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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
—— 4-methoxy-2-(<i>tert</i>-pentylsulfanyl-methyl)-phenol 100532-77-2 C13H20O2S
4-methoxy-2-(<i>tert</i>-pentylsulfanyl-methyl)-phenol
—— 2-ethynyl-4-fluorophenol 1622092-93-6 C8H5FO
2-ethynyl-4-fluorophenol
—— (2-hydroxy-3-methoxybenzylideneamino)acetonitrile 1279019-01-0 C10H10N2O2
(2-hydroxy-3-methoxybenzylideneamino)acetonitrile
—— dimethyl (4-bromo-3-methylphenylamino)(3-hydroxy-4-methoxyphenyl)methylphosphonate 1364003-39-3 C17H21BrNO5P
dimethyl (4-bromo-3-methylphenylamino)(3-hydroxy-4-methoxyphenyl)methylphosphonate
—— 1159714-88-1 C41H32N4O2
—— Phenol, 4-(aminocyclopropylmethyl)-2-chloro-6-methoxy- 1704122-18-8 C11H14ClNO2
Phenol, 4-(aminocyclopropylmethyl)-2-chloro-6-methoxy-
—— (5R,6R)-5-Benzyl-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-1-(3-methyl-butyryl)-6-(2-trimethylsilanyl-ethoxymethoxy)-[1,2,4]triazepan-3-one 871905-09-8 C38H53N3O8Si
(5R,6R)-5-Benzyl-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-1-(3-methyl-butyryl)-6-(2-trimethylsilanyl-ethoxymethoxy)-[1,2,4]triazepan-3-one
—— 2-Methoxy-5-allyl-1,4-hydrochinon 19772-34-0 C10H12O3
2-Methoxy-5-allyl-1,4-hydrochinon
—— 2-hydroxy-3,5,6-trimethylbenzene-1,4-dicarbonitrile 128540-75-0 C11H10N2O
2-hydroxy-3,5,6-trimethylbenzene-1,4-dicarbonitrile
—— 4-(1,2,5-Trimethyl-1,2,3,6-tetrahydro-[4]pyridyl)-phenol 101113-96-6 C14H19NO
4-(1,2,5-Trimethyl-1,2,3,6-tetrahydro-[4]pyridyl)-phenol
—— 6-(3,4-dihydroxy-phenyl)-hexanoic acid methyl ester 132858-52-7 C13H18O4
6-(3,4-dihydroxy-phenyl)-hexanoic acid methyl ester
—— 5-butyl-2-[2-[(2-hydroxy-3-methoxyphenyl)methylidene]hydrazinyl]-4-methyl-1H-pyrimidin-6-one 36361-98-5 C17H22N4O3
5-butyl-2-[2-[(2-hydroxy-3-methoxyphenyl)methylidene]hydrazinyl]-4-methyl-1H-pyrimidin-6-one
—— 1-{3-(N-isobutyl-N-methylamino)propyl}-4-(4-hydroxyphenyl)-1,2,5,6-tetrahydropyridine 137884-27-6 C19H30N2O
1-{3-(N-isobutyl-N-methylamino)propyl}-4-(4-hydroxyphenyl)-1,2,5,6-tetrahydropyridine
—— 2-Methyl-3-methoxyphenol-4,6-d2 77357-42-7 C8H10O2
2-Methyl-3-methoxyphenol-4,6-d2
—— H2tbhsBr 109874-23-9 C14H11BrN2OS
H2tbhsBr
—— 32246-42-7 C16H18O4
—— 5-(2,3-dihydroxy-5-trifluoromethylbenzylidene)-3-(2-ethylbutyl)thiazolidine-2,4-dione 1372864-93-1 C17H18F3NO4S
