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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
—— (1R,5S)-6,6-dimethyl-1-propan-2-yl-2-oxabicyclo[3.1.0]hexan-3-one —— C10H16O2
(1R,5S)-6,6-dimethyl-1-propan-2-yl-2-oxabicyclo[3.1.0]hexan-3-one
—— (1S,6S)-6-propan-2-yl-2-oxabicyclo[4.1.0]heptan-3-one —— C9H14O2
(1S,6S)-6-propan-2-yl-2-oxabicyclo[4.1.0]heptan-3-one
—— (1S,4S)-4,7,7-trimethyl-3-oxo-N-propyl-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C13H21NO3
(1S,4S)-4,7,7-trimethyl-3-oxo-N-propyl-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1R,5S)-1-propan-2-yl-3-oxabicyclo[3.1.0]hexane-2,4-dione —— C8H10O3
(1R,5S)-1-propan-2-yl-3-oxabicyclo[3.1.0]hexane-2,4-dione
—— (3R,5S)-3,5-dimethyloxolane-2,4-dione —— C6H8O3
(3R,5S)-3,5-dimethyloxolane-2,4-dione
—— (1S,4S)-4,7,7-trimethyl-3-oxo-N-(2,2,6,6-tetramethylpiperidin-4-yl)-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C19H32N2O3
(1S,4S)-4,7,7-trimethyl-3-oxo-N-(2,2,6,6-tetramethylpiperidin-4-yl)-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— methyl (1S,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate —— C11H16O4
methyl (1S,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
—— pyridin-3-yl (1R,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate —— C15H17NO4
pyridin-3-yl (1R,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
—— cyclohexyl (1S,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate —— C16H24O4
cyclohexyl (1S,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
—— (1S,4S)-N,N,4,7,7-pentamethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C12H19NO3
(1S,4S)-N,N,4,7,7-pentamethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-N-methoxy-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C11H17NO4
(1S,4S)-N-methoxy-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— cyclohexyl (1R,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate —— C16H24O4
cyclohexyl (1R,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
—— (1S,4S)-4,7,7-trimethyl-3-oxo-N-[[(2S)-oxolan-2-yl]methyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C15H23NO4
(1S,4S)-4,7,7-trimethyl-3-oxo-N-[[(2S)-oxolan-2-yl]methyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— pyridin-3-yl (1S,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate —— C15H17NO4
pyridin-3-yl (1S,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
—— (1S,4S)-N-[(2-chlorophenyl)methyl]-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C17H20ClNO3
(1S,4S)-N-[(2-chlorophenyl)methyl]-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-4,7,7-trimethyl-1-(4-methylpiperazine-1-carbonyl)-2-oxabicyclo[2.2.1]heptan-3-one —— C15H24N2O3
(1S,4S)-4,7,7-trimethyl-1-(4-methylpiperazine-1-carbonyl)-2-oxabicyclo[2.2.1]heptan-3-one
—— (1S,4S)-4,7,7-trimethyl-3-oxo-N-(2-phenylethyl)-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C18H23NO3
(1S,4S)-4,7,7-trimethyl-3-oxo-N-(2-phenylethyl)-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-4,7,7-trimethyl-N-(3-morpholin-4-ylpropyl)-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C17H28N2O4
(1S,4S)-4,7,7-trimethyl-N-(3-morpholin-4-ylpropyl)-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-4,7,7-trimethyl-3-oxo-N-[(1S)-1-phenylethyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C18H23NO3
(1S,4S)-4,7,7-trimethyl-3-oxo-N-[(1S)-1-phenylethyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-N-(1-adamantyl)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C20H29NO3
(1S,4S)-N-(1-adamantyl)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-4,7,7-trimethyl-3-oxo-N-(pyridin-3-ylmethyl)-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C16H20N2O3
(1S,4S)-4,7,7-trimethyl-3-oxo-N-(pyridin-3-ylmethyl)-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-N-(furan-2-ylmethyl)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C15H19NO4
(1S,4S)-N-(furan-2-ylmethyl)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-N,N-bis(cyanomethyl)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C14H17N3O3
