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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
—— 5-isohexyl-resorcinol 860504-71-8 C12H18O2
5-isohexyl-resorcinol
—— (2,3-dihydroxybenzylidene)-2-hydroxybenzohydrazide —— C14H12N2O4
(2,3-dihydroxybenzylidene)-2-hydroxybenzohydrazide
—— 1,3-dihydroxy-2-methyl-5-(7-bromoheptyl)benzene 219630-94-1 C14H21BrO2
1,3-dihydroxy-2-methyl-5-(7-bromoheptyl)benzene
—— 1-(3,6-dimethoxy-1,4-benzoquinon-2-yl)-16-(3,5-dihydroxyphenyl)-8-Z-hexadecene 219630-90-7 C30H42O6
1-(3,6-dimethoxy-1,4-benzoquinon-2-yl)-16-(3,5-dihydroxyphenyl)-8-Z-hexadecene
—— 1-(3,6-dimethoxy-1,4-benzoquinon-2-yl)-16-(3,5-dihydroxy-4-methylphenyl)-8-Z-hexadecene 219630-97-4 C31H44O6
1-(3,6-dimethoxy-1,4-benzoquinon-2-yl)-16-(3,5-dihydroxy-4-methylphenyl)-8-Z-hexadecene
—— ardisiaquinone E 99621-87-1 C29H40O6
ardisiaquinone E
—— 1-bromo-7-(3,5-dihydroxyphenyl)heptane 219630-86-1 C13H19BrO2
1-bromo-7-(3,5-dihydroxyphenyl)heptane
—— 6-[(furan-2-ylmethylamino)methylidene]cyclohexa-2,4-dien-1-one 76152-10-8 C12H11NO2
6-[(furan-2-ylmethylamino)methylidene]cyclohexa-2,4-dien-1-one
—— malon-di-<(p-hydroxy)benzylidene amino>amide 92514-61-9 C17H16N4O4
malon-di-<(p-hydroxy)benzylidene amino>amide
—— 4-(3-fluoro-4-hydroxy-phenyl)-butyric acid 588-25-0 C10H11FO3
4-(3-fluoro-4-hydroxy-phenyl)-butyric acid
—— 3,5-dimethyl-2,6-dinitrophenol 99584-19-7 C8H8N2O5
3,5-dimethyl-2,6-dinitrophenol
—— 4-[(2,4-Diamino-6-propylpyrimidin-5-yl)methyl]-2,6-dimethoxyphenol 73576-45-1 C16H22N4O3
4-[(2,4-Diamino-6-propylpyrimidin-5-yl)methyl]-2,6-dimethoxyphenol
—— 55380-55-7 C21H30O3
—— 3-[(2-hydroxy-3-methoxybenzylidene)hydrazo]-1,3-dihydroindol-2-one 326884-73-5 C16H13N3O3
3-[(2-hydroxy-3-methoxybenzylidene)hydrazo]-1,3-dihydroindol-2-one
—— ethyl(4,5-dimethoxy-2-hydroxyphenyl)acetate 76322-30-0 C12H16O5
ethyl(4,5-dimethoxy-2-hydroxyphenyl)acetate
—— 5-[4-(1,2-cis-hexen-1-yl)tetrahydro-2H-pyran-4-yl]resorcinol 1605281-06-8 C17H24O3
5-[4-(1,2-cis-hexen-1-yl)tetrahydro-2H-pyran-4-yl]resorcinol
—— 4-(3,5-dihydroxyphenyl)tetrahydro-2H-pyran-4-carbonitrile 1605281-02-4 C12H13NO3
4-(3,5-dihydroxyphenyl)tetrahydro-2H-pyran-4-carbonitrile
—— 3-dimethylamino-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 187877-87-8 C13H17NO4
3-dimethylamino-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one
—— 3-(3-bromo-4-hydroxyphenyl)-2-oxo-N-(2-sulfanylethyl)propanamide 1356929-90-2 C11H12BrNO3S
3-(3-bromo-4-hydroxyphenyl)-2-oxo-N-(2-sulfanylethyl)propanamide
