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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-(4-(Benzyloxy)phenoxy)-N'-(2,4-dihydroxybenzylidene)acetohydrazide 303085-14-5 C22H20N2O5
2-(4-(Benzyloxy)phenoxy)-N'-(2,4-dihydroxybenzylidene)acetohydrazide
—— (+/-)-2-phenyl-(3a<i>r</i>,21a<i>t</i>)-3a,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,21a-eicosahydro-cycloeicosoxazole; picrate 124245-84-7 C6H3N3O7*C27H43NO
(+/-)-2-phenyl-(3a<i>r</i>,21a<i>t</i>)-3a,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,21a-eicosahydro-cycloeicosoxazole; picrate
—— [2-(4-hydroxy-phenoxy)-ethyl]-dimethyl-octyl-ammonium; bromide 112377-10-3 Br*C18H32NO2
[2-(4-hydroxy-phenoxy)-ethyl]-dimethyl-octyl-ammonium; bromide
—— N,N'-bis(salicylidene)thiosemicarbazide 752205-83-7 C15H13N3O2S
N,N'-bis(salicylidene)thiosemicarbazide
—— 26,27,28-trihydroxy-5,17-dimethylcalix<4>arene 175349-00-5 C30H28O3
26,27,28-trihydroxy-5,17-dimethylcalix<4>arene
—— 3-Amino-5-fluorophenol hydrobromide 2243515-02-6 C6H7BrFNO
3-Amino-5-fluorophenol hydrobromide
—— N'-[1-{5-[3-(Benzylsulfanylthiocarbonyl-hydrazonomethyl)-4-hydroxy-phenyldisulfanyl]-2-hydroxy-phenyl}-meth-(E)-ylidene]-hydrazinecarbodithioic acid benzyl ester 161959-15-5 C30H26N4O2S6
N'-[1-{5-[3-(Benzylsulfanylthiocarbonyl-hydrazonomethyl)-4-hydroxy-phenyldisulfanyl]-2-hydroxy-phenyl}-meth-(E)-ylidene]-hydrazinecarbodithioic acid benzyl ester
—— 2-(3-hydroxybenzylidene)cyclopentanone 171796-55-7 C12H12O2
2-(3-hydroxybenzylidene)cyclopentanone
—— (+/-)-(4b<i>r</i>,9b<i>c</i>)-4b,5,9b,10-tetrahydro-indeno[2,1-<i>a</i>]indene-2,7-diol 111115-05-0 C16H14O2
(+/-)-(4b<i>r</i>,9b<i>c</i>)-4b,5,9b,10-tetrahydro-indeno[2,1-<i>a</i>]indene-2,7-diol
—— (E,4aS,5S)-3-(4-hydroxy-3-methoxybenzylidene)-octahydro-5-hydroxy-1,4a-methylennaphthalen-2(3H)-one 897020-65-4 C20H26O4
(E,4aS,5S)-3-(4-hydroxy-3-methoxybenzylidene)-octahydro-5-hydroxy-1,4a-methylennaphthalen-2(3H)-one
—— 4-[2-(3-cyclopropyl-[1,2,4]oxadiazol-5-yl)-vinyl]-benzene-1,2-diol 1332498-49-3 C13H12N2O3
4-[2-(3-cyclopropyl-[1,2,4]oxadiazol-5-yl)-vinyl]-benzene-1,2-diol
—— 3-(2-Hydroxy-4-methyl-benzoyl-methylen)-piperazinon-(2) 109846-05-1 C13H14N2O3
3-(2-Hydroxy-4-methyl-benzoyl-methylen)-piperazinon-(2)
—— <4.6-Dibrom-3-hydroxy-2.5-dimethyl-phenyl>-phosphonsaeure-diaethylester 100248-62-2 C12H17Br2O4P
<4.6-Dibrom-3-hydroxy-2.5-dimethyl-phenyl>-phosphonsaeure-diaethylester
—— 5-benzoyl-4-(3',4'-dihydroxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one 1370052-81-5 C18H16N2O4
