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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
—— 6a-Hydroxy-6,9a-dimethyl-3,3a,4,5,6,7,8,9b-octahydroazuleno[8,7-b]furan-2,9-dione —— C14H20O4
6a-Hydroxy-6,9a-dimethyl-3,3a,4,5,6,7,8,9b-octahydroazuleno[8,7-b]furan-2,9-dione
—— (3S,3aR,4S,9aR,9bS)-3,4,6,9-tetramethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione —— C16H20O3
(3S,3aR,4S,9aR,9bS)-3,4,6,9-tetramethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
—— (3S,3aS,4S,9aS,9bS)-3,4,6,9-tetramethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione —— C16H20O3
(3S,3aS,4S,9aS,9bS)-3,4,6,9-tetramethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
—— (3S)-3-[[(3R)-2-oxooxolan-3-yl]disulfanyl]oxolan-2-one —— C8H10O4S2
(3S)-3-[[(3R)-2-oxooxolan-3-yl]disulfanyl]oxolan-2-one
—— 3-(5-hydroxy-4,4,5-trimethyl-2-oxooxolan-3-yl)-N,N-dimethylpropanamide —— C12H21NO4
3-(5-hydroxy-4,4,5-trimethyl-2-oxooxolan-3-yl)-N,N-dimethylpropanamide
—— (3S)-3-bromooxan-2-one —— C5H7BrO2
(3S)-3-bromooxan-2-one
—— 2-[(3S,4E)-4-(1-chloroethylidene)-5-oxooxolan-3-yl]acetic acid —— C8H9ClO4
2-[(3S,4E)-4-(1-chloroethylidene)-5-oxooxolan-3-yl]acetic acid
—— (3R)-3-bromooxan-2-one —— C5H7BrO2
(3R)-3-bromooxan-2-one
—— 2-[(3R,4E)-4-(1-chloroethylidene)-5-oxooxolan-3-yl]acetic acid —— C8H9ClO4
2-[(3R,4E)-4-(1-chloroethylidene)-5-oxooxolan-3-yl]acetic acid
—— (3E,5S)-3-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-5-hydroxyoxolan-2-one —— C20H30O3
(3E,5S)-3-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-5-hydroxyoxolan-2-one
—— (3S)-5,5-dimethyl-2-oxo-3-prop-2-enyloxolane-3-carboxylic acid —— C10H14O4
(3S)-5,5-dimethyl-2-oxo-3-prop-2-enyloxolane-3-carboxylic acid
—— (3R,5R)-3-acetyl-5-ethyloxolan-2-one —— C8H12O3
(3R,5R)-3-acetyl-5-ethyloxolan-2-one
—— (5R)-5-(cyclohexen-1-yl)oxolan-2-one —— C10H14O2
(5R)-5-(cyclohexen-1-yl)oxolan-2-one
—— (5S)-5-(cyclohexen-1-yl)oxolan-2-one —— C10H14O2
(5S)-5-(cyclohexen-1-yl)oxolan-2-one
—— (3R)-3-acetyl-3-[2-(chloromethyl)prop-2-enyl]oxolan-2-one —— C10H13ClO3
(3R)-3-acetyl-3-[2-(chloromethyl)prop-2-enyl]oxolan-2-one
—— (3R,5R)-3-acetyl-5-(chloromethyl)oxolan-2-one —— C7H9ClO3
(3R,5R)-3-acetyl-5-(chloromethyl)oxolan-2-one
—— (3R,5S)-3-acetyl-5-(chloromethyl)oxolan-2-one —— C7H9ClO3
(3R,5S)-3-acetyl-5-(chloromethyl)oxolan-2-one
—— (2R)-2-[(2R,3R,4R)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetic acid —— C6H8O7
(2R)-2-[(2R,3R,4R)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetic acid
—— (2S)-3,3-dimethyl-5-oxooxolane-2-carbonyl chloride —— C7H9ClO3
(2S)-3,3-dimethyl-5-oxooxolane-2-carbonyl chloride
—— (5S)-3-methylidene-5-propyloxolan-2-one —— C8H12O2
(5S)-3-methylidene-5-propyloxolan-2-one
—— (2R)-3,3-dimethyl-5-oxooxolane-2-carbonyl chloride —— C7H9ClO3
(2R)-3,3-dimethyl-5-oxooxolane-2-carbonyl chloride
—— (5R,8R)-2-amino-8-methyl-7-oxa-1-thia-3-azaspiro[4.4]non-2-ene-4,6-dione —— C7H8N2O3S
(5R,8R)-2-amino-8-methyl-7-oxa-1-thia-3-azaspiro[4.4]non-2-ene-4,6-dione
—— (5S,8S)-2-amino-8-methyl-7-oxa-1-thia-3-azaspiro[4.4]non-2-ene-4,6-dione —— C7H8N2O3S
(5S,8S)-2-amino-8-methyl-7-oxa-1-thia-3-azaspiro[4.4]non-2-ene-4,6-dione
—— (5S,8R)-2-amino-8-methyl-7-oxa-1-thia-3-azaspiro[4.4]non-2-ene-4,6-dione —— C7H8N2O3S
(5S,8R)-2-amino-8-methyl-7-oxa-1-thia-3-azaspiro[4.4]non-2-ene-4,6-dione
—— (5R,8S)-2-amino-8-methyl-7-oxa-1-thia-3-azaspiro[4.4]non-2-ene-4,6-dione —— C7H8N2O3S
(5R,8S)-2-amino-8-methyl-7-oxa-1-thia-3-azaspiro[4.4]non-2-ene-4,6-dione
