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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
—— <i>N</i>-[5-(4-vanillylidenehydrazino-benzenesulfonyl)-thiazol-2-yl]-acetamide 108477-89-0 C19H18N4O5S2
<i>N</i>-[5-(4-vanillylidenehydrazino-benzenesulfonyl)-thiazol-2-yl]-acetamide
—— 1-(3-Brom-4-hydroxy-5-methoxyphenyl)-1-ethanol 55182-67-7 C9H11BrO3
1-(3-Brom-4-hydroxy-5-methoxyphenyl)-1-ethanol
—— 6-methoxy-2-(2-methyl-1-penten-5-yl)phenol 123974-03-8 C13H18O2
6-methoxy-2-(2-methyl-1-penten-5-yl)phenol
—— 2-(2-allyl-1,1-divinyl-pent-4-enyloxymethyl)-phenol 697744-51-7 C19H24O2
2-(2-allyl-1,1-divinyl-pent-4-enyloxymethyl)-phenol
—— 4-(3-chloropropyl)-2,5-dimethoxyphenol 111112-98-2 C11H15ClO3
4-(3-chloropropyl)-2,5-dimethoxyphenol
—— (4S)-4-benzyl-3-[3-(4-hydroxyphenyl)propanoyl]-1,3-oxazolidin-2-one 1224882-66-9 C19H19NO4
(4S)-4-benzyl-3-[3-(4-hydroxyphenyl)propanoyl]-1,3-oxazolidin-2-one
—— phenethyl 2-(3,4-dihydroxyphenyl)acetate 1425795-73-8 C16H16O4
phenethyl 2-(3,4-dihydroxyphenyl)acetate
—— [3-(4-Hydroxy-2-methoxy-phenyl)-propyl]-carbamic acid methyl ester 111113-01-0 C12H17NO4
[3-(4-Hydroxy-2-methoxy-phenyl)-propyl]-carbamic acid methyl ester
—— (5Z)-2-[(2,6-dichlorophenyl)amino]-5-[(3-hydroxy-4-nitrophenyl)methylidene]-1,3-thiazol-4(5H)-one 864275-13-8 C16H9Cl2N3O4S
(5Z)-2-[(2,6-dichlorophenyl)amino]-5-[(3-hydroxy-4-nitrophenyl)methylidene]-1,3-thiazol-4(5H)-one
—— 2,5-dibromo-3,4,6-trichloro-phenol 119916-55-1 C6HBr2Cl3O
2,5-dibromo-3,4,6-trichloro-phenol
—— 1,5-Diphenyl-3-(2-hydroxy-5,6-dimethoxy-phenyl)-pyrazolin 95433-11-7 C23H22N2O3
1,5-Diphenyl-3-(2-hydroxy-5,6-dimethoxy-phenyl)-pyrazolin
—— (+)-9-hydroxy-4,6-bis(4-hydroxyphenyl)-9,11-dimethyltricyclo-[5.2.2.0<sup>2,6</sup>]undeca-4,10-diene-3,8-dione 1414335-80-0 C25H22O5
(+)-9-hydroxy-4,6-bis(4-hydroxyphenyl)-9,11-dimethyltricyclo-[5.2.2.0<sup>2,6</sup>]undeca-4,10-diene-3,8-dione
—— 2,4-Dichlor-orcinol-3-benzylaether 106472-53-1 C14H12Cl2O2
2,4-Dichlor-orcinol-3-benzylaether
—— 3,3-Bis-<4-hydroxy-phenyl>-5,6-dihydro-3H-isobenzofuran-1-on 96057-85-1 C20H16O4
3,3-Bis-<4-hydroxy-phenyl>-5,6-dihydro-3H-isobenzofuran-1-on
—— 1-[(2-hydroxy-5-nitro-phenyl)-methanesulfonyl]-piperidine 58661-99-7 C12H16N2O5S
1-[(2-hydroxy-5-nitro-phenyl)-methanesulfonyl]-piperidine
—— bis(isonicotinamidosalicylaldimine)diisothiocyanatodioxouranium(VI) 155642-15-2 C28H22N8O6S2U
bis(isonicotinamidosalicylaldimine)diisothiocyanatodioxouranium(VI)
—— 2-<i>tert</i>-Butyl-4-(2,3-epoxy-propoxy)-phenol 7020-07-7 C13H18O3
2-<i>tert</i>-Butyl-4-(2,3-epoxy-propoxy)-phenol
—— 2-methyl-5-(p-hydroxybenzyl)-1,3,4-oxadiazole 119192-14-2 C10H10N2O2
2-methyl-5-(p-hydroxybenzyl)-1,3,4-oxadiazole
