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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
—— (2S)-2-[(6-acetyl-1,3-benzodioxol-5-yl)-[2-(benzotriazol-1-yl)acetyl]amino]-2-(4-hydroxy-3-methoxyphenyl)-N-[[(2S)-oxolan-2-yl]methyl]acetamide —— C31H31N5O8
(2S)-2-[(6-acetyl-1,3-benzodioxol-5-yl)-[2-(benzotriazol-1-yl)acetyl]amino]-2-(4-hydroxy-3-methoxyphenyl)-N-[[(2S)-oxolan-2-yl]methyl]acetamide
—— (2S)-2-[[2-(benzotriazol-1-yl)acetyl]-[(4-methoxyphenyl)methyl]amino]-2-(4-hydroxy-3-methoxyphenyl)-N-[[(2R)-oxolan-2-yl]methyl]acetamide —— C30H33N5O6
(2S)-2-[[2-(benzotriazol-1-yl)acetyl]-[(4-methoxyphenyl)methyl]amino]-2-(4-hydroxy-3-methoxyphenyl)-N-[[(2R)-oxolan-2-yl]methyl]acetamide
—— (2S)-2-[[2-(benzotriazol-1-yl)acetyl]-[(4-methoxyphenyl)methyl]amino]-2-(4-hydroxy-3-methoxyphenyl)-N-[[(2S)-oxolan-2-yl]methyl]acetamide —— C30H33N5O6
(2S)-2-[[2-(benzotriazol-1-yl)acetyl]-[(4-methoxyphenyl)methyl]amino]-2-(4-hydroxy-3-methoxyphenyl)-N-[[(2S)-oxolan-2-yl]methyl]acetamide
—— (2Z)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-[1,3]thiazolo[3,2-a]benzimidazol-1-one —— C17H11BrN2O3S
(2Z)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-[1,3]thiazolo[3,2-a]benzimidazol-1-one
—— 2-[(2Z)-2-hydroxyiminopropyl]-3,5-dimethoxyphenol —— C11H15NO4
2-[(2Z)-2-hydroxyiminopropyl]-3,5-dimethoxyphenol
—— 2-[(2Z)-2-hydroxyiminopropyl]-5-methoxyphenol —— C10H13NO3
2-[(2Z)-2-hydroxyiminopropyl]-5-methoxyphenol
—— 2-[(2Z)-2-hydroxyiminopropyl]-4-methoxyphenol —— C10H13NO3
2-[(2Z)-2-hydroxyiminopropyl]-4-methoxyphenol
—— (2R)-N-cyclohexyl-2-(2-fluoro-N-[2-(5-thiophen-2-yltetrazol-2-yl)acetyl]anilino)-2-(4-hydroxy-3-methoxyphenyl)acetamide —— C28H29FN6O4S
(2R)-N-cyclohexyl-2-(2-fluoro-N-[2-(5-thiophen-2-yltetrazol-2-yl)acetyl]anilino)-2-(4-hydroxy-3-methoxyphenyl)acetamide
—— 4-[(2Z)-2-hydroxyiminopropyl]-2,6-dimethoxyphenol —— C11H15NO4
4-[(2Z)-2-hydroxyiminopropyl]-2,6-dimethoxyphenol
—— (2S)-N-cyclohexyl-2-(2-fluoro-N-[2-(5-thiophen-2-yltetrazol-2-yl)acetyl]anilino)-2-(4-hydroxy-3-methoxyphenyl)acetamide —— C28H29FN6O4S
(2S)-N-cyclohexyl-2-(2-fluoro-N-[2-(5-thiophen-2-yltetrazol-2-yl)acetyl]anilino)-2-(4-hydroxy-3-methoxyphenyl)acetamide
—— ethyl (5Z)-2-(4-chloroanilino)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-oxothiophene-3-carboxylate —— C21H18ClNO5S
ethyl (5Z)-2-(4-chloroanilino)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-oxothiophene-3-carboxylate
—— 2-[(5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2,4-dimethylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]propanedinitrile —— C22H16BrN3O3S
2-[(5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2,4-dimethylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]propanedinitrile
—— (2E,5E)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-2-[(3,4-dimethylphenyl)imino]-3-methyl-1,3-thiazolidin-4-one —— C20H19BrN2O3S
(2E,5E)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-2-[(3,4-dimethylphenyl)imino]-3-methyl-1,3-thiazolidin-4-one
—— (5Z)-5-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(2,3-dichlorophenyl)imino-1,3-thiazolidin-4-one —— C17H10Br2Cl2N2O3S
(5Z)-5-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(2,3-dichlorophenyl)imino-1,3-thiazolidin-4-one
—— (5E)-5-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(2,3-dichloroanilino)-1,3-thiazol-4-one —— C17H10Br2Cl2N2O3S
(5E)-5-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(2,3-dichloroanilino)-1,3-thiazol-4-one
—— (2E,5E)-3-ethyl-2-[(4-ethylphenyl)imino]-5-(2-hydroxy-3-methoxybenzylidene)-1,3-thiazolidin-4-one —— C21H22N2O3S
(2E,5E)-3-ethyl-2-[(4-ethylphenyl)imino]-5-(2-hydroxy-3-methoxybenzylidene)-1,3-thiazolidin-4-one
—— ethyl (5Z)-2-(4-chloroanilino)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-4-oxothiophene-3-carboxylate —— C21H18ClNO5S
ethyl (5Z)-2-(4-chloroanilino)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-4-oxothiophene-3-carboxylate
—— 2-methoxy-4-[(1S,2S,5R,6S,9R)-6,8,9-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol —— C18H24O3
2-methoxy-4-[(1S,2S,5R,6S,9R)-6,8,9-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol
—— (1R,6R)-N-[(Z)-(3-hydroxyphenyl)methylideneamino]bicyclo[4.1.0]heptane-7-carboxamide —— C15H18N2O2
(1R,6R)-N-[(Z)-(3-hydroxyphenyl)methylideneamino]bicyclo[4.1.0]heptane-7-carboxamide
—— ethyl (2E,5R)-2-[(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18BrClN2O4S
ethyl (2E,5R)-2-[(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N,N'-bis[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]decanediamide —— C26H34N4O6
N,N'-bis[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]decanediamide
—— ethyl (2Z,5S)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(4-ethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H25BrN2O6S
ethyl (2Z,5S)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(4-ethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[(4R)-3-methyl-5-oxo-1,4-dihydropyrazol-4-yl]propanamide —— C15H18N4O4
N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[(4R)-3-methyl-5-oxo-1,4-dihydropyrazol-4-yl]propanamide
—— N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C10H12N2O3
N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— 4-[(2S)-decan-2-yl]phenol —— C16H26O
4-[(2S)-decan-2-yl]phenol
—— N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[(4S)-3-methyl-5-oxo-1,4-dihydropyrazol-4-yl]propanamide —— C15H18N4O4
N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[(4S)-3-methyl-5-oxo-1,4-dihydropyrazol-4-yl]propanamide
—— ethyl (2Z,5R)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(4-ethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H25BrN2O6S
ethyl (2Z,5R)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(4-ethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-[(2Z)-2-hydroxyiminopropyl]-2,3-dimethoxyphenol —— C11H15NO4
5-[(2Z)-2-hydroxyiminopropyl]-2,3-dimethoxyphenol
—— 4-[(2Z)-2-hydroxyiminopropyl]-2-methoxyphenol —— C10H13NO3
4-[(2Z)-2-hydroxyiminopropyl]-2-methoxyphenol
—— 2,4,6-tris[(2S)-nonan-2-yl]phenol —— C33H60O
2,4,6-tris[(2S)-nonan-2-yl]phenol
—— 2,4-bis[(2R)-nonan-2-yl]-6-[(2S)-nonan-2-yl]phenol —— C33H60O
2,4-bis[(2R)-nonan-2-yl]-6-[(2S)-nonan-2-yl]phenol
—— 5-[(Z)-C-(1,3-benzothiazol-2-yl)carbonohydrazonoyl]-2-methoxyphenol —— C15H13N3O2S
5-[(Z)-C-(1,3-benzothiazol-2-yl)carbonohydrazonoyl]-2-methoxyphenol
—— 2-bromo-4-[(2Z)-2-hydroxyiminopropyl]-6-methoxyphenol —— C10H12BrNO3
2-bromo-4-[(2Z)-2-hydroxyiminopropyl]-6-methoxyphenol
—— 4-[(2R)-nonan-2-yl]-2,6-bis[(2S)-nonan-2-yl]phenol —— C33H60O
4-[(2R)-nonan-2-yl]-2,6-bis[(2S)-nonan-2-yl]phenol
—— N-(2-fluorophenyl)-2-[(5E)-5-(4-hydroxy-3-nitrobenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C18H12FN3O6S
