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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
—— (3Z)-3-[(3,4-dihydroxy-5-methoxyphenyl)methylidene]-1-methylindol-2-one —— C17H15NO4
(3Z)-3-[(3,4-dihydroxy-5-methoxyphenyl)methylidene]-1-methylindol-2-one
—— 2-[(E)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5-(4-methylphenyl)-3H-thieno[2,3-d]pyrimidin-4-one —— C22H17ClN2O3S
2-[(E)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5-(4-methylphenyl)-3H-thieno[2,3-d]pyrimidin-4-one
—— ethyl 2-[(E)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5-methyl-4-oxo-3H-thieno[2,3-d]pyrimidine-6-carboxylate —— C19H17ClN2O5S
ethyl 2-[(E)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5-methyl-4-oxo-3H-thieno[2,3-d]pyrimidine-6-carboxylate
—— 5-[(Z)-2-(5-chloro-1,3-benzoxazol-2-yl)ethenyl]-2-methoxyphenol —— C16H12ClNO3
5-[(Z)-2-(5-chloro-1,3-benzoxazol-2-yl)ethenyl]-2-methoxyphenol
—— (Z)-2-(2,5-dibromophenyl)sulfonyl-3-(4-hydroxy-3-methoxyphenyl)prop-2-enenitrile —— C16H11Br2NO4S
(Z)-2-(2,5-dibromophenyl)sulfonyl-3-(4-hydroxy-3-methoxyphenyl)prop-2-enenitrile
—— ethyl 2-[(Z)-2-(2-bromo-5-hydroxy-4-methoxyphenyl)ethenyl]-5-methyl-4-oxo-3H-thieno[2,3-d]pyrimidine-6-carboxylate —— C19H17BrN2O5S
ethyl 2-[(Z)-2-(2-bromo-5-hydroxy-4-methoxyphenyl)ethenyl]-5-methyl-4-oxo-3H-thieno[2,3-d]pyrimidine-6-carboxylate
—— 4-chloro-2-[(Z)-2-methyl-3-[methyl-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]amino]prop-1-enyl]phenol —— C15H18ClN3O2
4-chloro-2-[(Z)-2-methyl-3-[methyl-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]amino]prop-1-enyl]phenol
—— (Z)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(4-methylphenyl)sulfonylprop-2-enenitrile —— C17H15NO5S
(Z)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(4-methylphenyl)sulfonylprop-2-enenitrile
—— 4-[(Z)-3-[(3R)-3-(2-hydroxyethyl)-4-(thiophen-2-ylmethyl)piperazin-1-yl]prop-1-enyl]-2-methoxyphenol —— C21H28N2O3S
4-[(Z)-3-[(3R)-3-(2-hydroxyethyl)-4-(thiophen-2-ylmethyl)piperazin-1-yl]prop-1-enyl]-2-methoxyphenol
—— 5-[(Z)-2-(5-ethylsulfonyl-1,3-benzoxazol-2-yl)ethenyl]-2-methoxyphenol —— C18H17NO5S
5-[(Z)-2-(5-ethylsulfonyl-1,3-benzoxazol-2-yl)ethenyl]-2-methoxyphenol
—— 1-[(3S)-1-[(Z)-3-(5-chloro-2-hydroxyphenyl)-2-methylprop-2-enyl]piperidin-3-yl]pyrrolidin-2-one —— C19H25ClN2O2
1-[(3S)-1-[(Z)-3-(5-chloro-2-hydroxyphenyl)-2-methylprop-2-enyl]piperidin-3-yl]pyrrolidin-2-one
—— 2-[(E)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1-ethylbenzimidazole-5-carboxylic acid —— C19H17ClN2O4
2-[(E)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1-ethylbenzimidazole-5-carboxylic acid
—— 5-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-8-thia-4,6-diazatricyclo[7.5.0.02,7]tetradeca-1(9),2(7),5-trien-3-one —— C20H20N2O3S
5-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-8-thia-4,6-diazatricyclo[7.5.0.02,7]tetradeca-1(9),2(7),5-trien-3-one
—— 2-[(E)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5,6,7,8-tetrahydro-3H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C19H17ClN2O3S
2-[(E)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5,6,7,8-tetrahydro-3H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— 2-methoxy-5-[(Z)-2-[4-(4-methylphenyl)-1,3-thiazol-2-yl]ethenyl]phenol —— C19H17NO2S
2-methoxy-5-[(Z)-2-[4-(4-methylphenyl)-1,3-thiazol-2-yl]ethenyl]phenol
—— 2-methoxy-5-[(Z)-2-(6-nitro-1,3-benzothiazol-2-yl)ethenyl]phenol —— C16H12N2O4S
2-methoxy-5-[(Z)-2-(6-nitro-1,3-benzothiazol-2-yl)ethenyl]phenol