5-(2,3-dihydroxy-5-trifluoromethylbenzylidene)-3-(2-ethylbutyl)thiazolidine-2,4-dione
—— 4-[[[4,6-Di(piperidin-1-yl)-1,3,5-triazin-2-yl]hydrazinylidene]methyl]benzene-1,2-diol 5679-77-6 C20H27N7O2
4-[[[4,6-Di(piperidin-1-yl)-1,3,5-triazin-2-yl]hydrazinylidene]methyl]benzene-1,2-diol
—— decanoic acid [5-(4-hydroxy-3,5-dimethoxy-benzylidene)-2-(4-methoxy phenyl)-4-oxo-thiazolidin-3-yl]amide 1290139-35-3 C29H38N2O6S
decanoic acid [5-(4-hydroxy-3,5-dimethoxy-benzylidene)-2-(4-methoxy phenyl)-4-oxo-thiazolidin-3-yl]amide
—— (E)-3-(4-Bromo-thiophen-2-yl)-1-(2-hydroxy-5-nitro-phenyl)-propenone 18791-83-8 C13H8BrNO4S
(E)-3-(4-Bromo-thiophen-2-yl)-1-(2-hydroxy-5-nitro-phenyl)-propenone
—— 2(pyridylazo)resorcinol 69904-41-2 C11H9N3O2
2(pyridylazo)resorcinol
—— 1-(1-Adamantyl)-3-[(2-hydroxy-3,5-diiodophenyl)methylideneamino]thiourea 32403-38-6 C18H21I2N3OS
1-(1-Adamantyl)-3-[(2-hydroxy-3,5-diiodophenyl)methylideneamino]thiourea
—— N'-(5-chloro-2-hydroxyphenyl)-N,N-diethylformamidine 1383437-53-3 C11H15ClN2O
N'-(5-chloro-2-hydroxyphenyl)-N,N-diethylformamidine
—— 2-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-5-methoxy-phenol 112156-66-8 C13H18O5
2-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-5-methoxy-phenol
—— 2-(4-Octoxyphenyl)ethanol 1000573-06-7 C16H26O2
2-(4-Octoxyphenyl)ethanol
—— 6-(N,N-Dimethyl-thiocarbamoyl-mercaptomethyl)-4,5-dimethyl-3-pentadecyl-brenzcatechin 16273-27-1 C27H47NO2S2
6-(N,N-Dimethyl-thiocarbamoyl-mercaptomethyl)-4,5-dimethyl-3-pentadecyl-brenzcatechin
—— 1,4-Bis-(4-hydroxy-3,5-dimethyl-phenyl)-trans-but-2-en 15385-36-1 C20H24O2
1,4-Bis-(4-hydroxy-3,5-dimethyl-phenyl)-trans-but-2-en
—— pyrrolidine-1-carboxamide;2,4,6-trinitrophenol 87454-58-8 C5H10N2O*C6H3N3O7
pyrrolidine-1-carboxamide;2,4,6-trinitrophenol
—— ethyl 2-hydroxy-3-methyl-5-chlorodihydrocinnamate 80515-83-9 C12H15ClO3
ethyl 2-hydroxy-3-methyl-5-chlorodihydrocinnamate
—— 3-chloro-4,N-dihydroxy-5-methylbenzamidine 944327-00-8 C8H9ClN2O2
3-chloro-4,N-dihydroxy-5-methylbenzamidine
—— (((4-(2-(octyloxy)ethyl)-1,2-phenylene)bis(oxy))bis(methylene))dibenzene 1191117-31-3 C30H38O3
(((4-(2-(octyloxy)ethyl)-1,2-phenylene)bis(oxy))bis(methylene))dibenzene
—— 2(3,5-Dibrom-2-hydroxybenzylidenamino)-butan-1-ol 4936-87-2 C11H13Br2NO2
2(3,5-Dibrom-2-hydroxybenzylidenamino)-butan-1-ol
—— 4-amino-2-fluorobenzene-1,3-diol 1431533-33-3 C6H6FNO2
4-amino-2-fluorobenzene-1,3-diol
