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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-(5-phenylthiophen-2-yl)phenol 1078733-84-2 C16H12OS
3-(5-phenylthiophen-2-yl)phenol
—— 3-(difluoro(5-phenylthiophen-2-yl)methyl)phenol 1617505-93-7 C17H12F2OS
3-(difluoro(5-phenylthiophen-2-yl)methyl)phenol
—— 3-(2-hydroxy-5-methyl-8-bromophenyl)-5-(4-methoxyphenyl)-Δ<sup>2</sup>-isoxazoline 29976-89-4 C17H16BrNO3
3-(2-hydroxy-5-methyl-8-bromophenyl)-5-(4-methoxyphenyl)-Δ<sup>2</sup>-isoxazoline
—— 2-Hydroxy-4,6-dimethoxy-benzaldehyde oxime 71253-52-6 C9H11NO4
2-Hydroxy-4,6-dimethoxy-benzaldehyde oxime
—— N<sup>2</sup>-ortho-hydroxyphenyl-N',N'-dimethylformamidine 64452-07-9 C9H12N2O
N<sup>2</sup>-ortho-hydroxyphenyl-N',N'-dimethylformamidine
—— 3-Methoxy-4-propyl-phenol 77934-55-5 C10H14O2
3-Methoxy-4-propyl-phenol
—— 3-hydroxy-N-[2-(4-hydroxy-3-methoxyphenyl)-ethyl]-2-(4-chlorophenyl)acrylamide 384823-10-3 C18H18ClNO4
3-hydroxy-N-[2-(4-hydroxy-3-methoxyphenyl)-ethyl]-2-(4-chlorophenyl)acrylamide
—— 2-nitro-6-(pyrrolidine-1-sulfonyl)-phenol 928196-55-8 C10H12N2O5S
2-nitro-6-(pyrrolidine-1-sulfonyl)-phenol
—— 1,1-Diethyl-3-[1-(2-hydroxyphenyl)ethylideneamino]thiourea 166036-46-0 C13H19N3OS
1,1-Diethyl-3-[1-(2-hydroxyphenyl)ethylideneamino]thiourea
—— 2-[(3-Chloro-4-hydroxy-5-methoxyphenyl)methylideneamino]-1-hydroxyguanidine —— C9H11ClN4O3
2-[(3-Chloro-4-hydroxy-5-methoxyphenyl)methylideneamino]-1-hydroxyguanidine
—— 5,5-dimethyl-6-hydroxy-6-(3',5'-dimethoxy-4'-hydroxyphenyl)-1-hexene 116911-85-4 C16H24O4
5,5-dimethyl-6-hydroxy-6-(3',5'-dimethoxy-4'-hydroxyphenyl)-1-hexene
—— trans-2-(3',5'-dimethoxy-4'-hydroxyphenyl)-1,1,3-trimethylcyclopentane 116911-87-6 C16H24O3
trans-2-(3',5'-dimethoxy-4'-hydroxyphenyl)-1,1,3-trimethylcyclopentane
—— Undecanamide, 11,11'-dithiobis(N-vanillyl- 102612-99-7 C38H60N2O6S2
Undecanamide, 11,11'-dithiobis(N-vanillyl-
—— Vanillin-dibenzyldithioacetal 32188-52-6 C22H22O2S2
Vanillin-dibenzyldithioacetal
—— 5,13-dibromo-8,16-dihydroxy<2.2>metacyclophane 144072-17-3 C16H14Br2O2
5,13-dibromo-8,16-dihydroxy<2.2>metacyclophane
—— N'-[1-(2-hydroxyphenyl)ethylideneamino]-N,N-dipropylcarbamimidothioic acid 166036-47-1 C15H23N3OS
N'-[1-(2-hydroxyphenyl)ethylideneamino]-N,N-dipropylcarbamimidothioic acid
—— N-[1-(2-hydroxyphenyl)ethylideneamino]piperidine-1-carbothioamide 166036-48-2 C14H19N3OS
N-[1-(2-hydroxyphenyl)ethylideneamino]piperidine-1-carbothioamide
—— 2-tert-butyl-4-[(4-hydroxy-3-methoxyphenyl)methyl]-6H-pyrazolo[1,5-a][1,3]benzodiazepin-5-one 1318763-29-9 C23H25N3O3
2-tert-butyl-4-[(4-hydroxy-3-methoxyphenyl)methyl]-6H-pyrazolo[1,5-a][1,3]benzodiazepin-5-one