—— [(1S,3S,7R,8R,8aS)-3-(hydroxymethyl)-8-[2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate —— C25H38O6
[(1S,3S,7R,8R,8aS)-3-(hydroxymethyl)-8-[2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate
—— [(1R,3S,7R,8R,8aS)-3-(hydroxymethyl)-8-[2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate —— C25H38O6
[(1R,3S,7R,8R,8aS)-3-(hydroxymethyl)-8-[2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate
—— (3R,5R)-5-hexyl-3-hydroxyoxolan-2-one —— C10H18O3
(3R,5R)-5-hexyl-3-hydroxyoxolan-2-one
—— (3R,4S,5R)-3-hydroxy-4-methyl-5-propan-2-yloxolan-2-one —— C8H14O3
(3R,4S,5R)-3-hydroxy-4-methyl-5-propan-2-yloxolan-2-one
—— [(1R,3R,7R,8R,8aS)-3-(hydroxymethyl)-8-[2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate —— C25H38O6
[(1R,3R,7R,8R,8aS)-3-(hydroxymethyl)-8-[2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate
—— [(1S,3R,7R,8R,8aS)-3-(hydroxymethyl)-8-[2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate —— C25H38O6
[(1S,3R,7R,8R,8aS)-3-(hydroxymethyl)-8-[2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate
—— (3S,4R,5R)-3-hydroxy-4-methyl-5-propan-2-yloxolan-2-one —— C8H14O3
(3S,4R,5R)-3-hydroxy-4-methyl-5-propan-2-yloxolan-2-one
—— (2S,3S,4S,5S)-4-amino-2,5-dimethyl-6-oxooxane-3-carboxylic acid —— C8H13NO4
(2S,3S,4S,5S)-4-amino-2,5-dimethyl-6-oxooxane-3-carboxylic acid
—— (3S)-3-(2-methoxyethyl)oxolan-2-one —— C7H12O3
(3S)-3-(2-methoxyethyl)oxolan-2-one
—— 2-[(3R)-2-oxooxolan-3-yl]acetic acid —— C6H8O4
2-[(3R)-2-oxooxolan-3-yl]acetic acid
—— (3R)-3-(2-methoxyethyl)oxolan-2-one —— C7H12O3
(3R)-3-(2-methoxyethyl)oxolan-2-one
—— 2-[(3S)-2-oxooxolan-3-yl]acetic acid —— C6H8O4
2-[(3S)-2-oxooxolan-3-yl]acetic acid
—— (3R)-3-hydroxy-3,5,5-trimethyloxolan-2-one —— C7H12O3
(3R)-3-hydroxy-3,5,5-trimethyloxolan-2-one
—— (3aS,6aS)-2-oxo-3,3a,6,6a-tetrahydrocyclopenta[b]furan-4-carbaldehyde —— C8H8O3
(3aS,6aS)-2-oxo-3,3a,6,6a-tetrahydrocyclopenta[b]furan-4-carbaldehyde
—— (3aR,6aR)-2-oxo-3,3a,6,6a-tetrahydrocyclopenta[b]furan-4-carbaldehyde —— C8H8O3
(3aR,6aR)-2-oxo-3,3a,6,6a-tetrahydrocyclopenta[b]furan-4-carbaldehyde
—— (3S)-3-hydroxy-3,5,5-trimethyloxolan-2-one —— C7H12O3
(3S)-3-hydroxy-3,5,5-trimethyloxolan-2-one
—— (5S)-3-methylidene-5-propan-2-yloxolan-2-one —— C8H12O2
(5S)-3-methylidene-5-propan-2-yloxolan-2-one
—— (5R)-3-methylidene-5-propan-2-yloxolan-2-one —— C8H12O2
(5R)-3-methylidene-5-propan-2-yloxolan-2-one
—— (5S,6R)-4,7-dioxadispiro[4.0.46.25]dodecane-3,8-dione —— C10H12O4
(5S,6R)-4,7-dioxadispiro[4.0.46.25]dodecane-3,8-dione
—— (5S,6S)-4,7-dioxadispiro[4.0.46.25]dodecane-3,8-dione —— C10H12O4
(5S,6S)-4,7-dioxadispiro[4.0.46.25]dodecane-3,8-dione
—— (5R,6R)-4,7-dioxadispiro[4.0.46.25]dodecane-3,8-dione —— C10H12O4
(5R,6R)-4,7-dioxadispiro[4.0.46.25]dodecane-3,8-dione
—— (4R,7R,9S,11R)-11-hydroxy-9-methyl-3-oxatricyclo[5.3.1.04,11]undec-1(10)-en-2-one —— C11H14O3
(4R,7R,9S,11R)-11-hydroxy-9-methyl-3-oxatricyclo[5.3.1.04,11]undec-1(10)-en-2-one
—— (3S)-3-acetyloxepan-2-one —— C8H12O3
(3S)-3-acetyloxepan-2-one
—— (1R,5R)-3,3-dibromo-5-(bromomethyl)-8,8-dimethyl-6-oxabicyclo[3.2.1]octane-4,7-dione —— C10H11Br3O3
(1R,5R)-3,3-dibromo-5-(bromomethyl)-8,8-dimethyl-6-oxabicyclo[3.2.1]octane-4,7-dione
—— (2R,4S,5S,7S,9R,13S,14S)-7-methyl-12-methylidene-3,6,10,15-tetraoxapentacyclo[12.2.1.02,4.05,7.09,13]heptadec-1(17)-ene-11,16-dione —— C15H14O6
(2R,4S,5S,7S,9R,13S,14S)-7-methyl-12-methylidene-3,6,10,15-tetraoxapentacyclo[12.2.1.02,4.05,7.09,13]heptadec-1(17)-ene-11,16-dione