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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
—— 2-Methoxy-phenol; compound with piperazine 93990-77-3 C4H10N2*C7H8O2
2-Methoxy-phenol; compound with piperazine
—— N-2-hydroxy-5-nitrophenyl-N'-butylthiourea 78720-29-3 C11H15N3O3S
N-2-hydroxy-5-nitrophenyl-N'-butylthiourea
—— 5-Iodo-2-methoxy-4-[(4-octyltriazol-1-yl)methyl]phenol 1003840-83-2 C18H26IN3O2
5-Iodo-2-methoxy-4-[(4-octyltriazol-1-yl)methyl]phenol
—— 2,6-Dimethyl-α,α-bis(trifluormethyl)-α-methylamino-p-kresol 16867-74-6 C12H13F6NO
2,6-Dimethyl-α,α-bis(trifluormethyl)-α-methylamino-p-kresol
—— 4-(1,2,4,5-tetrazin-3-yl)phenol 58884-34-7 C8H6N4O
4-(1,2,4,5-tetrazin-3-yl)phenol
—— 2,4,6-Tris-azepan-1-ylmethyl-benzene-1,3,5-triol 7366-58-7 C27H45N3O3
2,4,6-Tris-azepan-1-ylmethyl-benzene-1,3,5-triol
—— 4'-hydroxy-3,3',5,5'-tetramethyl-[1,1'-biphenyl]-4(1H)-one 6818-66-2 C16H18O2
4'-hydroxy-3,3',5,5'-tetramethyl-[1,1'-biphenyl]-4(1H)-one
—— 2-(1-(isopropylimino)ethyl)-5-methoxyphenol 803745-44-0 C12H17NO2
2-(1-(isopropylimino)ethyl)-5-methoxyphenol
—— N-{2-(4-hydroxybenzylidenehydrazino)-ethyl}-2-aminothiazole 1330187-61-5 C12H14N4OS
N-{2-(4-hydroxybenzylidenehydrazino)-ethyl}-2-aminothiazole
—— 2,4-dibromo-5-methylsulfanyl-phenol 861076-84-8 C7H6Br2OS
2,4-dibromo-5-methylsulfanyl-phenol
—— (4R)-4-hydroxy-4-(2-hydroxy-3-methoxy-phenyl)-butan-2-one 1162642-16-1 C11H14O4
(4R)-4-hydroxy-4-(2-hydroxy-3-methoxy-phenyl)-butan-2-one
—— <5,5-(2)H2>-2-(2,4-pentadienyl)-3-bromo-4,6-dimethoxy-5-methylphenol 105103-93-3 C14H17BrO3
<5,5-(2)H2>-2-(2,4-pentadienyl)-3-bromo-4,6-dimethoxy-5-methylphenol
—— 5-(3-hydroxy-4-methoxyphenyl)-4,4-dimethyl-2-(piperidin-4-yl)-2,4-dihydro-3H-pyrazol-3-one 1227153-79-8 C17H23N3O3
5-(3-hydroxy-4-methoxyphenyl)-4,4-dimethyl-2-(piperidin-4-yl)-2,4-dihydro-3H-pyrazol-3-one
—— tert-butyl (4-hydroxybenzyl)(methyl)carbamate 1046818-38-5 C13H19NO3
tert-butyl (4-hydroxybenzyl)(methyl)carbamate
—— 1361118-13-9 C15H16O2
—— 2-[[2-[[(2-Hydroxy-3-methoxyphenyl)methylideneamino]methyl]-3-pyridin-2-ylpropyl]iminomethyl]-6-methoxyphenol 219510-19-7 C25H27N3O4
2-[[2-[[(2-Hydroxy-3-methoxyphenyl)methylideneamino]methyl]-3-pyridin-2-ylpropyl]iminomethyl]-6-methoxyphenol
