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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
—— 3-hydroxy-4-methoxy-benzaldehyde-(4-nitro-phenylhydrazone) 303065-71-6 C14H13N3O4
3-hydroxy-4-methoxy-benzaldehyde-(4-nitro-phenylhydrazone)
—— 2-(2,4-dibromo-6-methoxyphenoxy)-N'-[(E)-(5-hydroxy-2-nitrophenyl)methylidene]acetohydrazide —— C16H13Br2N3O6
2-(2,4-dibromo-6-methoxyphenoxy)-N'-[(E)-(5-hydroxy-2-nitrophenyl)methylidene]acetohydrazide
—— N'-[(E)-(5-hydroxy-2-nitrophenyl)methylidene]-2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]acetohydrazide —— C23H29N3O5
N'-[(E)-(5-hydroxy-2-nitrophenyl)methylidene]-2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]acetohydrazide
—— 2-(2,4-dichlorophenoxy)-N'-[(E)-(3-hydroxy-4-nitrophenyl)methylidene]acetohydrazide —— C15H11Cl2N3O5
2-(2,4-dichlorophenoxy)-N'-[(E)-(3-hydroxy-4-nitrophenyl)methylidene]acetohydrazide
—— N'-[(E)-(3-hydroxy-4-nitrophenyl)methylidene]-2-(2,4,6-tribromophenoxy)acetohydrazide —— C15H10Br3N3O5
N'-[(E)-(3-hydroxy-4-nitrophenyl)methylidene]-2-(2,4,6-tribromophenoxy)acetohydrazide
—— (2E)-2-(3-hydroxy-4-methoxybenzylidene)-N'-nitrohydrazinecarboximidamide —— C9H11N5O4
(2E)-2-(3-hydroxy-4-methoxybenzylidene)-N'-nitrohydrazinecarboximidamide
—— 2-{N'-[(E)-(3-Hydroxyphenyl)methylidene]hydrazinecarbonyl}-N-(propan-2-YL)acetamide —— C13H17N3O3
2-{N'-[(E)-(3-Hydroxyphenyl)methylidene]hydrazinecarbonyl}-N-(propan-2-YL)acetamide
—— (NZ)-N-[(5E)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-4-oxo-3-prop-2-enyl-1,3-thiazolidin-2-ylidene]-4-nitrobenzenesulfonamide —— C19H14N4O8S2
(NZ)-N-[(5E)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-4-oxo-3-prop-2-enyl-1,3-thiazolidin-2-ylidene]-4-nitrobenzenesulfonamide
—— 2-{[(E)-(3-hydroxyphenyl)methylidene]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile —— C16H14N2OS
2-{[(E)-(3-hydroxyphenyl)methylidene]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile
—— N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-methyl-1,2,5-oxadiazole-3-carboxamide —— C12H12N4O4
N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-methyl-1,2,5-oxadiazole-3-carboxamide
—— [(E)-(2,4,6-tribromo-3-hydroxyphenyl)methylideneamino]urea —— C8H6Br3N3O2
[(E)-(2,4,6-tribromo-3-hydroxyphenyl)methylideneamino]urea
—— N-[(E)-(4-bromophenyl)methylideneamino]-2-[(4-hydroxy-3,5-dimethylphenyl)methylsulfanyl]acetamide —— C18H19BrN2O2S
N-[(E)-(4-bromophenyl)methylideneamino]-2-[(4-hydroxy-3,5-dimethylphenyl)methylsulfanyl]acetamide
—— 2,3-Dichloro-4-{2-[3-(4-hydroxyphenyl)propanoyl]hydrazono}but-2-enoic acid —— C13H12Cl2N2O4
