[(1R,2R,4R,5R)-5-[(3-tert-butyl-2-hydroxy-5-methoxyphenyl)methylideneamino]-2-bicyclo[2.2.2]octanyl]iminomethyl]-4-methoxyphenol
—— 3,3'-(((4-hydroxyphenyl)methylene)bis(sulfanediyl))dipropanoic acid 1033-50-7 C13H16O5S2
3,3'-(((4-hydroxyphenyl)methylene)bis(sulfanediyl))dipropanoic acid
—— 3-{[(R)-4,7-Dimethyl-1-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl]-hydroxy-methyl}-4-hydroxy-5-(4-hydroxy-phenyl)-1H-pyridin-2-one 71376-14-2 C27H33NO4
3-{[(R)-4,7-Dimethyl-1-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl]-hydroxy-methyl}-4-hydroxy-5-(4-hydroxy-phenyl)-1H-pyridin-2-one
—— 4-[6-(N-t-Butyloxycarbonyl)aminohexyloxy]-2,2',4'-trihydroxybenzophenone 174603-84-0 C24H31NO7
4-[6-(N-t-Butyloxycarbonyl)aminohexyloxy]-2,2',4'-trihydroxybenzophenone
—— 4-[(2-Chloro-4-hydroxy-3-iodo-5-methoxyphenyl)methylene]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one 828299-47-4 C18H14ClIN2O3
4-[(2-Chloro-4-hydroxy-3-iodo-5-methoxyphenyl)methylene]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one
—— 4-hydroxybenzonitrile-[cyano-14C] 67471-20-9 C7H5NO
4-hydroxybenzonitrile-[cyano-14C]
—— 4-bromo-5-fluoro-2-methylphenol 1600166-21-9 C7H6BrFO
4-bromo-5-fluoro-2-methylphenol
—— 3-chloro-5-hydroxy-6-methoxy-benzo[b]thiophene-2-carboxylic acid 1056555-62-4 C10H7ClO4S
3-chloro-5-hydroxy-6-methoxy-benzo[b]thiophene-2-carboxylic acid
—— m-(Dimethylphosphino)-phenol 38503-05-8 C8H11OP
m-(Dimethylphosphino)-phenol
—— 3-(2,4-dihydroxybenzyl)-1-benzylpyrrolidine-2,5-dione 1383105-32-5 C18H17NO4
3-(2,4-dihydroxybenzyl)-1-benzylpyrrolidine-2,5-dione
—— 1231945-61-1 C22H27NO6
—— 5-hydroxy-4-nitro-1,1-dioxidebenzo[b]thiophene 246177-25-3 C8H5NO5S
5-hydroxy-4-nitro-1,1-dioxidebenzo[b]thiophene
—— 2-Bromo-7-(5-chloro-2-hydroxy-phenylamino)-cyclohepta-2,4,6-trienone 93444-72-5 C13H9BrClNO2
2-Bromo-7-(5-chloro-2-hydroxy-phenylamino)-cyclohepta-2,4,6-trienone
—— 110625-36-0 C12H9N6NbO4
—— 2-(E)-(2-(2-aminoethylamino)methyl)-4-bromophenol 1613026-32-6 C11H16BrN3O
2-(E)-(2-(2-aminoethylamino)methyl)-4-bromophenol
—— (+/-)-6,7-di(3-hydroxy-4-methoxyphenyl)-1,2,3,5,8,8a-hexahydroindolizine 77513-56-5 C22H25NO4
(+/-)-6,7-di(3-hydroxy-4-methoxyphenyl)-1,2,3,5,8,8a-hexahydroindolizine
—— 2-(3,5-Dibrom-2-hydroxybenzyliden)-cyclohexanon-1 71039-33-3 C13H12Br2O2
2-(3,5-Dibrom-2-hydroxybenzyliden)-cyclohexanon-1
—— 2-methyl-6-[(2-morpholin-4-ylethylimino)methyl]phenol 1469902-17-7 C14H20N2O2
2-methyl-6-[(2-morpholin-4-ylethylimino)methyl]phenol
—— 3-(((5-chloro-2-hydroxyphenyl)(5-oxocyclopent-1-en-1-yl)methyl)thio)propanoic acid 1253909-70-4 C15H15ClO4S
3-(((5-chloro-2-hydroxyphenyl)(5-oxocyclopent-1-en-1-yl)methyl)thio)propanoic acid
—— 4-ethyl-2,6-bis(trimethylsilyl)phenol 145024-49-3 C14H26OSi2
4-ethyl-2,6-bis(trimethylsilyl)phenol
—— 3-Methoxy-4-hydroxy-benzaldehyd-<4-oxo-3-o-tolyl-thiazolin-2-yl-hydrazon> 802-00-6 C18H17N3O3S
3-Methoxy-4-hydroxy-benzaldehyd-<4-oxo-3-o-tolyl-thiazolin-2-yl-hydrazon>
—— 478400-79-2 C30H25NO4
—— 3-(4-hydroxy-phenyl)-2-(3-methyl-thiophen-2-yl)-4,5,6,6a-tetrahydro-3aH-pentalen-1-one 1104633-71-7 C19H18O2S
3-(4-hydroxy-phenyl)-2-(3-methyl-thiophen-2-yl)-4,5,6,6a-tetrahydro-3aH-pentalen-1-one
—— 4-Heptyl-6-[(hydroxyamino)methylidene]cyclohexa-2,4-dien-1-one 59661-88-0 C14H21NO2
4-Heptyl-6-[(hydroxyamino)methylidene]cyclohexa-2,4-dien-1-one
—— 4-methylsalicylaldehyde thiosemicarbazone 68696-07-1 C9H11N3OS
4-methylsalicylaldehyde thiosemicarbazone
—— 3-(3,5-difluoro-4-hydroxy-phenyl)-4,5,6,6a-tetrahydro-3aH-pentalen-1-one 1104634-43-6 C14H12F2O2
3-(3,5-difluoro-4-hydroxy-phenyl)-4,5,6,6a-tetrahydro-3aH-pentalen-1-one
—— 2,5-dihydroxy-3,4-dimethoxybromobenzene 93828-12-7 C8H9BrO4
2,5-dihydroxy-3,4-dimethoxybromobenzene
—— 2,8,14,20-Tetrakis(10-decylsulfanyldecyl)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 168568-88-5 C108H184O8S4
2,8,14,20-Tetrakis(10-decylsulfanyldecyl)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