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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-{4-[3,5-bis-(4-hydroxy-3-methoxy-benzylidene)-4-oxo-piperidin-1-yl]-4-oxo-butyrylamino}-propyl)-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester 1247874-45-8 C41H56N4O11
(3-{4-[3,5-bis-(4-hydroxy-3-methoxy-benzylidene)-4-oxo-piperidin-1-yl]-4-oxo-butyrylamino}-propyl)-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester
—— 2-(Hydroxymethoxymethyl)-5-methylphenol 6945-40-0 C9H12O3
2-(Hydroxymethoxymethyl)-5-methylphenol
—— N,N'-bis(3-methylsalicylidene)-1,2-phenilenediamine 6943-14-2 C22H20N2O2
N,N'-bis(3-methylsalicylidene)-1,2-phenilenediamine
—— (E)-tert-butyl 2-((2-(2-(hydroxyimino)-3-(4-hydroxyphenyl)-propanamido)ethyl)disulfanyl)ethylcarbamate 1395313-02-6 C18H27N3O5S2
(E)-tert-butyl 2-((2-(2-(hydroxyimino)-3-(4-hydroxyphenyl)-propanamido)ethyl)disulfanyl)ethylcarbamate
—— 2-{4-[2-(benzyloxy)ethoxy]phenyl}ethyl methanesulfonate 620599-96-4 C18H22O5S
2-{4-[2-(benzyloxy)ethoxy]phenyl}ethyl methanesulfonate
—— 2,6-dimethyl-4-(prop-1-en-1-yl)phenol 49583-11-1 C11H14O
2,6-dimethyl-4-(prop-1-en-1-yl)phenol
—— 1-(2,4,5-Trihydroxyphenyl)but-2-en-1-one 99059-11-7 C10H10O4
1-(2,4,5-Trihydroxyphenyl)but-2-en-1-one
—— N-acetyl-N-{2-[4-(2-ethoxyethyl)-2-methylphenoxy]ethyl}-4-chloro-1,3-dimethyl-5-pyrazolecarboxamide 160841-13-4 C21H28ClN3O4
N-acetyl-N-{2-[4-(2-ethoxyethyl)-2-methylphenoxy]ethyl}-4-chloro-1,3-dimethyl-5-pyrazolecarboxamide
—— nodosol 1012852-24-2 C16H20O
nodosol
—— 3,3’-(2,5-pyrazinediyl)bisphenol 855415-44-0 C16H12N2O2
3,3’-(2,5-pyrazinediyl)bisphenol
—— N-[3-(diethylamino)propyl]acetamide;2,4,6-trinitrophenol 7253-72-7 C15H23N5O8
N-[3-(diethylamino)propyl]acetamide;2,4,6-trinitrophenol
—— NSC 54162 4265-51-4 C11H12O5S2
NSC 54162
—— N',N'-diethyl-N-(2-nitrophenyl)propane-1,3-diamine;2,4,6-trinitrophenol 6938-47-2 C19H24N6O9
N',N'-diethyl-N-(2-nitrophenyl)propane-1,3-diamine;2,4,6-trinitrophenol
—— 2,6-Bis(1,3-dioxolan-2-yl)-4-methylphenol 773101-80-7 C13H16O5
2,6-Bis(1,3-dioxolan-2-yl)-4-methylphenol
—— 5-{4-[2-(4-Ethoxy-phenyl)-ethoxy]-benzyl}-thiazolidine-2,4-dione 74772-97-7 C20H21NO4S
5-{4-[2-(4-Ethoxy-phenyl)-ethoxy]-benzyl}-thiazolidine-2,4-dione
—— 2-Ethenyl-6-methoxy-4-methylphenol 6948-36-3 C10H12O2
2-Ethenyl-6-methoxy-4-methylphenol
—— 2-phenyl-4,5-dihydro-oxazole; picrate 7460-54-0 C6H3N3O7*C9H9NO
2-phenyl-4,5-dihydro-oxazole; picrate
—— 4-Hydroxy-3-methoxybenzaldehyde N-phenylthiosemicarbazone 20158-15-0 C15H15N3O2S
4-Hydroxy-3-methoxybenzaldehyde N-phenylthiosemicarbazone
—— 4-Chloro-2-(octadecyliminomethyl)phenol 6947-52-0 C25H42ClNO
4-Chloro-2-(octadecyliminomethyl)phenol
—— N,N-Diethyl-N'-<(4-hydroxy-phenoxy)-acetyl>-ethylendiamin 52662-27-8 C14H22N2O3
N,N-Diethyl-N'-<(4-hydroxy-phenoxy)-acetyl>-ethylendiamin
—— 1-Propan-2-ylpiperidine;2,4,6-trinitrophenol 7145-10-0 C14H20N4O7
1-Propan-2-ylpiperidine;2,4,6-trinitrophenol
—— 5-(4-hydroxy-benzylidene)-3-phenyl-2-thioxo-thiazolidin-4-one 13037-57-5 C16H11NO2S2
5-(4-hydroxy-benzylidene)-3-phenyl-2-thioxo-thiazolidin-4-one
—— 6-Allyl-2,4-dimethoxy-3-methylphenol 81457-16-1 C12H16O3
6-Allyl-2,4-dimethoxy-3-methylphenol
—— 4-(3,4-dihydroxy-5-methoxy-thiobenzoyl)-morpholine 70733-95-8 C12H15NO4S
4-(3,4-dihydroxy-5-methoxy-thiobenzoyl)-morpholine
—— 2,4,6-Trinitrophenol-4-{[(2-methylphenyl)sulfanyl]methyl}morpholine(1:1) 7355-40-0 C18H20N4O8S