5-benzoyl-4-(3',4'-dihydroxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one
—— 2,6-bis-(salicylidenamino-methyl)-phenol 110798-86-2 C22H20N2O3
2,6-bis-(salicylidenamino-methyl)-phenol
—— 4-allyloxy-3-(2-amino-1-methylethyl)-2-iodophenol hydrochloride 1203905-56-9 C12H16INO2*ClH
4-allyloxy-3-(2-amino-1-methylethyl)-2-iodophenol hydrochloride
—— 2-[5-(4'-nonylphenyl)-1,3,4-oxadiazol-2-yl]phenol 1384856-31-8 C23H28N2O2
2-[5-(4'-nonylphenyl)-1,3,4-oxadiazol-2-yl]phenol
—— 4-[2-(3-cyclohexyl-[1,2,4]oxadiazol-5-yl)-vinyl]-benzene-1,2-diol 1332498-64-2 C16H18N2O3
4-[2-(3-cyclohexyl-[1,2,4]oxadiazol-5-yl)-vinyl]-benzene-1,2-diol
—— 4-(1-hydroxypentyl)benzene-1,2-diol 6452-67-1 C11H16O3
4-(1-hydroxypentyl)benzene-1,2-diol
—— diisopropyl 5-fluoro-2-hydroxyphenylphosphonate 1592980-01-2 C12H18FO4P
diisopropyl 5-fluoro-2-hydroxyphenylphosphonate
—— 3-acetamidophenolate 74339-11-0 C8H8NO2
3-acetamidophenolate
—— 4-[3-(4-Hydroxy-phenoxy)-propoxy]-benzoic acid 150566-20-4 C16H16O5
4-[3-(4-Hydroxy-phenoxy)-propoxy]-benzoic acid
—— 2-Hydroxy-3-methoxybenzaldehyde N-(3-chlorophenyl)thiosemicarbazone 765284-86-4 C15H14ClN3O2S
2-Hydroxy-3-methoxybenzaldehyde N-(3-chlorophenyl)thiosemicarbazone
—— (4-Nitro-2-hydroxy-phenylhydrazono)-malonsaeure-diaethylester 21103-99-1 C13H15N3O7
(4-Nitro-2-hydroxy-phenylhydrazono)-malonsaeure-diaethylester
—— 2-[[(2-Hydroxy-5-methylphenyl)methylideneamino]methyliminomethyl]-4-methylphenol 3890-94-6 C17H18N2O2
2-[[(2-Hydroxy-5-methylphenyl)methylideneamino]methyliminomethyl]-4-methylphenol
—— (αS)-[α-(3)H1]tyramine hydrochloride 74447-55-5 C8H11NO*ClH
(αS)-[α-(3)H1]tyramine hydrochloride
—— 11-Hydroxy-1-(4'-hydroxy-3'-methoxyphenyl)-undeca-1Z,9Z-diene 132704-94-0 C18H26O3
11-Hydroxy-1-(4'-hydroxy-3'-methoxyphenyl)-undeca-1Z,9Z-diene
—— 2-amino-6-ethyl-4-methylphenol;hydrochloride 84942-29-0 C9H13NO*ClH
2-amino-6-ethyl-4-methylphenol;hydrochloride
—— N-(2-(3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydroisoxazol-5-yl)ethyl)-3-methylbutanamide 1187947-64-3 C16H21FN2O3
N-(2-(3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydroisoxazol-5-yl)ethyl)-3-methylbutanamide
—— Benzyl-(4-hydroxyphenyl)-methylsulfanium;thiophen-2-ylmethyl sulfate 1393884-46-2 C5H5O4S2*C14H15OS
Benzyl-(4-hydroxyphenyl)-methylsulfanium;thiophen-2-ylmethyl sulfate
—— (2-Hydroxy-5-methyl-phenyl)-phosphonic acid dihexyl ester 129529-34-6 C19H33O4P
(2-Hydroxy-5-methyl-phenyl)-phosphonic acid dihexyl ester
—— (1'S,2'S,3'S)-ethyl 2'-formyl-5'-hydroxy-1',2',3',6'-tetrahydro-[1,1':3',1''-terphenyl]-4'-carboxylate 1314236-49-1 C22H22O4
