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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
—— 4-chloro-5-fluoro-2,3-dimethylphenol 182011-15-0 C8H8ClFO
4-chloro-5-fluoro-2,3-dimethylphenol
—— (3Z,5E)-6-Dimethylamino-1,1,1-trifluoro-4-(2-hydroxy-4-methyl-phenylamino)-hexa-3,5-dien-2-one 196078-58-7 C15H17F3N2O2
(3Z,5E)-6-Dimethylamino-1,1,1-trifluoro-4-(2-hydroxy-4-methyl-phenylamino)-hexa-3,5-dien-2-one
—— 3-(3-hydroxy-4-methoxyphenyl)propionic acid benzyl ester 182249-52-1 C17H18O4
3-(3-hydroxy-4-methoxyphenyl)propionic acid benzyl ester
—— 5,11,17,23-Tetrabromo-2,8,14,20-tetrakis[4-(methoxymethoxy)butyl]pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol 174358-76-0 C52H68Br4O16
5,11,17,23-Tetrabromo-2,8,14,20-tetrakis[4-(methoxymethoxy)butyl]pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol
—— 3-hexadecyl-1,2-dihydroxybenzene 65216-88-8 C22H38O2
3-hexadecyl-1,2-dihydroxybenzene
—— 2-(3,5-diethyl-4-hydroxyphenyl)-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one 180090-40-8 C16H23NO3S
2-(3,5-diethyl-4-hydroxyphenyl)-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one
—— (R)-1,2,3,6-tetrahydro-4-(4-hydroxyphenyl)-1-{[3-(4-hydroxyphenyl)cyclohexen-1-yl]methyl}pyridine 216884-47-8 C24H27NO2
(R)-1,2,3,6-tetrahydro-4-(4-hydroxyphenyl)-1-{[3-(4-hydroxyphenyl)cyclohexen-1-yl]methyl}pyridine
—— 2-bromo-6-fluoro-3-methoxy-4,5-dimethylphenol 182010-41-9 C9H10BrFO2
2-bromo-6-fluoro-3-methoxy-4,5-dimethylphenol
—— 7,15-Ditert-butyl-3,11,19-trioxatetracyclo[19.3.1.15,9.113,17]heptacosa-1(25),5(27),6,8,13,15,17(26),21,23-nonaene-25,26,27-triol 206879-33-6 C32H40O6
7,15-Ditert-butyl-3,11,19-trioxatetracyclo[19.3.1.15,9.113,17]heptacosa-1(25),5(27),6,8,13,15,17(26),21,23-nonaene-25,26,27-triol
—— 2-Heptadecyl-4-methoxy-phenol 148665-84-3 C24H42O2
2-Heptadecyl-4-methoxy-phenol
—— 7-Bromo-15,23-ditert-butyl-3,11,19-trioxatetracyclo[19.3.1.15,9.113,17]heptacosa-1(24),5,7,9(27),13,15,17(26),21(25),22-nonaene-25,26,27-triol 206879-53-0 C32H39BrO6
7-Bromo-15,23-ditert-butyl-3,11,19-trioxatetracyclo[19.3.1.15,9.113,17]heptacosa-1(24),5,7,9(27),13,15,17(26),21(25),22-nonaene-25,26,27-triol
—— 2-(4-hydroxyphenyl)-3-(3-chloropropyl)-1,3-thiazolidin-4-one 180090-53-3 C12H14ClNO2S
2-(4-hydroxyphenyl)-3-(3-chloropropyl)-1,3-thiazolidin-4-one
—— 3,5-Dimethoxy-4-allylphenol 159427-01-7 C11H14O3
3,5-Dimethoxy-4-allylphenol
—— 5,11,17,23-tetrakis(1,1-dimethylundecyl)-25,26,27,28-tetrahydroxycalix[4]arene 189506-76-1 C80H128O4
5,11,17,23-tetrakis(1,1-dimethylundecyl)-25,26,27,28-tetrahydroxycalix[4]arene
—— 4-Chloro-2-hydroxy-5-(tetrahydro-pyran-2-yloxy)-benzonitrile 184766-73-2 C12H12ClNO3
