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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
—— methyl (4R)-2-oxo-1-oxaspiro[4.5]decane-4-carboxylate —— C11H16O4
methyl (4R)-2-oxo-1-oxaspiro[4.5]decane-4-carboxylate
—— methyl (4S)-2-oxo-1-oxaspiro[4.5]decane-4-carboxylate —— C11H16O4
methyl (4S)-2-oxo-1-oxaspiro[4.5]decane-4-carboxylate
—— (4S)-4-butyl-4-ethyloxolan-2-one —— C10H18O2
(4S)-4-butyl-4-ethyloxolan-2-one
—— (4R)-2-oxo-1-oxaspiro[4.4]nonane-4-carboxylic acid —— C9H12O4
(4R)-2-oxo-1-oxaspiro[4.4]nonane-4-carboxylic acid
—— (3R,4R)-4-phenyl-3-[(3S)-3-phenylbutanoyl]oxolan-2-one —— C20H20O3
(3R,4R)-4-phenyl-3-[(3S)-3-phenylbutanoyl]oxolan-2-one
—— (3R)-3-acetyl-3-methyloxolan-2-one —— C7H10O3
(3R)-3-acetyl-3-methyloxolan-2-one
—— (1R,2R,5S)-1,8,8-trimethyl-4-oxo-3-oxabicyclo[3.2.1]octane-2-carboxylate —— C11H15O4-
(1R,2R,5S)-1,8,8-trimethyl-4-oxo-3-oxabicyclo[3.2.1]octane-2-carboxylate
—— (3R)-3-(trifluoromethyl)oxolan-2-one —— C5H5F3O2
(3R)-3-(trifluoromethyl)oxolan-2-one
—— (3R)-3-methyloxolane-2,4-dione —— C5H6O3
(3R)-3-methyloxolane-2,4-dione
—— (1R,5S,6S)-1-bromo-4-oxo-3-oxabicyclo[3.1.0]hexane-6-carboxylate —— C6H4BrO4-
(1R,5S,6S)-1-bromo-4-oxo-3-oxabicyclo[3.1.0]hexane-6-carboxylate
—— (2R)-5-oxooxolane-2-carboxylate —— C5H5O4-
(2R)-5-oxooxolane-2-carboxylate
—— (3R,5S)-5-(hydroxymethyl)-3,5-dimethyloxolane-2,4-dione —— C7H10O4
(3R,5S)-5-(hydroxymethyl)-3,5-dimethyloxolane-2,4-dione
—— (4R)-4-(aminomethyl)oxolan-2-one —— C5H9NO2
(4R)-4-(aminomethyl)oxolan-2-one
—— (4S)-4-(aminomethyl)oxolan-2-one —— C5H9NO2
(4S)-4-(aminomethyl)oxolan-2-one
—— (5R)-5-[(1R)-1,2-dihydroxyethyl]-3-hydroxyoxolane-2,4-dione —— C6H8O6
(5R)-5-[(1R)-1,2-dihydroxyethyl]-3-hydroxyoxolane-2,4-dione
—— (1S,4R)-4,7,7-trimethyl-1-(thiomorpholine-4-carbonyl)-2-oxabicyclo[2.2.1]heptan-3-one —— C14H21NO3S
(1S,4R)-4,7,7-trimethyl-1-(thiomorpholine-4-carbonyl)-2-oxabicyclo[2.2.1]heptan-3-one
—— (2S,6S)-1-chloro-7-phenyl-8-oxatricyclo[4.3.0.02,7]nonan-9-one —— C14H13ClO2
(2S,6S)-1-chloro-7-phenyl-8-oxatricyclo[4.3.0.02,7]nonan-9-one
—— (2S,3R,4R)-3-hydroxy-4-methyl-2-(n-eicos-11′-yn-19′-enyl)butanolide —— C25H42O3
(2S,3R,4R)-3-hydroxy-4-methyl-2-(n-eicos-11′-yn-19′-enyl)butanolide
—— methyl 2-[(1S,3S,5R,7S,8S,9S,12S,13S)-13-(furan-3-yl)-5-hydroxy-6,6,8,12-tetramethyl-17-methylidene-15-oxo-2,14-dioxatetracyclo[7.7.1.01,12.03,8]heptadecan-7-yl]acetate —— C27H36O7
