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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-Nitro-5-benzylsulfonyl-phenol 23153-43-7 C13H11NO5S
2-Nitro-5-benzylsulfonyl-phenol
—— 2-[(4-tert-butylphenylimino)methyl]-4-nitrophenol 1207179-97-2 C17H18N2O3
2-[(4-tert-butylphenylimino)methyl]-4-nitrophenol
—— [(5-chloro-2-hydroxy-phenyl)-(3,5-dimethyl-1-phenyl-4,5-dihydro-1<i>H</i>-pyrazol-4-yl)-methyl]-malonic acid 73930-91-3 C21H21ClN2O5
[(5-chloro-2-hydroxy-phenyl)-(3,5-dimethyl-1-phenyl-4,5-dihydro-1<i>H</i>-pyrazol-4-yl)-methyl]-malonic acid
—— (E)-2-(2-hydroxy-3-methoxystyryl)-3-phenylpyrimido[4,5-d]pyrimidin-4(3H)-one 936744-18-2 C21H16N4O3
(E)-2-(2-hydroxy-3-methoxystyryl)-3-phenylpyrimido[4,5-d]pyrimidin-4(3H)-one
—— 5,11,17,23-tetrakis<(hydroxyimino)ethyl>-25,26,27,28-tetrahydroxycalix<4>arene 99033-57-5 C32H28N4O8
5,11,17,23-tetrakis<(hydroxyimino)ethyl>-25,26,27,28-tetrahydroxycalix<4>arene
—— methyl 2-hydroxy-4-(2-hydroxy-5-methoxyphenyl)butanoate 1094509-35-9 C12H16O5
methyl 2-hydroxy-4-(2-hydroxy-5-methoxyphenyl)butanoate
—— N’-(5-bromo-2-hydroxy-3-methoxybenzylidene)-3-chlorobenzohydrazide 405093-23-4 C15H12BrClN2O3
N’-(5-bromo-2-hydroxy-3-methoxybenzylidene)-3-chlorobenzohydrazide
—— 3-fluoro-4-hydroxybenzaldoxime 1071634-96-2 C7H6FNO2
3-fluoro-4-hydroxybenzaldoxime
—— p-OH-α-Me-Benzyliden-p-OH-anilin 73256-39-0 C14H13NO2
p-OH-α-Me-Benzyliden-p-OH-anilin
—— 6-cyclohexyl-4-hydroxy-6-[2-(4-hydroxyphenyl)ethyl]-5,6-dihydropyran-2-one 207736-89-8 C19H24O4
6-cyclohexyl-4-hydroxy-6-[2-(4-hydroxyphenyl)ethyl]-5,6-dihydropyran-2-one
—— 4-Methoxy-4.4-bis-<2-hydroxy-4-methoxy-phenyl>-crotonsaeure 97081-03-3 C19H20O7
4-Methoxy-4.4-bis-<2-hydroxy-4-methoxy-phenyl>-crotonsaeure
—— 5,11,17,13,29,35-hexa(diethoxyphosphoryl)-37,38,39,40,41,42-hexahydroxycalix[6]arene 1078121-73-9 C66H90O24P6
5,11,17,13,29,35-hexa(diethoxyphosphoryl)-37,38,39,40,41,42-hexahydroxycalix[6]arene
—— (S)-2-(4-bromo-3-hydroxybutyl)-4-fluorophenol 955124-72-8 C10H12BrFO2
(S)-2-(4-bromo-3-hydroxybutyl)-4-fluorophenol
—— 1,2-dihydroxy-3,6-diethoxy-4-methoxybenzene 91353-46-7 C11H16O5
1,2-dihydroxy-3,6-diethoxy-4-methoxybenzene
—— 4-(5-Hydroxy-2-iodo-3-methyl-phenyl)-butyric acid methyl ester 101909-35-7 C12H15IO3
4-(5-Hydroxy-2-iodo-3-methyl-phenyl)-butyric acid methyl ester
—— 3-(((triisopropylsilyl)ethynyl)thio)phenol 1443746-56-2 C17H26OSSi