(1'S,2'S,3'S)-ethyl 2'-formyl-5'-hydroxy-1',2',3',6'-tetrahydro-[1,1':3',1''-terphenyl]-4'-carboxylate
—— Benzo<b>cyclohepta<d>furan 5726-18-1 C13H10O
Benzo<b>cyclohepta<d>furan
—— 929903-42-4 C14H17NO2
—— 2,3,5,6-Tetramethyl-4-hydroxy-benzylmercaptan 59104-13-1 C11H16OS
2,3,5,6-Tetramethyl-4-hydroxy-benzylmercaptan
—— 4,4'-dinitro-2,2'-[(1,5-propanediyldioxy)bis(nitrilomethylidyne)]diphenol 1537214-62-2 C19H20N4O8
4,4'-dinitro-2,2'-[(1,5-propanediyldioxy)bis(nitrilomethylidyne)]diphenol
—— zinc[5-(4-hydroxy-3-methoxyphenyl)-10,15,20-triphenylporphyrinato] 358973-91-8 C45H30N4O2Zn
zinc[5-(4-hydroxy-3-methoxyphenyl)-10,15,20-triphenylporphyrinato]
—— 2-methoxy-6-(tridec-1-en-1-yl)phenol 1187759-61-0 C20H32O2
2-methoxy-6-(tridec-1-en-1-yl)phenol
—— 5-(13C)-5,7,11-trihydroxy-6H-benzo[b]fluoren-6-one 1167575-99-6 C17H10O4
5-(13C)-5,7,11-trihydroxy-6H-benzo[b]fluoren-6-one
—— salicylaldehyde-(2,3-dichloro-4,6-dinitro-phenylhydrazone) 96461-97-1 C13H8Cl2N4O5
salicylaldehyde-(2,3-dichloro-4,6-dinitro-phenylhydrazone)
—— 3-bromo-N′-(2-hydroxy-5-methoxybenzylidene)benzohydrazide 1322024-75-8 C15H13BrN2O3
3-bromo-N′-(2-hydroxy-5-methoxybenzylidene)benzohydrazide
—— ((E)-4-Penta-2,4-dienyl)-phenol 34632-84-3 C11H12O
((E)-4-Penta-2,4-dienyl)-phenol
—— 5-chloro-2-hydroxy-benzaldehyde-(1,4-dimethyl-6-oxo-1,6-dihydro-pyrimidin-2-ylhydrazone) 91762-61-7 C13H13ClN4O2
5-chloro-2-hydroxy-benzaldehyde-(1,4-dimethyl-6-oxo-1,6-dihydro-pyrimidin-2-ylhydrazone)
—— 4-[2-(3-hexyl-[1,2,4]oxadiazol-5-yl)-vinyl]-benzene-1,2-diol 1332498-53-9 C16H20N2O3
4-[2-(3-hexyl-[1,2,4]oxadiazol-5-yl)-vinyl]-benzene-1,2-diol
—— 2-(4-hydroxyphenyl)-5-dodecyloxypyrimidine 115770-81-5 C22H32N2O2
2-(4-hydroxyphenyl)-5-dodecyloxypyrimidine
—— (propan-2-ylideneamino) N-(3-hydroxyphenyl)carbamate 34207-27-7 C10H12N2O3
(propan-2-ylideneamino) N-(3-hydroxyphenyl)carbamate
—— methyl 3-{4-[2-(2-fluorophenyl)ethyloxy]-3-(1-methyl-1H-indazol-5-yl)phenyl}-propionate 591252-95-8 C26H25FN2O3
methyl 3-{4-[2-(2-fluorophenyl)ethyloxy]-3-(1-methyl-1H-indazol-5-yl)phenyl}-propionate
—— 4-((2E,4E)-Hexa-2,4-dienyl)-3-methyl-phenol 3280-54-4 C13H16O
4-((2E,4E)-Hexa-2,4-dienyl)-3-methyl-phenol
—— 6-<N-<2-(3,4-dihydroxyphenyl)-ethyl>-N-methylamino>-pyridazin-3(2H)-one 140628-44-0 C13H15N3O3
6-<N-<2-(3,4-dihydroxyphenyl)-ethyl>-N-methylamino>-pyridazin-3(2H)-one
—— [2-(4-hydroxy-phenoxy)-ethyl]-dimethyl-octadecyl-ammonium; bromide 121991-17-1 Br*C28H52NO2
[2-(4-hydroxy-phenoxy)-ethyl]-dimethyl-octadecyl-ammonium; bromide