methyl 2-[(1S,3S,5R,7S,8S,9S,12S,13S)-13-(furan-3-yl)-5-hydroxy-6,6,8,12-tetramethyl-17-methylidene-15-oxo-2,14-dioxatetracyclo[7.7.1.01,12.03,8]heptadecan-7-yl]acetate
—— [(1R,3S,7S,8R,8aR)-8-[2-[(2S,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate —— C25H38O5
[(1R,3S,7S,8R,8aR)-8-[2-[(2S,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate
—— (1S,5S)-2-[(E)-but-2-enyl]-3-methyl-6-oxabicyclo[3.2.0]hept-2-en-7-one —— C11H14O2
(1S,5S)-2-[(E)-but-2-enyl]-3-methyl-6-oxabicyclo[3.2.0]hept-2-en-7-one
—— (1S,5R)-2-[(E)-but-2-enyl]-3-methyl-6-oxabicyclo[3.2.0]hept-2-en-7-one —— C11H14O2
(1S,5R)-2-[(E)-but-2-enyl]-3-methyl-6-oxabicyclo[3.2.0]hept-2-en-7-one
—— (1R,5R)-2-[(E)-but-2-enyl]-3-methyl-6-oxabicyclo[3.2.0]hept-2-en-7-one —— C11H14O2
(1R,5R)-2-[(E)-but-2-enyl]-3-methyl-6-oxabicyclo[3.2.0]hept-2-en-7-one
—— (1R,5S)-2-[(E)-but-2-enyl]-3-methyl-6-oxabicyclo[3.2.0]hept-2-en-7-one —— C11H14O2
(1R,5S)-2-[(E)-but-2-enyl]-3-methyl-6-oxabicyclo[3.2.0]hept-2-en-7-one
—— (6S)-6-[(E)-hex-3-enyl]oxan-2-one —— C11H18O2
(6S)-6-[(E)-hex-3-enyl]oxan-2-one
—— (1R,4R)-4,7,7-trimethyl-N-(3-morpholin-4-ium-4-ylpropyl)-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C17H29N2O4+
(1R,4R)-4,7,7-trimethyl-N-(3-morpholin-4-ium-4-ylpropyl)-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1R,4R,7R,10R)-5,12-dioxatetracyclo[5.5.2.04,13.010,14]tetradeca-2,8-diene-6,11-dione —— C12H10O4
(1R,4R,7R,10R)-5,12-dioxatetracyclo[5.5.2.04,13.010,14]tetradeca-2,8-diene-6,11-dione
—— Tocris-1965 —— C25H38O5
Tocris-1965
—— [(Z)-1-[(3R,5S)-5-(2-methylpropoxymethyl)-2-oxooxolan-3-yl]propan-2-ylideneamino]thiourea —— C13H23N3O3S
[(Z)-1-[(3R,5S)-5-(2-methylpropoxymethyl)-2-oxooxolan-3-yl]propan-2-ylideneamino]thiourea
—— [(2S)-pent-4-yn-2-yl] (1R,2S,3R,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylate —— C15H20O4
[(2S)-pent-4-yn-2-yl] (1R,2S,3R,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylate
—— (1R,4R)-N',N',4,7,7-pentamethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbohydrazide —— C12H20N2O3
(1R,4R)-N',N',4,7,7-pentamethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbohydrazide
—— [(2S,4R)-5-oxo-4-propyloxolan-2-yl]methyl carbamimidothioate —— C9H16N2O2S
[(2S,4R)-5-oxo-4-propyloxolan-2-yl]methyl carbamimidothioate
