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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
—— (E)-N-[(1S)-2-(cyclohexylamino)-1-(2-fluorophenyl)-2-oxoethyl]-4-(2-hydroxy-4-methoxyphenyl)-4-oxo-N-(thiophen-2-ylmethyl)but-2-enamide —— C30H31FN2O5S
(E)-N-[(1S)-2-(cyclohexylamino)-1-(2-fluorophenyl)-2-oxoethyl]-4-(2-hydroxy-4-methoxyphenyl)-4-oxo-N-(thiophen-2-ylmethyl)but-2-enamide
—— 5-[(2-Hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-dimethyl-2-sulfanylidene-1,3-diazinane-4,6-dione —— C15H16N2O5S
5-[(2-Hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-dimethyl-2-sulfanylidene-1,3-diazinane-4,6-dione
—— (5E)-5-[(3-bromo-5-chloro-4-hydroxyphenyl)methylidene]-3-(2-ethoxyethyl)-2-phenylimino-1,3-thiazolidin-4-one —— C20H18BrClN2O3S
(5E)-5-[(3-bromo-5-chloro-4-hydroxyphenyl)methylidene]-3-(2-ethoxyethyl)-2-phenylimino-1,3-thiazolidin-4-one
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-4-[(5Z)-4-oxo-2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-thiazolidin-3-yl]butanamide —— C20H20N2O4S3
N-[2-(3,4-dihydroxyphenyl)ethyl]-4-[(5Z)-4-oxo-2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-thiazolidin-3-yl]butanamide
—— (5E)-5-(3,4-dihydroxybenzylidene)-3-(3-hydroxyphenyl)-2-thioxo-1,3-thiazolidin-4-one —— C16H11NO4S2
(5E)-5-(3,4-dihydroxybenzylidene)-3-(3-hydroxyphenyl)-2-thioxo-1,3-thiazolidin-4-one
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-5-[(4-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C21H20N2O6S
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-5-[(4-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— 1-cyclohexyl-3-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]urea —— C18H21N3O4S2
1-cyclohexyl-3-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]urea
—— N'-[(1S)-1-(4-hydroxy-3-methoxyphenyl)-2-oxo-2-(thiophen-2-ylmethylamino)ethyl]-N'-(2-methylphenyl)-N-(1,3-thiazol-2-yl)butanediamide —— C28H28N4O5S2
N'-[(1S)-1-(4-hydroxy-3-methoxyphenyl)-2-oxo-2-(thiophen-2-ylmethylamino)ethyl]-N'-(2-methylphenyl)-N-(1,3-thiazol-2-yl)butanediamide
—— N'-[(1R)-1-(4-hydroxy-3-methoxyphenyl)-2-oxo-2-(thiophen-2-ylmethylamino)ethyl]-N'-(2-methylphenyl)-N-(1,3-thiazol-2-yl)butanediamide —— C28H28N4O5S2
N'-[(1R)-1-(4-hydroxy-3-methoxyphenyl)-2-oxo-2-(thiophen-2-ylmethylamino)ethyl]-N'-(2-methylphenyl)-N-(1,3-thiazol-2-yl)butanediamide
—— N'-(2,4-dimethylphenyl)-N'-[(1R)-1-(4-hydroxy-3-methoxyphenyl)-2-oxo-2-(thiophen-2-ylmethylamino)ethyl]-N-(1,3-thiazol-2-yl)butanediamide —— C29H30N4O5S2
N'-(2,4-dimethylphenyl)-N'-[(1R)-1-(4-hydroxy-3-methoxyphenyl)-2-oxo-2-(thiophen-2-ylmethylamino)ethyl]-N-(1,3-thiazol-2-yl)butanediamide
—— (E)-4-(1,3-benzothiazol-2-yl)-5-(3-hydroxy-4-methoxyphenyl)pent-4-enoic acid —— C19H17NO4S
(E)-4-(1,3-benzothiazol-2-yl)-5-(3-hydroxy-4-methoxyphenyl)pent-4-enoic acid
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-5-(2-fluorobenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetamide —— C20H17FN2O4S2
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-5-(2-fluorobenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetamide
—— 2-[(5Z)-5-[(3-chlorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide —— C20H17ClN2O5S
2-[(5Z)-5-[(3-chlorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide
—— N-[(E)-[2,5-bis(methylsulfanyl)-4-[(Z)-[(3,4,5-trihydroxybenzoyl)hydrazinylidene]methyl]thiophen-3-yl]methylideneamino]-3,4,5-trihydroxybenzamide —— C22H20N4O8S3
N-[(E)-[2,5-bis(methylsulfanyl)-4-[(Z)-[(3,4,5-trihydroxybenzoyl)hydrazinylidene]methyl]thiophen-3-yl]methylideneamino]-3,4,5-trihydroxybenzamide
—— (2E,5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-[2-(4-methoxyphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one —— C20H17NO5S
(2E,5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-[2-(4-methoxyphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one
—— 2-Methoxy-4-methyl-6-{[4-(2-phenylethenesulfonyl)piperazin-1-yl]methyl}phenol —— C21H26N2O4S