—— 6-[(2S,3R,4S,5R,8S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-2,4,8-trimethyl-nonyl]-2,4-dimethoxy-3-methyl-phenol 717916-68-2 C33H64O6Si2
6-[(2S,3R,4S,5R,8S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-2,4,8-trimethyl-nonyl]-2,4-dimethoxy-3-methyl-phenol
—— 1-(4,5-Dihydro-5-(4-hydroxy-3-methoxyphenyl)-3-(3,4, 5-trimethoxyphenyl)pyrazol-1-yl)ethanone 1415219-32-7 C21H24N2O6
1-(4,5-Dihydro-5-(4-hydroxy-3-methoxyphenyl)-3-(3,4, 5-trimethoxyphenyl)pyrazol-1-yl)ethanone
—— (2,2'-Dihydroxy-benzophenon)-benzaldehyd-azin 100354-53-8 C20H16N2O2
(2,2'-Dihydroxy-benzophenon)-benzaldehyd-azin
—— 2-(tert-butyldimethylsilyl)-4-(3-hydroxypropyl)phenol 1428317-39-8 C15H26O2Si
2-(tert-butyldimethylsilyl)-4-(3-hydroxypropyl)phenol
—— 4-{[(2-hydroxyphenyl)methylene]amino}-5-methyl-2-{[(2-morpholin-4-ylethyl)amino]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one 1402046-40-5 C17H24N6O3
4-{[(2-hydroxyphenyl)methylene]amino}-5-methyl-2-{[(2-morpholin-4-ylethyl)amino]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one
—— N'-(2-Hydroxy-3-methoxybenzylidene)-2-(4-propylphenoxy)acetohydrazide 303084-60-8 C19H22N2O4
N'-(2-Hydroxy-3-methoxybenzylidene)-2-(4-propylphenoxy)acetohydrazide
—— N'-[(Z)-(2-hydroxy-3-methoxyphenyl)methylidene]pyrazine-2-carbohydrazide 917777-49-2 C13H12N4O3
N'-[(Z)-(2-hydroxy-3-methoxyphenyl)methylidene]pyrazine-2-carbohydrazide
—— 4-(6-methyl-1,3-thiazolo[5,4-b]pyridin-2-yl)benzene-1,3-diol 1357359-25-1 C13H10N2O2S
4-(6-methyl-1,3-thiazolo[5,4-b]pyridin-2-yl)benzene-1,3-diol
—— 5,11,17,23,29,35-Hexa-tert-butyl-37,38,40,41-tetrahydroxy-39,42-<2,6-pyridinediylbis(methyleneoxy)>calix<6>arene 173845-08-4 C73H89NO6
5,11,17,23,29,35-Hexa-tert-butyl-37,38,40,41-tetrahydroxy-39,42-<2,6-pyridinediylbis(methyleneoxy)>calix<6>arene
—— 4-hydroxybenzyl-H-phosphinic acid butyl ester 1071907-28-2 C11H17O3P
4-hydroxybenzyl-H-phosphinic acid butyl ester
—— 3-(Furan-2-yl)-4-((4-hydroxy-3,5-dimethoxybenzylidene)amino)-1H-1,2,4-triazole-5(4H)-thione 478253-75-7 C15H14N4O4S
3-(Furan-2-yl)-4-((4-hydroxy-3,5-dimethoxybenzylidene)amino)-1H-1,2,4-triazole-5(4H)-thione
—— 2-methyl-5-(1-methyl-butylamino)-phenol 437702-35-7 C12H19NO
2-methyl-5-(1-methyl-butylamino)-phenol
—— 2,4,6-trinitrobenzene-1,3,5-triol, ammonia salt 104704-25-8 C6H3N3O9*H3N
2,4,6-trinitrobenzene-1,3,5-triol, ammonia salt
—— 2,5-bis(2-hydroxyphenyl)-1,3,4-thiadiazole 88203-22-9 C14H10N2O2S
2,5-bis(2-hydroxyphenyl)-1,3,4-thiadiazole
—— (4-Me-2-iPr2C6H3)2NRh(C6H5)OCOC(CH3)3 1352009-35-8 C37H54NO2P2Rh
(4-Me-2-iPr2C6H3)2NRh(C6H5)OCOC(CH3)3
—— 2,4-Bis(trifluoromethylsulfonyl)-5-chloro-6-nitrophenol 115848-49-2 C8H2ClF6NO7S2
