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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
—— 5-Acetyl-4-(4-hydroxy-3-methoxyphenyl)-6-hydroxy-3,6-dimethyl-4,5,6,7-tetrahydro-2,1-benzisoxazole 105826-84-4 C18H21NO5
5-Acetyl-4-(4-hydroxy-3-methoxyphenyl)-6-hydroxy-3,6-dimethyl-4,5,6,7-tetrahydro-2,1-benzisoxazole
—— 6-methoxy-1-[(1-methyl-3-methylenecyclohexyl)methyl]benzene-2,3-diol 1070795-45-7 C16H22O3
6-methoxy-1-[(1-methyl-3-methylenecyclohexyl)methyl]benzene-2,3-diol
—— N,N'-bis(4-methoxy-2-oxyacetophenylidene)ethylenediamine 259748-16-8 C20H24N2O4
N,N'-bis(4-methoxy-2-oxyacetophenylidene)ethylenediamine
—— 4-Bromo-2-{[(Z)-2,3,5,6-tetrafluoro-phenylimino]-methyl}-phenol 26672-12-8 C13H6BrF4NO
4-Bromo-2-{[(Z)-2,3,5,6-tetrafluoro-phenylimino]-methyl}-phenol
—— 3-hydroxy-4-methoxybenzothioamide 145736-69-2 C8H9NO2S
3-hydroxy-4-methoxybenzothioamide
—— 2-(2-Ethyl-but-1-enyl)-4-methyl-phenol 86847-38-3 C13H18O
2-(2-Ethyl-but-1-enyl)-4-methyl-phenol
—— trimethyl-[(<i>S</i>)-1-hydroxymethyl-2-(4-hydroxy-phenyl)-ethyl]-ammonium; iodide 64900-44-3 C12H20NO2*I
trimethyl-[(<i>S</i>)-1-hydroxymethyl-2-(4-hydroxy-phenyl)-ethyl]-ammonium; iodide
—— 4-chloro-2-{[6-(3-chloro-4-fluoro-phenylamino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]-hydrazonomethyl}-phenol 851661-47-7 C17H10Cl2FN7O2
4-chloro-2-{[6-(3-chloro-4-fluoro-phenylamino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]-hydrazonomethyl}-phenol
—— (2Z,5Z)-5-(2,4-dihydroxybenzylidene)-3-(2,3-dimethylphenyl)-2-(2,3-dimethylphenylimino)thiazolidin-4-one 1391631-61-0 C26H24N2O3S
(2Z,5Z)-5-(2,4-dihydroxybenzylidene)-3-(2,3-dimethylphenyl)-2-(2,3-dimethylphenylimino)thiazolidin-4-one
—— p-2-tellurienylphenol 75073-63-1 C10H8OTe
p-2-tellurienylphenol
—— (4R)-4-(2,3-dihydroxy-phenyl)-4-hydroxy-butan-2-one 1162642-00-3 C10H12O4
(4R)-4-(2,3-dihydroxy-phenyl)-4-hydroxy-butan-2-one
—— gallacetophenone phenylhydrazone 153866-67-2 C14H14N2O3
gallacetophenone phenylhydrazone
—— [3-(3,4-dimethoxyphenyl)-4,5-dihydropyrazol-1-yl]-(4-hydroxy-3-methoxyphenyl)methanone 1417707-62-0 C19H20N2O5
[3-(3,4-dimethoxyphenyl)-4,5-dihydropyrazol-1-yl]-(4-hydroxy-3-methoxyphenyl)methanone
—— 2-[2-(3-chlorophenyl)ethyl]-5-hydroxypyrimidin-4(3H)-one 1417817-37-8 C12H11ClN2O2
2-[2-(3-chlorophenyl)ethyl]-5-hydroxypyrimidin-4(3H)-one
—— 2,4-dihydroxy-3-nitrobenzamide 1197043-08-5 C7H6N2O5
2,4-dihydroxy-3-nitrobenzamide
