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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 (1S,6S,9R)-8-oxo-7-oxabicyclo[4.2.1]nonane-9-carboxylate —— C10H14O4
methyl (1S,6S,9R)-8-oxo-7-oxabicyclo[4.2.1]nonane-9-carboxylate
—— (3S)-3-(2-methylphenyl)oxane-2,6-dione —— C12H12O3
(3S)-3-(2-methylphenyl)oxane-2,6-dione
—— (3R)-3-(2-methylphenyl)oxane-2,6-dione —— C12H12O3
(3R)-3-(2-methylphenyl)oxane-2,6-dione
—— (1S,4S)-4,7,7-trimethyl-1-(thiomorpholine-4-carbonyl)-2-oxabicyclo[2.2.1]heptan-3-one —— C14H21NO3S
(1S,4S)-4,7,7-trimethyl-1-(thiomorpholine-4-carbonyl)-2-oxabicyclo[2.2.1]heptan-3-one
—— (1R,4R,5S)-5,7,7-trimethyl-4-propan-2-yl-3,6-dioxabicyclo[3.2.2]nonan-2-one —— C13H22O3
(1R,4R,5S)-5,7,7-trimethyl-4-propan-2-yl-3,6-dioxabicyclo[3.2.2]nonan-2-one
—— (1R,4S,5S)-5,7,7-trimethyl-4-propan-2-yl-3,6-dioxabicyclo[3.2.2]nonan-2-one —— C13H22O3
(1R,4S,5S)-5,7,7-trimethyl-4-propan-2-yl-3,6-dioxabicyclo[3.2.2]nonan-2-one
—— (1R,5S)-4,4-diethyl-5,7,7-trimethyl-3,6-dioxabicyclo[3.2.2]nonan-2-one —— C14H24O3
(1R,5S)-4,4-diethyl-5,7,7-trimethyl-3,6-dioxabicyclo[3.2.2]nonan-2-one
—— (1S,5R)-4,4,5,7,7-pentamethyl-3,6-dioxabicyclo[3.2.2]nonan-2-one —— C12H20O3
(1S,5R)-4,4,5,7,7-pentamethyl-3,6-dioxabicyclo[3.2.2]nonan-2-one
—— (1S,4S,5S)-4-[(R)-hydroxy(phenyl)methyl]-1,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one —— C17H22O3
(1S,4S,5S)-4-[(R)-hydroxy(phenyl)methyl]-1,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one
—— (1S,4R)-1-[(2S)-2-bromo-2-phenylethyl]-4,7,7-trimethyl-2-oxabicyclo[2.2.1]heptan-3-one —— C17H21BrO2
(1S,4R)-1-[(2S)-2-bromo-2-phenylethyl]-4,7,7-trimethyl-2-oxabicyclo[2.2.1]heptan-3-one
—— (1S,4S,5S)-4-[(R)-bromo(phenyl)methyl]-1,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one —— C17H21BrO2
(1S,4S,5S)-4-[(R)-bromo(phenyl)methyl]-1,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one
—— (1R,4S,5R)-4-[(R)-hydroxy(phenyl)methyl]-1,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one —— C17H22O3
(1R,4S,5R)-4-[(R)-hydroxy(phenyl)methyl]-1,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one
—— (1S,5R)-1-methyl-5-propan-2-yl-3,8-dioxabicyclo[3.2.1]octane-2,4-dione —— C10H14O4
(1S,5R)-1-methyl-5-propan-2-yl-3,8-dioxabicyclo[3.2.1]octane-2,4-dione
—— (1R,5S)-1-methyl-5-propan-2-yl-3,8-dioxabicyclo[3.2.1]octane-2,4-dione —— C10H14O4
(1R,5S)-1-methyl-5-propan-2-yl-3,8-dioxabicyclo[3.2.1]octane-2,4-dione
—— (1R,4S)-1-[(2S)-2-bromo-2-phenylethyl]-4,7,7-trimethyl-2-oxabicyclo[2.2.1]heptan-3-one —— C17H21BrO2
(1R,4S)-1-[(2S)-2-bromo-2-phenylethyl]-4,7,7-trimethyl-2-oxabicyclo[2.2.1]heptan-3-one
—— (3S,6R)-6-methyl-3-octanoyloxane-2,4-dione —— C14H22O4
(3S,6R)-6-methyl-3-octanoyloxane-2,4-dione
—— (1S,5S,6S,7R)-6,7-dichloro-3-oxabicyclo[3.2.0]heptane-2,4-dione —— C6H4Cl2O3
(1S,5S,6S,7R)-6,7-dichloro-3-oxabicyclo[3.2.0]heptane-2,4-dione
—— (3R,6S)-6-methyl-3-octanoyloxane-2,4-dione —— C14H22O4
(3R,6S)-6-methyl-3-octanoyloxane-2,4-dione
—— (3S,6S)-6-methyl-3-octanoyloxane-2,4-dione —— C14H22O4
(3S,6S)-6-methyl-3-octanoyloxane-2,4-dione
—— (1R,5R,6R,7S)-6,7-dichloro-3-oxabicyclo[3.2.0]heptane-2,4-dione —— C6H4Cl2O3
(1R,5R,6R,7S)-6,7-dichloro-3-oxabicyclo[3.2.0]heptane-2,4-dione
—— (3R,6R)-6-methyl-3-octanoyloxane-2,4-dione —— C14H22O4
(3R,6R)-6-methyl-3-octanoyloxane-2,4-dione
—— 3-[butylamino(sulfanyl)methylidene]oxolane-2,4-dione —— C9H13NO3S
3-[butylamino(sulfanyl)methylidene]oxolane-2,4-dione
—— 3-[(benzylamino)-sulfanylmethylidene]oxolane-2,4-dione —— C12H11NO3S
3-[(benzylamino)-sulfanylmethylidene]oxolane-2,4-dione
