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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
—— (3E,5E)-3,5-bis(3-hydroxybenzylidene)-tetrahydropyran-4-one —— C19H16O4
(3E,5E)-3,5-bis(3-hydroxybenzylidene)-tetrahydropyran-4-one
—— 2-(3-hydroxyphenyl)-2-morpholinoacetonitrile —— C12H14N2O2
2-(3-hydroxyphenyl)-2-morpholinoacetonitrile
—— 3,5-diacetyl-4-(3-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine —— C17H19NO3
3,5-diacetyl-4-(3-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine
—— 2-(4-chlorophenyl)-5-(4-hydroxy-3-methoxyphenyl)furo[3,2-c]pyridin-4(5H)-one —— C20H14ClNO4
2-(4-chlorophenyl)-5-(4-hydroxy-3-methoxyphenyl)furo[3,2-c]pyridin-4(5H)-one
—— (E)-3-((3-mercapto-5-(pyrazin-2-yl)-4H-1,2,4-triazol-4-ylimino)methyl)phenol 1528690-47-2 C13H10N6OS
(E)-3-((3-mercapto-5-(pyrazin-2-yl)-4H-1,2,4-triazol-4-ylimino)methyl)phenol
—— (3-hydroxyphenyl)methylene-2-thioxo-4-thiazolidinone —— C10H7NO2S2
(3-hydroxyphenyl)methylene-2-thioxo-4-thiazolidinone
—— 1-amino-1,2-dicyano-2-(3'-hydroxibenzilidenamine)ethene —— C11H8N4O
1-amino-1,2-dicyano-2-(3'-hydroxibenzilidenamine)ethene
—— 2-amino-4-(3-hydroxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile —— C18H18N2O3
2-amino-4-(3-hydroxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
—— 1,4-bis(3-phenol)-2,3-diaza-1,3-butadiene —— C14H12N2O2
1,4-bis(3-phenol)-2,3-diaza-1,3-butadiene
—— (S)-1-(3-hydroxyphenyl)-2-nitroethanol —— C8H9NO4
(S)-1-(3-hydroxyphenyl)-2-nitroethanol
—— 4-methyl-2-((5-methyl-1,3,4-thiadiazolylamino)methyl)phenol —— C11H13N3OS
4-methyl-2-((5-methyl-1,3,4-thiadiazolylamino)methyl)phenol
—— 2-tert-butylsulfenyl-6-methylphenol —— C11H16OS
2-tert-butylsulfenyl-6-methylphenol
—— 2-methyl-6-((5-methyl-1,3,4-thiadiazolylamino)methyl)phenol —— C11H13N3OS
2-methyl-6-((5-methyl-1,3,4-thiadiazolylamino)methyl)phenol
—— 4-hydroxy-3-methoxy-benzoic acid-(2-nitro-benzylidenehydrazide) —— C15H13N3O5
4-hydroxy-3-methoxy-benzoic acid-(2-nitro-benzylidenehydrazide)
—— (+/-)-dibenzyl [hydroxy(3-hydroxyphenyl)methyl]phosphonate —— C21H21O5P
(+/-)-dibenzyl [hydroxy(3-hydroxyphenyl)methyl]phosphonate
—— 2-(4-hydroxy-2-methoxyphenyl)-1,3-dithiolane —— C10H12O2S2
2-(4-hydroxy-2-methoxyphenyl)-1,3-dithiolane
—— 3-iodo-5-methylphenol —— C7H7IO
3-iodo-5-methylphenol
—— 5,28-di-tert-butyl-11,22,34,45-tetramethyl-15,18,38,41-tetrathiaheptacyclo[41.3.1.1<sup>3,7</sup>.1<sup>9,13</sup>.1<sup>20,24</sup>.1<sup>26,30</sup>.1<sup>32,36</sup>]dopentaconta-1(46),3(48),4,6,9(49),10,12,20(50),21,23,25(51),27,29,32(52),33,35,43(47),44-octadecaene-47,48,49,50,51,52-hexaol —— C60H72O6S4