—— beta-Resorcylaldehyde, 2-pyridylhydrazone 50286-85-6 C12H11N3O2
beta-Resorcylaldehyde, 2-pyridylhydrazone
—— 1-[(5-Bromo-2-hydroxyphenyl)methylideneamino]-3-hexadecylthiourea 7399-44-2 C24H40BrN3OS
1-[(5-Bromo-2-hydroxyphenyl)methylideneamino]-3-hexadecylthiourea
—— 4,5-Dimethyl-3-pentadecyl-6-<dimethylamino-methyl>-brenzcatechin 16273-21-5 C26H47NO2
4,5-Dimethyl-3-pentadecyl-6-<dimethylamino-methyl>-brenzcatechin
—— 1-[5-(2,4-Dinitro-phenylamino)-2-hydroxy-phenyl]-naphthalen-2-ol 40112-34-3 C22H15N3O6
1-[5-(2,4-Dinitro-phenylamino)-2-hydroxy-phenyl]-naphthalen-2-ol
—— 2-(Diethylaminomethyl)cyclohexanone picrate 101591-56-4 C17H24N4O8
2-(Diethylaminomethyl)cyclohexanone picrate
—— (R,R)-N,N'-bis(3-methyl-salicylidene)-1,2-cyclohexanediamine 336105-87-4 C22H26N2O2
(R,R)-N,N'-bis(3-methyl-salicylidene)-1,2-cyclohexanediamine
—— 2-bromo-6-ethylideneamino-4-nitro-phenol 53088-05-4 C8H7BrN2O3
2-bromo-6-ethylideneamino-4-nitro-phenol
—— Sodium; 4-(3-hydroxy-4,5-dimethoxy-2-methyl-6-sulfooxy-phenyl)-butyrate 103993-51-7 C13H16O9S*2Na
Sodium; 4-(3-hydroxy-4,5-dimethoxy-2-methyl-6-sulfooxy-phenyl)-butyrate
—— N,N'-bis(salicylidene)-(1S)-ortho-chlorophenyl-1,2-ethylenediamine 958635-04-6 C22H19ClN2O2
N,N'-bis(salicylidene)-(1S)-ortho-chlorophenyl-1,2-ethylenediamine
—— 3',4',5'-Trihydroxy-stilbazol-(3) 20934-89-8 C13H11NO3
3',4',5'-Trihydroxy-stilbazol-(3)
—— 2-oxido-p-benzosemiquinone 70128-21-1 C6H3O3
2-oxido-p-benzosemiquinone
—— 1-n-Octyl-2-(o-hydroxyphenyl)-Δ<sup>2</sup>-imidazolin 84354-92-7 C17H26N2O
1-n-Octyl-2-(o-hydroxyphenyl)-Δ<sup>2</sup>-imidazolin
—— 15466-49-6 C18H18N4O2S2
—— tert-butyl N-[(3-amino-6-chloro-2-hydroxyphenyl)methyl]carbamate 761448-07-1 C12H17ClN2O3
tert-butyl N-[(3-amino-6-chloro-2-hydroxyphenyl)methyl]carbamate
—— 255884-66-3 C12H21N2O2Pt
—— 72054-29-6 C15H13Cl3NO2
—— (2R,5S)-3-acetyl-2-(4-hydroxyphenyl)-5-(D-arabino-tetritol-1-yl)oxazolidine 1008747-39-4 C15H21NO7
(2R,5S)-3-acetyl-2-(4-hydroxyphenyl)-5-(D-arabino-tetritol-1-yl)oxazolidine
—— 3-(4-Hydroxy-3,5-dimethoxy-phenyl)-1,2-benzothiazol 53249-64-2 C15H13NO3S
3-(4-Hydroxy-3,5-dimethoxy-phenyl)-1,2-benzothiazol
—— (Z)-5'-hydroxy-2'-iodo-4'-methoxyacetophenone O-4-nitrobenzyl oxime 1072708-47-4 C16H15IN2O5