—— (1R,5R,8R)-8-(bromomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione —— C10H13BrO3
(1R,5R,8R)-8-(bromomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione
—— [(Z)-1-(4-hexyl-5-oxooxolan-2-yl)ethylideneamino]urea —— C13H23N3O3
[(Z)-1-(4-hexyl-5-oxooxolan-2-yl)ethylideneamino]urea
—— (1S,5S,6S)-5-hydroxy-3,7-dioxabicyclo[4.2.1]nonan-2-one —— C7H10O4
(1S,5S,6S)-5-hydroxy-3,7-dioxabicyclo[4.2.1]nonan-2-one
—— (1S,5S,6R)-5-hydroxy-3,7-dioxabicyclo[4.2.1]nonan-2-one —— C7H10O4
(1S,5S,6R)-5-hydroxy-3,7-dioxabicyclo[4.2.1]nonan-2-one
—— (1R,5S,6R)-5-hydroxy-3,7-dioxabicyclo[4.2.1]nonan-2-one —— C7H10O4
(1R,5S,6R)-5-hydroxy-3,7-dioxabicyclo[4.2.1]nonan-2-one
—— (1R,5S,6S)-5-hydroxy-3,7-dioxabicyclo[4.2.1]nonan-2-one —— C7H10O4
(1R,5S,6S)-5-hydroxy-3,7-dioxabicyclo[4.2.1]nonan-2-one
—— (1S,4R,7R,8S)-4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.04,8]undeca-5,9-diene-10-carboxamide —— C10H9NO5
(1S,4R,7R,8S)-4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.04,8]undeca-5,9-diene-10-carboxamide
—— (3R)-3-decyloxolan-2-one —— C14H26O2
(3R)-3-decyloxolan-2-one
—— (3S)-3-decyloxolan-2-one —— C14H26O2
(3S)-3-decyloxolan-2-one
—— (5S)-5-methyl-5-octyloxolan-2-one —— C13H24O2
(5S)-5-methyl-5-octyloxolan-2-one
—— (3S)-3-heptyloxan-2-one —— C12H22O2
(3S)-3-heptyloxan-2-one
—— (3R)-3-heptyloxan-2-one —— C12H22O2
(3R)-3-heptyloxan-2-one
—— (1R,5R,6R)-1-bromo-4-oxo-3-oxabicyclo[3.1.0]hexane-6-carboxylic acid —— C6H5BrO4
(1R,5R,6R)-1-bromo-4-oxo-3-oxabicyclo[3.1.0]hexane-6-carboxylic acid
—— 2-butoxyethyl (1S,2R,3R,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylate —— C16H26O5
2-butoxyethyl (1S,2R,3R,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylate
—— 2-butoxyethyl (1S,2S,3S,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylate —— C16H26O5
2-butoxyethyl (1S,2S,3S,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylate
—— (1S,5R,8S)-8-[(Z)-pent-2-enyl]-2-oxabicyclo[3.2.1]octan-3-one —— C12H18O2
(1S,5R,8S)-8-[(Z)-pent-2-enyl]-2-oxabicyclo[3.2.1]octan-3-one
—— (1S,4S)-4,7,7-trimethyl-3-oxo-N-[3-[[(1S,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-[3-[[(1S,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)-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,4S)-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,8R)-8-[(Z)-pent-2-enyl]-2-oxabicyclo[3.2.1]octan-3-one —— C12H18O2
(1S,5R,8R)-8-[(Z)-pent-2-enyl]-2-oxabicyclo[3.2.1]octan-3-one
—— (3S)-3-ethyloxolane-2,4-dione —— C6H8O3
(3S)-3-ethyloxolane-2,4-dione
—— (5Z,9E)-5,9-dimethyl-1-oxacycloundeca-5,9-dien-2-one —— C12H18O2
(5Z,9E)-5,9-dimethyl-1-oxacycloundeca-5,9-dien-2-one
—— (1S,4S)-4,7,7-trimethyl-N-(2-morpholin-4-ylethyl)-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C16H26N2O4
(1S,4S)-4,7,7-trimethyl-N-(2-morpholin-4-ylethyl)-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1R,3S,6R,9S)-3-methyl-5-oxatricyclo[4.2.1.03,9]nonan-4-one —— C9H12O2
(1R,3S,6R,9S)-3-methyl-5-oxatricyclo[4.2.1.03,9]nonan-4-one
—— (1R,3R,6R,9S)-3-methyl-5-oxatricyclo[4.2.1.03,9]nonan-4-one —— C9H12O2
(1R,3R,6R,9S)-3-methyl-5-oxatricyclo[4.2.1.03,9]nonan-4-one
—— (1R,3S,6S,8S,9R)-8-methyl-5-oxatricyclo[4.2.1.03,9]nonan-4-one —— C9H12O2
(1R,3S,6S,8S,9R)-8-methyl-5-oxatricyclo[4.2.1.03,9]nonan-4-one
—— ethyl (1S,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate —— C12H18O4
ethyl (1S,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
—— (1S,5R)-6,6-dimethyl-1-propan-2-yl-2-oxabicyclo[3.1.0]hexan-3-one —— C10H16O2
(1S,5R)-6,6-dimethyl-1-propan-2-yl-2-oxabicyclo[3.1.0]hexan-3-one