2-Methoxy-4-methyl-6-{[4-(2-phenylethenesulfonyl)piperazin-1-yl]methyl}phenol
—— 4-[(Z)-(2-bromo-5-hydroxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione —— C9H7BrN4OS
4-[(Z)-(2-bromo-5-hydroxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione
—— (2E)-2-[(1,5-dimethyl-1H-pyrazol-4-yl)methylidene]-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-N-phenyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide —— C27H25N5O4S
(2E)-2-[(1,5-dimethyl-1H-pyrazol-4-yl)methylidene]-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-N-phenyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
—— 4-[(Z)-(2-bromo-5-hydroxyphenyl)methylideneamino]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-thione —— C10H6BrF3N4OS
4-[(Z)-(2-bromo-5-hydroxyphenyl)methylideneamino]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-thione
—— 5-{(Z)-[3-(difluoromethyl)-6-methyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-ylidene]methyl}-2-methoxyphenol —— C14H12F2N4O2S
5-{(Z)-[3-(difluoromethyl)-6-methyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-ylidene]methyl}-2-methoxyphenol
—— 2-[(2Z)-2-hydroxyiminopropyl]-6-methoxyphenol —— C10H13NO3
2-[(2Z)-2-hydroxyiminopropyl]-6-methoxyphenol
—— (5Z)-2-[2-chloro-5-(trifluoromethyl)phenyl]imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C18H12ClF3N2O3S
(5Z)-2-[2-chloro-5-(trifluoromethyl)phenyl]imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 2-[(Z)-3,4-Dichloro-phenylimino]-5-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-thiazolidin-4-one 18101-19-4 C17H12Cl2N2O3S
2-[(Z)-3,4-Dichloro-phenylimino]-5-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-thiazolidin-4-one
—— N-(2-hydroxy-4-nitrophenyl)-6-[(5Z)-5-[(4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanamide —— C23H23N3O6S2
N-(2-hydroxy-4-nitrophenyl)-6-[(5Z)-5-[(4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanamide
—— 6-[(5Z)-5-[(3,4-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)hexanamide —— C24H25N3O7S2
6-[(5Z)-5-[(3,4-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)hexanamide
—— 6-[(5Z)-5-[(4-chlorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)hexanamide —— C22H20ClN3O5S2
6-[(5Z)-5-[(4-chlorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)hexanamide
—— N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-methoxybenzamide —— C16H16N2O4
N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-methoxybenzamide
—— (2E)-1-(4-ethylphenyl)-3-[(4-hydroxy-2-methylphenyl)amino]prop-2-en-1-one —— C18H19NO2
(2E)-1-(4-ethylphenyl)-3-[(4-hydroxy-2-methylphenyl)amino]prop-2-en-1-one
—— N-[(2-chlorophenyl)methyl]-N-[(1R)-2-(cyclopentylamino)-1-(4-hydroxy-3-methoxyphenyl)-2-oxoethyl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide —— C30H31ClN2O6
N-[(2-chlorophenyl)methyl]-N-[(1R)-2-(cyclopentylamino)-1-(4-hydroxy-3-methoxyphenyl)-2-oxoethyl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide
—— N-[(2-chlorophenyl)methyl]-N-[(1S)-2-(cyclopentylamino)-1-(4-hydroxy-3-methoxyphenyl)-2-oxoethyl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide —— C30H31ClN2O6
N-[(2-chlorophenyl)methyl]-N-[(1S)-2-(cyclopentylamino)-1-(4-hydroxy-3-methoxyphenyl)-2-oxoethyl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide
—— (2E)-3-[(4-hydroxy-2-methylphenyl)amino]-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one —— C19H21NO5
(2E)-3-[(4-hydroxy-2-methylphenyl)amino]-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
—— 1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]-5-propan-2-yltriazole-4-carboxamide —— C16H18N8O3
1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]-5-propan-2-yltriazole-4-carboxamide
—— 2-methoxyethyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-propoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C28H30N2O7S
2-methoxyethyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-propoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— propan-2-yl (2Z)-5-(4-butoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H32N2O6S
