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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-methoxy-2-hydroxy-α-methylstyrene 87307-81-1 C10H12O2
3-methoxy-2-hydroxy-α-methylstyrene
—— 2-benzyloxy-3-methoxyphenol 122450-20-8 C14H14O3
2-benzyloxy-3-methoxyphenol
—— 4,4'-(isoxazol-3,5-diyl)diphenol 22439-73-2 C15H11NO3
4,4'-(isoxazol-3,5-diyl)diphenol
—— (E)-3,5-bis(4-hydroxyphenyl )-4-(non-1-en-1-yl)isoxazole  1400414-26-7 C24H27NO3
(E)-3,5-bis(4-hydroxyphenyl )-4-(non-1-en-1-yl)isoxazole 
—— (E)-4-(3,3-dimethyl-but-1-E-en-1-yl)-3,5-bis(4-hydroxyphenyl )isoxazole 1400414-32-5 C21H21NO3
(E)-4-(3,3-dimethyl-but-1-E-en-1-yl)-3,5-bis(4-hydroxyphenyl )isoxazole
—— 2-Methoxy-6-methyl-4-propan-2-yl-phenol 1083004-16-3 C11H16O2
2-Methoxy-6-methyl-4-propan-2-yl-phenol
—— (E)-N-(4-hydroxy-3-methoxy-d3-benzyl)-8-methylnon-6-enamide 1217899-52-9 C18H27NO3
(E)-N-(4-hydroxy-3-methoxy-d3-benzyl)-8-methylnon-6-enamide
—— 4-methoxy-2-[6-hydroxy-E-1-hexenyl]phenol 252233-97-9 C13H18O3
4-methoxy-2-[6-hydroxy-E-1-hexenyl]phenol
—— 3-benzyloxy-2-methoxyphenol 1072844-44-0 C14H14O3
3-benzyloxy-2-methoxyphenol
—— 2-fluoro-6-((methylamino)methyl)-4-nitrophenol 1508296-29-4 C8H9FN2O3
2-fluoro-6-((methylamino)methyl)-4-nitrophenol
—— 2-hydroxy-5-nitrophenylacetic acid methyl ester 155388-58-2 C9H9NO5
2-hydroxy-5-nitrophenylacetic acid methyl ester
—— methyl 2-(3-bromo-2-hydroxyphenyl)acetate 628331-74-8 C9H9BrO3
methyl 2-(3-bromo-2-hydroxyphenyl)acetate
—— 4-methoxy-2-(methoxyethoxy)methoxyphenol 881027-28-7 C11H16O5
4-methoxy-2-(methoxyethoxy)methoxyphenol
—— 4-chloro-2-[(5-methyl-3-isoxazolyl)amino]methylphenol 1153622-49-1 C11H11ClN2O2
4-chloro-2-[(5-methyl-3-isoxazolyl)amino]methylphenol
—— (S)-4-(1-hydroxy-2-nitroethyl)phenol 1268725-97-8 C8H9NO4
(S)-4-(1-hydroxy-2-nitroethyl)phenol
—— tert-butyl 2-(2-hydroxy-3-methoxybenzoyl)acrylate 1351365-26-8 C15H18O5
tert-butyl 2-(2-hydroxy-3-methoxybenzoyl)acrylate
—— {(1-4-η)-5-(2-amino-6-hydroxy-5-methoxy-3,4-dimethylphenyl)cyclohexa-1,3-diene}tricarbonyliron 125937-42-0 C18H19FeNO5
{(1-4-η)-5-(2-amino-6-hydroxy-5-methoxy-3,4-dimethylphenyl)cyclohexa-1,3-diene}tricarbonyliron
—— 5,11,17,23-Tetrakis(3-hydroxypropoxymethyl)-2,8,14,20-tetrakis(2-methylpropyl)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 1274936-97-8 C60H88O16
5,11,17,23-Tetrakis(3-hydroxypropoxymethyl)-2,8,14,20-tetrakis(2-methylpropyl)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-(3-hydroxyphenyl)cyclopropyl cyclopropyl ketone 219521-18-3 C13H14O2
2-(3-hydroxyphenyl)cyclopropyl cyclopropyl ketone
—— 3-(3,4-dihydroxyphenyl)propyl acetate 1390634-11-3 C11H14O4
3-(3,4-dihydroxyphenyl)propyl acetate
—— 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