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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
—— ethyl 2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(2-propan-2-yloxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H28N2O6S
ethyl 2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(2-propan-2-yloxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (4S)-4-(4-hydroxy-3-methoxyphenyl)-1-(4-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C21H21N3O4S
(4S)-4-(4-hydroxy-3-methoxyphenyl)-1-(4-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— 10-(4-Hydroxy-3,5-dimethylphenyl)-4,13-dimethyl-2,4,6,11,13,15-hexazatetracyclo[7.7.0.02,6.011,15]hexadec-8-ene-3,5,12,14-tetrone —— C20H22N6O5
10-(4-Hydroxy-3,5-dimethylphenyl)-4,13-dimethyl-2,4,6,11,13,15-hexazatetracyclo[7.7.0.02,6.011,15]hexadec-8-ene-3,5,12,14-tetrone
—— (4S)-1-(4-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C20H18FN3O3S
(4S)-1-(4-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4R)-4-(4-hydroxy-3-methoxyphenyl)-1-(4-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C21H21N3O4S
(4R)-4-(4-hydroxy-3-methoxyphenyl)-1-(4-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4R)-1-(4-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C20H18ClN3O3S
(4R)-1-(4-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— 3-[[[4-[(3-Hydroxyphenyl)methylideneamino]-1,2,4-triazol-3-yl]hydrazinylidene]methyl]phenol —— C16H14N6O2
3-[[[4-[(3-Hydroxyphenyl)methylideneamino]-1,2,4-triazol-3-yl]hydrazinylidene]methyl]phenol
—— (4R)-1-(2-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C20H18ClN3O3S
(4R)-1-(2-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4S)-1-(4-ethylphenyl)-4-(3-hydroxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C21H21N3O2S
(4S)-1-(4-ethylphenyl)-4-(3-hydroxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4S)-1-(4-ethylphenyl)-4-(4-hydroxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C21H21N3O2S
(4S)-1-(4-ethylphenyl)-4-(4-hydroxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4R)-1-(4-ethylphenyl)-4-(4-hydroxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C21H21N3O2S
(4R)-1-(4-ethylphenyl)-4-(4-hydroxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4R)-1-(3-chloro-4-methylphenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C21H20ClN3O3S
(4R)-1-(3-chloro-4-methylphenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4R)-1-(4-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C20H18FN3O3S
(4R)-1-(4-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4R)-1-(4,6-dimethylpyrimidin-2-yl)-4-(4-hydroxy-2-methoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C20H21N5O3
(4R)-1-(4,6-dimethylpyrimidin-2-yl)-4-(4-hydroxy-2-methoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4S)-1-(4,6-dimethylpyrimidin-2-yl)-4-(4-hydroxy-2-methoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C20H21N5O3
(4S)-1-(4,6-dimethylpyrimidin-2-yl)-4-(4-hydroxy-2-methoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4S)-1-(4,6-dimethylpyrimidin-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C20H21N5O3
(4S)-1-(4,6-dimethylpyrimidin-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— 3-[Bis(dimethylamino)-pyridin-4-yl-lambda5-phosphanylidene]-1-(4-hydroxyphenyl)-1-methylthiourea —— C17H24N5OPS
3-[Bis(dimethylamino)-pyridin-4-yl-lambda5-phosphanylidene]-1-(4-hydroxyphenyl)-1-methylthiourea
—— 3-(4-Ethylphenyl)-2-(4-ethylphenyl)imino-5-[(2-hydroxy-5-nitrophenyl)methylidene]-1,3-thiazolidin-4-one —— C26H23N3O4S
3-(4-Ethylphenyl)-2-(4-ethylphenyl)imino-5-[(2-hydroxy-5-nitrophenyl)methylidene]-1,3-thiazolidin-4-one
—— 7-ethenyl-8-(2-hydroxy-4,6-dimethoxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C22H24O5
7-ethenyl-8-(2-hydroxy-4,6-dimethoxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 7-ethenyl-8-(4-hydroxy-3-iodo-5-methoxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H21IO4
7-ethenyl-8-(4-hydroxy-3-iodo-5-methoxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4R)-1-(1,3-benzothiazol-2-yl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C22H20N4O4S
(4R)-1-(1,3-benzothiazol-2-yl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— 5-[(4-Hydroxyphenyl)methylidene]-2-phenyl-1,3-dioxane-4,6-dione —— C17H12O5
5-[(4-Hydroxyphenyl)methylidene]-2-phenyl-1,3-dioxane-4,6-dione
—— 4-Bromo-2-[[[4-(2-bromo-4-methylanilino)-6-morpholin-4-yl-1,3,5-triazin-2-yl]hydrazinylidene]methyl]-6-nitrophenol —— C21H20Br2N8O4
4-Bromo-2-[[[4-(2-bromo-4-methylanilino)-6-morpholin-4-yl-1,3,5-triazin-2-yl]hydrazinylidene]methyl]-6-nitrophenol
—— 3-(2-Hydroxy-5-methylanilino)-5-(4-methoxyphenyl)cyclohex-3-en-1-one —— C20H21NO3
3-(2-Hydroxy-5-methylanilino)-5-(4-methoxyphenyl)cyclohex-3-en-1-one
—— 8-(3-bromo-4-hydroxy-5-methoxyphenyl)-7-ethenyl-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H21BrO4
