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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
—— 3-(4-chloro-2-fluoro-5-hydroxy-6-iodophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione 328959-26-8 C12H6ClF4IN2O3
3-(4-chloro-2-fluoro-5-hydroxy-6-iodophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione
—— 1-[(1-methyl-3-methylenecyclohexyl)methyl]benzene-2,3,6-triol 1070795-49-1 C15H20O3
1-[(1-methyl-3-methylenecyclohexyl)methyl]benzene-2,3,6-triol
—— 1-(5-bromo-2-hydroxyphenyl)but-2-en-1-one oxime 1206479-14-2 C10H10BrNO2
1-(5-bromo-2-hydroxyphenyl)but-2-en-1-one oxime
—— 2-hydroxy-3,5-dinitro-N-phenethylbenzamide 227946-84-1 C15H13N3O6
2-hydroxy-3,5-dinitro-N-phenethylbenzamide
—— 1191259-32-1 C9H7N3O4
—— 3-phenethyl-3,4-dihydro-quinazolin-8-ol 101279-90-7 C16H16N2O
3-phenethyl-3,4-dihydro-quinazolin-8-ol
—— 1-(o-Hydroxyphenyl)benzosuberan 107365-77-5 C17H18O
1-(o-Hydroxyphenyl)benzosuberan
—— 2-(3,5-Dibrom-2-hydroxyphenyl)thiophen 121789-78-4 C10H5Br3OS
2-(3,5-Dibrom-2-hydroxyphenyl)thiophen
—— 3-((2-(4-fluorophenyl)hydrazono)methyl)benzene-1,2-diol 391273-09-9 C13H11FN2O2
3-((2-(4-fluorophenyl)hydrazono)methyl)benzene-1,2-diol
—— [(S)-α-phenylethylamino][(R)-diethoxyphosphoryl]methyl-4-hydroxybenzene 879885-73-1 C19H26NO4P
[(S)-α-phenylethylamino][(R)-diethoxyphosphoryl]methyl-4-hydroxybenzene
—— 4-[6-(2-fluorobenzyloxy)pyrimidin-4-yl]-3-hydroxy-1-methyl-1,5-dihydropyrrol-2-one 500367-93-1 C16H14FN3O3
4-[6-(2-fluorobenzyloxy)pyrimidin-4-yl]-3-hydroxy-1-methyl-1,5-dihydropyrrol-2-one
—— 4-(benzyloxy)-3-bromo-6-methoxy-5-methyl-2-(2,4-pentadienyl)phenol 105104-31-2 C20H21BrO3
4-(benzyloxy)-3-bromo-6-methoxy-5-methyl-2-(2,4-pentadienyl)phenol
—— 4-(1(2)<i>H</i>-tetrazol-5-ylazo)-benzene-1,3-diol 53003-99-9 C7H6N6O2
4-(1(2)<i>H</i>-tetrazol-5-ylazo)-benzene-1,3-diol
—— 1-(2-hydroxy-4-methoxyphenyl)-3-(piperidin-1-yl)prop-2-en-1-one 1388223-86-6 C15H19NO3
1-(2-hydroxy-4-methoxyphenyl)-3-(piperidin-1-yl)prop-2-en-1-one
—— 89669-38-5 C36H37N5O4Sn
—— 4-(3-amino-propyl)-2-methoxy-phenol; hydrochloride 112798-57-9 C10H15NO2*ClH
4-(3-amino-propyl)-2-methoxy-phenol; hydrochloride
—— 1193988-06-5 C21H30N2O5
—— 4-{[(3-bromophenyl)methylidene]amino}phenol 389612-40-2 C13H10BrNO
4-{[(3-bromophenyl)methylidene]amino}phenol
—— n-Bu3Sn(Gal) 94435-71-9 C19H32O5Sn
n-Bu3Sn(Gal)
—— [(3,4-dihydroxyphenyl)-hydroxymethyl]-propa-1,2-dienylphosphinic acid 124910-32-3 C10H11O5P
[(3,4-dihydroxyphenyl)-hydroxymethyl]-propa-1,2-dienylphosphinic acid
—— N-phenethyl-2'-hydroxyacetophenonimine 5879-65-2 C16H17NO
N-phenethyl-2'-hydroxyacetophenonimine
—— 3-[(3-methoxy-2-hydroxybenzylidene)amino]-4-oxoimidazolidin-2-thione 1416895-83-4 C11H11N3O3S
3-[(3-methoxy-2-hydroxybenzylidene)amino]-4-oxoimidazolidin-2-thione
—— 1-((N-(2-hydroxy-3-methoxybenzyl)-N-ethylcarbamoyl)methyl)-3-(4-aminobenzyl)urea 1313213-61-4 C20H26N4O4
1-((N-(2-hydroxy-3-methoxybenzyl)-N-ethylcarbamoyl)methyl)-3-(4-aminobenzyl)urea
—— 4-(3,3,3-trifluoro-2-(4-(perfluoropropan-2-ylidene)-1,3-dithietan-2-yl)-2-(trifluoromethyl)propyl)phenol 66172-10-9 C15H8F12OS2
4-(3,3,3-trifluoro-2-(4-(perfluoropropan-2-ylidene)-1,3-dithietan-2-yl)-2-(trifluoromethyl)propyl)phenol
—— N-(2-hydroxy-3-methoxybenzylidene)-2,6-dimethylaniline 54220-55-2 C16H17NO2
N-(2-hydroxy-3-methoxybenzylidene)-2,6-dimethylaniline
—— 6-methoxy-N-vanillylidene-4-chromanamine 67858-20-2 C18H19NO4
