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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
—— 5-bromo-3-methyl-1,2-benzenediol 1779857-21-4 C7H7BrO2
5-bromo-3-methyl-1,2-benzenediol
—— 1-(phenylthio)methyl-2-bromo-3-hydroxy-4-methoxybenzene 1261119-23-6 C14H13BrO2S
1-(phenylthio)methyl-2-bromo-3-hydroxy-4-methoxybenzene
—— 5,11,17-tris(p-tert-butyl)-23-hydroxyphosphonomethyl-25,26,27,28-tetrahydroxycalix[4]arene sodium salt 1314876-44-2 C41H50O7P*Na
5,11,17-tris(p-tert-butyl)-23-hydroxyphosphonomethyl-25,26,27,28-tetrahydroxycalix[4]arene sodium salt
—— 111959-23-0 C22H29NO3.ClH
—— (R)-4-(2-((3-chlorobenzyl)amino)-1-hydroxyethyl)benzene-1,2-diol 1544695-74-0 C15H16ClNO3
(R)-4-(2-((3-chlorobenzyl)amino)-1-hydroxyethyl)benzene-1,2-diol
—— 2,6-bis-(4-hydroxy-3-methoxy-phenyl)-4-oxo-piperidine-3-carboxylic acid ethyl ester 50524-17-9 C22H25NO7
2,6-bis-(4-hydroxy-3-methoxy-phenyl)-4-oxo-piperidine-3-carboxylic acid ethyl ester
—— (Z)-diisopropyl α-(3,5-dimethoxy-4-hydroxyphenyl)-β-[N-(pyrazinyl)-amino]-vinylphosphonate 407583-17-9 C20H28N3O6P
(Z)-diisopropyl α-(3,5-dimethoxy-4-hydroxyphenyl)-β-[N-(pyrazinyl)-amino]-vinylphosphonate
—— N-salicylidene-D-glucosamine 75684-29-6 C13H17NO6
N-salicylidene-D-glucosamine
—— 2-Heptadecyl-5-methoxy-3,6-dimethyl-phenol 859782-46-0 C26H46O2
2-Heptadecyl-5-methoxy-3,6-dimethyl-phenol
—— N-(3,4-dimethoxybenzyl)-N-(4-hydroxy-3,5-dimethoxybenzyl)acetamide 1426853-46-4 C20H25NO6
N-(3,4-dimethoxybenzyl)-N-(4-hydroxy-3,5-dimethoxybenzyl)acetamide
—— 4-Bromo-2-{[(3,5-dimethoxyphenyl)imino]methyl}-6-methoxybenzenol 477848-22-9 C16H16BrNO4
4-Bromo-2-{[(3,5-dimethoxyphenyl)imino]methyl}-6-methoxybenzenol
—— 2-hydroxy-5-nitro-3-(2-(2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)hydrazinyl)benzenesulfonic acid 1389396-43-3 C10H7N5O9S
2-hydroxy-5-nitro-3-(2-(2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)hydrazinyl)benzenesulfonic acid
—— N-(4-(4-hydroxy-3-methoxyphenyl)thiazol-2-yl)thiazole-5-carboxamide 1334920-22-7 C14H11N3O3S2
N-(4-(4-hydroxy-3-methoxyphenyl)thiazol-2-yl)thiazole-5-carboxamide
—— diethyl β-(3-hydroxy-5-methoxy-4-methylphenyl)-β-[N-(3-pyridyl)-amino]-ethylphosphonate 420111-49-5 C19H27N2O5P
diethyl β-(3-hydroxy-5-methoxy-4-methylphenyl)-β-[N-(3-pyridyl)-amino]-ethylphosphonate
—— diethyl β-(2,4-dimethyl-3-hydroxyphenyl)-β-[N-(3-pyridyl)-amino]-ethylphosphonate 420111-46-2 C19H27N2O4P
diethyl β-(2,4-dimethyl-3-hydroxyphenyl)-β-[N-(3-pyridyl)-amino]-ethylphosphonate
—— cis-dichloro(3,4-diaminophenol)platinum(II) 88194-69-8 C6H8Cl2N2OPt
cis-dichloro(3,4-diaminophenol)platinum(II)
—— 145755-66-4 C28H26N8NiO12
—— N<sup>1</sup>-<4-Amino-3,5-dichlor-benzoyl>-N<sup>2</sup>-<2-hydroxy-3-methoxy-benzyliden>-hydrazin 2999-58-8 C15H13Cl2N3O3
N<sup>1</sup>-<4-Amino-3,5-dichlor-benzoyl>-N<sup>2</sup>-<2-hydroxy-3-methoxy-benzyliden>-hydrazin
—— 2-{(1S)-1-{[(1S)-1-phenyethyl]amino}ethyl}phenol 77382-98-0 C16H19NO
2-{(1S)-1-{[(1S)-1-phenyethyl]amino}ethyl}phenol
—— 5-Methoxy-6-[(methylamino)methylidene]cyclohexa-2,4-dien-1-one 917567-23-8 C9H11NO2
5-Methoxy-6-[(methylamino)methylidene]cyclohexa-2,4-dien-1-one
—— Tasimelteon metabolite M9 1448344-06-6 C15H19NO4
Tasimelteon metabolite M9
—— N,N-Diethyl-2-(2'-hydroxy-5'-nitrophenyl)ethylamine hydrochloride 129295-72-3 C12H18N2O3*ClH