2,4-Bis(trifluoromethylsulfonyl)-5-chloro-6-nitrophenol
—— 2,6-bis-[(2-hydroxy-ethylimino)-methyl]-4-methyl phenol 174504-82-6 C13H18N2O3
2,6-bis-[(2-hydroxy-ethylimino)-methyl]-4-methyl phenol
—— 5-Methyl-2-[5-((Z)-styryl)-isoxazol-3-yl]-phenol 104387-50-0 C18H15NO2
5-Methyl-2-[5-((Z)-styryl)-isoxazol-3-yl]-phenol
—— 143018-01-3 C75H110Br2O8
—— 4-[[[4-[[Bis[(4-hydroxy-3-iodo-5-methoxyphenyl)methyl]amino]methyl]phenyl]methyl-[(4-hydroxy-3-iodo-5-methoxyphenyl)methyl]amino]methyl]-2-iodo-6-methoxyphenol 1246672-87-6 C40H40I4N2O8
4-[[[4-[[Bis[(4-hydroxy-3-iodo-5-methoxyphenyl)methyl]amino]methyl]phenyl]methyl-[(4-hydroxy-3-iodo-5-methoxyphenyl)methyl]amino]methyl]-2-iodo-6-methoxyphenol
—— 3,5-Dibromo-2-(propan-2-ylamino)-6-(propan-2-yliminomethyl)phenol 1138152-11-0 C13H18Br2N2O
3,5-Dibromo-2-(propan-2-ylamino)-6-(propan-2-yliminomethyl)phenol
—— 4-methyl-6,9-dihydroxy-7,8-diallyl-3,3-dioxo-1,2,5,9b-tetrahydrothieno<3,2-a>naphthalene 125219-88-7 C19H22O4S
4-methyl-6,9-dihydroxy-7,8-diallyl-3,3-dioxo-1,2,5,9b-tetrahydrothieno<3,2-a>naphthalene
—— Bis-o-hydroxyphenylquecksilberverbindung der Diethylbarbitursaeure 100000-84-8 C20H20Hg2N2O5
Bis-o-hydroxyphenylquecksilberverbindung der Diethylbarbitursaeure
—— N,N'-bis(5-nitrosalicylidene)-1,12-dodecanediamine 1334545-45-7 C26H34N4O6
N,N'-bis(5-nitrosalicylidene)-1,12-dodecanediamine
—— 6-hydroxy-2,3-dimethylbenzonitrile 52911-63-4 C9H9NO
6-hydroxy-2,3-dimethylbenzonitrile
—— 2-[4-Bromo-5-(4-methoxy-phenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-4-methyl-phenol 83548-82-7 C23H21BrN2O2
2-[4-Bromo-5-(4-methoxy-phenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-4-methyl-phenol
—— N,N'-bis[3-(3,4-dihydroxyphenoxy)-2-hydroxypropyl]-1,4-diaminobutane 62950-82-7 C22H32N2O8
N,N'-bis[3-(3,4-dihydroxyphenoxy)-2-hydroxypropyl]-1,4-diaminobutane
—— (E)-4-hydroxy-3-methoxy-(1'-(2)H)cinnamic acid ethyl ester 902515-76-8 C12H14O4
(E)-4-hydroxy-3-methoxy-(1'-(2)H)cinnamic acid ethyl ester
—— 5,11,17,23-tetratert-butyl-28-hydrazinylidenepentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),4,9,11,13(27),15(26),16,18,21(25),22-decaene-25,26,27-triol 147226-42-4 C44H60N2O3
5,11,17,23-tetratert-butyl-28-hydrazinylidenepentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),4,9,11,13(27),15(26),16,18,21(25),22-decaene-25,26,27-triol
—— 2-<5-(3-Pyridyl)-furfurylideneamino>-phenol 38594-25-1 C16H12N2O2
2-<5-(3-Pyridyl)-furfurylideneamino>-phenol
—— (1S,9S,10R)-4-hydroxy-10-iodomethyl-10-methyl-11-oxatricyclo[7.2.1.0(2,7)]dodeca-2,4,6-triene 1315472-04-8 C13H15IO2
(1S,9S,10R)-4-hydroxy-10-iodomethyl-10-methyl-11-oxatricyclo[7.2.1.0(2,7)]dodeca-2,4,6-triene
—— 132043-50-6 C15H24O3