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    首页 分子通 按分子结构分类 有机化合物 有机杂环化合物 内酯类

    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
    —— (3aR,4R,5R,6aS)-5-hydroxy-4-[(3S)-3-hydroxy-5-phenylpent-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one —— C18H22O4
    (3aR,4R,5R,6aS)-5-hydroxy-4-[(3S)-3-hydroxy-5-phenylpent-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
    —— 2,5-di-O-methanesulfonyl-L-rhamnono-1,4-lactone 146331-65-9 C8H14O9S2
    2,5-di-O-methanesulfonyl-L-rhamnono-1,4-lactone
    —— 8α-hydroxyachillin 35879-92-6 C15H18O4
    8α-hydroxyachillin
    —— (5R,6S)-9-Dodec-(E)-ylidene-6-hydroxymethyl-1,7-dioxa-spiro[4.4]nonane-2,8-dione 154086-40-5 C20H32O5
    (5R,6S)-9-Dodec-(E)-ylidene-6-hydroxymethyl-1,7-dioxa-spiro[4.4]nonane-2,8-dione
    —— 3-[1-Trimethylsilanyl-meth-(E)-ylidene]-1-oxa-spiro[4.5]decan-2-one 142636-36-0 C13H22O2Si
    3-[1-Trimethylsilanyl-meth-(E)-ylidene]-1-oxa-spiro[4.5]decan-2-one
    —— 2,2,2-trifluoro-N-[(3S,4S)-4-methyl-5-oxooxolan-3-yl]acetamide 118456-80-7 C7H8F3NO3
    2,2,2-trifluoro-N-[(3S,4S)-4-methyl-5-oxooxolan-3-yl]acetamide
    —— (-)-simplactone A 252722-14-8 C7H12O3
    (-)-simplactone A
    —— 3-hydroxy-2,4(3H,5H)-furandione 34359-76-7 C4H4O4
    3-hydroxy-2,4(3H,5H)-furandione
    —— (R)-β-hydroxymethyl-β-propiolactone 227451-38-9 C4H6O3
    (R)-β-hydroxymethyl-β-propiolactone
    —— 3,4,4a,5-Tetrahydro-cyclopenta[c]pyran-1,6-dione 143121-33-9 C8H8O3
    3,4,4a,5-Tetrahydro-cyclopenta[c]pyran-1,6-dione
    —— (3S,4R)-4-Hydroxy-3-hydroxymethyl-3-methyl-dihydro-furan-2-one 155882-56-7 C6H10O4
    (3S,4R)-4-Hydroxy-3-hydroxymethyl-3-methyl-dihydro-furan-2-one
    —— 8,9-dimethoxy-7-phenyl-3-oxatricyclo<8.2.0.0<sup>1,5</sup>>dodeca-5,9,11-trien-4-one 144744-73-0 C19H18O4
    8,9-dimethoxy-7-phenyl-3-oxatricyclo<8.2.0.0<sup>1,5</sup>>dodeca-5,9,11-trien-4-one
    —— 2,2,2-trifluoro-N-[(3S,4R)-4-methyl-5-oxooxolan-3-yl]acetamide 118456-79-4 C7H8F3NO3
    2,2,2-trifluoro-N-[(3S,4R)-4-methyl-5-oxooxolan-3-yl]acetamide
    —— 7-Phenyl-3,4,4a,5-tetrahydro-cyclopenta[c]pyran-1,6-dione 143121-34-0 C14H12O3
    7-Phenyl-3,4,4a,5-tetrahydro-cyclopenta[c]pyran-1,6-dione
    —— (2S,4R,5S)-4-hydroxy-5-<(methanesulfonyl)oxy>-2-isopropyl-7-methyloctanoic acid, γ-lactone 144413-08-1 C13H24O5S
    (2S,4R,5S)-4-hydroxy-5-<(methanesulfonyl)oxy>-2-isopropyl-7-methyloctanoic acid, γ-lactone
    —— tert-butyl N-[(E,3S)-4-methyl-1-(2-oxooxan-4-yl)pent-1-en-3-yl]carbamate 143327-92-8 C16H27NO4
    tert-butyl N-[(E,3S)-4-methyl-1-(2-oxooxan-4-yl)pent-1-en-3-yl]carbamate
