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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
—— 6-benzyl-6-(2-hydroxy-3,5-dinitrobenzyl)-1,4,8,11-tetraoxacyclotetradecane 106419-39-0 C24H30N2O9
6-benzyl-6-(2-hydroxy-3,5-dinitrobenzyl)-1,4,8,11-tetraoxacyclotetradecane
—— 1-(3,5-dihydroxy-phenyl)-4-(4-methoxy-phenyl)-butan-1-ol 101747-02-8 C17H20O4
1-(3,5-dihydroxy-phenyl)-4-(4-methoxy-phenyl)-butan-1-ol
—— 3,5-dinitro-N-(pentafluorophenyl)salicylaldimine 1422157-77-4 C13H4F5N3O5
3,5-dinitro-N-(pentafluorophenyl)salicylaldimine
—— 934820-96-9 C19H23BrO4
—— 6-(2-hydroxy-5-nitrophenyl)-5,5-dimethyl-4,5-dihydro-3(2H)-pyridazinone 483323-98-4 C12H13N3O4
6-(2-hydroxy-5-nitrophenyl)-5,5-dimethyl-4,5-dihydro-3(2H)-pyridazinone
—— 3-hydroxy-4-methyl-2-nitro-N-(cyanoethyl)benzamide 159301-22-1 C11H11N3O4
3-hydroxy-4-methyl-2-nitro-N-(cyanoethyl)benzamide
—— 3-bromo-4-nitro-5-propylphenol 94102-93-9 C9H10BrNO3
3-bromo-4-nitro-5-propylphenol
—— ethyl 2-hydroxy-4-nitrobenzimidate hydrochloride 105430-50-0 C9H10N2O4*ClH
ethyl 2-hydroxy-4-nitrobenzimidate hydrochloride
—— 3-Bromo-4-hydroxy-5-methoxybenzaldehyde (4-nitrophenyl)hydrazone 303084-47-1 C14H12BrN3O4
3-Bromo-4-hydroxy-5-methoxybenzaldehyde (4-nitrophenyl)hydrazone
—— 5-(5-bromo-1H-indol-3-yl)-2-methoxy-4-methylphenol 1613299-10-7 C16H14BrNO2
5-(5-bromo-1H-indol-3-yl)-2-methoxy-4-methylphenol
—— 3,5-Dimethyl-4-(penta-2t,4-dienyl)-phenol 28070-20-4 C13H16O
3,5-Dimethyl-4-(penta-2t,4-dienyl)-phenol
—— 6-tert-butyl-9-hydroxy[3.3]metacyclophane 103665-36-7 C22H28O
6-tert-butyl-9-hydroxy[3.3]metacyclophane
—— 471296-69-2 C19H22N2O3
—— 4-Bromo-2-(5-hydroxypentyliminomethyl)phenol 1612762-70-5 C12H16BrNO2
4-Bromo-2-(5-hydroxypentyliminomethyl)phenol
—— 3,4-Bis-[1-(2-hydroxy-phenyl)-meth-(Z)-ylidene]-dihydro-furan-2,5-dione 111385-02-5 C18H12O5
3,4-Bis-[1-(2-hydroxy-phenyl)-meth-(Z)-ylidene]-dihydro-furan-2,5-dione
—— erythro and threo--guaiacylglycerol-β-coniferyl aldehyde ether triacetate 82701-29-9 C16H20O8
erythro and threo--guaiacylglycerol-β-coniferyl aldehyde ether triacetate
—— (R)-3-(1-(4-hydroxy-3-methoxyphenyl)-2-nitroethyl)pentane-2,4-dione 1608092-00-7 C14H17NO6
(R)-3-(1-(4-hydroxy-3-methoxyphenyl)-2-nitroethyl)pentane-2,4-dione
—— 5-(m-hydroxyphenyl)-6-undecanone 96649-59-1 C17H26O2
5-(m-hydroxyphenyl)-6-undecanone
—— 1-(3-hydroxyphenyl)-2-(thien-2-yl)cyclopropane 219521-13-8 C13H12OS
1-(3-hydroxyphenyl)-2-(thien-2-yl)cyclopropane
—— [2-(1(3)<i>H</i>-imidazole-4-carbonyloxy)-ethyl]-trimethyl-ammonium; dipicrate 122596-64-9 C6H2N3O7*C6H3N3O7*C9H16N3O2
[2-(1(3)<i>H</i>-imidazole-4-carbonyloxy)-ethyl]-trimethyl-ammonium; dipicrate
—— 2-[(E)-5-(3,3-Dimethyl-oxiranyl)-3-methyl-pent-2-enyl]-4-methoxy-phenol 191401-65-7 C17H24O3
2-[(E)-5-(3,3-Dimethyl-oxiranyl)-3-methyl-pent-2-enyl]-4-methoxy-phenol
—— 4-(4-hydroxyphenyl)furazan-3-carbonitrile 862608-11-5 C9H5N3O2
4-(4-hydroxyphenyl)furazan-3-carbonitrile
—— 2,4,N-trihydroxy-5-nitrobenzamide 941305-95-9 C7H6N2O6
2,4,N-trihydroxy-5-nitrobenzamide
—— 4-(3-chloro-6-hydroxy-2,4-dimethyl-phenyl)-butyric acid dimethylamide 100794-52-3 C14H20ClNO2
4-(3-chloro-6-hydroxy-2,4-dimethyl-phenyl)-butyric acid dimethylamide
—— 5-[5-(3,4-Dihydroxyphenyl)thiophen-2-yl]-3-iodobenzene-1,2-diol 1394840-56-2 C16H11IO4S
5-[5-(3,4-Dihydroxyphenyl)thiophen-2-yl]-3-iodobenzene-1,2-diol
