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内酯类

内酯类化合物是一类含有环状结构的化合物,通常通过一个碳氧双键将两个羟基连接在一个四元、五元或六元的内环中形成。这类化合物广泛存在于自然界中,并且在有机化学、化学化工以及生物医药领域有着重要的应用价值。

内酯的分类
  1. 按环大小划分:根据内酯环的大小,可以将其分为四元、五元和六元内酯。
  2. 按碳原子数划分:依据组成内酯的碳原子数量不同,可进一步划分为二、三、四等碳链长度不同的内酯。
结构特征
  • 内酯结构中通常包含一个或多个环状氧基团。其独特的环状结构使得它们在水溶液中能够以开环形式存在。
  • 在生物体内,某些内酯通过酶的催化作用可实现快速转化,在药物设计和研究领域具有重要应用价值。
应用
  1. 医药领域:许多抗生素、抗真菌药及抗癌药物都含有内酯结构。例如,四环素类抗生素就含有五元或六元内酯。
  2. 工业化学:内酯作为重要的化工原料,在合成树脂、塑料和涂料等领域有着广泛应用。
  3. 分析化学与生物传感器:利用内酯的可逆开环性质进行分析检测;通过构建特定识别分子对提高生物传感系统的特异性。
生物活性
  • 内酯化合物通常具有一定的药理活性,如抗炎、抗菌等作用。这与其独特的空间构象和极性有关。
  • 在细胞信号传导过程中,内酯的环开裂或闭合可以影响特定蛋白质之间的相互作用。

总之,内酯作为一种重要的化学结构单元,在多个领域发挥着不可替代的作用。

中文名称 英文名称 CAS号 化学式 结构式图片
—— β-bromo-γ-hydroxy-α-oxo-isovaleric acid-lactone 408319-86-8 C5H5BrO3
β-bromo-γ-hydroxy-α-oxo-isovaleric acid-lactone
—— 1,4-Monolacton d.D-Taloschleimsaeure-methylesters —— C7H10O7
1,4-Monolacton d.D-Taloschleimsaeure-methylesters
—— 2H-Pyran-2-one, 4-(3,5-dimethyl-4-isoxazolyl)tetrahydro- 1552231-29-4 C10H13NO3
2H-Pyran-2-one, 4-(3,5-dimethyl-4-isoxazolyl)tetrahydro-
—— 6-methyl-2-oxo-9-prop-1-en-2-yl-1-oxaspiro[4.4]nonane-3-carbaldehyde 145397-93-9 C13H18O3
6-methyl-2-oxo-9-prop-1-en-2-yl-1-oxaspiro[4.4]nonane-3-carbaldehyde
—— tert-butyl (1R,2S,5S)-7-oxo-6-oxabicyclo[3.2.1]oct-3-en-2-ylcarbamate 1334880-42-0 C12H17NO4
tert-butyl (1R,2S,5S)-7-oxo-6-oxabicyclo[3.2.1]oct-3-en-2-ylcarbamate
—— tert-butyl (1S,2S,5R)-7-oxo-6-oxabicyclo[3.2.1]oct-3-en-2-ylcarbamate 1334880-46-4 C12H17NO4
tert-butyl (1S,2S,5R)-7-oxo-6-oxabicyclo[3.2.1]oct-3-en-2-ylcarbamate
—— 3-Furancarboxaldehyde, tetrahydro-2-(2-methylenecyclopentyl)-5-oxo- 1824578-69-9 C11H14O3
3-Furancarboxaldehyde, tetrahydro-2-(2-methylenecyclopentyl)-5-oxo-
—— (4R)-4-methyltetrahydro-2H-pyran-2-one 61898-55-3 C6H10O2
(4R)-4-methyltetrahydro-2H-pyran-2-one
—— (+/-)-6,9-divinyl-1-oxaspiro[4.4]nonan-2-one 133620-22-1 C12H16O2
(+/-)-6,9-divinyl-1-oxaspiro[4.4]nonan-2-one
—— 5-Oxo-tetrahydro-furan-3-carboxylic acid tert-butyl ester 198995-92-5 C9H14O4
5-Oxo-tetrahydro-furan-3-carboxylic acid tert-butyl ester
—— 2-oxabicyclo[3.3.1]nonan-3-one 6051-04-3 C8H12O2
2-oxabicyclo[3.3.1]nonan-3-one
—— tetrahydro-3,3,6-trimethyl-2H-pyran-2-one 62581-36-6 C8H14O2
tetrahydro-3,3,6-trimethyl-2H-pyran-2-one
—— (3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]dihydro-3-methyl-2(3H)-furanone 326889-47-8 C11H22O3Si
(3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]dihydro-3-methyl-2(3H)-furanone