—— 1-(3'-methylbut-2'-enyl)-8-(triisopropylsilyloxy)-5,6-dihydronaphthalen-2-ol 1275584-73-0 C24H38O2Si
1-(3'-methylbut-2'-enyl)-8-(triisopropylsilyloxy)-5,6-dihydronaphthalen-2-ol
—— 2,4,6-trinitro-3-<(phenylsulfonyl)methyl>phenol 92241-37-7 C13H9N3O9S
2,4,6-trinitro-3-<(phenylsulfonyl)methyl>phenol
—— 2-(2-amino-1,3-thiazol-4-yl)-2-[3-(3,4-dihydroxybenzylidene)carbazoyl]methoxyiminoacetic acid.hydrochloride 105588-37-2 C14H13N5O6S*ClH
2-(2-amino-1,3-thiazol-4-yl)-2-[3-(3,4-dihydroxybenzylidene)carbazoyl]methoxyiminoacetic acid.hydrochloride
—— 2,4-dibromo-6-[(6-phenylamino-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl)-hydrazonomethyl]-phenol 851660-68-9 C17H11Br2N7O2
2,4-dibromo-6-[(6-phenylamino-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl)-hydrazonomethyl]-phenol
—— 2,4-Difluoro-3-hydroxymandelic acid 1806272-05-8 C8H6F2O4
2,4-Difluoro-3-hydroxymandelic acid
—— 2-(6-Hydroxy-indan-1-ylen)-acetonitril 25164-67-4 C11H9NO
2-(6-Hydroxy-indan-1-ylen)-acetonitril
—— (R)-4-(1-hydroxy-2-nitroethyl)phenol 1291099-38-1 C8H9NO4
(R)-4-(1-hydroxy-2-nitroethyl)phenol
—— 2-((2-(piperazin-1-yl)ethylimino)methyl)-4-chlorophenol 1245707-53-2 C13H18ClN3O
2-((2-(piperazin-1-yl)ethylimino)methyl)-4-chlorophenol
—— Sodium;2-hydroxyimino-2-(2-hydroxyphenyl)ethanesulfonate 1024789-05-6 C8H8NNaO5S
Sodium;2-hydroxyimino-2-(2-hydroxyphenyl)ethanesulfonate
—— 1410796-06-3 C43H50O7
—— Picric acid; compound with 2-[1-(2,5-dimethyl-phenyl)-1-methyl-ethyl]-isothiourea 39192-43-3 C6H3N3O7*C12H18N2S
Picric acid; compound with 2-[1-(2,5-dimethyl-phenyl)-1-methyl-ethyl]-isothiourea
—— methyl 3-(2-hydroxy-3-methoxyphenyl)-3-(3-methoxy-3-oxopropyl)sulfanylpropanoate 114106-28-4 C15H20O6S
methyl 3-(2-hydroxy-3-methoxyphenyl)-3-(3-methoxy-3-oxopropyl)sulfanylpropanoate
—— 4-((2-aminothiazol-5-yl)methyl)-2-(isoxazol-5-yl)phenol 1194551-89-7 C13H11N3O2S
4-((2-aminothiazol-5-yl)methyl)-2-(isoxazol-5-yl)phenol
—— 4-hydroxybenzenediazonium 1,1,2,3,3-pentacyanoprop-2-en-1-ide 1204613-28-4 C6H5N2O*C8N5
4-hydroxybenzenediazonium 1,1,2,3,3-pentacyanoprop-2-en-1-ide
—— 2,4-dibromo-6-{[6-(4-fluoro-phenylamino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]-hydrazonomethyl}-phenol 851661-12-6 C17H10Br2FN7O2
2,4-dibromo-6-{[6-(4-fluoro-phenylamino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]-hydrazonomethyl}-phenol
—— (2-hydroxyphenyl)(thiophen-2-yl)methanone O-acetyl oxime 97035-10-4 C13H11NO3S
