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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
—— (10R,15S)-10-(4-hydroxy-3,5-dimethoxyphenyl)-13-oxa-8-thia-11-azatetracyclo[7.7.0.02,7.011,15]hexadeca-1(9),2,4,6-tetraen-12-one 1379685-83-2 C21H19NO5S
(10R,15S)-10-(4-hydroxy-3,5-dimethoxyphenyl)-13-oxa-8-thia-11-azatetracyclo[7.7.0.02,7.011,15]hexadeca-1(9),2,4,6-tetraen-12-one
—— <i>N</i>,<i>N</i>'-disalicyl-hydrazine 86683-16-1 C14H16N2O2
<i>N</i>,<i>N</i>'-disalicyl-hydrazine
—— p-(2,2-dichloro-3,3-dimethylcyclopropyl)phenol 52178-76-4 C11H12Cl2O
p-(2,2-dichloro-3,3-dimethylcyclopropyl)phenol
—— 4-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 1398414-30-6 C13H19BO3
4-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
—— (E)-5-(2-hydroxyphenyl)pent-2-enyl methyl carbonate 229471-36-7 C13H16O4
(E)-5-(2-hydroxyphenyl)pent-2-enyl methyl carbonate
—— 3-(morpholinomethyl)-6-methylcatechol 54489-06-4 C12H17NO3
3-(morpholinomethyl)-6-methylcatechol
—— m-hydroxybenzaldazine 41097-50-1 C14H12N2O2
m-hydroxybenzaldazine
—— 4-hexadecyl-resorcinol 24305-58-6 C22H38O2
4-hexadecyl-resorcinol
—— 7-(Aminomethyl)bicyclo[4.2.0]octa-1,3,5-trien-3-ol 1132076-55-1 C9H11NO
7-(Aminomethyl)bicyclo[4.2.0]octa-1,3,5-trien-3-ol
—— 4-methoxyphenol-3-sulfonic acid 121000-02-0 C7H8O5S
4-methoxyphenol-3-sulfonic acid
—— methyl 2-(3,5-difluoro-4-hydroxyphenyl)propanoate 1255041-75-8 C10H10F2O3
methyl 2-(3,5-difluoro-4-hydroxyphenyl)propanoate
—— 2,5-bis(4-hydroxyphenylethynyl)thiophene 475560-85-1 C20H12O2S
2,5-bis(4-hydroxyphenylethynyl)thiophene
—— 2,4-dihydroxy-6-methylbenzonitrile 98554-73-5 C8H7NO2
2,4-dihydroxy-6-methylbenzonitrile
—— (3-bromo-5-hydroxyphenyl)acetic acid 934241-94-8 C8H7BrO3
(3-bromo-5-hydroxyphenyl)acetic acid
—— 5,11,17,19-tetrakis(tert-butyl)-24-thiahexacyclo[25.3.1.1<sup>3,7</sup>.1<sup>9,13</sup>.1<sup>15,19</sup>.1<sup>21,25</sup>]tetratriaconta-1(31),3(4),5,7(32),9(10),11,13(33),15(34),16,18,21(25),22,27(28),29-tetradecaene-31,32,33,34-tetraol 256510-66-4 C49H60O4S
5,11,17,19-tetrakis(tert-butyl)-24-thiahexacyclo[25.3.1.1<sup>3,7</sup>.1<sup>9,13</sup>.1<sup>15,19</sup>.1<sup>21,25</sup>]tetratriaconta-1(31),3(4),5,7(32),9(10),11,13(33),15(34),16,18,21(25),22,27(28),29-tetradecaene-31,32,33,34-tetraol
—— 4-methyl-2-(3-phenyl-4,5-dihydro-1H-pyrazol-5-yl)phenol 107095-36-3 C16H16N2O