4-Chloro-2-hydroxy-5-(tetrahydro-pyran-2-yloxy)-benzonitrile
—— 1-[(E)-2-(4-chlorophenyl)ethenyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]thiourea 184003-09-6 C17H17ClN2O2S
1-[(E)-2-(4-chlorophenyl)ethenyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]thiourea
—— 5-bromo-13-tert-butyl-8,16-dihydroxy[2.2]metacyclophane 201354-80-5 C20H23BrO2
5-bromo-13-tert-butyl-8,16-dihydroxy[2.2]metacyclophane
—— 2-Heptadecyl-5-methoxy-phenol 148665-83-2 C24H42O2
2-Heptadecyl-5-methoxy-phenol
—— 2,3,5,6-Tetrachloro-4-[(4-methoxyphenyl)-trimethylsilylmethoxy]phenol 172796-88-2 C17H18Cl4O3Si
2,3,5,6-Tetrachloro-4-[(4-methoxyphenyl)-trimethylsilylmethoxy]phenol
—— 2-Allyl-6-chloro-3-methoxy-4,5-dimethyl-phenol 1027205-05-5 C12H15ClO2
2-Allyl-6-chloro-3-methoxy-4,5-dimethyl-phenol
—— 5-{Hydroxy-[6-methoxy-2-(3,4,5-trimethoxy-phenyl)-benzo[b]thiophen-3-yl]-methyl}-2-methoxy-phenol 334708-29-1 C26H26O7S
5-{Hydroxy-[6-methoxy-2-(3,4,5-trimethoxy-phenyl)-benzo[b]thiophen-3-yl]-methyl}-2-methoxy-phenol
—— N-(5-bromo-2-hydroxy-3-methoxyphenyl)formamide 198280-96-5 C8H8BrNO3
N-(5-bromo-2-hydroxy-3-methoxyphenyl)formamide
—— Ethyl 2-(5-bromo-2-hydroxyphenyl)acetate 220801-65-0 C10H11BrO3
Ethyl 2-(5-bromo-2-hydroxyphenyl)acetate
—— 4,5-Dimethoxy-2-propylsulfanylmethyl-phenol 179630-60-5 C12H18O3S
4,5-Dimethoxy-2-propylsulfanylmethyl-phenol
—— 2-(3,5-dimethyl-4-hydroxyphenyl)-3-(3-chloropropyl)-1,3-thiazolidin-4-one 180090-54-4 C14H18ClNO2S
2-(3,5-dimethyl-4-hydroxyphenyl)-3-(3-chloropropyl)-1,3-thiazolidin-4-one
—— N-o-hydroxybenzyl-N-isopropylhydroxylamine 180265-67-2 C10H15NO2
N-o-hydroxybenzyl-N-isopropylhydroxylamine
—— 3-(1,4,5,6-Tetrahydropyrimidin-2-yl)phenol 848850-63-5 C10H12N2O
3-(1,4,5,6-Tetrahydropyrimidin-2-yl)phenol
—— (Z)-4-(5-Chloro-2-hydroxy-phenylamino)-1,1,1-trifluoro-pent-3-en-2-one 196078-53-2 C11H9ClF3NO2
(Z)-4-(5-Chloro-2-hydroxy-phenylamino)-1,1,1-trifluoro-pent-3-en-2-one
—— (3Z,5E)-6-Dimethylamino-1,1,1-trifluoro-4-(2-hydroxy-5-methyl-phenylamino)-hexa-3,5-dien-2-one 196078-57-6 C15H17F3N2O2
(3Z,5E)-6-Dimethylamino-1,1,1-trifluoro-4-(2-hydroxy-5-methyl-phenylamino)-hexa-3,5-dien-2-one
—— Phenol, 2-(1,2-dihydro-4,6-diphenyl-1,3,5-triazin-2-yl)-5-methoxy- 163392-76-5 C22H19N3O2
Phenol, 2-(1,2-dihydro-4,6-diphenyl-1,3,5-triazin-2-yl)-5-methoxy-
—— N-benzyl-3-(4-hydroxy-3-methoxyphenyl)-propionamide 391609-32-8 C17H19NO3
N-benzyl-3-(4-hydroxy-3-methoxyphenyl)-propionamide
—— 2-chloro-3-methoxy-5-methylphenol 57074-22-3 C8H9ClO2
2-chloro-3-methoxy-5-methylphenol
