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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
—— 4,4'-(1E,1'E)-(ethane-1,2-diylbis(azanylylidene))bis(methanylylidene)bis(2-methoxyphenol) 1257519-32-6 C18H20N2O4
4,4'-(1E,1'E)-(ethane-1,2-diylbis(azanylylidene))bis(methanylylidene)bis(2-methoxyphenol)
—— 1,3,7,9-tetramethyl-5-(4-hydroxy-3-methoxyphenyl)pyrimido[5',4':5,6]pyrido[2,3-d]pyrimidine-2,4,6,8(1H,3H,7H,9H)-tetraone 1605301-35-6 C20H19N5O6
1,3,7,9-tetramethyl-5-(4-hydroxy-3-methoxyphenyl)pyrimido[5',4':5,6]pyrido[2,3-d]pyrimidine-2,4,6,8(1H,3H,7H,9H)-tetraone
—— butylbis(N-salicylidene-3-aminopropyl)phosphine 97390-86-8 C24H33N2O2P
butylbis(N-salicylidene-3-aminopropyl)phosphine
—— diethyl-benzyl sulfonium , picrate 109591-52-8 C6H2N3O7*C11H17S
diethyl-benzyl sulfonium , picrate
—— (4-hydroxy-3-methoxyphenyl)ethylaldehyde propanedithioacetal 172547-01-2 C12H16O2S2
(4-hydroxy-3-methoxyphenyl)ethylaldehyde propanedithioacetal
—— [4-(4-{[1-(3-Hydroxy-4-methoxy-phenyl)-meth-(Z)-ylidene-hydrazinocarbonylmethyl]-amino}-benzenesulfonyl)-phenylamino]-acetic acid [1-(3-hydroxy-4-methoxy-phenyl)-meth-(Z)-ylidene]-hydrazide 114710-11-1 C32H32N6O8S
[4-(4-{[1-(3-Hydroxy-4-methoxy-phenyl)-meth-(Z)-ylidene-hydrazinocarbonylmethyl]-amino}-benzenesulfonyl)-phenylamino]-acetic acid [1-(3-hydroxy-4-methoxy-phenyl)-meth-(Z)-ylidene]-hydrazide
—— 2,8,14,20-tetradecylcalix[4]resorcinarene 276681-47-1 C68H104O8
2,8,14,20-tetradecylcalix[4]resorcinarene
—— (S)-(+)-<6>-2,2-difluoro-4,4-(1,3-propanedithioacetyl)gingerol-t-butyldimethylsilylether 172546-92-8 C26H42F2O4S2Si
(S)-(+)-<6>-2,2-difluoro-4,4-(1,3-propanedithioacetyl)gingerol-t-butyldimethylsilylether
—— 2,5-bis(α-methyl-2'-hydroxy-5'-methylbenzalamino)-1,3,4-thiadiazole 124983-66-0 C20H20N4O2S
2,5-bis(α-methyl-2'-hydroxy-5'-methylbenzalamino)-1,3,4-thiadiazole
—— 2-ethyl-6-methoxy-4-propylphenol 86253-73-8 C12H18O2
2-ethyl-6-methoxy-4-propylphenol
—— N-4-Chlorphenyl-S,S-diethylsulfimid-Pikrat 103376-00-7 C6H3N3O7*C10H14ClNS
N-4-Chlorphenyl-S,S-diethylsulfimid-Pikrat
—— 3-(3-Hydroxy-4-methyl-2-nitro-benzoylamino)-propionyl azide 121018-25-5 C11H11N5O5
3-(3-Hydroxy-4-methyl-2-nitro-benzoylamino)-propionyl azide
—— N-[2-(4-hydroxy-3-methoxyphenyl)-5-methyl-4-oxo-1,3-thiazolidin-3-yl]-2-[4-[4-[[2-[[2-(4-hydroxy-3-methoxyphenyl)-5-methyl-4-oxo-1,3-thiazolidin-3-yl]amino]-2-oxoethyl]amino]phenyl]sulfonylanilino]acetamide 114710-30-4 C38H40N6O10S3
