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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
—— (+/-)-heliotridane picrate 15861-67-3 C6H3N3O7*C8H15N
(+/-)-heliotridane picrate
—— 4-(2-(5-(1H-indol-3-yl)-1H-pyrazol-3-yl)hydrazono)-1,7-bis(4-hydroxy-3-methoxy-phenyl)hepta-1,6-diene-3,5-dione 1583301-93-2 C32H27N5O6
4-(2-(5-(1H-indol-3-yl)-1H-pyrazol-3-yl)hydrazono)-1,7-bis(4-hydroxy-3-methoxy-phenyl)hepta-1,6-diene-3,5-dione
—— N-(3-hydroxy-4-methoxybenzyl)-1H-pyrrole 1333534-08-9 C12H13NO2
N-(3-hydroxy-4-methoxybenzyl)-1H-pyrrole
—— 4-{[4-(4-chloro-phenyl)-thiazol-2-ylimino]-phenyl-methyl}-benzene-1,3-diol 64343-64-2 C22H15ClN2O2S
4-{[4-(4-chloro-phenyl)-thiazol-2-ylimino]-phenyl-methyl}-benzene-1,3-diol
—— trinitrophloroglucinol sodium salt 887511-63-9 C6H2N3O9*Na
trinitrophloroglucinol sodium salt
—— 1-[4-(Azidomethyl)-2-hydroxyphenyl]ethanone oxime 903556-87-6 C9H10N4O2
1-[4-(Azidomethyl)-2-hydroxyphenyl]ethanone oxime
—— (E)-4-methoxy-2-(3-methylhepta-2,6-dien-1-yl)phenol 1417913-00-8 C15H20O2
(E)-4-methoxy-2-(3-methylhepta-2,6-dien-1-yl)phenol
—— 2-Hex-5-enyl-3,4-dimethoxy-phenol 192124-72-4 C14H20O3
2-Hex-5-enyl-3,4-dimethoxy-phenol
—— 134667-75-7 C27H24Br2N2O6S2
—— N'-(3,4-dihydroxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 1456816-73-1 C15H20N2O3Se2
N'-(3,4-dihydroxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide
—— (2E,4E)-5-(3,4-dihydroxyphenyl)penta-2,4-dienoyl chloride 1073666-66-6 C11H9ClO3
(2E,4E)-5-(3,4-dihydroxyphenyl)penta-2,4-dienoyl chloride
—— N-salicylideneglycinato(3,5-dimethylpyrazole)copper(II) monohydrate 109850-43-3 C5H8N2*C9H7NO3*Cu*H2O
N-salicylideneglycinato(3,5-dimethylpyrazole)copper(II) monohydrate
—— 2-(1,2-dihydro-pyrido[3,4-<i>e</i>][1,2,4]triazin-3-yl)-phenol 60773-23-1 C12H10N4O
2-(1,2-dihydro-pyrido[3,4-<i>e</i>][1,2,4]triazin-3-yl)-phenol
—— 2,2-bis[3-(3,5-dimethylphenyl)-prop-2-ynyl]malonic acid diethyl ester 1338070-84-0 C29H32O4
2,2-bis[3-(3,5-dimethylphenyl)-prop-2-ynyl]malonic acid diethyl ester
—— dimethyl [2-methyl-1-(1,2,4-triazol-4-ylamino)propyl]phosphonate picrate 1392514-16-7 C6H3N3O7*C8H17N4O3P
dimethyl [2-methyl-1-(1,2,4-triazol-4-ylamino)propyl]phosphonate picrate
—— optically inactive 2,7-dimethyl-4,5-bis-(4-hydroxy-phenyl)-octane 114278-46-5 C22H30O2
optically inactive 2,7-dimethyl-4,5-bis-(4-hydroxy-phenyl)-octane
—— 3-Ethinyl-2,6-dimethoxyphenol 63604-90-0 C10H10O3
3-Ethinyl-2,6-dimethoxyphenol
—— 1-hydroxy-allogibberellic acid methyl ester 35316-62-2 C19H22O4
1-hydroxy-allogibberellic acid methyl ester
—— N,N'-bis(2-hydroxy-5-nitromethylbenzylidene)glutarodihydrazone 1062484-70-1 C21H22N6O8
N,N'-bis(2-hydroxy-5-nitromethylbenzylidene)glutarodihydrazone
—— 1-(p-Hydroxyphenyl)benzosuberan 107365-78-6 C17H18O
1-(p-Hydroxyphenyl)benzosuberan
—— N,N′-bis(4-methoxylsalicylidene)-p-phenylenediamine 157982-85-9 C22H20N2O4
N,N′-bis(4-methoxylsalicylidene)-p-phenylenediamine
—— 4-bromo-2-(((5-chloro-2-hydroxyphenyl)imino)methyl)phenol 1761-38-2 C13H9BrClNO2
4-bromo-2-(((5-chloro-2-hydroxyphenyl)imino)methyl)phenol
—— 2-((2-(dimethylamino)-ethylimino)methyl)-6-methoxyphenol 634590-22-0 C12H18N2O2
2-((2-(dimethylamino)-ethylimino)methyl)-6-methoxyphenol
—— 2-iodo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 1245635-34-0 C12H16BIO3
2-iodo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