—— (S)-5-dodecyldihydrofuran-2(3H)-one —— C16H30O2
(S)-5-dodecyldihydrofuran-2(3H)-one
—— (5E)-5-benzylidene-2-(2-oxooxolan-3-yl)sulfanyl-1,3-thiazol-4-one —— C14H11NO3S2
(5E)-5-benzylidene-2-(2-oxooxolan-3-yl)sulfanyl-1,3-thiazol-4-one
—— (2S,3R)-2-(5-methylfuran-2-yl)-5-oxooxolane-3-carboxylic acid —— C10H10O5
(2S,3R)-2-(5-methylfuran-2-yl)-5-oxooxolane-3-carboxylic acid
—— (2R,3S)-2-(furan-2-yl)-5-oxooxolane-3-carboxylic acid —— C9H8O5
(2R,3S)-2-(furan-2-yl)-5-oxooxolane-3-carboxylic acid
—— (2R,3R)-2-(furan-2-yl)-5-oxooxolane-3-carboxylic acid —— C9H8O5
(2R,3R)-2-(furan-2-yl)-5-oxooxolane-3-carboxylic acid
—— (2S,3S)-2-(5-methylfuran-2-yl)-5-oxooxolane-3-carboxylic acid —— C10H10O5
(2S,3S)-2-(5-methylfuran-2-yl)-5-oxooxolane-3-carboxylic acid
—— (2S,3S)-5-oxo-2-thiophen-2-yloxolane-3-carboxylic acid —— C9H8O4S
(2S,3S)-5-oxo-2-thiophen-2-yloxolane-3-carboxylic acid
—— (2R,3R)-5-oxo-2-thiophen-2-yloxolane-3-carboxylic acid —— C9H8O4S
(2R,3R)-5-oxo-2-thiophen-2-yloxolane-3-carboxylic acid
—— (2R,3S)-2-(5-methylfuran-2-yl)-5-oxooxolane-3-carboxylic acid —— C10H10O5
(2R,3S)-2-(5-methylfuran-2-yl)-5-oxooxolane-3-carboxylic acid
—— (2R,3S)-5-oxo-2-thiophen-2-yloxolane-3-carboxylic acid —— C9H8O4S
(2R,3S)-5-oxo-2-thiophen-2-yloxolane-3-carboxylic acid
—— (2S,3S)-2-(furan-2-yl)-5-oxooxolane-3-carboxylic acid —— C9H8O5
(2S,3S)-2-(furan-2-yl)-5-oxooxolane-3-carboxylic acid
—— (2S,3R)-2-(furan-2-yl)-5-oxooxolane-3-carboxylic acid —— C9H8O5
(2S,3R)-2-(furan-2-yl)-5-oxooxolane-3-carboxylic acid
—— (2R,3R)-2-(5-methylfuran-2-yl)-5-oxooxolane-3-carboxylic acid —— C10H10O5
(2R,3R)-2-(5-methylfuran-2-yl)-5-oxooxolane-3-carboxylic acid
—— (2S,3R)-5-oxo-2-thiophen-2-yloxolane-3-carboxylic acid —— C9H8O4S
(2S,3R)-5-oxo-2-thiophen-2-yloxolane-3-carboxylic acid
—— 4,7,7-Trimethyl-N-(3-methylbutyl)-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C15H25NO3
4,7,7-Trimethyl-N-(3-methylbutyl)-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— 3,5-Dideoxy-threo-pentonic acid, 1,4-lactone, TMS —— C8H16O3Si
3,5-Dideoxy-threo-pentonic acid, 1,4-lactone, TMS
—— 2-C-Methylerythronic acid, 1,4-lactone, TMS —— C11H24O4Si2
2-C-Methylerythronic acid, 1,4-lactone, TMS
—— 2-Deoxy-lyxo-hexonic acid, 1,4-lactone, TMS —— C15H34O5Si3
2-Deoxy-lyxo-hexonic acid, 1,4-lactone, TMS