—— tri(propan-2-yl)silyl N-[3-(4-hydroxy-3-methoxyphenyl)propyl]carbamate 391609-23-7 C20H35NO4Si
tri(propan-2-yl)silyl N-[3-(4-hydroxy-3-methoxyphenyl)propyl]carbamate
—— (1S,5S)-1-[2-(2-bromo-3-hydroxy-4-methoxyphenyl)ethyl]-2-[2-(4-methoxyphenoxy)ethyl]-6-oxabicyclo[3.2.1]oct-2-en-7-one 213390-20-6 C25H27BrO6
(1S,5S)-1-[2-(2-bromo-3-hydroxy-4-methoxyphenyl)ethyl]-2-[2-(4-methoxyphenoxy)ethyl]-6-oxabicyclo[3.2.1]oct-2-en-7-one
—— 2-Chloro-6-(2-hydroxyethyl)-4-methoxyphenol 359844-43-2 C9H11ClO3
2-Chloro-6-(2-hydroxyethyl)-4-methoxyphenol
—— [2-13C]-2-chloro-3-methoxy-5-methylphenol 426835-16-7 C8H9ClO2
[2-13C]-2-chloro-3-methoxy-5-methylphenol
—— isoplagiochin C 872607-47-1 C28H22O4
isoplagiochin C
—— 4,5-dimethoxy-2-[(E)-6-(4-nitrophenyl)hex-5-en-2-yl]phenol 143653-81-0 C20H23NO5
4,5-dimethoxy-2-[(E)-6-(4-nitrophenyl)hex-5-en-2-yl]phenol
—— 6-mercaptodopamine 72515-46-9 C8H11NO2S
6-mercaptodopamine
—— (R)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodecan-3-one 135272-33-2 C19H30O4
(R)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodecan-3-one
—— 2'-hydroxy-4',6'-dimethoxy-ω-cinnamylidene acetophenone 223502-94-1 C19H18O4
2'-hydroxy-4',6'-dimethoxy-ω-cinnamylidene acetophenone
—— 4-hydroxybenzocyclobutene 145967-35-7 C8H6O
4-hydroxybenzocyclobutene
—— 6-(cyclohexylmethyl)-2-methoxyphenol 586963-56-6 C14H20O2
6-(cyclohexylmethyl)-2-methoxyphenol
—— Tert-butyl-[2-[4,5-dimethoxy-2-(3-methylbutoxy)-1,3-benzodithiol-7-yl]ethoxy]-diphenylsilane 149625-07-0 C32H42O4S2Si
Tert-butyl-[2-[4,5-dimethoxy-2-(3-methylbutoxy)-1,3-benzodithiol-7-yl]ethoxy]-diphenylsilane
—— N-Acetyl-N-(phenylmethyl)-6-(3,5-dimethyl-4-hydroxyphenyl)hex-1-enamine 149777-43-5 C23H29NO2
N-Acetyl-N-(phenylmethyl)-6-(3,5-dimethyl-4-hydroxyphenyl)hex-1-enamine
—— 2-tert-butyl-4-(2-methoxyethyl)phenol 206059-20-3 C13H20O2
2-tert-butyl-4-(2-methoxyethyl)phenol
—— 5-[(E)-4-(4-Dimethylamino-phenyl)-but-1-en-3-ynyl]-2-nitro-phenol 193957-49-2 C18H16N2O3
5-[(E)-4-(4-Dimethylamino-phenyl)-but-1-en-3-ynyl]-2-nitro-phenol
—— 15,35,55,75-Tetrakis(chloromethyl)-2,4,6,8-tetrathia-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-12,32,52,72-tetraol 244087-92-1 C28H20Cl4O4S4
15,35,55,75-Tetrakis(chloromethyl)-2,4,6,8-tetrathia-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-12,32,52,72-tetraol
—— 2-[1-(4-Hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-butane-1,4-diol 186411-99-4 C12H16O4
2-[1-(4-Hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-butane-1,4-diol
—— 2-[2,2-Difluoro-1-((E)-3-trimethylsilanyl-allyloxy)-vinyl]-phenol 1026388-95-3 C14H18F2O2Si
2-[2,2-Difluoro-1-((E)-3-trimethylsilanyl-allyloxy)-vinyl]-phenol