2,3-Dichloro-4-{2-[3-(4-hydroxyphenyl)propanoyl]hydrazono}but-2-enoic acid
—— 2-(4-chlorophenoxy)-N'-[(E)-(3-hydroxy-4-nitrophenyl)methylidene]acetohydrazide —— C15H12ClN3O5
2-(4-chlorophenoxy)-N'-[(E)-(3-hydroxy-4-nitrophenyl)methylidene]acetohydrazide
—— 2-(3,4-dimethylphenoxy)-N'-[(E)-(3-hydroxy-4-nitrophenyl)methylidene]acetohydrazide —— C17H17N3O5
2-(3,4-dimethylphenoxy)-N'-[(E)-(3-hydroxy-4-nitrophenyl)methylidene]acetohydrazide
—— N'-[(E)-(3-hydroxy-4-nitrophenyl)methylidene]-2-(2-methylphenoxy)acetohydrazide —— C16H15N3O5
N'-[(E)-(3-hydroxy-4-nitrophenyl)methylidene]-2-(2-methylphenoxy)acetohydrazide
—— N'-[(E)-(5-hydroxy-2-nitrophenyl)methylidene]-2-(2-methylphenoxy)acetohydrazide —— C16H15N3O5
N'-[(E)-(5-hydroxy-2-nitrophenyl)methylidene]-2-(2-methylphenoxy)acetohydrazide
—— N'-[(E)-(3-hydroxy-4-nitrophenyl)methylidene]-2-(3-methylphenoxy)acetohydrazide —— C16H15N3O5
N'-[(E)-(3-hydroxy-4-nitrophenyl)methylidene]-2-(3-methylphenoxy)acetohydrazide
—— N'-[(E)-(5-hydroxy-2-nitrophenyl)methylidene]pyridine-3-carbohydrazide —— C13H10N4O4
N'-[(E)-(5-hydroxy-2-nitrophenyl)methylidene]pyridine-3-carbohydrazide
—— [2-[(E)-[(2-hydroxyphenyl)-[(E)-(2-oxoniophenyl)methylideneamino]methyl]iminomethyl]phenyl]oxidanium;zirconium —— C42H40N4O6Zr+4
[2-[(E)-[(2-hydroxyphenyl)-[(E)-(2-oxoniophenyl)methylideneamino]methyl]iminomethyl]phenyl]oxidanium;zirconium
—— copper;2-[[(2E)-2-[(3-methoxy-2-oxoniophenyl)methylidene]hydrazinyl]-oxoniumylidenemethyl]phenolate;hydrate —— C15H17CuN2O5+
copper;2-[[(2E)-2-[(3-methoxy-2-oxoniophenyl)methylidene]hydrazinyl]-oxoniumylidenemethyl]phenolate;hydrate
—— disodium;5-amino-2-anilinobenzenesulfonate;3-aminobenzenesulfonate;(4Z)-3-hydroxy-4-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]cyclohexa-2,5-dien-1-one;iron;4-nitroaniline —— C36H31FeN9Na2O15S2
disodium;5-amino-2-anilinobenzenesulfonate;3-aminobenzenesulfonate;(4Z)-3-hydroxy-4-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]cyclohexa-2,5-dien-1-one;iron;4-nitroaniline
—— (6E)-4-amino-6-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-5-oxonaphthalene-1-sulfonic acid —— C16H11N5O9S
(6E)-4-amino-6-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-5-oxonaphthalene-1-sulfonic acid
—— sodium;(6E)-4-amino-6-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-5-oxonaphthalene-1-sulfonate —— C16H10N5NaO9S
sodium;(6E)-4-amino-6-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-5-oxonaphthalene-1-sulfonate