—— 5,11,17,23-tetrabromo-2,8,14,20-tetramethylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25)3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol 83136-18-9 C32H28Br4O8
5,11,17,23-tetrabromo-2,8,14,20-tetramethylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25)3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol
—— 1357023-47-2 C20H24O6
—— 1-(tert-Butyl-diphenyl-silanyloxy)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-benzene 96013-92-2 C40H46O2Si2
1-(tert-Butyl-diphenyl-silanyloxy)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-benzene
—— calix<4>arene-acetone (1:1) clathrate 95309-25-4 C3H6O*C28H24O4
calix<4>arene-acetone (1:1) clathrate
—— PGMAC 748798-53-0 C27H37ClO5
PGMAC
—— 4-hydroxy-3-methoxy-benzoic acid-(5-hydroxy-1,5-dimethyl-hexylamide) 107152-53-4 C16H25NO4
4-hydroxy-3-methoxy-benzoic acid-(5-hydroxy-1,5-dimethyl-hexylamide)
—— 1-(5-Fluor-2-hydroxy-phenyl)-3-(4-hydroxy-3-methoxy-phenyl)-prop-2-enon-(2,4-dinitro-phenylhydrazon) 1764-10-9 C22H17FN4O7
1-(5-Fluor-2-hydroxy-phenyl)-3-(4-hydroxy-3-methoxy-phenyl)-prop-2-enon-(2,4-dinitro-phenylhydrazon)
—— p-cresol-3,5-d2-OH 2213-77-6 C7H8O
p-cresol-3,5-d2-OH
—— 4-{[(3-bromo-4-hydroxyphenyl)methylidene]amino}phenol 1453073-16-9 C13H10BrNO2
4-{[(3-bromo-4-hydroxyphenyl)methylidene]amino}phenol
—— Coniferylalkohol-2-d1 34382-88-2 C10H12O3
Coniferylalkohol-2-d1
—— 1-hydroxy-4,5-dihydro-6H-isoxazolo-[5,4-d][2]-benzazepine hydrobromide 131753-28-1 BrH*C11H10N2O2
1-hydroxy-4,5-dihydro-6H-isoxazolo-[5,4-d][2]-benzazepine hydrobromide
—— 2-(4-Hydroxy-3-methoxybenzyliden-hydrazono)-4-oxo-3-p-tolyl-thiazolidin 98654-77-4 C18H17N3O3S
2-(4-Hydroxy-3-methoxybenzyliden-hydrazono)-4-oxo-3-p-tolyl-thiazolidin
—— 28-hydro-25,26,27,28-tetrahydroxycalix[4]monoquinone-17-ethylene ketal 386223-93-4 C30H28O6
28-hydro-25,26,27,28-tetrahydroxycalix[4]monoquinone-17-ethylene ketal
—— N-[(2-hydroxy-6-methoxyphenyl)methylideneamino]benzamide 1235837-32-7 C15H14N2O3
N-[(2-hydroxy-6-methoxyphenyl)methylideneamino]benzamide
—— 3,5-Diisopropoxy-2-methyl-phenol 215163-08-9 C13H20O3
3,5-Diisopropoxy-2-methyl-phenol
—— 4-amino-2-iodo-5-methyl-phenol 861619-94-5 C7H8INO
4-amino-2-iodo-5-methyl-phenol
—— 7-(2,3-dihydroxyphenyl)heptyl bromide 53545-42-9 C13H19BrO2
7-(2,3-dihydroxyphenyl)heptyl bromide
—— 1-(2-Hydroxy-3-methyl-phenyl)-butan-1,3-dion-dioxim 56686-30-7 C11H14N2O3
1-(2-Hydroxy-3-methyl-phenyl)-butan-1,3-dion-dioxim
—— 2,4,6-triallyl-benzene-1,3,5-triol 845827-52-3 C15H18O3
2,4,6-triallyl-benzene-1,3,5-triol
—— rac-2-methoxy-5-(4,5,6,7-tetrahydrothieno[2,3-c]pyridin-7-ylmethyl)phenol 1394174-39-0 C15H17NO2S
rac-2-methoxy-5-(4,5,6,7-tetrahydrothieno[2,3-c]pyridin-7-ylmethyl)phenol
—— N-(3-hydroxy-4-methoxybenzyl)-N-methyl-4-hydroxy-3-methoxybenzamide 148234-93-9 C17H19NO5
N-(3-hydroxy-4-methoxybenzyl)-N-methyl-4-hydroxy-3-methoxybenzamide
—— 3-[2-[Bis[2-[(2,3-dihydroxyphenyl)methylideneamino]ethyl]amino]ethyliminomethyl]benzene-1,2-diol 141233-06-9 C27H30N4O6
3-[2-[Bis[2-[(2,3-dihydroxyphenyl)methylideneamino]ethyl]amino]ethyliminomethyl]benzene-1,2-diol
—— 3,5-dioxo-1,2-diphenyl-pyrazolidine-4-carbothioic acid 4-hydroxy-anilide 106599-55-7 C22H17N3O3S
3,5-dioxo-1,2-diphenyl-pyrazolidine-4-carbothioic acid 4-hydroxy-anilide
—— 160748-58-3 C18H19ClN2O2
—— 2-benzyloxy-5-methoxy-phenol 84354-18-7 C14H14O3
2-benzyloxy-5-methoxy-phenol