N-[2-(4-hydroxy-3-methoxyphenyl)-5-methyl-4-oxo-1,3-thiazolidin-3-yl]-2-[4-[4-[[2-[[2-(4-hydroxy-3-methoxyphenyl)-5-methyl-4-oxo-1,3-thiazolidin-3-yl]amino]-2-oxoethyl]amino]phenyl]sulfonylanilino]acetamide
—— 209853-34-9 C20H16N4O2S
—— N-(5-Allyl-2-hydroxy-3-methoxy-benzyl)-2-chloro-acetamide 52780-54-8 C13H16ClNO3
N-(5-Allyl-2-hydroxy-3-methoxy-benzyl)-2-chloro-acetamide
—— (E)-2-hydroxy-4-methoxybenzaldehyde oxime 155912-26-8 C8H9NO3
(E)-2-hydroxy-4-methoxybenzaldehyde oxime
—— 4-allyl-2-tert-amyl-6-methoxyphenol 139553-38-1 C15H22O2
4-allyl-2-tert-amyl-6-methoxyphenol
—— 6,6'-(((4-methyl-1,3-phenylene)bis(azaneylylidene))bis(methaneylylidene))bis(2,4-dibromophenol) 134668-03-4 C21H14Br4N2O2
6,6'-(((4-methyl-1,3-phenylene)bis(azaneylylidene))bis(methaneylylidene))bis(2,4-dibromophenol)
—— 2-(5-((3-hydroxybenzylidene)amino)-1,3,4-thiadiazol-2-yl)phenol 188969-53-1 C15H11N3O2S
2-(5-((3-hydroxybenzylidene)amino)-1,3,4-thiadiazol-2-yl)phenol
—— 134668-00-1 C23H22N2O4
—— 1415746-50-7 C19H33NO2
—— Ethyl-p-hydroxydithiobenzoat 24530-66-3 C9H10OS2
Ethyl-p-hydroxydithiobenzoat
—— 2-benzalamino-5-o-hydroxyphenyl-1,3,4-thiadiazole 133212-67-6 C15H11N3OS
2-benzalamino-5-o-hydroxyphenyl-1,3,4-thiadiazole
—— 4-(2-(tert-butoxy)propyl)-2-methoxyphenol 1446088-04-5 C14H22O3
4-(2-(tert-butoxy)propyl)-2-methoxyphenol
—— (E)-2-methoxy-5-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenol 1618099-61-8 C15H21BO4
(E)-2-methoxy-5-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenol
—— 2-amino-5-(4-hydroxy-3-iodo-5-methoxyphenyl)-1,3,4-thiadiazole 1449203-90-0 C9H8IN3O2S
2-amino-5-(4-hydroxy-3-iodo-5-methoxyphenyl)-1,3,4-thiadiazole
—— 3,3'-(4-methyl-1,3-phenylene)bis(2-(3-bromo-4-hydroxy-5-methoxyphenyl)-5-methylthiazolidin-4-one) 134667-89-3 C29H28Br2N2O6S2
3,3'-(4-methyl-1,3-phenylene)bis(2-(3-bromo-4-hydroxy-5-methoxyphenyl)-5-methylthiazolidin-4-one)
—— 2-methoxy-4-(2-methoxypropyl)phenol 83356-70-1 C11H16O3
2-methoxy-4-(2-methoxypropyl)phenol
—— 4-[4-(Dibutylamino)butyl]-2-methoxyphenol 1415746-48-3 C19H33NO2
4-[4-(Dibutylamino)butyl]-2-methoxyphenol
—— 1389320-79-9 C43H38N6O12S2
—— 3,3'-(4-methyl-1,3-phenylene)bis(2-(2-hydroxyphenyl)-5-methylthiazolidin-4-one) 134667-80-4 C27H26N2O4S2
