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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-(3',4'-dihydroxyphenyl)-4-hydroxy-5-<(4''-hydroxyphenyl)methylene>furan-2(5H)-one 131146-40-2 C17H12O6
3-(3',4'-dihydroxyphenyl)-4-hydroxy-5-<(4''-hydroxyphenyl)methylene>furan-2(5H)-one
—— 3-(3',4'-dihydroxyphenyl)-5-(4''-hydroxyphenyl)methylene-4-methoxyfuran-2(5H)-one 131146-38-8 C18H14O6
3-(3',4'-dihydroxyphenyl)-5-(4''-hydroxyphenyl)methylene-4-methoxyfuran-2(5H)-one
—— (+-)-4-<2,3-Dibrom-4,5-dihydroxy-phenyl>-4-hydroxy-butan-2-on 70625-27-3 C10H10Br2O4
(+-)-4-<2,3-Dibrom-4,5-dihydroxy-phenyl>-4-hydroxy-butan-2-on
—— 5-<o-hydroxyphenyl(dicyanomethyl)methyl>thiazolidine-2,4-dithione 98664-33-6 C13H9N3OS3
5-<o-hydroxyphenyl(dicyanomethyl)methyl>thiazolidine-2,4-dithione
—— 2,8,14,20-Tetrakis(2-methylpropyl)-5,11,17,23-tetrakis(pent-4-enoxymethyl)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 1094618-93-5 C68H96O12
2,8,14,20-Tetrakis(2-methylpropyl)-5,11,17,23-tetrakis(pent-4-enoxymethyl)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(pent-4-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 1094618-97-9 C68H88O12
2,8,14,20-Tetrakis(2-methylpropyl)-5,11,17,23-tetrakis(pent-4-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
—— 2-bromo-3-hydroxy-6-methoxybenzaldehyde 311312-49-9 C8H7BrO3
2-bromo-3-hydroxy-6-methoxybenzaldehyde
—— 4-(2-((tert-butyldimethylsilyl)oxy)pent-4-yn-1-yl)phenol 1190958-14-5 C17H26O2Si
4-(2-((tert-butyldimethylsilyl)oxy)pent-4-yn-1-yl)phenol
—— 4-allyl-2,3-dimethoxyphenol 29445-64-5 C11H14O3
4-allyl-2,3-dimethoxyphenol
—— 6-allyl-2,3-dimethoxyphenol 450357-58-1 C11H14O3
6-allyl-2,3-dimethoxyphenol
—— 1-(5-bromo-2-hydroxyphenyl)ethan-1-one oxime 42524-21-0 C8H8BrNO2
1-(5-bromo-2-hydroxyphenyl)ethan-1-one oxime
—— (2E,2'E)-N,N-[2,2'-disulfanediylbis(hexane-6,1-diyl)]bis[3-(3-bromo-4-hydroxyphenyl)-2-(hydroxyimino)propanamide] 1071822-36-0 C30H40Br2N4O6S2
(2E,2'E)-N,N-[2,2'-disulfanediylbis(hexane-6,1-diyl)]bis[3-(3-bromo-4-hydroxyphenyl)-2-(hydroxyimino)propanamide]
—— (2E,2'E)-N,N-[2,2'-disulfanediylbis(pentane-5,1-diyl)]bis[3-(3-bromo-4-hydroxyphenyl)-2-(hydroxyimino)propanamide] 1071822-35-9 C28H36Br2N4O6S2
(2E,2'E)-N,N-[2,2'-disulfanediylbis(pentane-5,1-diyl)]bis[3-(3-bromo-4-hydroxyphenyl)-2-(hydroxyimino)propanamide]
—— (2E,2'E)-N,N-[2,2'-disulfanediylbis(butane-4,1-diyl)]bis[3-(3-bromo-4-hydroxyphenyl)-2-(hydroxyimino)propanamide] 1071822-34-8 C26H32Br2N4O6S2
(2E,2'E)-N,N-[2,2'-disulfanediylbis(butane-4,1-diyl)]bis[3-(3-bromo-4-hydroxyphenyl)-2-(hydroxyimino)propanamide]
—— methyl 3-(3-bromo-4-hydroxyphenyl)-2-(hydroxyimino)-propanoate 1407513-66-9 C10H10BrNO4
