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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,4R)-4,7,7-trimethyl-1-(morpholine-4-carbonyl)-2-oxabicyclo[2.2.1]heptan-3-one —— C14H21NO4
(1R,4R)-4,7,7-trimethyl-1-(morpholine-4-carbonyl)-2-oxabicyclo[2.2.1]heptan-3-one
—— (6S)-5,5-diethyl-3,3-dimethyl-6-thiophen-2-yloxane-2,4-dione —— C15H20O3S
(6S)-5,5-diethyl-3,3-dimethyl-6-thiophen-2-yloxane-2,4-dione
—— (1R,4R)-N,N,4,7,7-pentamethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C12H19NO3
(1R,4R)-N,N,4,7,7-pentamethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,1aR,3aS,7aR)-1-ethyl-1-methyl-1a,3a,6,7-tetrahydrocyclopropa[c][2]benzofuran-3-one —— C12H16O2
(1S,1aR,3aS,7aR)-1-ethyl-1-methyl-1a,3a,6,7-tetrahydrocyclopropa[c][2]benzofuran-3-one
—— (1R,1aR,3aS,7aR)-1-ethyl-1-methyl-1a,3a,6,7-tetrahydrocyclopropa[c][2]benzofuran-3-one —— C12H16O2
(1R,1aR,3aS,7aR)-1-ethyl-1-methyl-1a,3a,6,7-tetrahydrocyclopropa[c][2]benzofuran-3-one
—— (1S,4S)-4,7,7-trimethyl-3-oxo-N-(2,2,2-trifluoroethyl)-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C12H16F3NO3
(1S,4S)-4,7,7-trimethyl-3-oxo-N-(2,2,2-trifluoroethyl)-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-4,7,7-trimethyl-N,N-bis(2-methylpropyl)-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C18H31NO3
(1S,4S)-4,7,7-trimethyl-N,N-bis(2-methylpropyl)-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-4,7,7-trimethyl-3-oxo-N-[(2S)-2-[[(1R,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]amino]propyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C23H34N2O6
(1S,4S)-4,7,7-trimethyl-3-oxo-N-[(2S)-2-[[(1R,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]amino]propyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-N-benzyl-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C17H21NO3
(1S,4S)-N-benzyl-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-4,7,7-trimethyl-N-(4-methylpiperazin-1-yl)-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C15H25N3O3
(1S,4S)-4,7,7-trimethyl-N-(4-methylpiperazin-1-yl)-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-4,7,7-trimethyl-3-oxo-N-[(2R)-2-[[(1R,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]amino]propyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C23H34N2O6
(1S,4S)-4,7,7-trimethyl-3-oxo-N-[(2R)-2-[[(1R,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]amino]propyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-N',N',4,7,7-pentamethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbohydrazide —— C12H20N2O3
(1S,4S)-N',N',4,7,7-pentamethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbohydrazide
—— Majorynolide —— C17H26O3
Majorynolide
—— (1S,4S)-4,7,7-trimethyl-3-oxo-N,N-dipyridin-2-yl-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C20H21N3O3
(1S,4S)-4,7,7-trimethyl-3-oxo-N,N-dipyridin-2-yl-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-4,7,7-trimethyl-1-[4-[(1R,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]piperazine-1-carbonyl]-2-oxabicyclo[2.2.1]heptan-3-one —— C24H34N2O6
(1S,4S)-4,7,7-trimethyl-1-[4-[(1R,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]piperazine-1-carbonyl]-2-oxabicyclo[2.2.1]heptan-3-one
—— (1S,5S)-6-oxabicyclo[3.2.1]octan-7-one —— C7H10O2
(1S,5S)-6-oxabicyclo[3.2.1]octan-7-one
—— (1R,5R)-6-oxabicyclo[3.2.1]octan-7-one —— C7H10O2
(1R,5R)-6-oxabicyclo[3.2.1]octan-7-one
—— (1S,4S)-4,7,7-trimethyl-3-oxo-N-[(2S)-2-[[(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]amino]propyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C23H34N2O6
(1S,4S)-4,7,7-trimethyl-3-oxo-N-[(2S)-2-[[(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]amino]propyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-4,7,7-trimethyl-3-oxo-N-[(2R)-2-[[(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]amino]propyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C23H34N2O6
(1S,4S)-4,7,7-trimethyl-3-oxo-N-[(2R)-2-[[(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]amino]propyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— 10-[(E)-2-[(2S,3S)-3-[(Z)-but-2-enyl]oxiran-2-yl]vinyl]oxecan-2-one —— C17H26O3
10-[(E)-2-[(2S,3S)-3-[(Z)-but-2-enyl]oxiran-2-yl]vinyl]oxecan-2-one
—— (1R,5R,8S)-8-(bromomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione —— C10H13BrO3
(1R,5R,8S)-8-(bromomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione
—— (1R,5S,8S)-8-(bromomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione —— C10H13BrO3
(1R,5S,8S)-8-(bromomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione
—— (3S,4R,5S)-3,4-dibromo-5-hydroxyoxolan-2-one —— C4H4Br2O3
(3S,4R,5S)-3,4-dibromo-5-hydroxyoxolan-2-one
—— (3S,4S,5S)-3,4-dibromo-5-hydroxyoxolan-2-one —— C4H4Br2O3
(3S,4S,5S)-3,4-dibromo-5-hydroxyoxolan-2-one
—— (3R,4S,5S)-3,4-dibromo-5-hydroxyoxolan-2-one —— C4H4Br2O3