(Z)-5'-hydroxy-2'-iodo-4'-methoxyacetophenone O-4-nitrobenzyl oxime
—— 2-Aethoxycarbonyl-3-phenyl-5-<3-brom-5-fluor-2-hydroxyphenyl>-cyclohex-5-en-1-on 3967-83-7 C21H18BrFO4
2-Aethoxycarbonyl-3-phenyl-5-<3-brom-5-fluor-2-hydroxyphenyl>-cyclohex-5-en-1-on
—— 2-[(1-butyl-1H-tetrazol-5-yl)-(3-imidazol-1-yl-propylamino)-methyl]-4-methyl-phenol 1025366-32-8 C19H27N7O
2-[(1-butyl-1H-tetrazol-5-yl)-(3-imidazol-1-yl-propylamino)-methyl]-4-methyl-phenol
—— 2,2'-Dithio-bis-(4-chlor-resorcinol) 2517-83-1 C12H8Cl2O4S2
2,2'-Dithio-bis-(4-chlor-resorcinol)
—— 6-isopropenyl-2-methoxy-3-methyl-phenol 1384950-08-6 C11H14O2
6-isopropenyl-2-methoxy-3-methyl-phenol
—— N,N'-bis{2-[(2-ethylimino)methyl]-5-bromophenol}piperazine 1207281-37-5 C22H26Br2N4O2
N,N'-bis{2-[(2-ethylimino)methyl]-5-bromophenol}piperazine
—— 2,5-di-methyl-4-[(dibutylphenylsilyl)methylthio]phenol 1230389-06-6 C23H34OSSi
2,5-di-methyl-4-[(dibutylphenylsilyl)methylthio]phenol
—— 2-(5-fluoro-4-(4-methoxyphenethoxy)-1-methyl-1H-indol-3-yl)-N-methylethanamine 1265217-80-8 C21H25FN2O2
2-(5-fluoro-4-(4-methoxyphenethoxy)-1-methyl-1H-indol-3-yl)-N-methylethanamine
—— 4-{2-[(pyridin-4-ylmethylene)-amino]-ethyl}-phenol 510714-46-2 C14H14N2O
4-{2-[(pyridin-4-ylmethylene)-amino]-ethyl}-phenol
—— (+/-)-Δ8-<8>gingerol 77334-09-9 C19H28O4
(+/-)-Δ8-<8>gingerol
—— N-(3-hydroxy-4-methoxyphenethyl)-N-(4-hydroxy-3-methoxyphenethyl)trifluoroacetamide 75608-46-7 C20H22F3NO5
N-(3-hydroxy-4-methoxyphenethyl)-N-(4-hydroxy-3-methoxyphenethyl)trifluoroacetamide
—— 6-dimethoxymethyl-5-(2-hydroxy-5-nitro-benzyl)-2-thioxo-2,3-dihydro-1<i>H</i>-pyrimidin-4-one 31349-18-5 C14H15N3O6S
6-dimethoxymethyl-5-(2-hydroxy-5-nitro-benzyl)-2-thioxo-2,3-dihydro-1<i>H</i>-pyrimidin-4-one
—— 4,4'-dichloro-2,2'-(piperazine-1,4-diyldiimino-dimethyl)-bis-phenol 19774-89-1 C18H18Cl2N4O2
4,4'-dichloro-2,2'-(piperazine-1,4-diyldiimino-dimethyl)-bis-phenol
—— (3-hydroxy-phenyl)-dimethyl sulfonium ; iodide 57556-25-9 C8H11OS*I
(3-hydroxy-phenyl)-dimethyl sulfonium ; iodide
—— 4-(2,4-Diamino-6-methoxy-pyrimidin-5-ylmethyl)-2,6-dimethoxy-phenol 73576-14-4 C14H18N4O4
4-(2,4-Diamino-6-methoxy-pyrimidin-5-ylmethyl)-2,6-dimethoxy-phenol
—— α-(3-Hydroxybenzyliden)-butyrolacton 1570-89-4 C11H10O3
α-(3-Hydroxybenzyliden)-butyrolacton