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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-(4-hydroxy-3-methoxyphenyl)-5-phenyl-2,3-dihydro-1H-thieno[2,3-d]pyrimidin-4-one —— C19H16N2O3S
(2S)-2-(4-hydroxy-3-methoxyphenyl)-5-phenyl-2,3-dihydro-1H-thieno[2,3-d]pyrimidin-4-one
—— (2R,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
(2R,7R)-2-(3-hydroxy-4-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2S,7S)-2-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C18H19ClN2O3S
(2S,7S)-2-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2S)-2,3,3,3-tetrafluoro-N-(2-hydroxy-4-nitrophenyl)propanamide —— C9H6F4N2O4
(2S)-2,3,3,3-tetrafluoro-N-(2-hydroxy-4-nitrophenyl)propanamide
—— 2-methoxy-5-[[[(3S)-3-morpholin-4-ylthiolan-3-yl]methylamino]methyl]phenol —— C17H26N2O3S
2-methoxy-5-[[[(3S)-3-morpholin-4-ylthiolan-3-yl]methylamino]methyl]phenol
—— 2-methoxy-5-[[[(3R)-3-morpholin-4-ylthiolan-3-yl]methylamino]methyl]phenol —— C17H26N2O3S
2-methoxy-5-[[[(3R)-3-morpholin-4-ylthiolan-3-yl]methylamino]methyl]phenol
—— 4-(1,3-Dibenzyl-1,3-diazinane-1,3-diium-2-yl)-2-methoxyphenol —— C25H30N2O2+2
4-(1,3-Dibenzyl-1,3-diazinane-1,3-diium-2-yl)-2-methoxyphenol
—— (2R)-2-(2-hydroxy-3-methoxyphenyl)-2-[(3S)-5-methyl-3-phenyl-3,4-dihydropyrazol-2-yl]acetonitrile —— C19H19N3O2
(2R)-2-(2-hydroxy-3-methoxyphenyl)-2-[(3S)-5-methyl-3-phenyl-3,4-dihydropyrazol-2-yl]acetonitrile
—— (5E)-2-[(2S,6S)-2,6-dimethylmorpholin-4-yl]-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazol-4-one —— C16H18N2O3S
(5E)-2-[(2S,6S)-2,6-dimethylmorpholin-4-yl]-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazol-4-one
—— (5S)-5-(3-hydroxy-4-methoxyphenyl)-11-propan-2-yl-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C19H23N3O3S
(5S)-5-(3-hydroxy-4-methoxyphenyl)-11-propan-2-yl-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5R)-11-benzyl-5-(3-hydroxy-4-methoxyphenyl)-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C23H23N3O3S
(5R)-11-benzyl-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)-11-benzyl-5-(2-hydroxy-3-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C23H24N3O3S+
(5R)-11-benzyl-5-(2-hydroxy-3-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5R)-11-benzyl-5-(3-hydroxy-4-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C23H24N3O3S+
(5R)-11-benzyl-5-(3-hydroxy-4-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[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-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C19H23N3O3S
(5R)-5-(3-hydroxy-4-methoxyphenyl)-11-propan-2-yl-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5S)-11-benzyl-5-(2-hydroxy-3-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C23H24N3O3S+
(5S)-11-benzyl-5-(2-hydroxy-3-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5S)-11-benzyl-5-(2-hydroxy-3-methoxyphenyl)-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C23H23N3O3S
(5S)-11-benzyl-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-benzyl-5-(2-hydroxy-3-methoxyphenyl)-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C23H23N3O3S
(5R)-11-benzyl-5-(2-hydroxy-3-methoxyphenyl)-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (2R)-2-[(3S)-3,5-diphenyl-3,4-dihydropyrazol-2-yl]-2-(4-hydroxy-3-methoxyphenyl)acetonitrile —— C24H21N3O2
(2R)-2-[(3S)-3,5-diphenyl-3,4-dihydropyrazol-2-yl]-2-(4-hydroxy-3-methoxyphenyl)acetonitrile
—— (5S)-11-benzyl-5-(3-hydroxy-4-methoxyphenyl)-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C23H23N3O3S
(5S)-11-benzyl-5-(3-hydroxy-4-methoxyphenyl)-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5S)-5-(5-chloro-2-hydroxy-3-methoxyphenyl)-11-ethyl-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C18H20ClN3O3S
(5S)-5-(5-chloro-2-hydroxy-3-methoxyphenyl)-11-ethyl-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5S)-5-(5-chloro-2-hydroxy-3-methoxyphenyl)-11-ethyl-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C18H21ClN3O3S+
(5S)-5-(5-chloro-2-hydroxy-3-methoxyphenyl)-11-ethyl-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5R)-5-(5-chloro-2-hydroxy-3-methoxyphenyl)-11-ethyl-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C18H20ClN3O3S
(5R)-5-(5-chloro-2-hydroxy-3-methoxyphenyl)-11-ethyl-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5R)-5-(5-chloro-2-hydroxy-3-methoxyphenyl)-11-ethyl-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C18H21ClN3O3S+
(5R)-5-(5-chloro-2-hydroxy-3-methoxyphenyl)-11-ethyl-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5R)-11-ethyl-5-(2-hydroxy-3-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C18H22N3O3S+