N-(2-fluorophenyl)-2-[(5E)-5-(4-hydroxy-3-nitrobenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— (5E)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-3-(2-ethylphenyl)-2-(2-ethylphenyl)imino-1,3-thiazolidin-4-one —— C27H25ClN2O3S
(5E)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-3-(2-ethylphenyl)-2-(2-ethylphenyl)imino-1,3-thiazolidin-4-one
—— (Z,4E)-2,3-dichloro-4-[3-(4-hydroxyphenyl)propanoylhydrazinylidene]but-2-enoic acid —— C13H12Cl2N2O4
(Z,4E)-2,3-dichloro-4-[3-(4-hydroxyphenyl)propanoylhydrazinylidene]but-2-enoic acid
—— (2E)-3-[(2-hydroxy-4-methylphenyl)amino]-1-(4-methoxyphenyl)prop-2-en-1-one —— C17H17NO3
(2E)-3-[(2-hydroxy-4-methylphenyl)amino]-1-(4-methoxyphenyl)prop-2-en-1-one
—— (2R)-2-[N-[2-(benzotriazol-1-yl)acetyl]-3-(trifluoromethyl)anilino]-N-cyclohexyl-2-(3-hydroxy-4-methoxyphenyl)acetamide —— C30H30F3N5O4
(2R)-2-[N-[2-(benzotriazol-1-yl)acetyl]-3-(trifluoromethyl)anilino]-N-cyclohexyl-2-(3-hydroxy-4-methoxyphenyl)acetamide
—— (Z,4Z)-2,3-dichloro-4-[3-(4-hydroxyphenyl)propanoylhydrazinylidene]but-2-enoic acid —— C13H12Cl2N2O4
(Z,4Z)-2,3-dichloro-4-[3-(4-hydroxyphenyl)propanoylhydrazinylidene]but-2-enoic acid
—— (2R)-2-(N-[2-(benzotriazol-1-yl)acetyl]-4-chloroanilino)-N-cyclohexyl-2-(3-hydroxy-4-methoxyphenyl)acetamide —— C29H30ClN5O4
(2R)-2-(N-[2-(benzotriazol-1-yl)acetyl]-4-chloroanilino)-N-cyclohexyl-2-(3-hydroxy-4-methoxyphenyl)acetamide
—— (2Z)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-N-phenyl-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide —— C25H18N4O5S2
(2Z)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-N-phenyl-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
—— 3,4,5-trihydroxy-N'-[1-(4-oxocyclohexa-2,5-dien-1-ylidene)propyl]benzohydrazide —— C16H16N2O5
3,4,5-trihydroxy-N'-[1-(4-oxocyclohexa-2,5-dien-1-ylidene)propyl]benzohydrazide
—— 2,3,5-trichloro-6-[(2E)-2-[5-(2,4,5-trichloro-3,6-dihydroxyphenyl)-3H-1,3-thiazol-2-ylidene]-3H-1,3-thiazol-5-yl]cyclohexa-2,5-diene-1,4-dione —— C18H6Cl6N2O4S2
2,3,5-trichloro-6-[(2E)-2-[5-(2,4,5-trichloro-3,6-dihydroxyphenyl)-3H-1,3-thiazol-2-ylidene]-3H-1,3-thiazol-5-yl]cyclohexa-2,5-diene-1,4-dione
—— ethyl (2Z)-2-(2-hydroxy-5-nitrobenzylidene)-7-methyl-3-oxo-5-(thiophen-2-yl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H17N3O6S2
ethyl (2Z)-2-(2-hydroxy-5-nitrobenzylidene)-7-methyl-3-oxo-5-(thiophen-2-yl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-2-[(2-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-methylphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26N2O6S
ethyl (2Z)-2-[(2-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-methylphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (4Z)-1-(3-chloro-4-methylphenyl)-4-[(3,4-dihydroxyphenyl)methylidene]pyrazolidine-3,5-dione —— C17H13ClN2O4
(4Z)-1-(3-chloro-4-methylphenyl)-4-[(3,4-dihydroxyphenyl)methylidene]pyrazolidine-3,5-dione
—— 2-[(Z)-(2-chloro-3-hydroxy-4-methoxyphenyl)methylideneamino]-1-hydroxyguanidine —— C9H11ClN4O3
2-[(Z)-(2-chloro-3-hydroxy-4-methoxyphenyl)methylideneamino]-1-hydroxyguanidine
—— (2E,5E)-5-(2,3-dibromo-4-hydroxy-5-methoxybenzylidene)-2-[(4-ethylphenyl)imino]-1,3-thiazolidin-4-one —— C19H16Br2N2O3S
(2E,5E)-5-(2,3-dibromo-4-hydroxy-5-methoxybenzylidene)-2-[(4-ethylphenyl)imino]-1,3-thiazolidin-4-one
—— methyl (4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-(2-phenylethyl)pyrrole-3-carboxylate —— C23H23NO5
methyl (4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-(2-phenylethyl)pyrrole-3-carboxylate