3-(((triisopropylsilyl)ethynyl)thio)phenol
—— 1228931-07-4 C20H26O4S
—— (4E)-2-(1,3-benzothiazol-2-yl)-4-{[4-hydroxy-3-methoxyphenyl]methylidene}-5-methyl-2,4-dihydro-3H-pyrazol-3-one 874989-57-8 C19H15N3O3S
(4E)-2-(1,3-benzothiazol-2-yl)-4-{[4-hydroxy-3-methoxyphenyl]methylidene}-5-methyl-2,4-dihydro-3H-pyrazol-3-one
—— 3-Chlor-salicylaldehyd-benzylimin 92290-63-6 C14H12ClNO
3-Chlor-salicylaldehyd-benzylimin
—— 1.2-Bis-<2'.3'.4'-trihydroxy-benzoyl>-aethylen 92965-53-2 C16H12O8
1.2-Bis-<2'.3'.4'-trihydroxy-benzoyl>-aethylen
—— 4-Hydroxy-2-methyl-benzamidine 84436-95-3 C8H10N2O
4-Hydroxy-2-methyl-benzamidine
—— (E)-2-({[4-(dimethylamino)phenyl]imino}methyl)-4-nitrophenol 52741-45-4 C15H15N3O3
(E)-2-({[4-(dimethylamino)phenyl]imino}methyl)-4-nitrophenol
—— 3-((5-(5-(tert-butylamino)imidazo[2,1-b]thiazole-6-yl)thiophene-2-yl)ethynyl)phenol 950521-63-8 C21H19N3OS2
3-((5-(5-(tert-butylamino)imidazo[2,1-b]thiazole-6-yl)thiophene-2-yl)ethynyl)phenol
—— N,N'-bis-(2-hydroxybenzylidene)benzene-1,4-diamine 5344-68-3 C20H16N2O2
N,N'-bis-(2-hydroxybenzylidene)benzene-1,4-diamine
—— (2S,4R)-4-hydroxy-2-(4-hydroxyphenyl)decanenitrile 403996-38-3 C16H23NO2
(2S,4R)-4-hydroxy-2-(4-hydroxyphenyl)decanenitrile
—— 4-[(E)-2-(4-Hydroxy-phenyl)-vinyl]-5,5-dimethyl-2-oxo-2,5-dihydro-furan-3-carbonitrile 125208-25-5 C15H13NO3
4-[(E)-2-(4-Hydroxy-phenyl)-vinyl]-5,5-dimethyl-2-oxo-2,5-dihydro-furan-3-carbonitrile
—— 3-Isopropylsulfanyl-4-nitro-phenol 776-65-8 C9H11NO3S
3-Isopropylsulfanyl-4-nitro-phenol
—— 1234474-69-1 C16H18N8O2S4
—— 2-bromo-4-(2,2-dibromo-1-dibromomethyl-vinyl)-6-methyl-phenol 861576-30-9 C10H7Br5O
2-bromo-4-(2,2-dibromo-1-dibromomethyl-vinyl)-6-methyl-phenol
—— 3-(3-Chloro-4-hydroxyphenyl)-5-isoxazolecarboxylic acid 1211585-15-7 C10H6ClNO4
3-(3-Chloro-4-hydroxyphenyl)-5-isoxazolecarboxylic acid
—— (E)-1-(2-hydroxy-5-methylbenzylidene)thiosemicarbazide 53851-95-9 C9H11N3OS
(E)-1-(2-hydroxy-5-methylbenzylidene)thiosemicarbazide
—— 6-[2-(4-Chloro-2-nitrophenyl)hydrazinylidene]-4-(2,4,4-trimethylpentan-2-yl)cyclohexa-2,4-dien-1-one 56361-61-6 C20H24ClN3O3
6-[2-(4-Chloro-2-nitrophenyl)hydrazinylidene]-4-(2,4,4-trimethylpentan-2-yl)cyclohexa-2,4-dien-1-one
—— 142274-57-5 C21H16ClN5O5
—— 3,4-dihydroxy-mandelamidine; hydrochloride 24536-36-5 C8H10N2O3*ClH
3,4-dihydroxy-mandelamidine; hydrochloride
—— 1262209-46-0 C28H21Br2ClN6O4S2
—— 2-(3,4-dihydroxyphenyl)-2-(3-methylimidazolium)butyl acetate bromide 1241840-11-8 Br*C16H21N2O4