5,28-di-tert-butyl-11,22,34,45-tetramethyl-15,18,38,41-tetrathiaheptacyclo[41.3.1.1<sup>3,7</sup>.1<sup>9,13</sup>.1<sup>20,24</sup>.1<sup>26,30</sup>.1<sup>32,36</sup>]dopentaconta-1(46),3(48),4,6,9(49),10,12,20(50),21,23,25(51),27,29,32(52),33,35,43(47),44-octadecaene-47,48,49,50,51,52-hexaol
—— 3,5-dibromo-2-methyl-hydroquinone —— C7H6Br2O2
3,5-dibromo-2-methyl-hydroquinone
—— 5,11,22,28,34,45-hexamethyl-15,18,38,41-tetrathiaheptacyclo[41.3.1.1<sup>3,7</sup>.1<sup>9,13</sup>.1<sup>20,24</sup>.1<sup>26,30</sup>.1<sup>32,36</sup>]dopentaconta-1(46),3(48),4,6,9(49),10,12,20(50),21,23,25(51),27,29,32(52),33,35,43(47),44-octadecaene-47,48,49,50,51,52-hexaol —— C54H60O6S4
5,11,22,28,34,45-hexamethyl-15,18,38,41-tetrathiaheptacyclo[41.3.1.1<sup>3,7</sup>.1<sup>9,13</sup>.1<sup>20,24</sup>.1<sup>26,30</sup>.1<sup>32,36</sup>]dopentaconta-1(46),3(48),4,6,9(49),10,12,20(50),21,23,25(51),27,29,32(52),33,35,43(47),44-octadecaene-47,48,49,50,51,52-hexaol
—— 5,11,22,28,34,45-hexa-tert-butyl-15,18,38,41-tetrathiaheptacyclo[41.3.1.1<sup>3,7</sup>.1<sup>9,13</sup>.1<sup>20,24</sup>.1<sup>26,30</sup>.1<sup>32,36</sup>]dopentaconta-1(46),3(48),4,6,9(49),10,12,20(50),21,23,25(51),27,29,32(52),33,35,43(47),44-octadecaene-47,48,49,50,51,52-hexaol —— C72H96O6S4
5,11,22,28,34,45-hexa-tert-butyl-15,18,38,41-tetrathiaheptacyclo[41.3.1.1<sup>3,7</sup>.1<sup>9,13</sup>.1<sup>20,24</sup>.1<sup>26,30</sup>.1<sup>32,36</sup>]dopentaconta-1(46),3(48),4,6,9(49),10,12,20(50),21,23,25(51),27,29,32(52),33,35,43(47),44-octadecaene-47,48,49,50,51,52-hexaol
—— 4-(1,3-dithiolan-2-yl)benzene-1,3-diol —— C9H10O2S2
4-(1,3-dithiolan-2-yl)benzene-1,3-diol
—— 2-{[ethyl(methyl)amino]methyl}-4-methoxyphenol —— C11H17NO2
2-{[ethyl(methyl)amino]methyl}-4-methoxyphenol
—— 3-(2-hydroxy-5-bromobenzyl)-1,5,9-triazacyclododecane —— C16H26BrN3O
3-(2-hydroxy-5-bromobenzyl)-1,5,9-triazacyclododecane
—— 3-[1-(methylethylamino)ethyl]phenol —— C11H17NO
3-[1-(methylethylamino)ethyl]phenol
—— 2,2'-(1E,1'E)-(2,2'-azanediylbis(ethane-1,2-diyl)bis(azan-1-yl-1-ylidene))bis(methan-1-yl-1-ylidene)bis(4-chlorophenol) —— C18H19Cl2N3O2
2,2'-(1E,1'E)-(2,2'-azanediylbis(ethane-1,2-diyl)bis(azan-1-yl-1-ylidene))bis(methan-1-yl-1-ylidene)bis(4-chlorophenol)
—— 3-(cyclopentyloxy)-4-methoxyphenol —— C12H16O3
3-(cyclopentyloxy)-4-methoxyphenol
—— 2,2’-((1E,1’E)-((azanediylbis(ethane-2,1-diyl))bis(azanylylidene))bis(methanylylidene))diphenol —— C18H21N3O2
2,2’-((1E,1’E)-((azanediylbis(ethane-2,1-diyl))bis(azanylylidene))bis(methanylylidene))diphenol
—— 2,8,14,20-tetrahexylpentacyclo[19.3.1.1<sup>3,7</sup>,1<sup>9,13</sup>,1<sup>15,19</sup>]octacosa-1(25),3,7(28),9,13(27),15,19(26),21-dodecane-5,11,17,23-tetrachloro-4,6,10,12,16,18,22,24-octol —— C52H68Cl4O8