3,3'-(4-methyl-1,3-phenylene)bis(2-(2-hydroxyphenyl)-5-methylthiazolidin-4-one)
—— selenodiphenol 94783-98-9 C12H10O2Se
selenodiphenol
—— (S)-(-)-<6>-2,2-difluorogingerol-t-butyldimethylsilylether 172546-93-9 C23H38F2O4Si
(S)-(-)-<6>-2,2-difluorogingerol-t-butyldimethylsilylether
—— 134667-87-1 C29H30N2O6S2
—— 4-(3-hydroxypropyl)-2-methoxy-6-prop-1-enylphenol 854665-55-7 C13H18O3
4-(3-hydroxypropyl)-2-methoxy-6-prop-1-enylphenol
—— (E)-ethyl 4-(4-hydroxy-3-methoxyphenyl)but-2-enoate 1209476-90-3 C13H16O4
(E)-ethyl 4-(4-hydroxy-3-methoxyphenyl)but-2-enoate
—— 110095-49-3 C28H54N8Ni2*4ClO4
—— 2-methoxy-4-(1,4,7,8-tetrahydro-3,5-dimethyldipyrazolo-[3,4-b:4',3'-e]pyridin-4-yl)phenol 1346445-98-4 C16H17N5O2
2-methoxy-4-(1,4,7,8-tetrahydro-3,5-dimethyldipyrazolo-[3,4-b:4',3'-e]pyridin-4-yl)phenol
—— 1-(4-hydroxy-3-methoxyphenyl)-propan-2-one oxime 319914-08-4 C10H13NO3
1-(4-hydroxy-3-methoxyphenyl)-propan-2-one oxime
—— 3-methoxy-4-hydroxybenzaldehyde 5-trifluoromethyl-2-pyridylhydrazone 304685-79-8 C14H12F3N3O2
3-methoxy-4-hydroxybenzaldehyde 5-trifluoromethyl-2-pyridylhydrazone
—— N-(2-hydroxyethoxy)ethyliminomethylphenol 1269665-22-6 C11H15NO3
N-(2-hydroxyethoxy)ethyliminomethylphenol
—— 4-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol;sulfuric acid;dihydrate 6078-56-4 C11H23NO9S
4-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol;sulfuric acid;dihydrate
—— 4-chloro-2-[(2-propynoxyimino)methyl]phenol 103742-85-4 C10H8ClNO2
4-chloro-2-[(2-propynoxyimino)methyl]phenol
—— 1-(1H-benzo[d]imidazol-2-yl)-N-(4-fluorophenyl)-2-(4-hydroxy-3-methoxyphenyl)ethenesulfonamide 1430475-81-2 C22H18FN3O4S
1-(1H-benzo[d]imidazol-2-yl)-N-(4-fluorophenyl)-2-(4-hydroxy-3-methoxyphenyl)ethenesulfonamide
—— (E)-4-bromo-2-(((2-hydroxyethyl)imino)methyl)phenol 942199-85-1 C9H10BrNO2
(E)-4-bromo-2-(((2-hydroxyethyl)imino)methyl)phenol
—— 4-Brom-2-chlormethyl-6-nitrophenol 39554-69-3 C7H5BrClNO3
4-Brom-2-chlormethyl-6-nitrophenol
—— (C2H5)3SnC6H4-o-OH 855423-00-6 C12H20OSn
(C2H5)3SnC6H4-o-OH
—— 4-Pentachlorophenyloxymethyl-phenol 120677-39-6 C13H7Cl5O2
4-Pentachlorophenyloxymethyl-phenol
—— 2-((1-(1-adamantan-1-yl)ethyl)iminomethyl)-5-methoxyphenol 1346265-89-1 C20H27NO2
2-((1-(1-adamantan-1-yl)ethyl)iminomethyl)-5-methoxyphenol
—— (4-hydroxy-3-methoxybenzyloxy)triethylsilane 1352841-02-1 C14H24O3Si
(4-hydroxy-3-methoxybenzyloxy)triethylsilane