—— (2E)-3-(3-bromo-4-hydroxyphenyl)-N-[2-[2-[[(2E)-3-(3-bromo-4-hydroxyphenyl)-2-hydrazinylidenepropanoyl]amino]ethyldisulfanyl]ethyl]-2-hydrazinylidenepropanamide 1356929-94-6 C22H26Br2N6O4S2
(2E)-3-(3-bromo-4-hydroxyphenyl)-N-[2-[2-[[(2E)-3-(3-bromo-4-hydroxyphenyl)-2-hydrazinylidenepropanoyl]amino]ethyldisulfanyl]ethyl]-2-hydrazinylidenepropanamide
—— (2E)-3-(3-bromo-4-hydroxyphenyl)-N-[3-[2-[[(2E)-3-(3-bromo-4-hydroxyphenyl)-2-hydroxyiminopropanoyl]amino]ethylsulfanyl]propyl]-2-hydroxyiminopropanamide 1356930-33-0 C23H26Br2N4O6S
(2E)-3-(3-bromo-4-hydroxyphenyl)-N-[3-[2-[[(2E)-3-(3-bromo-4-hydroxyphenyl)-2-hydroxyiminopropanoyl]amino]ethylsulfanyl]propyl]-2-hydroxyiminopropanamide
—— (2E)-3-(3-bromo-4-hydroxyphenyl)-2-methoxyimino-N-(2-sulfanylethyl)propanamide 1356929-84-4 C12H15BrN2O3S
(2E)-3-(3-bromo-4-hydroxyphenyl)-2-methoxyimino-N-(2-sulfanylethyl)propanamide
—— (E)-3-(3-bromo-4-hydroxyphenyl)-2-hydrazono-N-(2-(methylthio)ethyl)propanamide 1356929-92-4 C12H16BrN3O2S
(E)-3-(3-bromo-4-hydroxyphenyl)-2-hydrazono-N-(2-(methylthio)ethyl)propanamide
—— (R)-3-(3,5-dibromo-4-hydroxy-phenyl)-2-hydroxy-propionic acid methyl ester 866087-54-9 C10H10Br2O4
(R)-3-(3,5-dibromo-4-hydroxy-phenyl)-2-hydroxy-propionic acid methyl ester
—— 3,6-dihydroxy-1,2-dihydrobenzocyclobutene 77627-60-2 C8H8O2
3,6-dihydroxy-1,2-dihydrobenzocyclobutene
—— 2-[4-hydroxy-3-pentylphenyl]acetic acid 1254646-35-9 C13H18O3
2-[4-hydroxy-3-pentylphenyl]acetic acid
—— (5R)-5-(2-hydroxy-3-methoxyphenyl)-1',3',7-trimethyl-3,3a,5,6-tetrahydro-2H,2'H-spiro[1-benzothiophene-4,5'-pyrimidine]-2',4',6'(1'H,3'H)-trione 1,1-dioxide 1185843-41-7 C21H24N2O7S
(5R)-5-(2-hydroxy-3-methoxyphenyl)-1',3',7-trimethyl-3,3a,5,6-tetrahydro-2H,2'H-spiro[1-benzothiophene-4,5'-pyrimidine]-2',4',6'(1'H,3'H)-trione 1,1-dioxide
—— 3-hydroxy-4-nitroacetanilide 712-34-5 C8H8N2O4
3-hydroxy-4-nitroacetanilide
—— (4-chloro-2-hydroxy-6-methylphenyl)boronic acid 1207961-50-9 C7H8BClO3
(4-chloro-2-hydroxy-6-methylphenyl)boronic acid
—— 1-chloro-3-<4-(2-cyclopropylmethoxy)ethyl>phenoxypropan-2-ol 169613-99-4 C15H21ClO3
1-chloro-3-<4-(2-cyclopropylmethoxy)ethyl>phenoxypropan-2-ol
—— [(2S)-1-chloro-3-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]propan-2-yl] acetate 169614-01-1 C17H23ClO4
[(2S)-1-chloro-3-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]propan-2-yl] acetate
—— 11b-benzyl-9-hydroxy-1,2,5,6,7,11b-hexahydro-dibenzo[a,c]cyclohepten-3-one 1400924-57-3 C22H22O2