2,8,14,20-tetrahexylpentacyclo[19.3.1.1<sup>3,7</sup>,1<sup>9,13</sup>,1<sup>15,19</sup>]octacosa-1(25),3,7(28),9,13(27),15,19(26),21-dodecane-5,11,17,23-tetrachloro-4,6,10,12,16,18,22,24-octol
—— tert-butyl (2-hydroxybenzyl)(methyl)carbamate 1487444-34-7 C13H19NO3
tert-butyl (2-hydroxybenzyl)(methyl)carbamate
—— 4-hydroxy-3-methoxy-benzoic acid-(3-nitro-benzylidenehydrazide) —— C15H13N3O5
4-hydroxy-3-methoxy-benzoic acid-(3-nitro-benzylidenehydrazide)
—— 2-[2,2,2-trichloro-1-(methylamino)ethyl]phenol —— C9H10Cl3NO
2-[2,2,2-trichloro-1-(methylamino)ethyl]phenol
—— 4-[(1-pentylsulfanyl)methyl]-1,2-benzenediol —— C12H18O2S
4-[(1-pentylsulfanyl)methyl]-1,2-benzenediol
—— 2-(bis(pentylthio)methyl)phenol —— C17H28OS2
2-(bis(pentylthio)methyl)phenol
—— 5-fluoro-2-methyl-4-nitrophenol —— C7H6FNO3
5-fluoro-2-methyl-4-nitrophenol
—— 2-(3,3-dichloro-1-methyl-allyl)-phenol —— C10H10Cl2O
2-(3,3-dichloro-1-methyl-allyl)-phenol
—— (p-hydroxyphenyl)dimethylsulfonium perchlorate —— C8H11OS*ClO4
(p-hydroxyphenyl)dimethylsulfonium perchlorate
—— 2-methoxy-6-phenylsulfonyl-1,4-hydroquinone —— C13H12O5S
2-methoxy-6-phenylsulfonyl-1,4-hydroquinone
—— 3-methoxy-5-(phenylsulfonyl)benzene-1,2-diol —— C13H12O5S
3-methoxy-5-(phenylsulfonyl)benzene-1,2-diol
—— 2-methoxy-5-phenylsulfonyl-1,4-hydroquinone —— C13H12O5S
2-methoxy-5-phenylsulfonyl-1,4-hydroquinone
—— 5-[(3,4-dihydroxy-5-nitrophenyl)methylidene]-3-methyl-2-thioxothiazolidin-4-one —— C11H8N2O5S2
5-[(3,4-dihydroxy-5-nitrophenyl)methylidene]-3-methyl-2-thioxothiazolidin-4-one
—— 5-(3,4-dihydroxy-5-nitrobenzylidene)3-ethylthiazolidine-2,4-dione —— C12H10N2O6S
5-(3,4-dihydroxy-5-nitrobenzylidene)3-ethylthiazolidine-2,4-dione
—— 4-(6-chlorohexyloxy)-2,3,6-trimethylphenol —— C15H23ClO2
4-(6-chlorohexyloxy)-2,3,6-trimethylphenol
—— 4-(10-chlorodecyloxy)-2,3,6-trimethylphenol —— C19H31ClO2
4-(10-chlorodecyloxy)-2,3,6-trimethylphenol
—— 4-(4-chlorobutoxy)-2,3,6-trimethylphenol —— C13H19ClO2
4-(4-chlorobutoxy)-2,3,6-trimethylphenol
—— 4-(8-bromooctyloxy)-2,3,6-trimethylphenol —— C17H27BrO2
4-(8-bromooctyloxy)-2,3,6-trimethylphenol
—— 4-(((4-iodo-2,5-dimethoxyphenethyl)amino)methyl)-3-methoxyphenol 1800475-17-5 C18H22INO4
4-(((4-iodo-2,5-dimethoxyphenethyl)amino)methyl)-3-methoxyphenol
—— N-(p-hydroxybenzylidene)-m-hydroxyaniline —— C13H11NO2
N-(p-hydroxybenzylidene)-m-hydroxyaniline
—— (E)-2-(((3-hydroxyphenyl)imino)methyl)-4-nitrophenol —— C13H10N2O4
(E)-2-(((3-hydroxyphenyl)imino)methyl)-4-nitrophenol
—— 2-chloro-N-(3-hydroxyphenyl)isonicotinamidine —— C12H10ClN3O
2-chloro-N-(3-hydroxyphenyl)isonicotinamidine