8-(3-bromo-4-hydroxy-5-methoxyphenyl)-7-ethenyl-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 4-(1H-benzimidazol-2-ylsulfanyl)-2,6-dinitrophenol —— C13H8N4O5S
4-(1H-benzimidazol-2-ylsulfanyl)-2,6-dinitrophenol
—— 2-Methylpropyl 4-(4-hydroxy-3-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate —— C17H22N2O5
2-Methylpropyl 4-(4-hydroxy-3-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate
—— Butan-2-yl 4-(4-hydroxy-3-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate —— C17H22N2O5
Butan-2-yl 4-(4-hydroxy-3-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate
—— Cyclohexyl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate —— C19H23BrN2O5
Cyclohexyl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate
—— 2-Allyl-5-hydroxy-4-methoxybenzaldehyde —— C11H12O3
2-Allyl-5-hydroxy-4-methoxybenzaldehyde
—— 5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-[(4-methoxy-N-methylanilino)methyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C20H20N2O4S2
5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-[(4-methoxy-N-methylanilino)methyl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— N-[[5-(4-bromophenyl)furan-2-yl]methylideneamino]-3-(2-hydroxy-4-methoxyphenyl)butanamide —— C22H21BrN2O4
N-[[5-(4-bromophenyl)furan-2-yl]methylideneamino]-3-(2-hydroxy-4-methoxyphenyl)butanamide
—— 7-ethenyl-8-(2-hydroxy-3-methoxyphenyl)-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H22O4
7-ethenyl-8-(2-hydroxy-3-methoxyphenyl)-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 5-[(2-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(2-chloro-6-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione —— C18H12BrClFNO4S
5-[(2-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(2-chloro-6-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione
—— 7-ethenyl-8-(4-hydroxy-3,5-dimethoxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C23H26O5
7-ethenyl-8-(4-hydroxy-3,5-dimethoxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 5-[(3-Hydroxy-4-methoxyphenyl)methylidene]-3-(3-phenylpropyl)-1,3-thiazolidine-2,4-dione —— C20H19NO4S
5-[(3-Hydroxy-4-methoxyphenyl)methylidene]-3-(3-phenylpropyl)-1,3-thiazolidine-2,4-dione
—— 4-(4-Hydroxy-3-methoxyphenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarbonitrile —— C16H15N3O2
4-(4-Hydroxy-3-methoxyphenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarbonitrile
—— 5-[(2-Hydroxy-5-nitrophenyl)methylidene]-2-morpholin-4-yl-1,3-thiazol-4-one —— C14H13N3O5S
5-[(2-Hydroxy-5-nitrophenyl)methylidene]-2-morpholin-4-yl-1,3-thiazol-4-one
—— 5-(1H-benzimidazol-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-6-phenyl-3,4-dihydro-1H-pyrimidin-2-one —— C24H20N4O3
5-(1H-benzimidazol-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-6-phenyl-3,4-dihydro-1H-pyrimidin-2-one
—— 3-(2-Hydroxyphenyl)-5-[(3-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H11NO3S2
3-(2-Hydroxyphenyl)-5-[(3-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 7-ethenyl-8-(3-hydroxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H22O3
7-ethenyl-8-(3-hydroxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-N-(2-methylphenyl)-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide —— C27H23N3O4S2
2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-N-(2-methylphenyl)-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
—— 1-[(2R)-2-(2-hydroxy-5-nitrophenyl)-5-(2-nitrophenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C16H12N4O7
1-[(2R)-2-(2-hydroxy-5-nitrophenyl)-5-(2-nitrophenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— N-[(3-hydroxyphenyl)methylideneamino]heptanamide —— C14H20N2O2
N-[(3-hydroxyphenyl)methylideneamino]heptanamide
—— 1-[(2S)-2-(2-hydroxy-5-nitrophenyl)-5-(2-nitrophenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C16H12N4O7
1-[(2S)-2-(2-hydroxy-5-nitrophenyl)-5-(2-nitrophenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(2-chloro-4-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione —— C18H12BrClFNO4S
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(2-chloro-4-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione
—— 3-[(4-Bromophenyl)methyl]-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C19H16BrNO5S
3-[(4-Bromophenyl)methyl]-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— ethyl 2-[(4-hydroxy-3-iodo-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-propan-2-yloxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H27IN2O6S
ethyl 2-[(4-hydroxy-3-iodo-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-propan-2-yloxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-Cyclohexyl-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H15Br2NO2S2
3-Cyclohexyl-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 4-[(2-Bromo-5-hydroxyphenyl)methylidene]-1-(3-chloro-4-methylphenyl)pyrazolidine-3,5-dione —— C17H12BrClN2O3
4-[(2-Bromo-5-hydroxyphenyl)methylidene]-1-(3-chloro-4-methylphenyl)pyrazolidine-3,5-dione