—— sodium;iron(3+);5-nitro-3-[(2Z)-2-[3-[(4-nitro-2-sulfonatophenyl)diazenyl]-4-oxido-6-oxocyclohexa-2,4-dien-1-ylidene]hydrazinyl]-2-oxidobenzenesulfonate —— C18H8FeN6NaO13S2
sodium;iron(3+);5-nitro-3-[(2Z)-2-[3-[(4-nitro-2-sulfonatophenyl)diazenyl]-4-oxido-6-oxocyclohexa-2,4-dien-1-ylidene]hydrazinyl]-2-oxidobenzenesulfonate
—— (1Z)-1-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]naphthalen-2-one —— C16H10N4O6
(1Z)-1-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]naphthalen-2-one
—— sodium;chromium(3+);(2Z)-2-[(5-nitro-2-oxido-3-sulfonatophenyl)hydrazinylidene]-3-oxo-N-phenylbutanimidate;hydroxide —— C16H12CrN4NaO9S
sodium;chromium(3+);(2Z)-2-[(5-nitro-2-oxido-3-sulfonatophenyl)hydrazinylidene]-3-oxo-N-phenylbutanimidate;hydroxide
—— (6E)-3-(diethylamino)-6-[(2-hydroxy-5-nitrophenyl)hydrazinylidene]cyclohexa-2,4-dien-1-one —— C16H18N4O4
(6E)-3-(diethylamino)-6-[(2-hydroxy-5-nitrophenyl)hydrazinylidene]cyclohexa-2,4-dien-1-one
—— (2Z,5Z)-3-allyl-2-(1,3-benzothiazol-2-ylimino)-5-[(2-hydroxy-3-methoxy-phenyl)methylene]thiazolidin-4-one —— C21H17N3O3S2
(2Z,5Z)-3-allyl-2-(1,3-benzothiazol-2-ylimino)-5-[(2-hydroxy-3-methoxy-phenyl)methylene]thiazolidin-4-one
—— 3-[2-(5-benzoylimino-3-methyl-6-oxocyclohexa-1,3-dien-1-yl)hydrazinyl]-2-hydroxy-5-nitrobenzenesulfonic acid —— C20H16N4O8S
3-[2-(5-benzoylimino-3-methyl-6-oxocyclohexa-1,3-dien-1-yl)hydrazinyl]-2-hydroxy-5-nitrobenzenesulfonic acid
—— (3-endo,4-endo,6-exo)-2,7-Bis(4-hydroxybenzyl)-3,6-dibenzyl-8-oxa-2,7-diaza-1-phosphabicyclo[3.2.1]octan-4-ol-1-oxide —— C32H33N2O5P
(3-endo,4-endo,6-exo)-2,7-Bis(4-hydroxybenzyl)-3,6-dibenzyl-8-oxa-2,7-diaza-1-phosphabicyclo[3.2.1]octan-4-ol-1-oxide
—— 1-[(E)-(2-chloro-3-hydroxy-4-methoxy-phenyl)methyleneamino]-3-hydroxy-guanidine; 4-methylbenzenesulfonic acid —— C16H19ClN4O6S
1-[(E)-(2-chloro-3-hydroxy-4-methoxy-phenyl)methyleneamino]-3-hydroxy-guanidine; 4-methylbenzenesulfonic acid
—— 2-[(E)-1-(3-hydroxyphenyl)ethylideneamino]guanidine —— C9H12N4O
2-[(E)-1-(3-hydroxyphenyl)ethylideneamino]guanidine
—— (5Z)-5-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-6-oxonaphthalene-2-sulfonic acid —— C16H10N4O9S
(5Z)-5-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-6-oxonaphthalene-2-sulfonic acid
—— 1-amino-3-[(Z)-[1-(3-hydroxy-4-methoxyphenyl)-2-(3-hydroxy-2-oxo-1H-indol-3-yl)ethylidene]amino]urea —— C18H19N5O5
1-amino-3-[(Z)-[1-(3-hydroxy-4-methoxyphenyl)-2-(3-hydroxy-2-oxo-1H-indol-3-yl)ethylidene]amino]urea
—— 2-(1-adamantyl)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C20H26N2O3
2-(1-adamantyl)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— N'-[(E)-(3-hydroxyphenyl)methylidene]-3-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)propanehydrazide —— C14H16N4O3