11b-benzyl-9-hydroxy-1,2,5,6,7,11b-hexahydro-dibenzo[a,c]cyclohepten-3-one
—— 3-(4,5-dihydro-3<i>H</i>-pyrrol-2-yl)-phenol 102236-69-1 C10H11NO
3-(4,5-dihydro-3<i>H</i>-pyrrol-2-yl)-phenol
—— 4-[[Tert-butyl(dimethyl)silyl]oxymethyl]-2-[2-(1-hydroxycyclohexyl)ethynyl]-6-methoxyphenol 343309-53-5 C22H34O4Si
4-[[Tert-butyl(dimethyl)silyl]oxymethyl]-2-[2-(1-hydroxycyclohexyl)ethynyl]-6-methoxyphenol
—— 2,6-bis(dihydroxyphosphonyl)methyl 4-methyl phenol 147608-61-5 C9H14O7P2
2,6-bis(dihydroxyphosphonyl)methyl 4-methyl phenol
—— 2-(2,4,6-trimethoxyphenyl)ethan-1-ol 832-87-1 C11H16O4
2-(2,4,6-trimethoxyphenyl)ethan-1-ol
—— 1-(3-ethyl-2-hydroxy-4,6-dimethoxyphenyl)but-2-en-1-one 144688-19-7 C14H18O4
1-(3-ethyl-2-hydroxy-4,6-dimethoxyphenyl)but-2-en-1-one
—— 4-hydroxy-3-methoxybenz-[14C]-aldehyde 15212-09-6 C8H8O3
4-hydroxy-3-methoxybenz-[14C]-aldehyde
—— ethyl 3,5-dibromo-4-hydroxybenzyl(methyl)phosphinate 1282618-55-6 C10H13Br2O3P
ethyl 3,5-dibromo-4-hydroxybenzyl(methyl)phosphinate
—— 5-Amino-2,4-dimethoxy-3-methyl-6-prop-2-enylphenol 206766-44-1 C12H17NO3
5-Amino-2,4-dimethoxy-3-methyl-6-prop-2-enylphenol
—— 2,6-dibromo-3,4,5-trichloro-phenol 339364-72-6 C6HBr2Cl3O
2,6-dibromo-3,4,5-trichloro-phenol
—— 2-(3,5-dihydroxyphenyl)-1,3-oxazoline 24207-30-5 C9H9NO3
2-(3,5-dihydroxyphenyl)-1,3-oxazoline
—— 4-[3-[2-(1H-imidazol-5-yl)ethyl-methylamino]butyl]phenol 126376-96-3 C16H23N3O
4-[3-[2-(1H-imidazol-5-yl)ethyl-methylamino]butyl]phenol
—— 4-[3-[ethyl-[2-(1H-imidazol-5-yl)ethyl]amino]butyl]phenol 126376-97-4 C17H25N3O
4-[3-[ethyl-[2-(1H-imidazol-5-yl)ethyl]amino]butyl]phenol
—— 4-[3-[2-(1H-imidazol-5-yl)ethyl-propylamino]butyl]phenol 126376-99-6 C18H27N3O
4-[3-[2-(1H-imidazol-5-yl)ethyl-propylamino]butyl]phenol
—— 3-amino-6-bromo-2-fluoro-4-nitrophenol 1210047-88-3 C6H4BrFN2O3
3-amino-6-bromo-2-fluoro-4-nitrophenol
—— Pentanitro-phenol 322765-69-5 C6HN5O11
Pentanitro-phenol
—— 3,5-bis(diethylphosphonomethyl)phenol 1236355-59-1 C16H28O7P2
3,5-bis(diethylphosphonomethyl)phenol
—— 2,2,7,7,13,13,18,18-Octamethyl-24,26-diazapentacyclo[17.3.1.13,6.18,12.114,17]hexacosa-1(23),3,5,8(25),9,11,14,16,19,21-decaene-10,21-diol 1357909-88-6 C32H38N2O2
2,2,7,7,13,13,18,18-Octamethyl-24,26-diazapentacyclo[17.3.1.13,6.18,12.114,17]hexacosa-1(23),3,5,8(25),9,11,14,16,19,21-decaene-10,21-diol
—— 4-(2-(2-hydroxyphenylamino)thiazol-4-yl)benzene-1,3-diol 1173282-19-3 C15H12N2O3S
4-(2-(2-hydroxyphenylamino)thiazol-4-yl)benzene-1,3-diol