methyl 3-(3-bromo-4-hydroxyphenyl)-2-(hydroxyimino)-propanoate
—— 3-(3-ethyl-4-hydroxy-5-methylphenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one 910814-19-6 C23H28O2S
3-(3-ethyl-4-hydroxy-5-methylphenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one
—— 4-Butyl-2-methylphenol 17269-95-3 C11H16O
4-Butyl-2-methylphenol
—— iso-gomphidic acid 104222-55-1 C18H12O9
iso-gomphidic acid
—— 3-(4-hydroxy-3-methyl-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one 910814-13-0 C21H24O2S
3-(4-hydroxy-3-methyl-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one
—— 3-(4-hydroxy-2,3,5-trimethyl-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one 910814-31-2 C23H28O2S
3-(4-hydroxy-2,3,5-trimethyl-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one
—— 3-(4-hydroxy-2-methoxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one 875012-99-0 C21H24O3S
3-(4-hydroxy-2-methoxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one
—— 3-(3-chloro-4-hydroxy-5-methyl-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclo-propa[a]pentalen-4-yl)-propan-1-one 910814-27-6 C21H23ClO2S
3-(3-chloro-4-hydroxy-5-methyl-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclo-propa[a]pentalen-4-yl)-propan-1-one
—— 3-(4-hydroxy-2,6-dimethyl-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one 910814-34-5 C22H26O2S
3-(4-hydroxy-2,6-dimethyl-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one
—— 3-(3,5-dimethoxy-4-hydroxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one 910814-23-2 C22H26O4S
3-(3,5-dimethoxy-4-hydroxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one
—— 3-(4-hydroxy-3-methoxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one 910814-17-4 C21H24O3S
3-(4-hydroxy-3-methoxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one
—— 3-allyl-5-fluoro-phenol 1079398-93-8 C9H9FO
3-allyl-5-fluoro-phenol
—— 6-fluoro-2-(3-hydroxy-4-methoxyphenyl)benzothiazole 916606-28-5 C14H10FNO2S
6-fluoro-2-(3-hydroxy-4-methoxyphenyl)benzothiazole
—— 2-(4-Hydroxyhex-5-enyl)-6-methoxyphenol 1356337-98-8 C13H18O3
2-(4-Hydroxyhex-5-enyl)-6-methoxyphenol
—— (E)-3'-hydroxy-4'-methoxyacetophenone O-4-nitrobenzyl oxime 1072708-42-9 C16H16N2O5
(E)-3'-hydroxy-4'-methoxyacetophenone O-4-nitrobenzyl oxime
—— 2-(1-Amino-2-methylpropan-2-yl)-4-methoxyphenol 1219098-67-5 C11H17NO2
2-(1-Amino-2-methylpropan-2-yl)-4-methoxyphenol
—— 2-[1-(Dimethoxyphosphorylamino)-2-methylpropan-2-yl]-4-methoxyphenol 1219098-68-6 C13H22NO5P
2-[1-(Dimethoxyphosphorylamino)-2-methylpropan-2-yl]-4-methoxyphenol
