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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-(3,4-dimethoxyphenyl)-N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide —— C17H17N3O6
2-(3,4-dimethoxyphenyl)-N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide
—— methyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate —— C20H19N3O4
methyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate
—— 2,6-Dimethoxy-4-[[4-[(2-nitrophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol —— C20H27N3O5+2
2,6-Dimethoxy-4-[[4-[(2-nitrophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol
—— (2Z,5E)-2-[(4-fluorophenyl)imino]-5-(3-hydroxy-4-methoxybenzylidene)-1,3-thiazolidin-4-one —— C17H13FN2O3S
(2Z,5E)-2-[(4-fluorophenyl)imino]-5-(3-hydroxy-4-methoxybenzylidene)-1,3-thiazolidin-4-one
—— (7R)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-N-(2-methylphenyl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C21H21N5O3
(7R)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-N-(2-methylphenyl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— 2-Methoxy-6-[(4-methyl-1,4-diazepane-1,4-diium-1-yl)methyl]phenol —— C14H24N2O2+2
2-Methoxy-6-[(4-methyl-1,4-diazepane-1,4-diium-1-yl)methyl]phenol
—— 6-[5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-2-phenyl-1H-1,2,4-triazol-3-ylidene]cyclohexa-2,4-dien-1-one —— C23H19N3O3
6-[5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-2-phenyl-1H-1,2,4-triazol-3-ylidene]cyclohexa-2,4-dien-1-one
—— (5E)-1-(2-fluorophenyl)-5-(4-hydroxy-3-nitrobenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione —— C17H10FN3O5S
(5E)-1-(2-fluorophenyl)-5-(4-hydroxy-3-nitrobenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
—— (2E,6S)-2-[(2-hydroxy-4-methylanilino)methylidene]-6-methylcyclohexan-1-one —— C15H19NO2
(2E,6S)-2-[(2-hydroxy-4-methylanilino)methylidene]-6-methylcyclohexan-1-one
—— 3-{[(2E,5Z)-5-(4-hydroxy-3-nitrobenzylidene)-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]amino}benzoic acid —— C18H13N3O6S
3-{[(2E,5Z)-5-(4-hydroxy-3-nitrobenzylidene)-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]amino}benzoic acid
—— (4S,7S)-7-(3-hydroxyphenyl)-6-imino-3-methyl-4-phenyl-5,7-dihydro-4H-1,2-benzoxazole-5-carbonitrile —— C21H17N3O2
(4S,7S)-7-(3-hydroxyphenyl)-6-imino-3-methyl-4-phenyl-5,7-dihydro-4H-1,2-benzoxazole-5-carbonitrile
—— methyl (5Z)-5-[(4-hydroxyphenyl)methylidene]-2-methyl-4-oxo-3H-pyrrole-3-carboxylate —— C14H13NO4
methyl (5Z)-5-[(4-hydroxyphenyl)methylidene]-2-methyl-4-oxo-3H-pyrrole-3-carboxylate
—— 2-Methoxy-6-[[[1-methyl-2-(piperidin-1-ium-1-ylmethyl)benzimidazol-5-yl]amino]methyl]phenol —— C22H29N4O2+
2-Methoxy-6-[[[1-methyl-2-(piperidin-1-ium-1-ylmethyl)benzimidazol-5-yl]amino]methyl]phenol
—— methyl (2S)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-(2-methoxyanilino)propanoate —— C19H20F3NO6
methyl (2S)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-(2-methoxyanilino)propanoate
—— methyl (2R)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-(2-methoxyanilino)propanoate —— C19H20F3NO6
methyl (2R)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-(2-methoxyanilino)propanoate
—— (3R)-3-(4-hydroxy-3-methoxyphenyl)-4,4-dimethyl-2-oxaspiro[5.5]undecane-1,5-dione —— C19H24O5
(3R)-3-(4-hydroxy-3-methoxyphenyl)-4,4-dimethyl-2-oxaspiro[5.5]undecane-1,5-dione
—— (5Z)-2-(4-ethylpiperazin-1-yl)-5-(4-hydroxy-3-methoxybenzylidene)-1,3-thiazol-4(5H)-one —— C17H21N3O3S
(5Z)-2-(4-ethylpiperazin-1-yl)-5-(4-hydroxy-3-methoxybenzylidene)-1,3-thiazol-4(5H)-one
—— (5E)-5-(2-hydroxy-5-nitrobenzylidene)-1-(prop-2-en-1-yl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione —— C14H11N3O5S
(5E)-5-(2-hydroxy-5-nitrobenzylidene)-1-(prop-2-en-1-yl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
—— N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]-1,3-benzodioxole-5-carboxamide —— C15H11N3O6
N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]-1,3-benzodioxole-5-carboxamide
—— (2S)-3-(4-hydroxy-3-methoxyphenyl)-N-(3-methoxyphenyl)-2-(2H-tetrazol-5-yl)propanamide —— C18H19N5O4
(2S)-3-(4-hydroxy-3-methoxyphenyl)-N-(3-methoxyphenyl)-2-(2H-tetrazol-5-yl)propanamide
—— methyl (2R)-3,3,3-trifluoro-2-hydroxy-2-(4-hydroxy-2,3-dimethylphenyl)propanoate —— C12H13F3O4
methyl (2R)-3,3,3-trifluoro-2-hydroxy-2-(4-hydroxy-2,3-dimethylphenyl)propanoate
—— 2-[(3S)-3-methylthian-1-ium-1-yl]benzene-1,4-diol —— C12H17O2S+
2-[(3S)-3-methylthian-1-ium-1-yl]benzene-1,4-diol
—— (2S,7R)-2-(3-hydroxy-4-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C18H20N2O3S
(2S,7R)-2-(3-hydroxy-4-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (5S)-11-ethyl-5-(2-hydroxy-3-methoxyphenyl)-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C18H21N3O3S