(1S,4S)-N,N-bis(cyanomethyl)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-4,7,7-trimethyl-3-oxo-N-[(1R)-1-phenylethyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C18H23NO3
(1S,4S)-4,7,7-trimethyl-3-oxo-N-[(1R)-1-phenylethyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-N-[(4-chlorophenyl)methyl]-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C17H20ClNO3
(1S,4S)-N-[(4-chlorophenyl)methyl]-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1R,4R)-N-(1-adamantyl)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C20H29NO3
(1R,4R)-N-(1-adamantyl)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-N-[(Z)-(2-chlorophenyl)methylideneamino]-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C17H19ClN2O3
(1S,4S)-N-[(Z)-(2-chlorophenyl)methylideneamino]-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-4,7,7-trimethyl-N-(3-methylbutyl)-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C15H25NO3
(1S,4S)-4,7,7-trimethyl-N-(3-methylbutyl)-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-N,N-bis(2-cyanoethyl)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C16H21N3O3
(1S,4S)-N,N-bis(2-cyanoethyl)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1R,4S,5S)-1,4-dimethyl-6,8-dioxabicyclo[3.2.1]octan-7-one —— C8H12O3
(1R,4S,5S)-1,4-dimethyl-6,8-dioxabicyclo[3.2.1]octan-7-one
—— (1R,4R,5S)-1,4-dimethyl-6,8-dioxabicyclo[3.2.1]octan-7-one —— C8H12O3
(1R,4R,5S)-1,4-dimethyl-6,8-dioxabicyclo[3.2.1]octan-7-one
—— (1S,4S)-N-[(Z)-1-(4-bromophenyl)ethylideneamino]-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C18H21BrN2O3
(1S,4S)-N-[(Z)-1-(4-bromophenyl)ethylideneamino]-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— ethyl (1R,5R)-2-oxospiro[3-oxabicyclo[3.1.0]hexane-4,1'-cyclohexane]-1-carboxylate —— C13H18O4
ethyl (1R,5R)-2-oxospiro[3-oxabicyclo[3.1.0]hexane-4,1'-cyclohexane]-1-carboxylate
—— ethyl (1S,5S)-2-oxospiro[3-oxabicyclo[3.1.0]hexane-4,1'-cyclohexane]-1-carboxylate —— C13H18O4
ethyl (1S,5S)-2-oxospiro[3-oxabicyclo[3.1.0]hexane-4,1'-cyclohexane]-1-carboxylate
—— (4S,5S)-4,5-dichlorooxolan-2-one —— C4H4Cl2O2
(4S,5S)-4,5-dichlorooxolan-2-one
—— (4R,5R)-4,5-dichlorooxolan-2-one —— C4H4Cl2O2
(4R,5R)-4,5-dichlorooxolan-2-one
—— (4R,5S)-4,5-dichlorooxolan-2-one —— C4H4Cl2O2
(4R,5S)-4,5-dichlorooxolan-2-one
—— (4S,5R)-4,5-dichlorooxolan-2-one —— C4H4Cl2O2
(4S,5R)-4,5-dichlorooxolan-2-one
—— (1R,5S)-1-acetyl-5-ethenyl-3-oxabicyclo[3.1.0]hexan-2-one —— C9H10O3
(1R,5S)-1-acetyl-5-ethenyl-3-oxabicyclo[3.1.0]hexan-2-one
—— (1R,2S,5R,7S,8R)-5-acetyl-3-oxatricyclo[6.2.1.02,7]undec-9-ene-4,6-dione —— C12H12O4
(1R,2S,5R,7S,8R)-5-acetyl-3-oxatricyclo[6.2.1.02,7]undec-9-ene-4,6-dione
—— (1R,2S,5R,7R,8R)-5-acetyl-3-oxatricyclo[6.2.1.02,7]undec-9-ene-4,6-dione —— C12H12O4
(1R,2S,5R,7R,8R)-5-acetyl-3-oxatricyclo[6.2.1.02,7]undec-9-ene-4,6-dione
—— (1R,2S,5S,7R,8R)-5-acetyl-3-oxatricyclo[6.2.1.02,7]undec-9-ene-4,6-dione —— C12H12O4
(1R,2S,5S,7R,8R)-5-acetyl-3-oxatricyclo[6.2.1.02,7]undec-9-ene-4,6-dione
—— (1R,2S,5S,7S,8R)-5-acetyl-3-oxatricyclo[6.2.1.02,7]undec-9-ene-4,6-dione —— C12H12O4
(1R,2S,5S,7S,8R)-5-acetyl-3-oxatricyclo[6.2.1.02,7]undec-9-ene-4,6-dione
—— (1R,5R,6R)-6-methyl-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylic acid —— C7H8O4
(1R,5R,6R)-6-methyl-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylic acid
—— (1R,6S)-2-oxo-3-oxabicyclo[4.1.0]heptane-1-carboxylic acid —— C7H8O4
(1R,6S)-2-oxo-3-oxabicyclo[4.1.0]heptane-1-carboxylic acid
—— (1R,5R,6S)-6-methyl-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylic acid —— C7H8O4
(1R,5R,6S)-6-methyl-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylic acid
—— (2R)-5-oxooxolane-2-carboperoxoic acid —— C5H6O5
(2R)-5-oxooxolane-2-carboperoxoic acid
—— (2S)-5-oxooxolane-2-carboperoxoic acid —— C5H6O5
(2S)-5-oxooxolane-2-carboperoxoic acid
—— (3R)-2-oxooxolane-3-carboperoxoic acid —— C5H6O5
(3R)-2-oxooxolane-3-carboperoxoic acid
—— (3S)-2-oxooxolane-3-carboperoxoic acid —— C5H6O5
(3S)-2-oxooxolane-3-carboperoxoic acid