(5R)-11-ethyl-5-(2-hydroxy-3-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5S)-11-ethyl-5-(2-hydroxy-3-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C18H22N3O3S+
(5S)-11-ethyl-5-(2-hydroxy-3-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5R)-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
(5R)-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
—— (5S)-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
(5S)-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)-11-ethyl-5-(4-hydroxy-3-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C18H22N3O3S+
(5R)-11-ethyl-5-(4-hydroxy-3-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5S)-11-ethyl-5-(4-hydroxy-3-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C18H22N3O3S+
(5S)-11-ethyl-5-(4-hydroxy-3-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[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-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C18H22N3O3S+
(5R)-11-ethyl-5-(3-hydroxy-4-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5R)-11-ethyl-5-(4-hydroxy-3-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-(4-hydroxy-3-methoxyphenyl)-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5S)-11-ethyl-5-(3-hydroxy-4-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C18H22N3O3S+
(5S)-11-ethyl-5-(3-hydroxy-4-methoxyphenyl)-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-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C19H23ClN3O3S+
(5S)-5-(5-chloro-2-hydroxy-3-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
—— (5R)-5-(5-chloro-2-hydroxy-3-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 —— C19H23ClN3O3S+
(5R)-5-(5-chloro-2-hydroxy-3-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
—— ethyl (5R)-5-(3-hydroxy-4-methoxyphenyl)-3-oxo-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-diene-11-carboxylate —— C19H21N3O5S
ethyl (5R)-5-(3-hydroxy-4-methoxyphenyl)-3-oxo-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-diene-11-carboxylate
—— (5R)-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
(5R)-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
—— (2R,7S)-2-(3-hydroxy-4-methoxyphenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C22H28N2O3S
(2R,7S)-2-(3-hydroxy-4-methoxyphenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2S,7R)-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,7R)-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
—— (5S)-5-(4-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 —— C19H23N3O3S
(5S)-5-(4-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-(5-hydroxy-2-nitrophenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C21H25N3O4S
(2S,7S)-2-(5-hydroxy-2-nitrophenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (5R)-5-(4-hydroxy-3-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-(4-hydroxy-3-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
—— (2R,7S)-2-(5-hydroxy-2-nitrophenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C21H25N3O4S
(2R,7S)-2-(5-hydroxy-2-nitrophenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2R,7R)-2-(5-hydroxy-2-nitrophenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C21H25N3O4S
(2R,7R)-2-(5-hydroxy-2-nitrophenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (5E)-3-[(2S)-butan-2-yl]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C15H17NO4S
(5E)-3-[(2S)-butan-2-yl]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— (2S)-2-[(3S)-3,5-diphenyl-3,4-dihydropyrazol-2-yl]-2-(2-hydroxy-3-methoxyphenyl)acetonitrile —— C24H21N3O2
(2S)-2-[(3S)-3,5-diphenyl-3,4-dihydropyrazol-2-yl]-2-(2-hydroxy-3-methoxyphenyl)acetonitrile
—— (2R)-2-[(3S)-3,5-diphenyl-3,4-dihydropyrazol-2-yl]-2-(2-hydroxy-3-methoxyphenyl)acetonitrile —— C24H21N3O2
(2R)-2-[(3S)-3,5-diphenyl-3,4-dihydropyrazol-2-yl]-2-(2-hydroxy-3-methoxyphenyl)acetonitrile
—— (3R,4R)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3-pyridin-1-ium-1-yl-3,4-dihydro-1H-pyridine-5-carbonitrile —— C18H16N3O4+
(3R,4R)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3-pyridin-1-ium-1-yl-3,4-dihydro-1H-pyridine-5-carbonitrile
—— (3S,4R)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3-pyridin-1-ium-1-yl-3,4-dihydro-1H-pyridine-5-carbonitrile —— C18H16N3O4+
(3S,4R)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3-pyridin-1-ium-1-yl-3,4-dihydro-1H-pyridine-5-carbonitrile
—— (5E)-3-[(2R)-butan-2-yl]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C15H17NO4S
(5E)-3-[(2R)-butan-2-yl]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— (2S)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-(3-methylphenyl)propanamide —— C18H18N2O3
(2S)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-(3-methylphenyl)propanamide