N'-[(E)-(3-hydroxyphenyl)methylidene]-3-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)propanehydrazide
—— 3-[(E)-[(5-phenyl-1,2,4-triazin-3-yl)hydrazinylidene]methyl]phenol —— C16H13N5O
3-[(E)-[(5-phenyl-1,2,4-triazin-3-yl)hydrazinylidene]methyl]phenol
—— sodium;3-[(2E)-2-(1-anilino-1,3-dioxobutan-2-ylidene)hydrazinyl]-2-hydroxy-5-nitrobenzenesulfonate;chromium —— C16H13CrN4NaO8S
sodium;3-[(2E)-2-(1-anilino-1,3-dioxobutan-2-ylidene)hydrazinyl]-2-hydroxy-5-nitrobenzenesulfonate;chromium
—— 3-[(2E)-2-(1-anilino-1,3-dioxobutan-2-ylidene)hydrazinyl]-2-hydroxy-5-nitrobenzenesulfonic acid —— C16H14N4O8S
3-[(2E)-2-(1-anilino-1,3-dioxobutan-2-ylidene)hydrazinyl]-2-hydroxy-5-nitrobenzenesulfonic acid
—— N-[(E)-(3-hydroxyphenyl)methylideneamino]-2-imidazo[2,1-b][1,3]thiazol-6-ylacetamide —— C14H12N4O2S
N-[(E)-(3-hydroxyphenyl)methylideneamino]-2-imidazo[2,1-b][1,3]thiazol-6-ylacetamide
—— N'-[(E)-(5-bromothiophen-2-yl)methylidene]-3,4,5-trihydroxybenzohydrazide —— C12H9BrN2O4S
N'-[(E)-(5-bromothiophen-2-yl)methylidene]-3,4,5-trihydroxybenzohydrazide
—— N'-{(E)-[3-(benzyloxy)phenyl]methylidene}-3,4,5-trihydroxybenzohydrazide —— C21H18N2O5
N'-{(E)-[3-(benzyloxy)phenyl]methylidene}-3,4,5-trihydroxybenzohydrazide
—— 5-[(E)-{[3-(3,5-dimethyl-1H-pyrazol-1-yl)-5-methyl-4H-1,2,4-triazol-4-yl]imino}methyl]-2-methoxyphenol —— C16H18N6O2
5-[(E)-{[3-(3,5-dimethyl-1H-pyrazol-1-yl)-5-methyl-4H-1,2,4-triazol-4-yl]imino}methyl]-2-methoxyphenol
—— N'-[(E)-(3,4-dichlorophenyl)methylidene]-3,4,5-trihydroxybenzohydrazide —— C14H10Cl2N2O4
N'-[(E)-(3,4-dichlorophenyl)methylidene]-3,4,5-trihydroxybenzohydrazide
—— N-[(E)-(3-hydroxyphenyl)methylideneamino]-2-(5-methylpyrazol-1-yl)acetamide —— C13H14N4O2
N-[(E)-(3-hydroxyphenyl)methylideneamino]-2-(5-methylpyrazol-1-yl)acetamide
—— N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]pentanediamide —— C21H24N4O6
N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]pentanediamide
—— 3-[(E)-[(5,6-dichloropyridazin-4-yl)hydrazinylidene]methyl]phenol —— C11H8Cl2N4O
3-[(E)-[(5,6-dichloropyridazin-4-yl)hydrazinylidene]methyl]phenol
—— N-[(3-hydroxyphenyl)methylideneamino]-N'-[(E)-(3-hydroxyphenyl)methylideneamino]pentanediamide —— C19H20N4O4
N-[(3-hydroxyphenyl)methylideneamino]-N'-[(E)-(3-hydroxyphenyl)methylideneamino]pentanediamide
—— 1-hexadecyl-3-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]thiourea —— C25H43N3O2S
1-hexadecyl-3-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]thiourea