(3R,4S,5S)-3,4-dibromo-5-hydroxyoxolan-2-one
—— (1R,5R)-5,8,8-trimethyl-2,4-dioxo-N-(2,2,2-trifluoroethyl)-3-oxabicyclo[3.2.1]octane-1-carboxamide —— C13H16F3NO4
(1R,5R)-5,8,8-trimethyl-2,4-dioxo-N-(2,2,2-trifluoroethyl)-3-oxabicyclo[3.2.1]octane-1-carboxamide
—— (1R,4R)-4,7,7-trimethyl-3-oxo-N-[5-[[(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]amino]pentyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C25H38N2O6
(1R,4R)-4,7,7-trimethyl-3-oxo-N-[5-[[(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]amino]pentyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1R,5R)-5,8,8-trimethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide —— C11H15NO4
(1R,5R)-5,8,8-trimethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide
—— (1R,4R)-4,7,7-trimethyl-3-oxo-N-[(1R)-1-phenylethyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C18H23NO3
(1R,4R)-4,7,7-trimethyl-3-oxo-N-[(1R)-1-phenylethyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1R,4R)-4,7,7-trimethyl-3-oxo-N-[(1S)-1-phenylethyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C18H23NO3
(1R,4R)-4,7,7-trimethyl-3-oxo-N-[(1S)-1-phenylethyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-N-cyclohexyl-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C16H25NO3
(1S,4S)-N-cyclohexyl-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4S)-N,N-diethyl-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C14H23NO3
(1S,4S)-N,N-diethyl-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4R)-4,7,7-trimethyl-3-oxo-N-[5-[[(1S,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]amino]pentyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C25H38N2O6
(1S,4R)-4,7,7-trimethyl-3-oxo-N-[5-[[(1S,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]amino]pentyl]-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,5R)-N,N,5,8,8-pentamethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide —— C13H19NO4
(1S,5R)-N,N,5,8,8-pentamethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide
—— (1R,5S)-N,5,8,8-tetramethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide —— C12H17NO4
(1R,5S)-N,5,8,8-tetramethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide
—— (1S,5R)-N,5,8,8-tetramethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide —— C12H17NO4
(1S,5R)-N,5,8,8-tetramethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide
—— (1R,5R)-1-(bromomethyl)-8,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione —— C10H13BrO3
(1R,5R)-1-(bromomethyl)-8,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione
—— (1R,5S)-5,8,8-trimethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide —— C11H15NO4
(1R,5S)-5,8,8-trimethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide
—— (1<sup>1</sup>-bromo-(+)-camphoric acid )-anhydride —— C10H13BrO3
(1<sup>1</sup>-bromo-(+)-camphoric acid )-anhydride
—— (1R,5R,8R)-1,8-bis(bromomethyl)-8-methyl-3-oxabicyclo[3.2.1]octane-2,4-dione —— C10H12Br2O3
(1R,5R,8R)-1,8-bis(bromomethyl)-8-methyl-3-oxabicyclo[3.2.1]octane-2,4-dione
—— (1R,5S)-1-(bromomethyl)-8,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione —— C10H13BrO3
(1R,5S)-1-(bromomethyl)-8,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione
—— (1S,5S)-N,N,5,8,8-pentamethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide —— C13H19NO4
(1S,5S)-N,N,5,8,8-pentamethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide
—— (1S,5S)-N,5,8,8-tetramethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide —— C12H17NO4
(1S,5S)-N,5,8,8-tetramethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide
—— (1R,5S)-N,N,5,8,8-pentamethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide —— C13H19NO4
(1R,5S)-N,N,5,8,8-pentamethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide
—— (1S,5R)-1-(bromomethyl)-8,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione —— C10H13BrO3
(1S,5R)-1-(bromomethyl)-8,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione
—— (1R,5S,8S)-1,8-bis(bromomethyl)-8-methyl-3-oxabicyclo[3.2.1]octane-2,4-dione —— C10H12Br2O3
(1R,5S,8S)-1,8-bis(bromomethyl)-8-methyl-3-oxabicyclo[3.2.1]octane-2,4-dione
—— (1R,5R)-N,N,5,8,8-pentamethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide —— C13H19NO4
(1R,5R)-N,N,5,8,8-pentamethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide
—— (1S,2R,3S,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylic acid —— C10H14O4
(1S,2R,3S,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylic acid
—— (1S,2R,3R,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylic acid —— C10H14O4
(1S,2R,3R,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylic acid
—— (1R,5R,8S)-1,8-bis(bromomethyl)-8-methyl-3-oxabicyclo[3.2.1]octane-2,4-dione —— C10H12Br2O3
(1R,5R,8S)-1,8-bis(bromomethyl)-8-methyl-3-oxabicyclo[3.2.1]octane-2,4-dione