(5S)-11-ethyl-5-(2-hydroxy-3-methoxyphenyl)-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5R)-11-ethyl-5-(3-hydroxy-4-methoxyphenyl)-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C18H21N3O3S
(5R)-11-ethyl-5-(3-hydroxy-4-methoxyphenyl)-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5R)-5-(3-hydroxy-4-methoxyphenyl)-11-propan-2-yl-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C19H24N3O3S+
(5R)-5-(3-hydroxy-4-methoxyphenyl)-11-propan-2-yl-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5S)-5-(5-chloro-2-hydroxy-3-methoxyphenyl)-11-propan-2-yl-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C19H22ClN3O3S
(5S)-5-(5-chloro-2-hydroxy-3-methoxyphenyl)-11-propan-2-yl-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (2S,7S)-2-(2-hydroxy-3-methoxyphenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C22H28N2O3S
(2S,7S)-2-(2-hydroxy-3-methoxyphenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (3S,4S)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3-pyridin-1-ium-1-yl-3,4-dihydro-1H-pyridine-5-carbonitrile —— C18H16N3O4+
(3S,4S)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3-pyridin-1-ium-1-yl-3,4-dihydro-1H-pyridine-5-carbonitrile
—— N'-[(E)-(5-Hydroxy-2-nitrophenyl)methylidene]-2-[(2-methylphenyl)amino]acetohydrazide —— C16H16N4O4
N'-[(E)-(5-Hydroxy-2-nitrophenyl)methylidene]-2-[(2-methylphenyl)amino]acetohydrazide
—— N'-[(E)-(6-bromo-1,3-benzodioxol-5-yl)methylidene]-2-hydroxy-5-nitrobenzohydrazide —— C15H10BrN3O6
N'-[(E)-(6-bromo-1,3-benzodioxol-5-yl)methylidene]-2-hydroxy-5-nitrobenzohydrazide
—— (4S)-1-(4-fluorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C21H18FNO6
(4S)-1-(4-fluorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4R)-1-(3-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C20H16FNO5
(4R)-1-(3-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4R)-1-(3-chlorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C21H18ClNO6
(4R)-1-(3-chlorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— 5-[(3S)-3-(2-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-5-oxopentanoate —— C18H17N2O4S-
5-[(3S)-3-(2-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-5-oxopentanoate
—— furan-2-yl-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]methanone —— C19H16N2O4S
furan-2-yl-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]methanone
—— methyl (4S)-4-(4-hydroxyphenyl)-2-methyl-5,5-dioxo-3,4-dihydro-[1]benzothiolo[3,2-b]pyridine-3-carboxylate —— C20H17NO5S
methyl (4S)-4-(4-hydroxyphenyl)-2-methyl-5,5-dioxo-3,4-dihydro-[1]benzothiolo[3,2-b]pyridine-3-carboxylate
—— 2-(4-Methoxyphenyl)ethyl 3-methyl-1-benzofuran-2-carboxylate —— C19H18O4
2-(4-Methoxyphenyl)ethyl 3-methyl-1-benzofuran-2-carboxylate
—— 2-ethylsulfanylethyl (4S)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C17H21ClN2O5S
2-ethylsulfanylethyl (4S)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-phenoxyethyl (4S)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C20H19N3O7
2-phenoxyethyl (4S)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-O-ethyl 4-O-[2-(4-methoxyphenyl)ethyl] 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylate —— C19H23NO5
2-O-ethyl 4-O-[2-(4-methoxyphenyl)ethyl] 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylate
—— 2-[(3R)-2-methylsulfonyl-5-thiophen-2-yl-3,4-dihydropyrazol-3-yl]phenol —— C14H14N2O3S2
2-[(3R)-2-methylsulfonyl-5-thiophen-2-yl-3,4-dihydropyrazol-3-yl]phenol
—— 1-[(3R)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]propan-1-one —— C18H18N2O2
1-[(3R)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]propan-1-one
—— 2-[(5R)-3-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-5-yl]-6-methoxyphenol —— C16H15ClN2O2
2-[(5R)-3-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-5-yl]-6-methoxyphenol
—— 4-bromo-2-[(5S)-3-(furan-3-yl)-4,5-dihydro-1H-pyrazol-5-yl]phenol —— C13H11BrN2O2
4-bromo-2-[(5S)-3-(furan-3-yl)-4,5-dihydro-1H-pyrazol-5-yl]phenol
—— 4-bromo-2-[(5R)-3-(furan-3-yl)-4,5-dihydro-1H-pyrazol-5-yl]phenol —— C13H11BrN2O2
4-bromo-2-[(5R)-3-(furan-3-yl)-4,5-dihydro-1H-pyrazol-5-yl]phenol
—— 2-[(5S)-2-(benzylidenehydrazinylidene)-3-(4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-5-yl]acetate —— C18H14N3O4S-
2-[(5S)-2-(benzylidenehydrazinylidene)-3-(4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-5-yl]acetate
—— Dimethyl-[[11,17,23-tris[(dimethylazaniumyl)methyl]-25,26,27,28-tetrahydroxy-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]methyl]azanium —— C40H56N4O4+4
Dimethyl-[[11,17,23-tris[(dimethylazaniumyl)methyl]-25,26,27,28-tetrahydroxy-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]methyl]azanium
—— 2,6-dimethoxy-4-[[[(1R)-1-phenylethyl]amino]methyl]phenol —— C17H21NO3
2,6-dimethoxy-4-[[[(1R)-1-phenylethyl]amino]methyl]phenol
—— 1-[(3S)-3-(4-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone —— C15H14N2O2S
1-[(3S)-3-(4-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone