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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
—— 2-(2-Hydroxy-benzyl)-cyclohexanon 100611-99-2 C13H16O2
2-(2-Hydroxy-benzyl)-cyclohexanon
—— 4-(2-aminohexafluoro-2-propyl)-2,6-dimethylphenol 14355-85-2 C11H11F6NO
4-(2-aminohexafluoro-2-propyl)-2,6-dimethylphenol
—— N-(3-hydroxybenzyl)acetamide 34190-44-8 C9H11NO2
N-(3-hydroxybenzyl)acetamide
—— (R)-3-(4-benzyl-4,5-dihydrooxazol-2-yl)phenol 1072880-54-6 C16H15NO2
(R)-3-(4-benzyl-4,5-dihydrooxazol-2-yl)phenol
—— 3-hydroxy-benzamidine 24722-35-8 C7H8N2O
3-hydroxy-benzamidine
—— 3,3',4,4'-tetrahydroxybenzaldazine 14414-34-7 C14H12N2O4
3,3',4,4'-tetrahydroxybenzaldazine
—— (S)-3-(4-phenyl-4,5-dihydrooxazol-2-yl)phenol 186584-59-8 C15H13NO2
(S)-3-(4-phenyl-4,5-dihydrooxazol-2-yl)phenol
—— (S)-3-(4-benzyl-4,5-dihydrooxazol-2-yl)phenol 1072880-52-4 C16H15NO2
(S)-3-(4-benzyl-4,5-dihydrooxazol-2-yl)phenol
—— 3-hydroxybenzaldoxime 22241-18-5 C7H7NO2
3-hydroxybenzaldoxime
—— 3,6-bis(3-hydroxyphenyl)-1,2,4,5-tetrazine 71123-38-1 C14H10N4O2
3,6-bis(3-hydroxyphenyl)-1,2,4,5-tetrazine
—— 3-Iminomethyl-phenol 61022-59-1 C7H7NO
3-Iminomethyl-phenol
—— o-hydroxyphenyldiazomethane 99557-54-7 C7H6N2O
o-hydroxyphenyldiazomethane
—— 2-(phenylethynyl)cardanol 943753-74-0 C29H40O
2-(phenylethynyl)cardanol
—— sodium 2-(5-chloro-2-fluoro-4-hydroxyphenyl)-2-hydroxyacetate 1169484-20-1 C8H5ClFO4*Na
sodium 2-(5-chloro-2-fluoro-4-hydroxyphenyl)-2-hydroxyacetate
—— 5,11,17,23,29,35,41,47-Octatert-butyl-50,59-dioxaundecacyclo[23.23.12.13,7.19,13.115,19.127,31.133,37.139,43.021,60.045,49.052,57]hexahexaconta-1(48),3,5,7(66),9,11,13(65),15(64),16,18,21,23,25(60),27,29,31(63),33(62),34,36,39(61),40,42,45(49),46,52,54,56-heptacosaene-61,62,63,64,65,66-hexol 176210-45-0 C96H118O8
5,11,17,23,29,35,41,47-Octatert-butyl-50,59-dioxaundecacyclo[23.23.12.13,7.19,13.115,19.127,31.133,37.139,43.021,60.045,49.052,57]hexahexaconta-1(48),3,5,7(66),9,11,13(65),15(64),16,18,21,23,25(60),27,29,31(63),33(62),34,36,39(61),40,42,45(49),46,52,54,56-heptacosaene-61,62,63,64,65,66-hexol
—— 1-(2,4-dihydroxy-phenyl)-2-methoxy-ethanone-imine; hydrochloride 63549-24-6 C9H11NO3*ClH
1-(2,4-dihydroxy-phenyl)-2-methoxy-ethanone-imine; hydrochloride
—— 2,3-dimethoxy-1,6-dihydroxybenzene 13077-75-3 C8H10O4
2,3-dimethoxy-1,6-dihydroxybenzene
—— sawaranospirolide C 128508-30-5 C14H16O7
sawaranospirolide C
—— 5,11,17,23,29,35,41,47-Octatert-butyl-50,58-dioxaundecacyclo[23.23.11.13,7.19,13.115,19.127,31.133,37.139,43.152,56.021,59.045,49]hexahexaconta-1(48),3,5,7(66),9,11,13(65),15(64),16,18,21,23,25(59),27,29,31(63),33(62),34,36,39(61),40,42,45(49),46,52,54,56(60)-heptacosaene-61,62,63,64,65,66-hexol 507488-86-0 C96H118O8
5,11,17,23,29,35,41,47-Octatert-butyl-50,58-dioxaundecacyclo[23.23.11.13,7.19,13.115,19.127,31.133,37.139,43.152,56.021,59.045,49]hexahexaconta-1(48),3,5,7(66),9,11,13(65),15(64),16,18,21,23,25(59),27,29,31(63),33(62),34,36,39(61),40,42,45(49),46,52,54,56(60)-heptacosaene-61,62,63,64,65,66-hexol
—— 5,11,17,23,29,35,41,47-Octatert-butyl-50,57-dioxaundecacyclo[25.21.10.252,55.13,7.19,13.115,19.121,25.133,37.139,43.031,58.045,49]hexahexaconta-1(49),3,5,7(66),9,11,13(65),15(64),16,18,21(63),22,24,27(58),28,30,33,35,37(62),39(61),40,42,45,47,52,54,59-heptacosaene-61,62,63,64,65,66-hexol 176210-43-8 C96H118O8
5,11,17,23,29,35,41,47-Octatert-butyl-50,57-dioxaundecacyclo[25.21.10.252,55.13,7.19,13.115,19.121,25.133,37.139,43.031,58.045,49]hexahexaconta-1(49),3,5,7(66),9,11,13(65),15(64),16,18,21(63),22,24,27(58),28,30,33,35,37(62),39(61),40,42,45,47,52,54,59-heptacosaene-61,62,63,64,65,66-hexol
—— 4-(2-methylthiazol-4-yl)benzene-1,3-diol 1067911-22-1 C10H9NO2S
4-(2-methylthiazol-4-yl)benzene-1,3-diol
—— 5-(2-methyl-4-thiazolyl)-3-nitropyrocatechol hydrobromide 134610-81-4 BrH*C10H8N2O4S
5-(2-methyl-4-thiazolyl)-3-nitropyrocatechol hydrobromide
—— 2-Amino-4-chloro-3,5-dimethyl-phenol hydrochloride 1052530-87-6 C8H11Cl2NO
2-Amino-4-chloro-3,5-dimethyl-phenol hydrochloride
—— Tris-(diaethylamino)-(o-hydroxy-phenyl)-phosphoniumchlorid 18110-22-0 C18H35N3OP*Cl
Tris-(diaethylamino)-(o-hydroxy-phenyl)-phosphoniumchlorid
—— 4-bromophenol-2,6-d<sub>2</sub> 98600-50-1 C6H5BrO
4-bromophenol-2,6-d<sub>2</sub>
—— bis(4-hydroxyphenyl)diethyllsilane 3011-56-1 C16H20O2Si
bis(4-hydroxyphenyl)diethyllsilane
—— 4-(1H,1H,2H,2H-perfluorodecyl)phenol 171182-91-5 C16H9F17O
4-(1H,1H,2H,2H-perfluorodecyl)phenol
—— 2-(cyclohexylmethyl)phenol 5899-19-4 C13H18O
2-(cyclohexylmethyl)phenol
—— tert-butyl 4-(4-hydroxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate 742067-11-4 C16H21NO3
tert-butyl 4-(4-hydroxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate
—— 1-(4-hydroxyphenyl)-2-(4-pyrimidinyl)ethanol 185848-14-0 C12H12N2O2
1-(4-hydroxyphenyl)-2-(4-pyrimidinyl)ethanol
—— 4-(Dimethylboranyl)phenol 885475-27-4 C8H11BO
4-(Dimethylboranyl)phenol
—— 2-(2,2,2-trifluoroethyl)amino-5-nitrophenol 329229-63-2 C8H7F3N2O3
2-(2,2,2-trifluoroethyl)amino-5-nitrophenol
—— 2-Hydroxyphenyl 2-pyridyl disulfide 1227258-47-0 C11H9NOS2
2-Hydroxyphenyl 2-pyridyl disulfide
—— (E)-3-(dimethylamino)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one 89807-39-6 C12H15NO2
(E)-3-(dimethylamino)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one
—— 3-Ethyl-5-methyl-4-aminophenol 112730-54-8 C9H13NO
3-Ethyl-5-methyl-4-aminophenol
—— 6-(4-fluoro-phenyl)-3-(4-hydroxy-3-methoxy-phenyl)-3H-thieno[3,2-d]pyrimidin-4-one 1408284-99-0 C19H13FN2O3S
6-(4-fluoro-phenyl)-3-(4-hydroxy-3-methoxy-phenyl)-3H-thieno[3,2-d]pyrimidin-4-one
—— 2-Bromo-4-(trifluoromethoxy)phenol 200956-13-4 C7H4BrF3O2
2-Bromo-4-(trifluoromethoxy)phenol
—— 4-(2-pyridylazo)resorcinol 113964-55-9 C11H9N3O2
4-(2-pyridylazo)resorcinol
—— (E)-2-(3-hydroxy-4-methoxyphenyl)vinylboronic acid 863479-40-7 C9H11BO4
(E)-2-(3-hydroxy-4-methoxyphenyl)vinylboronic acid
—— 2-bromo-5-hydroxy-4-methoxybenzyl alcohol 655238-34-9 C8H9BrO3
2-bromo-5-hydroxy-4-methoxybenzyl alcohol
—— Phenol;trifluoroborane 462-05-5 C12H12BF3O2
Phenol;trifluoroborane
—— 5-[1-(4-hydroxyphenyl)but-2-yn-1-yl]-2,2-dimethyl-1,3-dioxane-4,6-dione 865233-33-6 C16H16O5
5-[1-(4-hydroxyphenyl)but-2-yn-1-yl]-2,2-dimethyl-1,3-dioxane-4,6-dione
—— 2-Methyl-4-propargyl-phenol 1807-45-0 C10H10O
2-Methyl-4-propargyl-phenol
—— 3-(3-bromopropyl)phenol 1971-83-1 C9H11BrO
3-(3-bromopropyl)phenol
—— 1-(4-hydroxy-3-methoxy-phenyl)-prop-2-yn-1-ol 276884-27-6 C10H10O3
1-(4-hydroxy-3-methoxy-phenyl)-prop-2-yn-1-ol
—— 4,4'-(1,2,4-thiadiazole-3,5-diyl)diphenol 1122660-12-1 C14H10N2O2S
4,4'-(1,2,4-thiadiazole-3,5-diyl)diphenol
—— 2-hydroxy-3-methoxy-5-(pyridin-3-ylethynyl)benzaldehyde 1093119-15-3 C15H11NO3
2-hydroxy-3-methoxy-5-(pyridin-3-ylethynyl)benzaldehyde
—— 5-ethynyl-2-hydroxy-3-methoxybenzaldehyde 1093120-68-3 C10H8O3
5-ethynyl-2-hydroxy-3-methoxybenzaldehyde
—— 4-Nitrocatechol sulfate (dipotassium salt) —— C6H3K2NO7S
4-Nitrocatechol sulfate (dipotassium salt)
—— 6-amino-4-(3-hydroxyphenyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile 89607-42-1 C14H12N4O2
6-amino-4-(3-hydroxyphenyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile