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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
—— (6S)-6-(bromomethyl)-5-oxaspiro[2.4]heptan-4-one —— C7H9BrO2
(6S)-6-(bromomethyl)-5-oxaspiro[2.4]heptan-4-one
—— (6S)-6-(bromomethyl)-5-oxaspiro[2.5]octan-4-one —— C8H11BrO2
(6S)-6-(bromomethyl)-5-oxaspiro[2.5]octan-4-one
—— (6R)-6-(bromomethyl)-5-oxaspiro[2.4]heptan-4-one —— C7H9BrO2
(6R)-6-(bromomethyl)-5-oxaspiro[2.4]heptan-4-one
—— (7R)-7-(aminomethyl)-6-oxaspiro[3.4]octan-5-one —— C8H13NO2
(7R)-7-(aminomethyl)-6-oxaspiro[3.4]octan-5-one
—— (7S)-7-(aminomethyl)-6-oxaspiro[3.4]octan-5-one —— C8H13NO2
(7S)-7-(aminomethyl)-6-oxaspiro[3.4]octan-5-one
—— (6R)-6-(bromomethyl)-5-oxaspiro[2.5]octan-4-one —— C8H11BrO2
(6R)-6-(bromomethyl)-5-oxaspiro[2.5]octan-4-one
—— 3,3-Dibromo-5-bromomethyl-8,8-dimethyl-6-oxa-bicyclo[3.2.1]octane-4,7-dione —— C10H11Br3O3
3,3-Dibromo-5-bromomethyl-8,8-dimethyl-6-oxa-bicyclo[3.2.1]octane-4,7-dione
—— 3-[1-Hydroxy-1-(2-oxooxepan-3-yl)ethyl]oxepan-2-one —— C14H22O5
3-[1-Hydroxy-1-(2-oxooxepan-3-yl)ethyl]oxepan-2-one
—— 7-(2-Oxocyclohexylidene)oxepan-2-one —— C12H16O3
7-(2-Oxocyclohexylidene)oxepan-2-one
—— (1-Bromo-10-methyl-5-oxo-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-yl) but-2-enoate —— C14H15BrO4
(1-Bromo-10-methyl-5-oxo-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-yl) but-2-enoate
—— (3R,5S)-5-[(1R,3R)-1-azido-3-(hydroxymethyl)-4-methylpentyl]-3-propan-2-yloxolan-2-one —— C14H25N3O3
(3R,5S)-5-[(1R,3R)-1-azido-3-(hydroxymethyl)-4-methylpentyl]-3-propan-2-yloxolan-2-one
—— (3R,5R)-5-[(1R,3R)-1-azido-3-(hydroxymethyl)-4-methylpentyl]-3-propan-2-yloxolan-2-one —— C14H25N3O3
(3R,5R)-5-[(1R,3R)-1-azido-3-(hydroxymethyl)-4-methylpentyl]-3-propan-2-yloxolan-2-one
—— (3S,4R)-3-bromo-4-hydroxyoxolan-2-one —— C4H5BrO3
(3S,4R)-3-bromo-4-hydroxyoxolan-2-one
—— (3S,5S)-5-[(1R,3R)-1-azido-3-(hydroxymethyl)-4-methylpentyl]-3-propan-2-yloxolan-2-one —— C14H25N3O3
(3S,5S)-5-[(1R,3R)-1-azido-3-(hydroxymethyl)-4-methylpentyl]-3-propan-2-yloxolan-2-one
—— [(1R,3R,7R,8R,8aR)-8-[2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (3R)-3-hydroxy-2,2-dimethylbutanoate —— C25H38O6
[(1R,3R,7R,8R,8aR)-8-[2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (3R)-3-hydroxy-2,2-dimethylbutanoate
—— (3R,4R)-3-bromo-4-hydroxyoxolan-2-one —— C4H5BrO3
(3R,4R)-3-bromo-4-hydroxyoxolan-2-one
—— [(1S,3R,7R,8R,8aR)-8-[2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (3R)-3-hydroxy-2,2-dimethylbutanoate —— C25H38O6
[(1S,3R,7R,8R,8aR)-8-[2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (3R)-3-hydroxy-2,2-dimethylbutanoate
—— [(1S,3S,7R,8R,8aR)-8-[2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (3R)-3-hydroxy-2,2-dimethylbutanoate —— C25H38O6
[(1S,3S,7R,8R,8aR)-8-[2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (3R)-3-hydroxy-2,2-dimethylbutanoate
—— [(1R,3S,7R,8R,8aR)-8-[2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (3R)-3-hydroxy-2,2-dimethylbutanoate —— C25H38O6
[(1R,3S,7R,8R,8aR)-8-[2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (3R)-3-hydroxy-2,2-dimethylbutanoate
—— (3aR,6aR)-5-methylidene-3a,4,6,6a-tetrahydro-1H-cyclopenta[c]furan-3-one —— C8H10O2
(3aR,6aR)-5-methylidene-3a,4,6,6a-tetrahydro-1H-cyclopenta[c]furan-3-one
—— (3S,5S)-5-[(2S,4R)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidin-2-one —— C14H23NO3
(3S,5S)-5-[(2S,4R)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidin-2-one
—— (3R,5S)-5-[(2S,4R)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidin-2-one —— C14H23NO3
(3R,5S)-5-[(2S,4R)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidin-2-one
—— (3S,5R)-5-[(2S,4R)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidin-2-one —— C14H23NO3
(3S,5R)-5-[(2S,4R)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidin-2-one
—— 5-(1,2-Dihydroxyethyl)-4-hydroxyoxolane-2,3-dione —— C6H8O6
5-(1,2-Dihydroxyethyl)-4-hydroxyoxolane-2,3-dione
—— 3-[1-(propylamino)ethylidene]oxolane-2,4-dione —— C9H13NO3
3-[1-(propylamino)ethylidene]oxolane-2,4-dione
—— 12-epi-Eupalmerin acetate —— C22H32O5
12-epi-Eupalmerin acetate
—— (5R,6S)-3,5-dimethyl-6-[(2R)-pentan-2-yl]-3-phenylseleninyloxan-2-one —— C18H26O3Se
(5R,6S)-3,5-dimethyl-6-[(2R)-pentan-2-yl]-3-phenylseleninyloxan-2-one
—— 3-[(1-benzyl-3,4-dihydro-2H-pyrrol-1-ium-5-yl)sulfanyl]oxolan-2-one;bromide —— Br*C15H18NO2S
3-[(1-benzyl-3,4-dihydro-2H-pyrrol-1-ium-5-yl)sulfanyl]oxolan-2-one;bromide
—— (2S)-4-methylidene-5-oxo-2-tridecyloxolane-3-carboxylic acid —— C19H32O4
(2S)-4-methylidene-5-oxo-2-tridecyloxolane-3-carboxylic acid
—— 3-Butyl-4-pentyl-3-trimethylsilyloxetan-2-one —— C15H30O2Si
3-Butyl-4-pentyl-3-trimethylsilyloxetan-2-one
—— ethyl (2S,3R)-2,4,4-trimethyl-2-(2-methylpropyl)-5-oxooxolane-3-carboxylate —— C14H24O4
ethyl (2S,3R)-2,4,4-trimethyl-2-(2-methylpropyl)-5-oxooxolane-3-carboxylate
—— methyl (3R,5R)-5-methyl-2-oxooxolane-3-carboxylate —— C7H10O4
methyl (3R,5R)-5-methyl-2-oxooxolane-3-carboxylate
—— methyl (3R,5S)-5-methyl-2-oxooxolane-3-carboxylate —— C7H10O4
methyl (3R,5S)-5-methyl-2-oxooxolane-3-carboxylate
—— (3S)-3-[(E,2R)-2-hydroxy-3-methyl-4-nitrobut-3-en-2-yl]oxan-2-one —— C10H15NO5
(3S)-3-[(E,2R)-2-hydroxy-3-methyl-4-nitrobut-3-en-2-yl]oxan-2-one
—— (3R,3aS,5S,6R,6aR)-6-bromo-3,5-dihydroxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one —— C7H9BrO4
(3R,3aS,5S,6R,6aR)-6-bromo-3,5-dihydroxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
—— 4-Hexan-2-yl-3-trimethylsilyloxetan-2-one —— C12H24O2Si
4-Hexan-2-yl-3-trimethylsilyloxetan-2-one
—— (3R,5S)-5-((R)-1-Hydroxy-3-methyl-butyl)-3-isopropyl-dihydro-furan-2-one —— C12H22O3
(3R,5S)-5-((R)-1-Hydroxy-3-methyl-butyl)-3-isopropyl-dihydro-furan-2-one
—— (1R,5S)-2-oxo-6-phenyl-3-oxabicyclo[3.1.0]hexane-1-carboxylic acid —— C12H10O4
(1R,5S)-2-oxo-6-phenyl-3-oxabicyclo[3.1.0]hexane-1-carboxylic acid
—— (4aS,7aS)-3-Methylene-decahydro-azuleno[6,5-b]furan-2-one —— C13H18O2
(4aS,7aS)-3-Methylene-decahydro-azuleno[6,5-b]furan-2-one
—— (5S)-3-methylidene-4-prop-2-enoxy-5-propyloxolan-2-one —— C11H16O3
(5S)-3-methylidene-4-prop-2-enoxy-5-propyloxolan-2-one
—— 4-Ethyl-4-methyl-3-trimethylsilyloxetan-2-one —— C9H18O2Si
4-Ethyl-4-methyl-3-trimethylsilyloxetan-2-one
—— (1R,5R)-1-Methoxy-6-oxa-bicyclo[3.2.0]heptan-7-one —— C7H10O3
(1R,5R)-1-Methoxy-6-oxa-bicyclo[3.2.0]heptan-7-one
—— [(1R,3R,7S,9R)-8-[tert-butyl(dimethyl)silyl]oxy-5,5,11,11-tetramethyl-4,6,10,12-tetraoxatricyclo[7.3.0.03,7]dodecan-2-yl] (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate —— C28H46O9Si
[(1R,3R,7S,9R)-8-[tert-butyl(dimethyl)silyl]oxy-5,5,11,11-tetramethyl-4,6,10,12-tetraoxatricyclo[7.3.0.03,7]dodecan-2-yl] (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
—— (4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-phenylselanyloxolan-2-one —— C23H40O4SeSi2
(4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-phenylselanyloxolan-2-one
—— 2-Oxo-4-phenyl-5-tridecyl-tetrahydro-furan-3-carboxylic acid —— C24H36O4
2-Oxo-4-phenyl-5-tridecyl-tetrahydro-furan-3-carboxylic acid
—— Acalycixeniolide H —— C21H30O5
Acalycixeniolide H
—— (3S,4S)-3-[(2E)-2-[ethoxy(trimethylsilyloxy)methylidene]butyl]-4-propan-2-yloxetan-2-one —— C16H30O4Si
(3S,4S)-3-[(2E)-2-[ethoxy(trimethylsilyloxy)methylidene]butyl]-4-propan-2-yloxetan-2-one
—— (5R,6S)-5-diethoxyphosphoryl-6-(furan-2-yl)oxan-2-one —— C13H19O6P
(5R,6S)-5-diethoxyphosphoryl-6-(furan-2-yl)oxan-2-one
—— (2S,3R,4R)-4-Methyl-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid allylamide —— C17H29NO3
(2S,3R,4R)-4-Methyl-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid allylamide
—— 5-[2-[3-[2-(6-Oxooxan-3-yl)ethoxy]propoxy]ethyl]oxan-2-one —— C17H28O6
5-[2-[3-[2-(6-Oxooxan-3-yl)ethoxy]propoxy]ethyl]oxan-2-one