4-methyl-2-(3-phenyl-4,5-dihydro-1H-pyrazol-5-yl)phenol
—— 10,16,22,28-tetrakis(tert-butyl)-31-thiahexacyclo[24.3.1.1<sup>3,6</sup>.1<sup>8,12</sup>.1<sup>14,18</sup>.1<sup>20,24</sup>]tetratriaconta-1(29),3(4),5,8(9),10,12(32),14(15),16,18(33),20(21),24(34),26(30),27-tetradecaene-30,32,33,34-tetraol 256510-65-3 C49H60O4S
10,16,22,28-tetrakis(tert-butyl)-31-thiahexacyclo[24.3.1.1<sup>3,6</sup>.1<sup>8,12</sup>.1<sup>14,18</sup>.1<sup>20,24</sup>]tetratriaconta-1(29),3(4),5,8(9),10,12(32),14(15),16,18(33),20(21),24(34),26(30),27-tetradecaene-30,32,33,34-tetraol
—— 4-n-Decyl-2-methyl-phenol 110025-88-2 C17H28O
4-n-Decyl-2-methyl-phenol
—— 2-(3-methoxymethoxyprop-1-ynyl)phenol 882507-68-8 C11H12O3
2-(3-methoxymethoxyprop-1-ynyl)phenol
—— 3-(4-Hydroxyphenyl)-2-(1-ethyl-4-pyridinio)-2-propenesulfonate 111260-15-2 C16H17NO4S
3-(4-Hydroxyphenyl)-2-(1-ethyl-4-pyridinio)-2-propenesulfonate
—— 3-(2-Hydroxyphenyl)-2-(1-ethyl-4-pyridinio)-2-propenesulfonate 111260-16-3 C16H17NO4S
3-(2-Hydroxyphenyl)-2-(1-ethyl-4-pyridinio)-2-propenesulfonate
—— N-(2,2-dimethoxyethyl)-2,2,2-trifluoro-N-(2-hydroxybenzyl)acetamide 817160-27-3 C13H16F3NO4
N-(2,2-dimethoxyethyl)-2,2,2-trifluoro-N-(2-hydroxybenzyl)acetamide
—— 3-Chloro-4-ethoxy-5-fluorophenol 1017778-82-3 C8H8ClFO2
3-Chloro-4-ethoxy-5-fluorophenol
—— Salfuride 16915-70-1 C12H7N5O9
Salfuride
—— 3-(2-bromo-5-hydroxy-phenyl)-propionic acid methyl ester 936758-64-4 C10H11BrO3
3-(2-bromo-5-hydroxy-phenyl)-propionic acid methyl ester
—— 3-(3-hydroxy-3-methylbutyl)phenol 189019-50-9 C11H16O2
3-(3-hydroxy-3-methylbutyl)phenol
—— 3-(3-Hydroxy-3-methylbutyl)-2,6-dimethylphenol 189019-54-3 C13H20O2
3-(3-Hydroxy-3-methylbutyl)-2,6-dimethylphenol
—— 4-Bromo-3-(3-hydroxy-3-methylbutyl)phenol 189019-51-0 C11H15BrO2
4-Bromo-3-(3-hydroxy-3-methylbutyl)phenol
—— tert-butyl 3-(5-bromo-2-hydroxyphenyl)-3-hydroxy-2-methylenenpropanoate 548756-58-7 C14H17BrO4
tert-butyl 3-(5-bromo-2-hydroxyphenyl)-3-hydroxy-2-methylenenpropanoate
—— tert-butyl 3-(3,5-dibromo-2-hydroxyphenyl)-3-hydroxy-2-methylenenpropanoate 548756-59-8 C14H16Br2O4
tert-butyl 3-(3,5-dibromo-2-hydroxyphenyl)-3-hydroxy-2-methylenenpropanoate
—— 4-hydroxy-3-isopropenyl-5-nitrobenzonitrile 942216-08-2 C10H8N2O3
4-hydroxy-3-isopropenyl-5-nitrobenzonitrile