6-methoxy-N-vanillylidene-4-chromanamine
—— 4-Fluoro-5-(1-hydroxy-2-methylamino-ethyl)-benzene-1,2-diol; compound with oxalic acid 115562-28-2 C2H2O4*2C9H12FNO3
4-Fluoro-5-(1-hydroxy-2-methylamino-ethyl)-benzene-1,2-diol; compound with oxalic acid
—— 2-(3,4,5-tribenzyloxyphenyl)ethanol 1428976-95-7 C29H28O4
2-(3,4,5-tribenzyloxyphenyl)ethanol
—— (5-Phenyl-[1,3,4]oxadiazol-2-ylamino)-acetic acid [1-(2-hydroxy-phenyl)-meth-(E)-ylidene]-hydrazide 36949-13-0 C17H15N5O3
(5-Phenyl-[1,3,4]oxadiazol-2-ylamino)-acetic acid [1-(2-hydroxy-phenyl)-meth-(E)-ylidene]-hydrazide
—— 35316-65-5 C19H24O6
—— 5-ethoxy-3-<i>tert</i>-butyl-pyrocatechol 857425-95-7 C12H18O3
5-ethoxy-3-<i>tert</i>-butyl-pyrocatechol
—— N-(3,5-dibromo-4-hydroxybenzyl)-N-isopropylmethacrylamide 1612841-39-0 C14H17Br2NO2
N-(3,5-dibromo-4-hydroxybenzyl)-N-isopropylmethacrylamide
—— 6-(4-hydroxy-3-methoxybenzylidene)hydrazinocarbonyl-5-hydroxy-2-phenylpyridazin-3(2H)-one 121582-98-7 C19H16N4O5
6-(4-hydroxy-3-methoxybenzylidene)hydrazinocarbonyl-5-hydroxy-2-phenylpyridazin-3(2H)-one
—— 4-(1,1-Dimethoxy-allyl)-2,6-dimethoxy-phenol 66463-75-0 C13H18O5
4-(1,1-Dimethoxy-allyl)-2,6-dimethoxy-phenol
—— methyl 3-(2-hydroxy-3-nitrophenyl)-3-(3-methoxy-3-oxopropyl)sulfanylpropanoate 114106-32-0 C14H17NO7S
methyl 3-(2-hydroxy-3-nitrophenyl)-3-(3-methoxy-3-oxopropyl)sulfanylpropanoate
—— 3,5-dimethyl-7-(3,5-dihydroxy-phenyl)-4H-[1,2]diazepine 1428250-89-8 C13H14N2O2
3,5-dimethyl-7-(3,5-dihydroxy-phenyl)-4H-[1,2]diazepine
—— alatusol A 1578237-39-4 C13H18O6
alatusol A
—— 5-[1-(4-Hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-3-phenyl-2,5-dihydro-1H-[1,2,4]triazin-6-one 116247-48-4 C17H15N3O3
5-[1-(4-Hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-3-phenyl-2,5-dihydro-1H-[1,2,4]triazin-6-one
—— 2-hydroxy-3-nitrobenzenethiol 167481-41-6 C6H5NO3S
2-hydroxy-3-nitrobenzenethiol
—— 4-<(3-tert.-Butylthiopropyl)thio>-3,5-xylenol 37708-53-5 C15H24OS2
4-<(3-tert.-Butylthiopropyl)thio>-3,5-xylenol
—— 3,5-Bis[(3-hydroxyphenyl)methylidene]thian-4-one 1095827-41-0 C19H16O3S
3,5-Bis[(3-hydroxyphenyl)methylidene]thian-4-one
—— ethyl 3-(o-hydroxyphenyl)propoxyacetate 77420-29-2 C13H18O4
ethyl 3-(o-hydroxyphenyl)propoxyacetate
—— (E,Z)-cyano-{3-ethyl-5-[(E,Z)-1-(4-hydroxy-3-nitro-phenylamino)-methylene]-4-oxo-thiazolidin-2-ylidene}-acetic acid ethyl ester 851646-10-1 C17H16N4O6S
(E,Z)-cyano-{3-ethyl-5-[(E,Z)-1-(4-hydroxy-3-nitro-phenylamino)-methylene]-4-oxo-thiazolidin-2-ylidene}-acetic acid ethyl ester
—— 4-carbamimidoyl-2,6-dimethoxyphenol 95065-45-5 C9H12N2O3
4-carbamimidoyl-2,6-dimethoxyphenol
—— neodymium(III) 2-((2-hydroxybenzylidene)amino)phenolate 2-((2-oxidobenzylidene)amino)phenolate 65465-04-5 C13H9NO2*C13H10NO2*Nd
neodymium(III) 2-((2-hydroxybenzylidene)amino)phenolate 2-((2-oxidobenzylidene)amino)phenolate
—— 1-(2-fluoro-ethyl)-3-(3-hydroxy-benzyl)-urea 1044257-26-2 C10H13FN2O2
1-(2-fluoro-ethyl)-3-(3-hydroxy-benzyl)-urea
—— 5-methyl-2-phenyl-2H-pyrazole-3,4-dione 4-[(2-hydroxy-5-nitro-phenyl)-hydrazone] 18921-89-6 C16H13N5O4
5-methyl-2-phenyl-2H-pyrazole-3,4-dione 4-[(2-hydroxy-5-nitro-phenyl)-hydrazone]
—— 5-Salicyliden-2-thion-1,3-thiazanon-4 27990-55-2 C11H9NO2S2
5-Salicyliden-2-thion-1,3-thiazanon-4
—— 2-Isopropylamino-3,5-dinitrophenol 32418-16-9 C9H11N3O5
2-Isopropylamino-3,5-dinitrophenol
—— 37970-40-4 C17H15N3O3