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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-(2-Propinylthio)-3,5-xylenol 5579-36-2 C11H12OS
4-(2-Propinylthio)-3,5-xylenol
—— 4-[5-(6-diethylamino-5-methyl-pyridin-3-yl)-[1,3,4]oxadiazol-2-yl]-2-ethyl-6-methyl-phenol 1186617-84-4 C21H26N4O2
4-[5-(6-diethylamino-5-methyl-pyridin-3-yl)-[1,3,4]oxadiazol-2-yl]-2-ethyl-6-methyl-phenol
—— 4-(3-ethyl-1,4-dimethyl-1,2,5,6-tetrahydro-pyridin-2-ylmethyl)-phenol 64088-87-5 C16H23NO
4-(3-ethyl-1,4-dimethyl-1,2,5,6-tetrahydro-pyridin-2-ylmethyl)-phenol
—— Dimethyl-α,α-bis-(4-hydroxyphenyl)-n-octadecylphosphonat 31662-01-8 C32H51O5P
Dimethyl-α,α-bis-(4-hydroxyphenyl)-n-octadecylphosphonat
—— 1622386-20-2 C18H18N4O8
—— 2-(2-hydroxy-1-methyl-ethyl)-5-iodo-4-methoxy-phenol 865305-59-5 C10H13IO3
2-(2-hydroxy-1-methyl-ethyl)-5-iodo-4-methoxy-phenol
—— (5R,6R)-5-Benzyl-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-1-(4-thiophen-2-yl-butyryl)-6-(2-trimethylsilanyl-ethoxymethoxy)-[1,2,4]triazepan-3-one 871905-29-2 C41H53N3O8SSi
(5R,6R)-5-Benzyl-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-1-(4-thiophen-2-yl-butyryl)-6-(2-trimethylsilanyl-ethoxymethoxy)-[1,2,4]triazepan-3-one
—— ((7a<i>S</i>)-(7a<i>r</i>)-hexahydropyrrolizin-1<i>t</i>-yl)-methanol; picrate 97358-92-4 C6H3N3O7*C8H15NO
((7a<i>S</i>)-(7a<i>r</i>)-hexahydropyrrolizin-1<i>t</i>-yl)-methanol; picrate
—— 4-[2-(3-benzyl-[1,2,4]oxadiazol-5-yl)-vinyl]-benzene-1,2-diol 1332498-24-4 C17H14N2O3
4-[2-(3-benzyl-[1,2,4]oxadiazol-5-yl)-vinyl]-benzene-1,2-diol
—— Thioschwefligesaeure-bis-(6-hydroxy-3-methyl-benzylester) 53055-32-6 C16H18O4S2
Thioschwefligesaeure-bis-(6-hydroxy-3-methyl-benzylester)
—— 1,4-dichloro-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2,3-naphthodiol 116393-15-8 C14H18Cl2O2
1,4-dichloro-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2,3-naphthodiol
—— (E)-3-(benzyloxy)-4-methoxy-2-(prop-1-enyl)phenol 1247734-42-4 C17H18O3
(E)-3-(benzyloxy)-4-methoxy-2-(prop-1-enyl)phenol
—— 2-(1-(4-methoxyphenylimino)ethyl)-4-nitrophenol 1382679-78-8 C15H14N2O4
2-(1-(4-methoxyphenylimino)ethyl)-4-nitrophenol
—— 3-Aethyl-4-<2-hydroxy-phenyl>-5-<4-hydroxy-phenyl>-isoxazol 1035-38-7 C17H15NO3
3-Aethyl-4-<2-hydroxy-phenyl>-5-<4-hydroxy-phenyl>-isoxazol
—— 2233-68-3 C21H17N3O2S
—— 4'-methyl-8-morpholin-4-yl-spiro[bicyclo[4.2.0]octa-1,3,5-triene-7,1'-cyclohex-3'-ene]-2,5-diol 6996-74-3 C18H23NO3
4'-methyl-8-morpholin-4-yl-spiro[bicyclo[4.2.0]octa-1,3,5-triene-7,1'-cyclohex-3'-ene]-2,5-diol
—— 4,5-Dibromo-2-ethyl-phenol 52016-85-0 C8H8Br2O
