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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 5-(3-ethoxy-4-prop-2-enoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H30N2O7S
ethyl 5-(3-ethoxy-4-prop-2-enoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl 2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-(3-ethoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H29BrN2O7S
ethyl 2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-(3-ethoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 1-[3-(2-Hydroxyphenyl)propanoylamino]-3-phenylthiourea —— C16H17N3O2S
1-[3-(2-Hydroxyphenyl)propanoylamino]-3-phenylthiourea
—— ethyl 2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-5-(4-methylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H24N2O5S
ethyl 2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-5-(4-methylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 4-bromo-2-methoxy-6-[[4-[(Z)-3-phenylprop-2-enyl]piperazin-1-yl]methyl]phenol —— C21H25BrN2O2
4-bromo-2-methoxy-6-[[4-[(Z)-3-phenylprop-2-enyl]piperazin-1-yl]methyl]phenol
—— 2-(benzotriazol-1-yl)-N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]propanamide —— C17H17N5O3
2-(benzotriazol-1-yl)-N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]propanamide
—— (2R)-2-[(4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanyl-2-phenylacetic acid —— C25H20N2O5S
(2R)-2-[(4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanyl-2-phenylacetic acid
—— (2S)-2-[(4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanylbutanoic acid —— C21H20N2O5S
(2S)-2-[(4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanylbutanoic acid
—— (2S)-2-[(4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanyl-2-phenylacetic acid —— C25H20N2O5S
(2S)-2-[(4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanyl-2-phenylacetic acid
—— (2S)-2-[(4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanyl-2-phenylacetic acid —— C25H20N2O5S
(2S)-2-[(4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanyl-2-phenylacetic acid
—— 5-[(3,5-Dibromo-2-hydroxyphenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione —— C16H9Br2NO3S
5-[(3,5-Dibromo-2-hydroxyphenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione
—— (2S)-2-[(4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanylpropanoic acid —— C20H18N2O5S
(2S)-2-[(4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanylpropanoic acid
—— (2R)-2-[(4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanylpropanoic acid —— C20H18N2O5S
(2R)-2-[(4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanylpropanoic acid
—— (2S)-2-[(4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanylpropanoic acid —— C20H18N2O5S
(2S)-2-[(4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanylpropanoic acid
—— (2S)-2-[(4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanylbutanoic acid —— C21H20N2O5S
(2S)-2-[(4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanylbutanoic acid
—— (2R)-2-[(4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanylbutanoic acid —— C21H20N2O5S
(2R)-2-[(4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanylbutanoic acid
—— (2R)-2-[(4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanylbutanoic acid —— C21H20N2O5S
(2R)-2-[(4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanylbutanoic acid
—— 6-[(S)-[4-[(S)-(6-hydroxy-1,3-benzodioxol-5-yl)-(3-hydroxy-4-methoxyphenyl)methyl]piperazin-1-yl]-(3-hydroxy-4-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol —— C34H34N2O10
6-[(S)-[4-[(S)-(6-hydroxy-1,3-benzodioxol-5-yl)-(3-hydroxy-4-methoxyphenyl)methyl]piperazin-1-yl]-(3-hydroxy-4-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol
—— 6-[(R)-[4-[(R)-(6-hydroxy-1,3-benzodioxol-5-yl)-(2-hydroxy-3-methoxyphenyl)methyl]piperazin-1-yl]-(2-hydroxy-3-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol —— C34H34N2O10
6-[(R)-[4-[(R)-(6-hydroxy-1,3-benzodioxol-5-yl)-(2-hydroxy-3-methoxyphenyl)methyl]piperazin-1-yl]-(2-hydroxy-3-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol
—— 6-[(S)-[4-[(S)-(6-hydroxy-1,3-benzodioxol-5-yl)-(4-hydroxy-3-methoxyphenyl)methyl]piperazin-1-yl]-(4-hydroxy-3-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol —— C34H34N2O10
6-[(S)-[4-[(S)-(6-hydroxy-1,3-benzodioxol-5-yl)-(4-hydroxy-3-methoxyphenyl)methyl]piperazin-1-yl]-(4-hydroxy-3-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol
—— 6-[(S)-[4-[(R)-(6-hydroxy-1,3-benzodioxol-5-yl)-(4-hydroxy-3-methoxyphenyl)methyl]piperazin-1-yl]-(4-hydroxy-3-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol —— C34H34N2O10
6-[(S)-[4-[(R)-(6-hydroxy-1,3-benzodioxol-5-yl)-(4-hydroxy-3-methoxyphenyl)methyl]piperazin-1-yl]-(4-hydroxy-3-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol
—— 6-Amino-4-(3,5-dibromo-4-hydroxyphenyl)-3-ethyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile —— C15H12Br2N4O2
6-Amino-4-(3,5-dibromo-4-hydroxyphenyl)-3-ethyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
—— 6-[(R)-[4-[(R)-(6-hydroxy-1,3-benzodioxol-5-yl)-(3-hydroxy-4-methoxyphenyl)methyl]piperazin-1-yl]-(3-hydroxy-4-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol —— C34H34N2O10
6-[(R)-[4-[(R)-(6-hydroxy-1,3-benzodioxol-5-yl)-(3-hydroxy-4-methoxyphenyl)methyl]piperazin-1-yl]-(3-hydroxy-4-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol
—— Methyl 3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-(3-methylpiperazine-1,4-diium-1-yl)propanoate —— C17H25F3N2O5+2
Methyl 3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-(3-methylpiperazine-1,4-diium-1-yl)propanoate
—— 7-ethenyl-8-(4-hydroxy-2-methoxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C22H24O4
7-ethenyl-8-(4-hydroxy-2-methoxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(4-ethylanilino)-1,3-thiazolidin-4-one —— C19H19BrN2O3S
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(4-ethylanilino)-1,3-thiazolidin-4-one
—— 2-(4-Hydroxy-3-methoxyphenyl)-3-(2-piperidin-1-ium-1-ylethyl)-1,3-thiazolidin-4-one —— C17H25N2O3S+
2-(4-Hydroxy-3-methoxyphenyl)-3-(2-piperidin-1-ium-1-ylethyl)-1,3-thiazolidin-4-one
—— 11-(4-Chlorophenyl)-14-[(4-hydroxy-3,5-dinitrophenyl)methylidene]-15-thia-12,17-diazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,16-pentaen-13-one —— C27H17ClN4O6S
11-(4-Chlorophenyl)-14-[(4-hydroxy-3,5-dinitrophenyl)methylidene]-15-thia-12,17-diazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,16-pentaen-13-one
—— Propionic acid, 2-amino-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-, methyl ester —— C12H14F3NO5
Propionic acid, 2-amino-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-, methyl ester
—— [1,1,1-Trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-methoxy-3-oxopropan-2-yl]azanium —— C12H15F3NO5+
[1,1,1-Trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-methoxy-3-oxopropan-2-yl]azanium
—— 4-Bromo-2-[6-(4-bromophenyl)-2-(4-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol —— C22H17Br2FN2O
4-Bromo-2-[6-(4-bromophenyl)-2-(4-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol
—— 4-Bromo-2-[6-(4-bromophenyl)-2-(4-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol —— C22H18Br2FN2O+
4-Bromo-2-[6-(4-bromophenyl)-2-(4-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol
—— 5-[(3-Hydroxy-4-methoxyphenyl)methylidene]-3-(3-methoxypropyl)-1,3-thiazolidine-2,4-dione —— C15H17NO5S
5-[(3-Hydroxy-4-methoxyphenyl)methylidene]-3-(3-methoxypropyl)-1,3-thiazolidine-2,4-dione
—— 6-Amino-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(2-thienyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile —— C18H13BrN4O3S
6-Amino-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(2-thienyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
—— 5-[(5-Bromo-2-hydroxy-3-methoxyphenyl)methylidene]-2-phenyl-1,3-thiazol-4-one —— C17H12BrNO3S
5-[(5-Bromo-2-hydroxy-3-methoxyphenyl)methylidene]-2-phenyl-1,3-thiazol-4-one
—— 4-Bromo-2-[2-(4-fluorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol —— C23H21BrFN2O+
4-Bromo-2-[2-(4-fluorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol
—— 4-Bromo-2-[6-(4-methylphenyl)-2-propan-2-yl-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol —— C20H24BrN2O+
4-Bromo-2-[6-(4-methylphenyl)-2-propan-2-yl-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol
—— 4-Bromo-2-[2-(2-chlorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol —— C23H21BrClN2O+
4-Bromo-2-[2-(2-chlorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol
—— 4-Bromo-2-[2-(4-bromophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol —— C23H20Br2N2O
4-Bromo-2-[2-(4-bromophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol
—— 4-Chloro-2-[2-(4-fluorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol —— C23H21ClFN2O+
4-Chloro-2-[2-(4-fluorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol
—— 4-Chloro-2-[2-(4-fluorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol —— C23H20ClFN2O
4-Chloro-2-[2-(4-fluorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol
—— 2-[2-(4-Bromophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-4-chlorophenol —— C23H20BrClN2O
2-[2-(4-Bromophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-4-chlorophenol
—— 4-Bromo-2-[6-(4-methylphenyl)-2-propan-2-yl-1,2,3,4-tetrahydropyrimidin-4-yl]phenol —— C20H23BrN2O
4-Bromo-2-[6-(4-methylphenyl)-2-propan-2-yl-1,2,3,4-tetrahydropyrimidin-4-yl]phenol
—— 2-[2-(4-Bromophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-4-chlorophenol —— C23H21BrClN2O+
2-[2-(4-Bromophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-4-chlorophenol
—— 4-Bromo-2-[2-(4-fluorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol —— C23H20BrFN2O
4-Bromo-2-[2-(4-fluorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(3-bromophenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H11Br2NO3S2
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(3-bromophenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 4-Bromo-2-[2-(2-chlorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol —— C23H20BrClN2O
4-Bromo-2-[2-(2-chlorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol
—— 5-[(5-Bromo-2-hydroxy-3-nitrophenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione —— C16H9BrN2O5S
5-[(5-Bromo-2-hydroxy-3-nitrophenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione
—— [4-(4-Hydroxyphenyl)but-1-en-2-ylamino]urea —— C11H15N3O2
[4-(4-Hydroxyphenyl)but-1-en-2-ylamino]urea
—— N-[(3,5-dibromo-2-hydroxyphenyl)methylideneamino]-2-(3,5-dimethyl-1H-pyrazol-4-yl)acetamide —— C14H14Br2N4O2
N-[(3,5-dibromo-2-hydroxyphenyl)methylideneamino]-2-(3,5-dimethyl-1H-pyrazol-4-yl)acetamide