—— 5-[(Z)-2-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]ethenyl]-2-methoxyphenol —— C18H14FNO2S
5-[(Z)-2-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]ethenyl]-2-methoxyphenol
—— ethyl (3E,5E)-3,5-bis[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxopiperidine-1-carboxylate —— C24H25NO7
ethyl (3E,5E)-3,5-bis[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxopiperidine-1-carboxylate
—— (2Z,5Z)-2,5-bis[(3-hydroxyphenyl)methylidene]cyclopentan-1-one —— C19H16O3
(2Z,5Z)-2,5-bis[(3-hydroxyphenyl)methylidene]cyclopentan-1-one
—— (2Z,5E)-2,5-bis[(3-hydroxyphenyl)methylidene]cyclopentan-1-one —— C19H16O3
(2Z,5E)-2,5-bis[(3-hydroxyphenyl)methylidene]cyclopentan-1-one
—— (2E,5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-3-methyl-2-[2-(2-methylphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one —— C22H21NO5S
(2E,5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-3-methyl-2-[2-(2-methylphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one
—— (2E,5Z)-2-[2-(furan-2-yl)-2-oxoethylidene]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C17H13NO5S
(2E,5Z)-2-[2-(furan-2-yl)-2-oxoethylidene]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (Z)-3-(2-bromo-5-hydroxy-4-methoxyphenyl)-2-methylsulfonylprop-2-enenitrile —— C11H10BrNO4S
(Z)-3-(2-bromo-5-hydroxy-4-methoxyphenyl)-2-methylsulfonylprop-2-enenitrile
—— (2Z,5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-3-methyl-2-[2-(2-methylphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one —— C22H21NO5S
(2Z,5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-3-methyl-2-[2-(2-methylphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one
—— (3E,5E)-3,5-bis[(3-hydroxy-4-methoxyphenyl)methylidene]thian-4-one —— C21H20O5S
(3E,5E)-3,5-bis[(3-hydroxy-4-methoxyphenyl)methylidene]thian-4-one
—— (2E,5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-3-methyl-2-[2-(2-methylphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one —— C22H21NO5S
(2E,5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-3-methyl-2-[2-(2-methylphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one
—— 2-methoxy-5-[(Z)-2-(5-methyl-1,3-benzothiazol-2-yl)ethenyl]phenol —— C17H15NO2S
2-methoxy-5-[(Z)-2-(5-methyl-1,3-benzothiazol-2-yl)ethenyl]phenol
—— (2Z,5E)-2-[2-(furan-2-yl)-2-oxoethylidene]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C17H13NO5S
(2Z,5E)-2-[2-(furan-2-yl)-2-oxoethylidene]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (Z)-3-(3-hydroxy-4-methoxyphenyl)-2-methylsulfonylprop-2-enenitrile —— C11H11NO4S
(Z)-3-(3-hydroxy-4-methoxyphenyl)-2-methylsulfonylprop-2-enenitrile
—— (2E)-2-[(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]-N-(2-methoxyphenyl)acetamide —— C21H20N2O5S
(2E)-2-[(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]-N-(2-methoxyphenyl)acetamide
—— (Z)-3-(4-hydroxyphenyl)-2-methylsulfonylprop-2-enenitrile —— C10H9NO3S
(Z)-3-(4-hydroxyphenyl)-2-methylsulfonylprop-2-enenitrile
—— (3E)-6-fluoro-3-[(3-hydroxy-4-methoxyphenyl)methylidene]thiochromen-4-one —— C17H13FO3S
(3E)-6-fluoro-3-[(3-hydroxy-4-methoxyphenyl)methylidene]thiochromen-4-one
—— (5E)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-2-piperidin-1-yl-1,3-thiazol-4-one —— C17H20N2O2S
(5E)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-2-piperidin-1-yl-1,3-thiazol-4-one
—— (3E)-6-fluoro-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]thiochromen-4-one —— C18H15FO4S
(3E)-6-fluoro-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]thiochromen-4-one