2,4,6-Trinitrophenol-4-{[(2-methylphenyl)sulfanyl]methyl}morpholine(1:1)
—— 4-methyl-3-(butyl-4-ol-phenol) 117069-96-2 C11H16O2
4-methyl-3-(butyl-4-ol-phenol)
—— 2-hydroxyethaninium picrate 6627-48-1 C2H7NO*C6H3N3O7
2-hydroxyethaninium picrate
—— 3,6-di(1-propynyl)-1,2-benzenediol 1331730-58-5 C12H10O2
3,6-di(1-propynyl)-1,2-benzenediol
—— 2,4,6-Trinitrophenol-1,1'-cyclopenta-3,5-diene-1,3-diyldibenzene(1:1) 6942-64-9 C23H17N3O7
2,4,6-Trinitrophenol-1,1'-cyclopenta-3,5-diene-1,3-diyldibenzene(1:1)
—— (2,3-Dihydroxy-1,4-phenylene)bis(phosphonic acid) 91633-18-0 C6H8O8P2
(2,3-Dihydroxy-1,4-phenylene)bis(phosphonic acid)
—— 2,5-dihydroxyphenylthianium chloride 28374-64-3 C11H15O2S*Cl
2,5-dihydroxyphenylthianium chloride
—— 4-(4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine 90684-15-4 C11H13NO
4-(4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine
—— 1-[(2-Methylphenyl)sulfanylmethyl]piperidine;2,4,6-trinitrophenol 6631-91-0 C19H22N4O7S
1-[(2-Methylphenyl)sulfanylmethyl]piperidine;2,4,6-trinitrophenol
—— 1-(2,5-dihydroxyphenyl)thianium bromide 89706-15-0 Br*C11H15O2S
1-(2,5-dihydroxyphenyl)thianium bromide
—— 2-Methyl-4-propan-2-yloxybenzene-1,3-diol 1083312-72-4 C10H14O3
2-Methyl-4-propan-2-yloxybenzene-1,3-diol
—— (R/S)-3-((S)-1-(3-hydroxyphenyl)ethyl)-6-methyl-6-phenyl-1,3-oxazinan-2-one 1114064-73-1 C19H21NO3
(R/S)-3-((S)-1-(3-hydroxyphenyl)ethyl)-6-methyl-6-phenyl-1,3-oxazinan-2-one
—— (2,4-difluoro-3-hydroxy-benzyl)-carbamic acid tert-butyl ester 1401839-34-6 C12H15F2NO3
(2,4-difluoro-3-hydroxy-benzyl)-carbamic acid tert-butyl ester
—— 4-bromo-3,6-difluoro-2-nitrophenol 1394130-47-2 C6H2BrF2NO3
4-bromo-3,6-difluoro-2-nitrophenol
—— 2-chloro-3,4-dimethylphenol 10283-15-5 C8H9ClO
2-chloro-3,4-dimethylphenol
—— 4-Allyl-6-methoxy-2-(2,6-dimethyl-morpholinomethyl)-phenol 6972-89-0 C17H25NO3
4-Allyl-6-methoxy-2-(2,6-dimethyl-morpholinomethyl)-phenol
—— N,N'-((4-Hydroxy-3-methoxyphenyl)methylene)bis(2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxamide) 6950-42-1 C18H14N4O8
N,N'-((4-Hydroxy-3-methoxyphenyl)methylene)bis(2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxamide)
—— diethyl <2-(4-acetoxyphenoxy)ethyl>phosphonate 89210-98-0 C12H19O5P
diethyl <2-(4-acetoxyphenoxy)ethyl>phosphonate
—— 2-Methylnaphthalene; 2,4,6-trinitrophenol 5160-55-4 C17H13N3O7
2-Methylnaphthalene; 2,4,6-trinitrophenol
—— 2-(1H-benzimidazol-2-ylsulfanyl)-N-[2-(2-hydroxy-3-methoxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]acetamide 1226777-31-6 C19H18N4O4S2
2-(1H-benzimidazol-2-ylsulfanyl)-N-[2-(2-hydroxy-3-methoxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]acetamide
—— 6-{3-chloro-4-[3-(4-hydroxy-phenoxy)-propoxy]-phenyl}-4,5-dihydro-2H-pyridazin-3-one 705290-38-6 C19H19ClN2O4
6-{3-chloro-4-[3-(4-hydroxy-phenoxy)-propoxy]-phenyl}-4,5-dihydro-2H-pyridazin-3-one
—— [2-[[(2-Acetyloxy-3,5-dichlorophenyl)methyl-methylamino]methyl]-4,6-dimethylphenyl] acetate;2,4,6-trinitrophenol 6964-66-5 C27H26Cl2N4O11
[2-[[(2-Acetyloxy-3,5-dichlorophenyl)methyl-methylamino]methyl]-4,6-dimethylphenyl] acetate;2,4,6-trinitrophenol
—— Aziridinium-picrate —— C8H8N4O7
Aziridinium-picrate
—— (E)-3-Dimethylamino-1-(2-hydroxy-3,4-dimethoxy-phenyl)-propenone 73220-34-5 C13H17NO4
(E)-3-Dimethylamino-1-(2-hydroxy-3,4-dimethoxy-phenyl)-propenone
—— 4-Methoxy-2-tetradecyl-phenol 148665-98-9 C21H36O2
4-Methoxy-2-tetradecyl-phenol
—— 2-tetradecyl-hydroquinone 50677-17-3 C20H34O2
2-tetradecyl-hydroquinone