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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
—— (3Z,5R)-3-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-5-methoxyoxolan-2-one —— C21H32O3
(3Z,5R)-3-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-5-methoxyoxolan-2-one
—— (3Z,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-methoxyoxolan-2-one —— C21H32O3
(3Z,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-methoxyoxolan-2-one
—— (6S,9aR)-6-methyl-1,5,6,7,9,9a-hexahydrocycloocta[c]furan-3,8-dione —— C11H14O3
(6S,9aR)-6-methyl-1,5,6,7,9,9a-hexahydrocycloocta[c]furan-3,8-dione
—— (5S)-5-but-1-ynyloxolan-2-one —— C8H10O2
(5S)-5-but-1-ynyloxolan-2-one
—— (3R)-3-acetyloxepan-2-one —— C8H12O3
(3R)-3-acetyloxepan-2-one
—— (3aS,4R,6aS)-4-methoxy-3-methyl-2-oxido-4,6a-dihydro-3aH-furo[3,4-d][1,2]oxazol-2-ium-6-one —— C7H9NO5
(3aS,4R,6aS)-4-methoxy-3-methyl-2-oxido-4,6a-dihydro-3aH-furo[3,4-d][1,2]oxazol-2-ium-6-one
—— (3R)-3-[(2R)-3-methylbut-3-en-2-yl]oxolan-2-one —— C9H14O2
(3R)-3-[(2R)-3-methylbut-3-en-2-yl]oxolan-2-one
—— (4R,6S)-6-methyl-4-[(1S)-2,6,6-trimethylcyclohex-2-en-1-yl]oxan-2-one —— C15H24O2
(4R,6S)-6-methyl-4-[(1S)-2,6,6-trimethylcyclohex-2-en-1-yl]oxan-2-one
—— (3S)-3-[(2R)-6-methylheptan-2-yl]oxan-2-one —— C13H24O2
(3S)-3-[(2R)-6-methylheptan-2-yl]oxan-2-one
—— (4S,6S)-6-methyl-4-(2,6,6-trimethylcyclohexen-1-yl)oxan-2-one —— C15H24O2
(4S,6S)-6-methyl-4-(2,6,6-trimethylcyclohexen-1-yl)oxan-2-one
—— (3R)-3-[(2S)-6-methylheptan-2-yl]oxan-2-one —— C13H24O2
(3R)-3-[(2S)-6-methylheptan-2-yl]oxan-2-one
—— (4S,6R)-6-methyl-4-(2,6,6-trimethylcyclohexen-1-yl)oxan-2-one —— C15H24O2
(4S,6R)-6-methyl-4-(2,6,6-trimethylcyclohexen-1-yl)oxan-2-one
—— (3S)-3-[(2S)-6-methylheptan-2-yl]oxan-2-one —— C13H24O2
(3S)-3-[(2S)-6-methylheptan-2-yl]oxan-2-one
—— (4S,6S)-6-methyl-4-[(1S)-2,6,6-trimethylcyclohex-2-en-1-yl]oxan-2-one —— C15H24O2
(4S,6S)-6-methyl-4-[(1S)-2,6,6-trimethylcyclohex-2-en-1-yl]oxan-2-one
—— (5S)-5-[(2R)-2,6-dimethylheptyl]oxolan-2-one —— C13H24O2
(5S)-5-[(2R)-2,6-dimethylheptyl]oxolan-2-one
—— (3R,5S)-3-chloro-3,5-dimethyl-5-phenyloxolan-2-one —— C12H13ClO2
(3R,5S)-3-chloro-3,5-dimethyl-5-phenyloxolan-2-one
—— (3S,5S)-3-chloro-3,5-dimethyl-5-phenyloxolan-2-one —— C12H13ClO2
(3S,5S)-3-chloro-3,5-dimethyl-5-phenyloxolan-2-one
—— (3R,5S)-5-butyl-3-chlorooxolan-2-one —— C8H13ClO2
(3R,5S)-5-butyl-3-chlorooxolan-2-one
—— (3S,5R)-3-chloro-5-hexyl-3-methyloxolan-2-one —— C11H19ClO2
(3S,5R)-3-chloro-5-hexyl-3-methyloxolan-2-one