propan-2-yl (2Z)-5-(4-butoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— methyl (2Z)-5-(4-butoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H28N2O6S
methyl (2Z)-5-(4-butoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-Acetyl-2-(3-hydroxy-4-methylanilino)-6-methylpyran-4-one —— C15H15NO4
3-Acetyl-2-(3-hydroxy-4-methylanilino)-6-methylpyran-4-one
—— (2R)-2-[1,3-benzodioxol-5-ylmethyl-[2-(benzotriazol-1-yl)acetyl]amino]-2-(4-hydroxy-3-methoxyphenyl)-N-[[(2S)-oxolan-2-yl]methyl]acetamide —— C30H31N5O7
(2R)-2-[1,3-benzodioxol-5-ylmethyl-[2-(benzotriazol-1-yl)acetyl]amino]-2-(4-hydroxy-3-methoxyphenyl)-N-[[(2S)-oxolan-2-yl]methyl]acetamide
—— 2-methylpropyl (2Z)-5-(4-ethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C28H30N2O6S
2-methylpropyl (2Z)-5-(4-ethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-methylpropyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-phenylmethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C33H32N2O6S
2-methylpropyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-phenylmethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— propan-2-yl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-pentoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C31H36N2O7S
propan-2-yl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-pentoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— benzyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-phenylmethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C36H30N2O6S
benzyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-phenylmethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2R)-2-[1,3-benzodioxol-5-ylmethyl-[2-(benzotriazol-1-yl)acetyl]amino]-2-(4-hydroxy-3-methoxyphenyl)-N-[[(2R)-oxolan-2-yl]methyl]acetamide —— C30H31N5O7
(2R)-2-[1,3-benzodioxol-5-ylmethyl-[2-(benzotriazol-1-yl)acetyl]amino]-2-(4-hydroxy-3-methoxyphenyl)-N-[[(2R)-oxolan-2-yl]methyl]acetamide
—— N-[(Z)-(6-chloro-1,3-benzodioxol-5-yl)methylideneamino]-2-hydroxy-5-nitrobenzamide —— C15H10ClN3O6
N-[(Z)-(6-chloro-1,3-benzodioxol-5-yl)methylideneamino]-2-hydroxy-5-nitrobenzamide
—— propan-2-yl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-propoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C28H30N2O6S
propan-2-yl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-propoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2S)-2-[1,3-benzodioxol-5-ylmethyl-[2-(benzotriazol-1-yl)acetyl]amino]-2-(4-hydroxy-3-methoxyphenyl)-N-[[(2R)-oxolan-2-yl]methyl]acetamide —— C30H31N5O7
(2S)-2-[1,3-benzodioxol-5-ylmethyl-[2-(benzotriazol-1-yl)acetyl]amino]-2-(4-hydroxy-3-methoxyphenyl)-N-[[(2R)-oxolan-2-yl]methyl]acetamide
—— (2R)-2-[(6-acetyl-1,3-benzodioxol-5-yl)-[2-(benzotriazol-1-yl)acetyl]amino]-2-(4-hydroxy-3-methoxyphenyl)-N-[[(2R)-oxolan-2-yl]methyl]acetamide —— C31H31N5O8
(2R)-2-[(6-acetyl-1,3-benzodioxol-5-yl)-[2-(benzotriazol-1-yl)acetyl]amino]-2-(4-hydroxy-3-methoxyphenyl)-N-[[(2R)-oxolan-2-yl]methyl]acetamide
—— 2-methoxyethyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-phenylmethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C33H32N2O8S
2-methoxyethyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-phenylmethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2R)-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
(2R)-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-[(6-acetyl-1,3-benzodioxol-5-yl)-[2-(benzotriazol-1-yl)acetyl]amino]-2-(4-hydroxy-3-methoxyphenyl)-N-[[(2R)-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-[[(2R)-oxolan-2-yl]methyl]acetamide
—— (2R)-2-[[2-(benzotriazol-1-yl)acetyl]-[(4-methoxyphenyl)methyl]amino]-2-(4-hydroxy-3-methoxyphenyl)-N-[[(2S)-oxolan-2-yl]methyl]acetamide —— C30H33N5O6
(2R)-2-[[2-(benzotriazol-1-yl)acetyl]-[(4-methoxyphenyl)methyl]amino]-2-(4-hydroxy-3-methoxyphenyl)-N-[[(2S)-oxolan-2-yl]methyl]acetamide