    —— 2-oxatricyclo[5.2.1.04,10]decane-3-one 69641-94-7 C9H12O2
    2-oxatricyclo[5.2.1.04,10]decane-3-one
    —— (S)-9-Methyl-8-oxa-1,4-dithia-spiro[4.5]decan-7-one 148066-70-0 C8H12O2S2
    (S)-9-Methyl-8-oxa-1,4-dithia-spiro[4.5]decan-7-one
    —— (S)-6-pentyl-5,6-dihydropyran-2(3H),4-dione 158732-49-1 C10H16O3
    (S)-6-pentyl-5,6-dihydropyran-2(3H),4-dione
    —— (5-Oxo-tetrahydro-furan-3-ylmethyl)-tetradecyl-phosphinic acid ethyl ester 1026173-02-3 C21H41O4P
    (5-Oxo-tetrahydro-furan-3-ylmethyl)-tetradecyl-phosphinic acid ethyl ester
    —— 4-Methyl-6-methylidenetetrahydro-2-pyranone 92911-99-4 C7H10O2
    4-Methyl-6-methylidenetetrahydro-2-pyranone
    —— (1S,7S,9R,10S)-1,9-Dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.03,7]tetradecane-5,12-dione 16983-23-6 C15H20O4
    (1S,7S,9R,10S)-1,9-Dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.03,7]tetradecane-5,12-dione
    —— (2S,3R,4S)-4-Methyl-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid 647830-61-3 C14H24O4
    (2S,3R,4S)-4-Methyl-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid
    —— 7-Methyl-3,4,4a,5-tetrahydro-cyclopenta[c]pyran-1,6-dione 143121-31-7 C9H10O3
    7-Methyl-3,4,4a,5-tetrahydro-cyclopenta[c]pyran-1,6-dione
    —— 6-methyl-3a,4-dihydro-1H-cyclopenta[c]furan-1,5(3H)-dione 143121-32-8 C8H8O3
    6-methyl-3a,4-dihydro-1H-cyclopenta[c]furan-1,5(3H)-dione
    —— (2S,3R,4R)-4-Methyl-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid 647830-62-4 C14H24O4
    (2S,3R,4R)-4-Methyl-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid
    —— 3-[1-Trimethylsilanyl-meth-(Z)-ylidene]-1-oxa-spiro[4.5]decan-2-one 142636-37-1 C13H22O2Si
    3-[1-Trimethylsilanyl-meth-(Z)-ylidene]-1-oxa-spiro[4.5]decan-2-one
    —— (1S,2S,8S,11R,13R,17R)-15,15-dimethyl-3,12,14,16-tetraoxatetracyclo[9.6.0.02,8.013,17]heptadecan-4-one 1026678-19-2 C15H22O5
    (1S,2S,8S,11R,13R,17R)-15,15-dimethyl-3,12,14,16-tetraoxatetracyclo[9.6.0.02,8.013,17]heptadecan-4-one
    —— (1S,2S,6S,8R,11R,13R,17R)-6,15,15-trimethyl-3,12,14,16-tetraoxatetracyclo[9.6.0.02,8.013,17]heptadecan-4-one 142133-33-3 C16H24O5
    (1S,2S,6S,8R,11R,13R,17R)-6,15,15-trimethyl-3,12,14,16-tetraoxatetracyclo[9.6.0.02,8.013,17]heptadecan-4-one
    —— (3S,4R,5S)-3-(2-Chloro-ethyl)-5-hydroxymethyl-4-vinyl-dihydro-furan-2-one 1026643-17-3 C9H13ClO3
    (3S,4R,5S)-3-(2-Chloro-ethyl)-5-hydroxymethyl-4-vinyl-dihydro-furan-2-one
    —— diethyl (+)-(1S,5R)-2-oxo-3-oxabicyclo[3.1.0]hexan-1-ylphosphonate 1253573-46-4 C9H15O5P
    diethyl (+)-(1S,5R)-2-oxo-3-oxabicyclo[3.1.0]hexan-1-ylphosphonate