N,N-Diethyl-2-(2'-hydroxy-5'-nitrophenyl)ethylamine hydrochloride
—— 3-hydroxy-2-nitro-N-(2-oxoethyl)-N-prop-2-ynylbenzamide 94324-73-9 C12H10N2O5
3-hydroxy-2-nitro-N-(2-oxoethyl)-N-prop-2-ynylbenzamide
—— 2-Isopropyl-5-hydroxy-6-nitro-toluol 1705-74-4 C10H13NO3
2-Isopropyl-5-hydroxy-6-nitro-toluol
—— N-(3-Hydroxy-4-methoxyphenethyl)-3.4-dimethoxyphenyl-acetamide 33710-70-2 C19H23NO5
N-(3-Hydroxy-4-methoxyphenethyl)-3.4-dimethoxyphenyl-acetamide
—— Phenol, 2,3,6-trimethyl-4-[(7-hydroxy-3,7-dimethyloctyl)oxy]- 1099470-48-0 C19H32O3
Phenol, 2,3,6-trimethyl-4-[(7-hydroxy-3,7-dimethyloctyl)oxy]-
—— 5-Methyl-4-nitroso-2-trityl-phenol 105001-22-7 C26H21NO2
5-Methyl-4-nitroso-2-trityl-phenol
—— methyl 1425494-14-9 C15H12N2OS
methyl
—— 2-nonylbenzene-1,3,5-triol 96756-21-7 C15H24O3
2-nonylbenzene-1,3,5-triol
—— 1-(5-Bromo-2-hydroxyphenyl)cyclopropane-1-carboxylicacid 1314661-12-5 C10H9BrO3
1-(5-Bromo-2-hydroxyphenyl)cyclopropane-1-carboxylicacid
—— methyl 2-(3-(2-hydroxy-4-methylphenyl)propanamido)acrylate 1352437-97-8 C14H17NO4
methyl 2-(3-(2-hydroxy-4-methylphenyl)propanamido)acrylate
—— 132820-10-1 C24H19BrN4O5
—— (E)-diisopropyl α-(3,5-dimethoxy-4-hydroxyphenyl)-β-[N-(pyrazinyl)-amino]-vinylphosphonate 407583-19-1 C20H28N3O6P
(E)-diisopropyl α-(3,5-dimethoxy-4-hydroxyphenyl)-β-[N-(pyrazinyl)-amino]-vinylphosphonate
—— 5-[(5-Bromo-2-hydroxyphenyl)methylidene]-4-sulfanylidene-1,3-thiazolidin-2-one 496020-82-7 C10H6BrNO2S2
5-[(5-Bromo-2-hydroxyphenyl)methylidene]-4-sulfanylidene-1,3-thiazolidin-2-one
—— 3,5-dibromo-2,4-diiodo-6-methyl-phenol 857784-24-8 C7H4Br2I2O
3,5-dibromo-2,4-diiodo-6-methyl-phenol
—— N-(5-Chlor-3-nitro-2-hydroxy-benzoyl)-N'-isonicotinoyl-hydrazin 5043-83-4 C13H9ClN4O5
N-(5-Chlor-3-nitro-2-hydroxy-benzoyl)-N'-isonicotinoyl-hydrazin
—— 9-<o-Hydroxy-phenyl>-1,5-diaza-bicyclo<3,3,1>nonan 96650-76-9 C13H18N2O
9-<o-Hydroxy-phenyl>-1,5-diaza-bicyclo<3,3,1>nonan
—— [3-[(2-Hydroxy-3,5-dinitrophenyl)methylideneamino]phenyl]boronic acid 1174064-41-5 C13H10BN3O7
[3-[(2-Hydroxy-3,5-dinitrophenyl)methylideneamino]phenyl]boronic acid
—— 3-Hydroxy-4-[(2-hydroxyanilino)(sulfanyl)methylidene]cyclohexa-2,5-dien-1-one 202977-74-0 C13H11NO3S
3-Hydroxy-4-[(2-hydroxyanilino)(sulfanyl)methylidene]cyclohexa-2,5-dien-1-one
—— 3-hydroxy-2,4,6-trimethyl-benzyl alcohol 17743-36-1 C10H14O2
3-hydroxy-2,4,6-trimethyl-benzyl alcohol
—— 2-dihydroxyboranyl-3-methoxy-phenol 98546-52-2 C7H9BO4
2-dihydroxyboranyl-3-methoxy-phenol
—— aquilarone A 1404479-44-2 C18H20O8
aquilarone A
—— 6-Hydroxy-5-methoxy-1-methylbenzimidazol 36110-60-8 C9H10N2O2
6-Hydroxy-5-methoxy-1-methylbenzimidazol
—— 4-(3-Methylpyridin-1-ium-1-yl)benzene-1,2-diol;bromide 76494-36-5 Br*C12H12NO2
4-(3-Methylpyridin-1-ium-1-yl)benzene-1,2-diol;bromide
—— 2,6-Dimethoxy-4-{[4-(4-methyl-benzyl)-piperazin-1-ylimino]-methyl}-phenol 303102-30-9 C21H27N3O3
2,6-Dimethoxy-4-{[4-(4-methyl-benzyl)-piperazin-1-ylimino]-methyl}-phenol
—— acetic acid-(2-hydroxy-4,5-dimethoxy-anilide) 7107-12-2 C10H13NO4
acetic acid-(2-hydroxy-4,5-dimethoxy-anilide)
—— 635750-53-7 C20H14Cl2N2O2
—— (4S)-3-((1R,2S)-2-(4-hydroxy-3-methoxyphenyl)cyclohex-3-enecarbonyl)-4-isopropyloxazolidin-2-one 1595280-40-2 C20H25NO5
(4S)-3-((1R,2S)-2-(4-hydroxy-3-methoxyphenyl)cyclohex-3-enecarbonyl)-4-isopropyloxazolidin-2-one
—— 1393826-20-4 C22H19FN2O4
—— 82056-87-9 C22H30Cl3MoN2O3