(2-hydroxyphenyl)(thiophen-2-yl)methanone O-acetyl oxime
—— 1,4-dibromo-4-(2-bromoethoxy)phenol 31406-91-4 C8H7Br3O2
1,4-dibromo-4-(2-bromoethoxy)phenol
—— 4-chloro-2-(dimethoxymethylideneamino)phenol 87054-08-8 C9H10ClNO3
4-chloro-2-(dimethoxymethylideneamino)phenol
—— 3-methyl-4-(5-piperidin-1-yl-penta-1,3-diynyl)-phenol 33834-06-9 C17H19NO
3-methyl-4-(5-piperidin-1-yl-penta-1,3-diynyl)-phenol
—— 4-(1,1-Diisobutyl-but-3-enyl)-phenol 38564-36-2 C18H28O
4-(1,1-Diisobutyl-but-3-enyl)-phenol
—— isonicotinic acid [1-(2-hydroxy-5-methoxy-phenyl)-ethylidene]hydrazide 1013567-49-1 C15H15N3O3
isonicotinic acid [1-(2-hydroxy-5-methoxy-phenyl)-ethylidene]hydrazide
—— 2,3-Dihydroxy-6-methoxybenzaldehyde 80832-55-9 C8H8O4
2,3-Dihydroxy-6-methoxybenzaldehyde
—— N-(2-hydroxy-5-nitro-1-salicylidene)-L-arginine 1285542-32-6 C13H17N5O5
N-(2-hydroxy-5-nitro-1-salicylidene)-L-arginine
—— aniline-N-carboxamidine picrate 4086-60-6 C6H3N3O7*C7H9N3
aniline-N-carboxamidine picrate
—— 2,4,6-tris(((tert-butyldimethylsilyl)oxy)methyl)phenol 848826-48-2 C27H54O4Si3
2,4,6-tris(((tert-butyldimethylsilyl)oxy)methyl)phenol
—— Picric acid; compound with (4-chloro-phenyl)-furan-2-ylmethyl-amine 95124-30-4 C6H3N3O7*C11H10ClNO
Picric acid; compound with (4-chloro-phenyl)-furan-2-ylmethyl-amine
—— 3-[(5-bromo-3-methoxy-2-hydroxybenzylidene)amino]-4-oxoimidazolidin-2-thione 1416895-84-5 C11H10BrN3O3S
3-[(5-bromo-3-methoxy-2-hydroxybenzylidene)amino]-4-oxoimidazolidin-2-thione
—— 3-chloro-4,6-dimethoxy-5-methyl-2-(2,4-pentadienyl)phenol 105104-28-7 C14H17ClO3
3-chloro-4,6-dimethoxy-5-methyl-2-(2,4-pentadienyl)phenol
—— 71407-33-5 C18H21N3O2*I4Th
—— (E)-1,1,4,4-tetramethyl-2-tetrazenium picrate 1332869-46-1 C4H12N4*C6H3N3O7
(E)-1,1,4,4-tetramethyl-2-tetrazenium picrate
—— N,N'-butylenebis(imidazole): (2,4,6-trinitrophenol)2 102599-12-2 2C6H3N3O7*C10H14N4
N,N'-butylenebis(imidazole): (2,4,6-trinitrophenol)2
—— 4-(5-ethoxypent-3-yn-1-yl)phenol 1449770-12-0 C13H16O2
4-(5-ethoxypent-3-yn-1-yl)phenol
—— N1-(2-((2-((2-aminoethyl)amino)ethyl)amino)ethyl)-N10-(3,4-dihydroxyphenethyl)decanediamide 1186221-80-6 C24H43N5O4
N1-(2-((2-((2-aminoethyl)amino)ethyl)amino)ethyl)-N10-(3,4-dihydroxyphenethyl)decanediamide
—— 1-(diaminomethylene)thiouron-1-ium picrate 859771-04-3 C2H6N4S*C6H3N3O7
1-(diaminomethylene)thiouron-1-ium picrate
—— 2,3,10,11-tetrahydrobotryllamide F 1219115-45-3 C18H21NO4
2,3,10,11-tetrahydrobotryllamide F