—— 4-(2-hydroxy-5-methylphenyl)-N,N-bis(1-methylethyl)-4-oxobut-2-ynamide 98153-19-6 C17H21NO3
4-(2-hydroxy-5-methylphenyl)-N,N-bis(1-methylethyl)-4-oxobut-2-ynamide
—— 4-Nitro-2-[(4-phenyl-1,3-thiazol-2-yl)iminomethyl]phenol 112120-10-2 C16H11N3O3S
4-Nitro-2-[(4-phenyl-1,3-thiazol-2-yl)iminomethyl]phenol
—— 2-(4-hydroxybenzyl)cyclopentan-1-one ethylene acetal 120647-36-1 C14H18O3
2-(4-hydroxybenzyl)cyclopentan-1-one ethylene acetal
—— 5-[[(5-chloro-2-hydroxyphenyl)-diethoxyphosphorylmethyl]amino]-1H-pyrimidine-2,4-dione 908089-94-1 C15H19ClN3O6P
5-[[(5-chloro-2-hydroxyphenyl)-diethoxyphosphorylmethyl]amino]-1H-pyrimidine-2,4-dione
—— 2-[5-(3-Bromo-phenyl)-isoxazol-3-yl]-4-methyl-phenol 651021-71-5 C16H12BrNO2
2-[5-(3-Bromo-phenyl)-isoxazol-3-yl]-4-methyl-phenol
—— Copper;2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol —— C16H16CuN2O2
Copper;2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol
—— Phenol, 2-((cyclohexylamino)methyl)-6-methoxy- 59004-61-4 C14H21NO2
Phenol, 2-((cyclohexylamino)methyl)-6-methoxy-
—— 2,6-Bis-morpholinomethyl-hydrochinon 93143-24-9 C16H24N2O4
2,6-Bis-morpholinomethyl-hydrochinon
—— Copper;2-(phenyliminomethyl)phenol 14363-27-0 C26H22CuN2O2
Copper;2-(phenyliminomethyl)phenol
—— 2-[2-[(2-Hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol;manganese —— C16H16MnN2O2
2-[2-[(2-Hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol;manganese
—— 4-hydroxy-3-methoxy-5-(pyrrolidin-1-ylmethyl)benzaldehyde 101913-36-4 C13H17NO3
4-hydroxy-3-methoxy-5-(pyrrolidin-1-ylmethyl)benzaldehyde
—— 4-Fluoro-2-((R)-1-hydroxy-ethyl)-phenol 156597-63-6 C8H9FO2
4-Fluoro-2-((R)-1-hydroxy-ethyl)-phenol
—— N-[(2,4-dihydroxyphenyl)methylideneamino]-3-phenylpropanamide 316133-04-7 C16H16N2O3
N-[(2,4-dihydroxyphenyl)methylideneamino]-3-phenylpropanamide
—— O-<4-Hydroxy-benzylidenamino>-glykolsaeure 90564-13-9 C9H9NO4
O-<4-Hydroxy-benzylidenamino>-glykolsaeure
—— 2-(Butyliminomethyl)phenol;copper 13986-33-9 C22H30CuN2O2
2-(Butyliminomethyl)phenol;copper
—— 2,3,5-Tris(morpholinomethyl)hydrochinon 6452-81-9 C21H33N3O5
2,3,5-Tris(morpholinomethyl)hydrochinon
—— 1-(2-hydroxy-5-methyl-phenyl)-4-methyl-pent-2-en-1-one 41873-83-0 C13H16O2
1-(2-hydroxy-5-methyl-phenyl)-4-methyl-pent-2-en-1-one
—— 2-Azanidylpropyl-[(2-hydroxyphenyl)methyl]azanide;nickel 6944-67-8 C20H28N4NiO2-4
2-Azanidylpropyl-[(2-hydroxyphenyl)methyl]azanide;nickel
—— 2,2'-{[2-(2-Hydroxy-3-methoxyphenyl)dihydropyrimidine-1,3(2H,4H)-diyl]bis(methylene)}bis(6-methoxyphenol) 5767-45-3 C27H32N2O6
2,2'-{[2-(2-Hydroxy-3-methoxyphenyl)dihydropyrimidine-1,3(2H,4H)-diyl]bis(methylene)}bis(6-methoxyphenol)