—— (3R,5R)-3-chloro-5-hexyl-3-methyloxolan-2-one —— C11H19ClO2
(3R,5R)-3-chloro-5-hexyl-3-methyloxolan-2-one
—— (5R)-5-[(2R)-6-methylheptan-2-yl]oxolan-2-one —— C12H22O2
(5R)-5-[(2R)-6-methylheptan-2-yl]oxolan-2-one
—— [(2Z)-10-hydroxy-2,11-dimethyl-6,12-dioxospiro[5,14-dioxatricyclo[9.2.1.04,8]tetradeca-1(13),2-diene-7,2'-oxirane]-9-yl] 2-methylprop-2-enoate —— C19H20O8
[(2Z)-10-hydroxy-2,11-dimethyl-6,12-dioxospiro[5,14-dioxatricyclo[9.2.1.04,8]tetradeca-1(13),2-diene-7,2'-oxirane]-9-yl] 2-methylprop-2-enoate
—— [(E)-1-[5-(2-methylpropoxymethyl)-2-oxooxolan-3-yl]propan-2-ylideneamino]thiourea —— C13H23N3O3S
[(E)-1-[5-(2-methylpropoxymethyl)-2-oxooxolan-3-yl]propan-2-ylideneamino]thiourea
—— (8Z)-10-hydroxy-3,8-dimethyl-12-methylidene-4,14-dioxatricyclo[9.3.0.03,5]tetradec-8-en-13-one —— C15H20O4
(8Z)-10-hydroxy-3,8-dimethyl-12-methylidene-4,14-dioxatricyclo[9.3.0.03,5]tetradec-8-en-13-one
—— (3R)-3-(2-bromoethyl)oxolan-2-one —— C6H9BrO2
(3R)-3-(2-bromoethyl)oxolan-2-one
—— (3R)-3-ethanethioyloxolan-2-one —— C6H8O2S
(3R)-3-ethanethioyloxolan-2-one
—— (3E,5S)-3-(dimethylaminomethylidene)-5-methyloxolane-2,4-dione —— C8H11NO3
(3E,5S)-3-(dimethylaminomethylidene)-5-methyloxolane-2,4-dione
—— (1R,1aS,3aR,7aR)-1-ethyl-1-methyl-1a,3a,6,7-tetrahydrocyclopropa[c][2]benzofuran-3-one —— C12H16O2
(1R,1aS,3aR,7aR)-1-ethyl-1-methyl-1a,3a,6,7-tetrahydrocyclopropa[c][2]benzofuran-3-one
—— [(1S,7S,8S,8aS)-8-[2-[(2S,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate —— C23H34O5
[(1S,7S,8S,8aS)-8-[2-[(2S,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate
—— (3S)-6-methylidene-3-propan-2-yloxan-2-one —— C9H14O2
(3S)-6-methylidene-3-propan-2-yloxan-2-one
—— (2E)-2-[4-(5-methyl-2-oxotetrahydrofuran-3-yl)butan-2-ylidene]hydrazinecarboxamide —— C10H17N3O3
(2E)-2-[4-(5-methyl-2-oxotetrahydrofuran-3-yl)butan-2-ylidene]hydrazinecarboxamide
—— [(1S,3R,7S,8S,8aS)-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
[(1S,3R,7S,8S,8aS)-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
—— (1R,4R,8R,9S,12R)-9-hydroxy-2-oxatricyclo[6.3.1.04,12]dodeca-5,10-dien-3-one —— C11H12O3
(1R,4R,8R,9S,12R)-9-hydroxy-2-oxatricyclo[6.3.1.04,12]dodeca-5,10-dien-3-one
—— 9-[(1E)-1-decenyl]-2-oxonanone —— C18H32O2
9-[(1E)-1-decenyl]-2-oxonanone
—— 3-(hydroxymethylene)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one —— C8H8O3
3-(hydroxymethylene)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one
—— (3E)-3-[[8-[[(Z)-(2-oxooxolan-3-ylidene)methyl]amino]octylamino]methylidene]oxolan-2-one —— C18H28N2O4