—— 4-methyl-3-(methylamino)phenol 6265-13-0 C8H11NO
4-methyl-3-(methylamino)phenol
—— seco-plakortolide N 1266187-49-8 C26H42O5
seco-plakortolide N
—— 3-methyl-2-(2,2,4,4-tetramethyl-1-oxo-1λ<sup>5</sup>-phosphetan-1-yloxy)-phenol 62451-26-7 C14H21O3P
3-methyl-2-(2,2,4,4-tetramethyl-1-oxo-1λ<sup>5</sup>-phosphetan-1-yloxy)-phenol
—— 3-(2,2,2-trifluoroacetylamino)methylphenol 226070-65-1 C9H8F3NO2
3-(2,2,2-trifluoroacetylamino)methylphenol
—— 4-(4'-Hydroxyphenoxy)-methyl-benzoesaeure 254116-46-6 C14H12O4
4-(4'-Hydroxyphenoxy)-methyl-benzoesaeure
—— 4-hydroxy-3-methoxybenzeneacetic acid 8-methylnonyl ester 240110-07-0 C19H30O4
4-hydroxy-3-methoxybenzeneacetic acid 8-methylnonyl ester
—— 2-(cyclohexylmethyl)-hydroquinone 94854-08-7 C13H18O2
2-(cyclohexylmethyl)-hydroquinone
—— (E)-3-(2-bromo-3-hydroxy-4-methoxyphenyl)prop-2-enenitrile 157330-37-5 C10H8BrNO2
(E)-3-(2-bromo-3-hydroxy-4-methoxyphenyl)prop-2-enenitrile
—— AG 974 148741-31-5 C10H5IN2O2
AG 974
—— (E,E)-6-(4-Hydroxyphenyl)-N-(2-methylpropyl)-2,4-hexadienamide 120231-90-5 C16H21NO2
(E,E)-6-(4-Hydroxyphenyl)-N-(2-methylpropyl)-2,4-hexadienamide
—— 4-[(4E)-4-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-methyl-5-oxoimidazol-1-yl]butanoic acid;piperazine 73043-53-5 C36H46N6O10
4-[(4E)-4-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-methyl-5-oxoimidazol-1-yl]butanoic acid;piperazine
—— 1-(4-(2-(Cyclopentylmethoxy)ethyl)phenoxy)-3-isopropylaminopropan-2-ol fumarate 63686-85-1 C44H70N2O10
1-(4-(2-(Cyclopentylmethoxy)ethyl)phenoxy)-3-isopropylaminopropan-2-ol fumarate
—— Phenol diisobutene 84848-74-8 C14H22O
Phenol diisobutene
—— 2-allyl-4-methoxy-3-(methoxymethoxy)phenol 1247734-20-8 C12H16O4
2-allyl-4-methoxy-3-(methoxymethoxy)phenol
—— 3-(Pentadec-7-en-1-yl)phenol 17793-52-1 C21H34O
3-(Pentadec-7-en-1-yl)phenol
—— 4-(tetrahydro-2H-pyran-2-yl)phenol 66123-79-3 C11H14O2
4-(tetrahydro-2H-pyran-2-yl)phenol
—— Phenol, 3-[2-amino-1-[(1-methylethyl)amino]ethyl]- 1780716-28-0 C11H18N2O
Phenol, 3-[2-amino-1-[(1-methylethyl)amino]ethyl]-
—— 2-Pyrrolidinone, 4-[[1-(2-hydroxyphenyl)ethyl]amino]- 1700175-49-0 C12H16N2O2
2-Pyrrolidinone, 4-[[1-(2-hydroxyphenyl)ethyl]amino]-
—— Bis(2,4,6-trichlorophenolato)diimidazolecopper(II) monohydrate 58748-61-1 C18H16Cl6CuN4O3
Bis(2,4,6-trichlorophenolato)diimidazolecopper(II) monohydrate