—— (2E)-2-[(5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]-N-(2-methoxyphenyl)acetamide —— C21H20N2O5S
(2E)-2-[(5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]-N-(2-methoxyphenyl)acetamide
—— (3E)-3-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-6-fluorothiochromen-4-one —— C17H12BrFO3S
(3E)-3-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-6-fluorothiochromen-4-one
—— 2-methoxyethyl 2-[(E)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5-methyl-4-oxo-3H-thieno[2,3-d]pyrimidine-6-carboxylate —— C20H19ClN2O6S
2-methoxyethyl 2-[(E)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5-methyl-4-oxo-3H-thieno[2,3-d]pyrimidine-6-carboxylate
—— (2E,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C18H21NO4S
(2E,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5E)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-2-piperidin-1-yl-1,3-thiazol-4-one —— C16H17ClN2O3S
(5E)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-2-piperidin-1-yl-1,3-thiazol-4-one
—— (10Z)-10-[(3-hydroxy-4-methoxyphenyl)methylidene]-4,5-dimethyl-6-thia-1,8-diazatricyclo[7.3.0.03,7]dodeca-3(7),4,8-trien-2-one —— C19H18N2O3S
(10Z)-10-[(3-hydroxy-4-methoxyphenyl)methylidene]-4,5-dimethyl-6-thia-1,8-diazatricyclo[7.3.0.03,7]dodeca-3(7),4,8-trien-2-one
—— (2Z,5E)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C18H21NO4S
(2Z,5E)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5R)-5-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-1,2,5,6-tetrahydropyrazolo[4,3-g]quinolin-7-one —— C19H17N3O3
(5R)-5-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-1,2,5,6-tetrahydropyrazolo[4,3-g]quinolin-7-one
—— (5S)-5-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-1,2,5,6-tetrahydropyrazolo[4,3-g]quinolin-7-one —— C19H17N3O3
(5S)-5-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-1,2,5,6-tetrahydropyrazolo[4,3-g]quinolin-7-one
—— 4-chloro-2-[(Z)-3-(3-ethyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)-2-methylprop-1-enyl]phenol —— C18H22ClN3O
4-chloro-2-[(Z)-3-(3-ethyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)-2-methylprop-1-enyl]phenol
—— [4-[1-[(Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl]piperidin-4-yl]oxyphenyl]-pyrrolidin-1-ylmethanone —— C26H32N2O4
[4-[1-[(Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl]piperidin-4-yl]oxyphenyl]-pyrrolidin-1-ylmethanone
—— 4-[(Z)-3-[(3S)-3-(2-hydroxyethyl)-4-[(5-methylfuran-2-yl)methyl]piperazin-1-yl]prop-1-enyl]-2-methoxyphenol —— C22H30N2O4
4-[(Z)-3-[(3S)-3-(2-hydroxyethyl)-4-[(5-methylfuran-2-yl)methyl]piperazin-1-yl]prop-1-enyl]-2-methoxyphenol
—— N-[[(3R)-1-[(Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl]piperidin-3-yl]methyl]furan-2-carboxamide —— C21H26N2O4
N-[[(3R)-1-[(Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl]piperidin-3-yl]methyl]furan-2-carboxamide
—— N-cyclopropyl-1-[1-[(Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl]piperidin-4-yl]piperidine-4-carboxamide —— C24H35N3O3
N-cyclopropyl-1-[1-[(Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl]piperidin-4-yl]piperidine-4-carboxamide
—— ethyl (3S)-1-[(Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl]-3-(2-methoxyethyl)piperidine-3-carboxylate —— C21H31NO5
ethyl (3S)-1-[(Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl]-3-(2-methoxyethyl)piperidine-3-carboxylate
—— ethyl (3R)-1-[(Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl]-3-(2-methoxyethyl)piperidine-3-carboxylate —— C21H31NO5
ethyl (3R)-1-[(Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl]-3-(2-methoxyethyl)piperidine-3-carboxylate