(3E)-3-[[8-[[(Z)-(2-oxooxolan-3-ylidene)methyl]amino]octylamino]methylidene]oxolan-2-one
—— (3Z)-3-[1-(1,3-thiazol-2-ylamino)ethylidene]oxolane-2,4-dione —— C9H8N2O3S
(3Z)-3-[1-(1,3-thiazol-2-ylamino)ethylidene]oxolane-2,4-dione
—— (6Z,10E)-3-[(dimethylamino)methyl]-7,10-dimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one —— C17H27NO2
(6Z,10E)-3-[(dimethylamino)methyl]-7,10-dimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one
—— (3E)-3-[(2-aminothiophen-3-yl)methylidene]oxolan-2-one —— C9H9NO2S
(3E)-3-[(2-aminothiophen-3-yl)methylidene]oxolan-2-one
—— (1'S,5R,7'R)-3-methylidenespiro[oxolane-5,4'-tricyclo[3.3.1.02,7]nonane]-2-one —— C13H16O2
(1'S,5R,7'R)-3-methylidenespiro[oxolane-5,4'-tricyclo[3.3.1.02,7]nonane]-2-one
—— (3Z)-3-[9-[(2S)-oxiran-2-yl]nonylidene]oxolan-2-one —— C15H24O3
(3Z)-3-[9-[(2S)-oxiran-2-yl]nonylidene]oxolan-2-one
—— (3R,5S)-5-methyl-3-[[2-[[(3R,5R)-5-methyl-2-oxooxolan-3-yl]methyl]phenyl]methyl]oxolan-2-one —— C18H22O4
(3R,5S)-5-methyl-3-[[2-[[(3R,5R)-5-methyl-2-oxooxolan-3-yl]methyl]phenyl]methyl]oxolan-2-one
—— (3R,3aR,7Z,9aS,9bR)-7-hydroxyimino-3,6,9-trimethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2-one —— C15H19NO3
(3R,3aR,7Z,9aS,9bR)-7-hydroxyimino-3,6,9-trimethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2-one
—— [(1S,7S,8S,8aS)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-3-methylidene-2,7,8,8a-tetrahydro-1H-naphthalen-1-yl] 2,2-dimethylbutanoate —— C25H36O5
[(1S,7S,8S,8aS)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-3-methylidene-2,7,8,8a-tetrahydro-1H-naphthalen-1-yl] 2,2-dimethylbutanoate
—— (3S,4R)-3-hydroxy-4-(hydroxymethyl)-3-[(E)-3-[(2S,3R)-3-methyloxiran-2-yl]prop-2-enoyl]oxolan-2-one —— C11H14O6
(3S,4R)-3-hydroxy-4-(hydroxymethyl)-3-[(E)-3-[(2S,3R)-3-methyloxiran-2-yl]prop-2-enoyl]oxolan-2-one
—— (3R,6E)-6-(bromomethylidene)-3-phenyloxan-2-one —— C12H11BrO2
(3R,6E)-6-(bromomethylidene)-3-phenyloxan-2-one
—— (3S,8aS)-3-methoxy-5-methyl-3-oxo-8,8a-dihydro-1H-furo[3,4-e][1,3,2]dioxaphosphepin-6-one —— C8H11O6P
(3S,8aS)-3-methoxy-5-methyl-3-oxo-8,8a-dihydro-1H-furo[3,4-e][1,3,2]dioxaphosphepin-6-one
—— methyl (2Z)-2-[(4S)-4,5,5-trimethyl-2-oxooxolan-3-ylidene]acetate —— C10H14O4
methyl (2Z)-2-[(4S)-4,5,5-trimethyl-2-oxooxolan-3-ylidene]acetate
—— (3Z)-3-(1-aminoethylidene)oxolane-2,4-dione —— C6H7NO3
(3Z)-3-(1-aminoethylidene)oxolane-2,4-dione
—— [(Z)-1-[(2R,4R)-4-heptyl-5-oxooxolan-2-yl]ethylideneamino]urea —— C14H25N3O3
[(Z)-1-[(2R,4R)-4-heptyl-5-oxooxolan-2-yl]ethylideneamino]urea