—— 2-(2-hydroxyphenyl)-2-[(5-pyridin-4-yl-1,3,4-oxadiazol-2-yl)amino]acetonitrile 117634-77-2 C15H11N5O2
2-(2-hydroxyphenyl)-2-[(5-pyridin-4-yl-1,3,4-oxadiazol-2-yl)amino]acetonitrile
—— 1-(3-hydroxy-pyridin-2-yl)-3-phenyl-propane-1,2-dione bis-[(2,4-dinitro-phenyl)-hydrazon] 36984-27-7 C26H19N9O9
1-(3-hydroxy-pyridin-2-yl)-3-phenyl-propane-1,2-dione bis-[(2,4-dinitro-phenyl)-hydrazon]
—— di(2,3,6-trimethyl-4-hydroxyphenyl) disulfide 85460-74-8 C18H22O2S2
di(2,3,6-trimethyl-4-hydroxyphenyl) disulfide
—— S-methyl 3-(5-bromo-2-hydroxyphenyl)methylenedithiocarbazate 42183-25-5 C9H9BrN2OS2
S-methyl 3-(5-bromo-2-hydroxyphenyl)methylenedithiocarbazate
—— (4-Methoxy-phenyl)-(2,4-dihydroxy-phenyl)-tellurdiiodid 126508-15-4 C13H12I2O3Te
(4-Methoxy-phenyl)-(2,4-dihydroxy-phenyl)-tellurdiiodid
—— 3,4-Bis(decoxy)phenol 161807-03-0 C26H46O3
3,4-Bis(decoxy)phenol
—— 5-[(3,4-Dihydroxyphenyl)methylideneamino]-1-methylimidazole-4-carbonitrile 1610624-74-2 C12H10N4O2
5-[(3,4-Dihydroxyphenyl)methylideneamino]-1-methylimidazole-4-carbonitrile
—— 4-({[(E)-(2-hydroxyphenyl)methylidene]amino}methyl)cyclohexanecarboxylic acid 924961-49-9 C15H19NO3
4-({[(E)-(2-hydroxyphenyl)methylidene]amino}methyl)cyclohexanecarboxylic acid
—— 2-ethylaminomethyl-3,4,6-trichloro-phenol 106783-61-3 C9H10Cl3NO
2-ethylaminomethyl-3,4,6-trichloro-phenol
—— trans-2-(4'-acetyl-1'-methyl-cyclohex-1'-yl)-4-methoxyphenol 89644-83-7 C16H22O3
trans-2-(4'-acetyl-1'-methyl-cyclohex-1'-yl)-4-methoxyphenol
—— 34269-71-1 C19H17N5O4S
—— 6-[(4-(3-ethoxycarbonyl)propyl-1-piperazinyl)methyl]-2,3-dimethoxyphenol 486450-76-4 C19H30N2O5
6-[(4-(3-ethoxycarbonyl)propyl-1-piperazinyl)methyl]-2,3-dimethoxyphenol
—— 1-cyanoimidazolium picrate 98993-75-0 C4H3N3*C6H3N3O7
1-cyanoimidazolium picrate
—— 2-(2-Hydroxy-3,4,5,6-tetrachlor-phenyl-hydrazono)-3-methylimino-buttersaeureaethylester 5352-18-1 C13H13Cl4N3O3
2-(2-Hydroxy-3,4,5,6-tetrachlor-phenyl-hydrazono)-3-methylimino-buttersaeureaethylester
—— 3-Fluoro-4-hydroxy-5-methoxybenzenepropanol 1000516-59-5 C10H13FO3
3-Fluoro-4-hydroxy-5-methoxybenzenepropanol
—— 5-Chlor-2-hydroxy-3-methoxy-benzaldehyd-phenylhydrazon 7740-08-1 C14H13ClN2O2
5-Chlor-2-hydroxy-3-methoxy-benzaldehyd-phenylhydrazon
—— 2-[C-methyl-N-(5-phenyl-1,3,4-oxadiazol-2-yl)carbonimidoyl]phenol 183486-14-8 C16H13N3O2
2-[C-methyl-N-(5-phenyl-1,3,4-oxadiazol-2-yl)carbonimidoyl]phenol
—— 2-Nitro-3-hydroxy-4-methyl-N-(n-octyl)-benzoesaeureamid 63435-37-0 C16H24N2O4
2-Nitro-3-hydroxy-4-methyl-N-(n-octyl)-benzoesaeureamid
—— 1313182-86-3 C11H17BrOSi
—— 1,5-bis(1-benzimidazolyl)-3-oxapentane 2,4,6-trinitrophenolate 1604045-79-5 C6H3N3O7*C18H18N4O
1,5-bis(1-benzimidazolyl)-3-oxapentane 2,4,6-trinitrophenolate
—— 2-hydroxy-<i>N</i>-(6-methoxy-pyridazin-3-yl)-4-nitro-benzamide 39614-95-4 C12H10N4O5
2-hydroxy-<i>N</i>-(6-methoxy-pyridazin-3-yl)-4-nitro-benzamide
—— 1356120-94-9 C14H15NO5
—— 4-[[3-[(4-Hydroxyphenyl)methylideneamino]-4-methylphenyl]iminomethyl]phenol 1262652-46-9 C21H18N2O2
4-[[3-[(4-Hydroxyphenyl)methylideneamino]-4-methylphenyl]iminomethyl]phenol
—— 5-Chlor-2-hydroxy-4,6-dimethoxy-benzamid 3187-08-4 C9H10ClNO4
5-Chlor-2-hydroxy-4,6-dimethoxy-benzamid
—— 4-(m-methoxy-p-hydroxybenzalamino)-3-methyl-5-styrylisoxazole 80650-27-7 C20H18N2O3
4-(m-methoxy-p-hydroxybenzalamino)-3-methyl-5-styrylisoxazole
—— <i>N</i>,<i>N</i>'-dimethyl-hydrazine; picrate 5968-80-9 C2H8N2*C6H3N3O7
<i>N</i>,<i>N</i>'-dimethyl-hydrazine; picrate