—— 1,3-Bis(4-methoxy-benzyl)-2-(5-nitro-2-hydroxy-phenyl)-hexahydropyrimidin 7355-43-3 C26H29N3O5
1,3-Bis(4-methoxy-benzyl)-2-(5-nitro-2-hydroxy-phenyl)-hexahydropyrimidin
—— 2-[[2-[4-[Bis(2-chloroethyl)amino]-2-chlorophenyl]-3-[(2-hydroxy-3-methoxyphenyl)methyl]-1,3-diazinan-1-yl]methyl]-6-methoxyphenol 5767-47-5 C30H36Cl3N3O4
2-[[2-[4-[Bis(2-chloroethyl)amino]-2-chlorophenyl]-3-[(2-hydroxy-3-methoxyphenyl)methyl]-1,3-diazinan-1-yl]methyl]-6-methoxyphenol
—— 2-(3-Hydroxy-4-methoxy-benzyliden)-thiazolo<3,2-a>benzimidazol-3-on 341956-68-1 C17H12N2O3S
2-(3-Hydroxy-4-methoxy-benzyliden)-thiazolo<3,2-a>benzimidazol-3-on
—— (2Z)-2-(4-hydroxy-3-methoxybenzylidene)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one 1443655-11-5 C17H12N2O3S
(2Z)-2-(4-hydroxy-3-methoxybenzylidene)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one
—— (2Z)-2-(3-hydroxy-4-methoxybenzylidene)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one 124301-09-3 C17H12N2O3S
(2Z)-2-(3-hydroxy-4-methoxybenzylidene)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one
—— 2-(p-hydroxy-m-methoxybenzylidene)thiazolo<3,2-a>benzimidazol-3(2H)-one 88498-93-5 C17H12N2O3S
2-(p-hydroxy-m-methoxybenzylidene)thiazolo<3,2-a>benzimidazol-3(2H)-one
—— 2-(2-Hydroxy-3-methoxy-phenyl)-1,3-bis-(4-<N,N-bis-(2-chlor-ethyl)-amino>-benzyl)-hexahydropyrimidin 16757-45-2 C33H42Cl4N4O2
2-(2-Hydroxy-3-methoxy-phenyl)-1,3-bis-(4-<N,N-bis-(2-chlor-ethyl)-amino>-benzyl)-hexahydropyrimidin
—— (2E,2'E)-2,2'-(2,5-Dihydroxycyclohexa-2,5-diene-1,4-diylidene)dihydrazinecarboximidamide 92352-38-0 C8H12N8O2
(2E,2'E)-2,2'-(2,5-Dihydroxycyclohexa-2,5-diene-1,4-diylidene)dihydrazinecarboximidamide
—— 3,4-Dihydroxybenzaldehyde guanylhydrazone 106694-40-0 C8H10N4O2
3,4-Dihydroxybenzaldehyde guanylhydrazone
—— 2-{1,3-Bis[(3,4-dimethoxyphenyl)methyl]hexahydropyrimidin-2-yl}-6-methoxyphenol 5767-51-1 C29H36N2O6
2-{1,3-Bis[(3,4-dimethoxyphenyl)methyl]hexahydropyrimidin-2-yl}-6-methoxyphenol
—— 5-carbamoyloxymethyl-3-(3-hydroxy-phenyl)-oxazolidin-2-one 42902-47-6 C11H12N2O5
5-carbamoyloxymethyl-3-(3-hydroxy-phenyl)-oxazolidin-2-one
—— 2,2'-{[2-{4-[Bis(2-chloroethyl)amino]phenyl}dihydropyrimidine-1,3(2H,4H)-diyl]bis(methylene)}bis(6-methoxyphenol) 5019-64-7 C30H37Cl2N3O4
2,2'-{[2-{4-[Bis(2-chloroethyl)amino]phenyl}dihydropyrimidine-1,3(2H,4H)-diyl]bis(methylene)}bis(6-methoxyphenol)
—— 2-[[3-[(2-Hydroxy-3-methoxyphenyl)methyl]-2-(2-hydroxyphenyl)-1,3-diazinan-1-yl]methyl]-6-methoxyphenol 5740-56-7 C26H30N2O5
2-[[3-[(2-Hydroxy-3-methoxyphenyl)methyl]-2-(2-hydroxyphenyl)-1,3-diazinan-1-yl]methyl]-6-methoxyphenol