—— 2(3H)-Furanone, 5-(6-hepten-1-yl)dihydro- 854737-08-9 C11H18O2
2(3H)-Furanone, 5-(6-hepten-1-yl)dihydro-
—— (3S,4S)-dihydro-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3-methyl-2(3H)-furanone 1141365-67-4 C23H30O3Si
(3S,4S)-dihydro-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3-methyl-2(3H)-furanone
—— acide ethyl-2 methyl-5 δ-caprolactone-2 carboxylique 92215-62-8 C10H16O4
acide ethyl-2 methyl-5 δ-caprolactone-2 carboxylique
—— 3-Decyl-4-undecyl-oxetan-2-one 872631-20-4 C24H46O2
3-Decyl-4-undecyl-oxetan-2-one
—— 6,6-dimethyl-4(R)-tribromomethyl-3-oxa-bicyclo(3,1,0)hexan-2-one 72345-90-5 C8H9Br3O2
6,6-dimethyl-4(R)-tribromomethyl-3-oxa-bicyclo(3,1,0)hexan-2-one
—— α-[hydroxy(5-norbornen-2-yl)methyl]-γ-butyrolactone 398488-19-2 C12H16O3
α-[hydroxy(5-norbornen-2-yl)methyl]-γ-butyrolactone
—— 6,6-dimethyl-4-trichloromethyl-3-oxa-bicyclo(3,1,0)-hexane-2-one 72345-89-2 C8H9Cl3O2
6,6-dimethyl-4-trichloromethyl-3-oxa-bicyclo(3,1,0)-hexane-2-one
—— 4-acetyl-5-methyl-dihydro-furan-2-one 89898-27-1 C7H10O3
4-acetyl-5-methyl-dihydro-furan-2-one
—— α-hydroxy-γ-butyrolactone-D<sub>2</sub> 1597493-79-2 C4H6O3
α-hydroxy-γ-butyrolactone-D<sub>2</sub>
—— cis-5-ethyl-3-hydroxydihydrofuran-2(3H)-one 81644-93-1 C6H10O3
cis-5-ethyl-3-hydroxydihydrofuran-2(3H)-one
—— dihydro-3-<<(methylsulfonyl)oxy>methylene>-2(3H)-furanone 113982-63-1 C6H8O5S
dihydro-3-<<(methylsulfonyl)oxy>methylene>-2(3H)-furanone
—— (trans,4R,5R,8R,9S)-9-mesyloxy-5,8-oxisotricos-12-en-1,4-olide 303053-19-2 C24H42O6S
(trans,4R,5R,8R,9S)-9-mesyloxy-5,8-oxisotricos-12-en-1,4-olide
—— (4R,5R,8R,9S,12R,13S)-12,13-dihydroxy-9-mesyloxy-5,8-oxidotricosa-1,4-olide 303052-91-7 C24H44O8S
(4R,5R,8R,9S,12R,13S)-12,13-dihydroxy-9-mesyloxy-5,8-oxidotricosa-1,4-olide
—— (4R,5R,8R,9S,12R,13R)-12,13-dihydroxy-9-mesyloxy-5,8-oxidotricosa-1,4-olide 172667-73-1 C24H44O8S
(4R,5R,8R,9S,12R,13R)-12,13-dihydroxy-9-mesyloxy-5,8-oxidotricosa-1,4-olide
—— (4R,5R)-8-hydroxy-5-(tert-butyldiphenylsilyloxy)octan-1,4-olide 303053-15-8 C24H32O4Si
(4R,5R)-8-hydroxy-5-(tert-butyldiphenylsilyloxy)octan-1,4-olide
—— (cis,trans,4R,5R)-5-tert-butyldiphenylsilyloxytricosa-8,12-dien-1,4-olide 303053-18-1 C39H58O3Si
(cis,trans,4R,5R)-5-tert-butyldiphenylsilyloxytricosa-8,12-dien-1,4-olide
—— (4R,5R)-tert-butyldiphenylsilyloxyoctan-1-al-5,8-olide 181803-16-7 C24H30O4Si
(4R,5R)-tert-butyldiphenylsilyloxyoctan-1-al-5,8-olide
—— 3-methyl-3-trimethylsilyloxyglutaric anhydride 81943-18-2 C9H16O4Si
3-methyl-3-trimethylsilyloxyglutaric anhydride
—— 5-(azidomethyl)dihydrofuran-2(3H)-one 179532-81-1 C5H7N3O2
5-(azidomethyl)dihydrofuran-2(3H)-one
—— 7-deoxy-L-glycero-L-galacto-heptono-1,4-lactone 161721-52-4 C7H12O6
7-deoxy-L-glycero-L-galacto-heptono-1,4-lactone
—— 1-oxaspiro[4.4]nonan-2-one 33448-80-5 C8H12O2
1-oxaspiro[4.4]nonan-2-one
—— L-Rhamnono-1,4-lactone 20031-16-7 C6H10O5
L-Rhamnono-1,4-lactone
—— cis-1,2-cyclopropanedicarboxylic acid anhydride 5617-74-3 C5H4O3
cis-1,2-cyclopropanedicarboxylic acid anhydride
—— (-)-7α-triethylsilyloxy-6β-triethylsilyloxymethyl-cis-2-oxabicyclo<3.3.0>octan-3-one 128948-09-4 C20H40O4Si2
(-)-7α-triethylsilyloxy-6β-triethylsilyloxymethyl-cis-2-oxabicyclo<3.3.0>octan-3-one
—— (-)-7α-triethylsilyloxy-6β-formyl-cis-2-oxabicyclo<3.3.0>octan-3-one 128948-10-7 C14H24O4Si
(-)-7α-triethylsilyloxy-6β-formyl-cis-2-oxabicyclo<3.3.0>octan-3-one
—— (3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((S,E)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one 1240483-15-1 C30H50O4Si2
(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((S,E)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one
—— (+/-)-5-oxo-2<i>c</i>-phenyl-tetrahydro-furan-3<i>r</i>-carboxylic acid 13389-88-3 C11H10O4
(+/-)-5-oxo-2<i>c</i>-phenyl-tetrahydro-furan-3<i>r</i>-carboxylic acid
—— 3-benzyl-glutaric acid-anhydride 91963-19-8 C12H12O3
3-benzyl-glutaric acid-anhydride
—— 4-Fluoro-5-phenyloxolan-2-one 1167421-95-5 C10H9FO2
4-Fluoro-5-phenyloxolan-2-one
—— (+/-)-5-oxo-2<i>r</i>-phenyl-tetrahydro-furan-3<i>t</i>-carboxylic acid 13389-88-3 C11H10O4
(+/-)-5-oxo-2<i>r</i>-phenyl-tetrahydro-furan-3<i>t</i>-carboxylic acid
—— 6-cyclopropylidene-5-oxaspiro<2.3>hexan-4-one 123674-87-3 C8H8O2
6-cyclopropylidene-5-oxaspiro<2.3>hexan-4-one
—— 5-oxo-2-trichloromethyl-tetrahydro-furan-3-carboxylic acid 5910-08-7 C6H5Cl3O4
5-oxo-2-trichloromethyl-tetrahydro-furan-3-carboxylic acid
—— 5,6-dihydro-2H-pyran-2,4-dione 33532-46-6 C5H6O3
5,6-dihydro-2H-pyran-2,4-dione
—— (S)-mevalonolactone 19022-60-7 C6H10O3
(S)-mevalonolactone
—— 5-hydroxy-4-propyldihydrofuran-2-one 357338-44-4 C7H12O3
5-hydroxy-4-propyldihydrofuran-2-one
—— ethyl (1S,5R)-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate 145032-58-2 C8H10O4
ethyl (1S,5R)-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate
—— (R)-4-allyldihydrofuran-2(3H)-one 80758-91-4 C7H10O2
(R)-4-allyldihydrofuran-2(3H)-one