4,5-Dibromo-2-ethyl-phenol
—— 4-(cyclopropylmethyl)-2,6-dimethylphenol 36161-19-0 C12H16O
4-(cyclopropylmethyl)-2,6-dimethylphenol
—— 2-Butyl-4,5-dichloro-phenol 52016-72-5 C10H12Cl2O
2-Butyl-4,5-dichloro-phenol
—— 4-methoxy-2,6-bis(2-phenylsulfinyl-2-propenyl)phenol 139371-11-2 C25H24O4S2
4-methoxy-2,6-bis(2-phenylsulfinyl-2-propenyl)phenol
—— 3,4,5-trihydroxy-N-[4-(4-hydroxy-phenyl)-5-methyl-thiazol-2-yl]-benzamide 1003312-88-6 C17H14N2O5S
3,4,5-trihydroxy-N-[4-(4-hydroxy-phenyl)-5-methyl-thiazol-2-yl]-benzamide
—— 5-Allyl-2-chlor-6-methyl-phenol 41389-66-6 C10H11ClO
5-Allyl-2-chlor-6-methyl-phenol
—— 4-(dec-1-ynyl)phenol 1418137-00-4 C16H22O
4-(dec-1-ynyl)phenol
—— 2-(1-Ethyl-hexyl)-4,6-dinitro-phenol; compound with morpholine 4307-90-8 C4H9NO*C14H20N2O5
2-(1-Ethyl-hexyl)-4,6-dinitro-phenol; compound with morpholine
—— N-Nonanoyl-4-hydroxy-3.5-dimethoxy-benzylamin 4973-55-1 C18H29NO4
N-Nonanoyl-4-hydroxy-3.5-dimethoxy-benzylamin
—— 11,23-dicyclohexyl-5,17-octano-25,26,27,28-tetrahydroxycalix<4>arene 115347-95-0 C48H58O4
11,23-dicyclohexyl-5,17-octano-25,26,27,28-tetrahydroxycalix<4>arene
—— 3-(6-Bromo-benzo[1,3]dioxol-5-yl)-N-[2-(3-hydroxy-4-methoxy-phenyl)-ethyl]-propionamide 92446-51-0 C19H20BrNO5
3-(6-Bromo-benzo[1,3]dioxol-5-yl)-N-[2-(3-hydroxy-4-methoxy-phenyl)-ethyl]-propionamide
—— (2-hydroxy-3-methoxy-5-bromobenzylideneamino)acetonitrile 1279019-06-5 C10H9BrN2O2
(2-hydroxy-3-methoxy-5-bromobenzylideneamino)acetonitrile
—— (5R,6R)-1-(3-Benzo[1,3]dioxol-5-yl-propionyl)-5-benzyl-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-6-(2-trimethylsilanyl-ethoxymethoxy)-[1,2,4]triazepan-3-one 871905-23-6 C43H53N3O10Si
(5R,6R)-1-(3-Benzo[1,3]dioxol-5-yl-propionyl)-5-benzyl-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-6-(2-trimethylsilanyl-ethoxymethoxy)-[1,2,4]triazepan-3-one
—— (1r,3R,4S)-3,4-bis((2-hydroxy-3-methoxybenzylidene)amino)-N-(4-methoxypyridin-3-yl)cyclopentane-1-carboxamide 1427204-47-4 C28H30N4O6
(1r,3R,4S)-3,4-bis((2-hydroxy-3-methoxybenzylidene)amino)-N-(4-methoxypyridin-3-yl)cyclopentane-1-carboxamide
—— 4-hydroxy-N-methylbenzothioamide 120951-39-5 C8H9NOS
4-hydroxy-N-methylbenzothioamide
—— 4-{[(E)-1,3-Dimethyl-butylimino]-methyl}-2-methoxy-phenol 30121-92-7 C14H21NO2
4-{[(E)-1,3-Dimethyl-butylimino]-methyl}-2-methoxy-phenol
—— [2-(2-Hydroxy-4,5-dimethoxy-phenyl)-ethyl]-carbamic acid 2-trimethylsilanyl-ethyl ester 141939-58-4 C16H27NO5Si
[2-(2-Hydroxy-4,5-dimethoxy-phenyl)-ethyl]-carbamic acid 2-trimethylsilanyl-ethyl ester
—— 3-(3,5-dimethylisoxazol-4-yl)-4-(4-hydroxyphenyl)thiophene-2-carbaldehyde oxime 1360604-75-6 C16H14N2O3S
3-(3,5-dimethylisoxazol-4-yl)-4-(4-hydroxyphenyl)thiophene-2-carbaldehyde oxime
—— 3.5-Dimethyl-2-dodecyl-phenol 7282-07-7 C20H34O
3.5-Dimethyl-2-dodecyl-phenol
—— 2-(2-Hydroxy-3-chlor-5-nitro-phenyl-hydrazono)-3-oxo-buttersaeureaethylester 5294-08-6 C12H12ClN3O6
2-(2-Hydroxy-3-chlor-5-nitro-phenyl-hydrazono)-3-oxo-buttersaeureaethylester
—— 4-Ethyl-3,5,7-trinitro-tropolon 2902-42-3 C9H7N3O8
4-Ethyl-3,5,7-trinitro-tropolon
—— 2,4,5-Trimethyl-6-thiomethoxymethyl-phenol 14093-79-9 C11H16OS
2,4,5-Trimethyl-6-thiomethoxymethyl-phenol
—— 3,3-diethyl-1-(4-hydroxy-3-methoxy-benzylideneamino)-5-methyl-piperidine-2,4-dione 39844-60-5 C18H24N2O4
3,3-diethyl-1-(4-hydroxy-3-methoxy-benzylideneamino)-5-methyl-piperidine-2,4-dione
—— 2,6-Dimethyl-4-(1,2,2,6,6-pentamethyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenol 42001-31-0 C18H27NO
2,6-Dimethyl-4-(1,2,2,6,6-pentamethyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenol
—— 81421-17-2 C36H34CoN8O8
—— benzyl 2-(2-hydroxy-4-(2-(2-methoxyethoxy)ethoxy)phenyl)-4-methyl-4,5-dihydrooxazole-4-carboxylate 1346427-72-2 C23H27NO7
benzyl 2-(2-hydroxy-4-(2-(2-methoxyethoxy)ethoxy)phenyl)-4-methyl-4,5-dihydrooxazole-4-carboxylate
—— [(S)-cyano-(4-hydroxy-3-methoxyphenyl)methyl] acetate 129313-30-0 C11H11NO4
[(S)-cyano-(4-hydroxy-3-methoxyphenyl)methyl] acetate
—— cobalt(II) 2,2'-((succinylbis(hydrazin-2-yl-1-ylidene))bis(methaneylylidene))diphenolate 62611-56-7 C18H16N4O4*Co
cobalt(II) 2,2'-((succinylbis(hydrazin-2-yl-1-ylidene))bis(methaneylylidene))diphenolate
—— 4-methyl-2-(4-morpholinylmethyleneamino)phenol 1323158-75-3 C12H16N2O2
4-methyl-2-(4-morpholinylmethyleneamino)phenol
—— monoaureate of 2,6-bis((diethylamino)methyl)-4-CN-phenol 141753-89-1 AuCl4*C17H28N3O
monoaureate of 2,6-bis((diethylamino)methyl)-4-CN-phenol
—— N-<5-methylsalicylidene>-benzylamine 53848-13-8 C15H15NO
N-<5-methylsalicylidene>-benzylamine
—— 6-(2-hydroxy-3,5-dinitrobenzyl)-6-(p-nitrobenzyl)-1,4,8,11-tetraoxacyclotetradecane 106420-04-6 C24H29N3O11
6-(2-hydroxy-3,5-dinitrobenzyl)-6-(p-nitrobenzyl)-1,4,8,11-tetraoxacyclotetradecane
—— 4-(6-Ethyl-4-hydroxymethyl-5-methyl-cyclohex-1-enyl)-phenol 25918-07-4 C16H22O2
4-(6-Ethyl-4-hydroxymethyl-5-methyl-cyclohex-1-enyl)-phenol
—— (1S,1'S)-N-(1'-phenylethyl)-1-(2''-hydroxy-3'',4''-dimethoxyphenyl)ethylamine hydroperchlorate 122078-31-3 C18H23NO3*ClHO4
(1S,1'S)-N-(1'-phenylethyl)-1-(2''-hydroxy-3'',4''-dimethoxyphenyl)ethylamine hydroperchlorate