—— 3-(4-hydroxy-3,5-dimethyl-phenyl)-1-(4-phenyl-5-trifluoromethyl-thiophen-2-yl)-propan-1-one 917873-20-2 C22H19F3O2S
3-(4-hydroxy-3,5-dimethyl-phenyl)-1-(4-phenyl-5-trifluoromethyl-thiophen-2-yl)-propan-1-one
—— <2-(p-hydroxyphenyl)-2-methylperhydropyran-3-yl>methylamine 142683-82-7 C13H19NO2
<2-(p-hydroxyphenyl)-2-methylperhydropyran-3-yl>methylamine
—— 2-(3-hydroxy-5-methylphenyl)acetic acid 367261-75-4 C9H10O3
2-(3-hydroxy-5-methylphenyl)acetic acid
—— 4-[(3-Aminopropylamino)methyl]-2-methoxyphenol 1178285-73-8 C11H18N2O2
4-[(3-Aminopropylamino)methyl]-2-methoxyphenol
—— 2,5-Dimethoxy-4-chlor-phenol 18211-01-3 C8H9ClO3
2,5-Dimethoxy-4-chlor-phenol
—— (S)-2-(1-(pyridin-3-yl)ethyl)phenol 1275593-47-9 C13H13NO
(S)-2-(1-(pyridin-3-yl)ethyl)phenol
—— 4,5-Diisopropoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 1265221-61-1 C18H29BO5
4,5-Diisopropoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
—— 3-benzyl-4-(4-hydroxyphenyl)-1H-pyrrole-2,5-dione 1220307-41-4 C17H13NO3
3-benzyl-4-(4-hydroxyphenyl)-1H-pyrrole-2,5-dione
—— 3-(4-bromo-3-hydroxy-phenyl)-propionic acid ethyl ester 702687-44-3 C11H13BrO3
3-(4-bromo-3-hydroxy-phenyl)-propionic acid ethyl ester
—— (2,5-Dioxopyrrolidin-1-yl) 3-(3-hydroxyphenyl)propanoate 131450-43-6 C13H13NO5
(2,5-Dioxopyrrolidin-1-yl) 3-(3-hydroxyphenyl)propanoate
—— (HO)2C6H3-C(H)(3,5-dimethylpyrazol-1-yl)2 1365833-36-8 C17H20N4O2
(HO)2C6H3-C(H)(3,5-dimethylpyrazol-1-yl)2
—— 3-(5-Amino-1,3,4-thiadiazol-2-yl)phenol 64405-79-4 C8H7N3OS
3-(5-Amino-1,3,4-thiadiazol-2-yl)phenol
—— 4-bromo-2-(4-phenyl-2,5-dihydrofuran-2-yl)phenol 1489099-93-5 C16H13BrO2
4-bromo-2-(4-phenyl-2,5-dihydrofuran-2-yl)phenol
—— 5-acetyl-4-(5-bromo-2-hydroxyphenyl)-6-methyl-3,4-dihydropyrimidine-2(1H)-thione 301169-98-2 C13H13BrN2O2S
5-acetyl-4-(5-bromo-2-hydroxyphenyl)-6-methyl-3,4-dihydropyrimidine-2(1H)-thione
—— 4-bromo-2-(((5-methylpyridin-2-yl)imino)methyl)phenol 918667-03-5 C13H11BrN2O
4-bromo-2-(((5-methylpyridin-2-yl)imino)methyl)phenol
—— tris[2-(5-bromosalicylideneamino)ethyl]amine 142066-85-1 C27H27Br3N4O3
tris[2-(5-bromosalicylideneamino)ethyl]amine
—— 5-amino-7-(5-bromo-2-hydroxyphenyl)-8-nitro-3,7-dihydro-2H-thiazolo[3,2-a]pyridine-6-carbonitrile 1349736-49-7 C14H11BrN4O3S
5-amino-7-(5-bromo-2-hydroxyphenyl)-8-nitro-3,7-dihydro-2H-thiazolo[3,2-a]pyridine-6-carbonitrile
—— 9-(5-bromo-2-hydroxyphenyl)-3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-2H-xanthene-1,8(5H,9H)-dione 312515-52-9 C23H25BrO4
9-(5-bromo-2-hydroxyphenyl)-3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-2H-xanthene-1,8(5H,9H)-dione
—— (5-hydroxy-2-nitro-phenyl)-acetic acid 141577-22-2 C8H7NO5
(5-hydroxy-2-nitro-phenyl)-acetic acid