—— 2-cyclopentyl-3-methoxyphenol 21712-96-9 C12H16O2
2-cyclopentyl-3-methoxyphenol
—— 4-<Tropyl-7>-resorcin 16235-35-1 C13H12O2
4-<Tropyl-7>-resorcin
—— 2-(2-Hydroxy-5-nitro-phenyl)-cyclopentanon 32345-08-7 C11H11NO4
2-(2-Hydroxy-5-nitro-phenyl)-cyclopentanon
—— 2-(5,6-di-pyridin-2-yl-[1,2,4]triazin-3-yl)-phenol 98363-92-9 C19H13N5O
2-(5,6-di-pyridin-2-yl-[1,2,4]triazin-3-yl)-phenol
—— (2S)-1-(4-hydroxyphenoxy)-3-<(1-methylethyl)(methylsulfonyl)amino>-2-propanol 72223-79-1 C13H21NO5S
(2S)-1-(4-hydroxyphenoxy)-3-<(1-methylethyl)(methylsulfonyl)amino>-2-propanol
—— 4-(Thiazolyl-2-azo)-6-pentylresorcin 14383-28-9 C14H17N3O2S
4-(Thiazolyl-2-azo)-6-pentylresorcin
—— 17646-34-3 C15H11FN4OS
—— 2,3-Dichloro-4-(2-methyl-3-oxo-1-pentenyl)phenol 25195-04-4 C12H12Cl2O2
2,3-Dichloro-4-(2-methyl-3-oxo-1-pentenyl)phenol
—— 1-Dodecyl-3-[(2-hydroxyphenyl)methylideneamino]thiourea 6340-19-8 C20H33N3OS
1-Dodecyl-3-[(2-hydroxyphenyl)methylideneamino]thiourea
—— 1-(2-iodo-5-methoxyphenyl)hept-2-yn-1-one 1261035-73-7 C14H15IO2
1-(2-iodo-5-methoxyphenyl)hept-2-yn-1-one
—— Ubisemihydroquinone 145523-82-6 C9H11O4
Ubisemihydroquinone
—— 4,4'-(6,6'-{5,5'-[5,5'-methylenebis(3-methylbenzofuran-7,5-diyl)]bis(1,3,4-thiadiazole-5,2-diyl)}bis[5-(4-methylphenyl)-3,3a,5,6-tetrahydro-2H-pyrazolo[3,4-d]thiazole-6,3-diyl])bis(2-methoxyphenol) 1268829-92-0 C59H50N10O6S4
4,4'-(6,6'-{5,5'-[5,5'-methylenebis(3-methylbenzofuran-7,5-diyl)]bis(1,3,4-thiadiazole-5,2-diyl)}bis[5-(4-methylphenyl)-3,3a,5,6-tetrahydro-2H-pyrazolo[3,4-d]thiazole-6,3-diyl])bis(2-methoxyphenol)
—— 2,3,6-trimethyl-4-[2-(dimethylphenylsilyl)ethyl]phenol 1230388-57-4 C19H26OSi
2,3,6-trimethyl-4-[2-(dimethylphenylsilyl)ethyl]phenol
—— 2-[(2-isopropylaminoethylimino)methyl]-4-methylphenol 1637473-62-1 C13H20N2O
2-[(2-isopropylaminoethylimino)methyl]-4-methylphenol
—— (((4-(2-butoxyethyl)-1,2-phenylene)bis(oxy))bis(methylene))dibenzene 1191117-29-9 C26H30O3
(((4-(2-butoxyethyl)-1,2-phenylene)bis(oxy))bis(methylene))dibenzene
—— 5-(2-hydroxy-benzylidene)-3-(1-methyl-2-phenyl-ethyl)-2-thioxo-thiazolidin-4-one 21222-52-6 C19H17NO2S2
5-(2-hydroxy-benzylidene)-3-(1-methyl-2-phenyl-ethyl)-2-thioxo-thiazolidin-4-one
—— 5-bromo-N-(3-hydroxybenzyl)-N-methylthiophene-2-sulfonamide 1282488-31-6 C12H12BrNO3S2
5-bromo-N-(3-hydroxybenzyl)-N-methylthiophene-2-sulfonamide