2-(3,4-dihydroxyphenyl)-2-(3-methylimidazolium)butyl acetate bromide
—— cis-1-(aminomethyl)-3,4-dihydro-5-hydroxy-1H-2-benzopyran 135393-82-7 C16H17NO2
cis-1-(aminomethyl)-3,4-dihydro-5-hydroxy-1H-2-benzopyran
—— 4-(3,4-Dihydroxyphenyl)-2-(3-pyridylamino)thiazole hydrochloride 79571-73-6 C14H11N3O2S*ClH
4-(3,4-Dihydroxyphenyl)-2-(3-pyridylamino)thiazole hydrochloride
—— 1-<4-Hydroxy-3,5-diiod-phenyl>-cyclopentan-carbonsaeure-(1) 91446-77-4 C12H12I2O3
1-<4-Hydroxy-3,5-diiod-phenyl>-cyclopentan-carbonsaeure-(1)
—— 2,5-Difluoro-3,4,6-tris-methylsulfanyl-phenol 60190-21-8 C9H10F2OS3
2,5-Difluoro-3,4,6-tris-methylsulfanyl-phenol
—— Acetic acid 3-nitro-phenoxymethyl ester 57440-13-8 C9H9NO5
Acetic acid 3-nitro-phenoxymethyl ester
—— 54305-33-8 C9H10ClN3O3
—— 2-ethoxy-3,4,6-trimethoxyphenol 94933-88-7 C11H16O5
2-ethoxy-3,4,6-trimethoxyphenol
—— 4,6,10,12,16,18,22,24-octahydroxy-5-[N-(2,2-dimethyl-3-oxoprop-1-yl)ethylamino-methyl]-2,8,14,20-tetraheptylpentacyclo[19.3.1.1(3,7).1(9,13).1(15,19)]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene 1239171-48-2 C64H95NO9
4,6,10,12,16,18,22,24-octahydroxy-5-[N-(2,2-dimethyl-3-oxoprop-1-yl)ethylamino-methyl]-2,8,14,20-tetraheptylpentacyclo[19.3.1.1(3,7).1(9,13).1(15,19)]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene
—— 3,9,15,21,27-Pentatert-butyl-32,32-dimethyl-31,33-dioxa-32-silaheptacyclo[27.5.1.17,11.113,17.119,23.05,34.025,30]octatriaconta-1,3,5(34),7,9,11(38),13,15,17(37),19(36),20,22,25(30),26,28-pentadecaene-36,37,38-triol 475476-34-7 C57H74O5Si
3,9,15,21,27-Pentatert-butyl-32,32-dimethyl-31,33-dioxa-32-silaheptacyclo[27.5.1.17,11.113,17.119,23.05,34.025,30]octatriaconta-1,3,5(34),7,9,11(38),13,15,17(37),19(36),20,22,25(30),26,28-pentadecaene-36,37,38-triol
—— 2-Hydroxy-4-methyl-3-nitro-benzenesulfonyl fluoride 22243-84-1 C7H6FNO5S
2-Hydroxy-4-methyl-3-nitro-benzenesulfonyl fluoride
—— 4-(3-hydroxy-5,6,7,8-tetrahydro-[2]naphthyl)-butyric acid 876482-68-7 C14H18O3
4-(3-hydroxy-5,6,7,8-tetrahydro-[2]naphthyl)-butyric acid
—— 3-Butylselanyl-phenol 86297-13-4 C10H14OSe
3-Butylselanyl-phenol
—— N'-(2-hydroxy-5-nonylbenzylidene)octanehydrazide 1074213-33-4 C24H40N2O2
N'-(2-hydroxy-5-nonylbenzylidene)octanehydrazide
—— 1-(2-Chlor-4,5-dihydroxyphenyl)-2-tert.butylamino-ethanol 69240-89-7 C12H18ClNO3
1-(2-Chlor-4,5-dihydroxyphenyl)-2-tert.butylamino-ethanol