    —— ethyl N-[(E,1R)-1-[(3S,4S,5S,6R)-6-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-4-hydroxy-3,5-dimethyl-2-oxooxan-3-yl]-4-hydroxy-3-methylbut-2-enyl]carbamate 221008-04-4 C21H35NO8
    ethyl N-[(E,1R)-1-[(3S,4S,5S,6R)-6-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-4-hydroxy-3,5-dimethyl-2-oxooxan-3-yl]-4-hydroxy-3-methylbut-2-enyl]carbamate
    —— (R)-4-Allyl-4-methyl-tetrahydro-pyran-2-one 200204-49-5 C9H14O2
    (R)-4-Allyl-4-methyl-tetrahydro-pyran-2-one
    —— (4S,5S)-4-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-3-methylene-5-pentyl-dihydro-furan-2-one 218908-81-7 C18H34O4Si
    (4S,5S)-4-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-3-methylene-5-pentyl-dihydro-furan-2-one
    —— 4-Methyl-3-phenylselanyl-7-propan-2-yloxepan-2-one 199797-27-8 C16H22O2Se
    4-Methyl-3-phenylselanyl-7-propan-2-yloxepan-2-one
    —— (2S,3S,4S)-4-Methyl-5-oxo-2-pentyl-tetrahydro-furan-3-carboxylic acid ethyl ester 203514-29-8 C13H22O4
    (2S,3S,4S)-4-Methyl-5-oxo-2-pentyl-tetrahydro-furan-3-carboxylic acid ethyl ester
    —— β-(iodomethyl)-δ-valerolactone 129352-62-1 C6H9IO2
    β-(iodomethyl)-δ-valerolactone
    —— methyl (2'R,3'S,4'S)-2-[4'-hydroxy-2'-octyltetrahydrofuran-5'-on-3'-yl] acetate 290347-29-4 C15H26O5
    methyl (2'R,3'S,4'S)-2-[4'-hydroxy-2'-octyltetrahydrofuran-5'-on-3'-yl] acetate
    —— (1R,2R,6R,8S)-8-(2-trimethylsilylethoxymethoxy)spiro[3,5,10-trioxatricyclo[6.2.1.02,6]undecane-4,1'-cyclohexane]-9-one 185900-09-8 C19H32O6Si
    (1R,2R,6R,8S)-8-(2-trimethylsilylethoxymethoxy)spiro[3,5,10-trioxatricyclo[6.2.1.02,6]undecane-4,1'-cyclohexane]-9-one
    —— (S)-4-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-5-oxo-tetrahydro-furan-2-yl)-butyraldehyde 182072-78-2 C24H30O4Si
    (S)-4-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-5-oxo-tetrahydro-furan-2-yl)-butyraldehyde
    —— ((S)-5-Oxo-tetrahydro-furan-3-yl)-acetaldehyde 150932-65-3 C6H8O3
    ((S)-5-Oxo-tetrahydro-furan-3-yl)-acetaldehyde
    —— methyl (1R,5S,6S,8R)-10,10-dimethyl-2-oxo-3-oxatricyclo[6.3.0.01,5]undecane-6-carboxylate 203188-75-4 C14H20O4
    methyl (1R,5S,6S,8R)-10,10-dimethyl-2-oxo-3-oxatricyclo[6.3.0.01,5]undecane-6-carboxylate
    —— (S)-4-(tert-Butyl-diphenyl-silanyloxy)-4-((R)-5-oxo-tetrahydro-furan-2-yl)-butyraldehyde 182072-77-1 C24H30O4Si
    (S)-4-(tert-Butyl-diphenyl-silanyloxy)-4-((R)-5-oxo-tetrahydro-furan-2-yl)-butyraldehyde
    —— 5-O[(tert-butyl)dimethylsilyl]-2,3-dideoxy-2-fluoro-3-{[(tert-butyl)dimethylsilyl]oxy(methyl)amino}arabino-1,4-lactone 219841-71-1 C18H38FNO4Si2
    5-O[(tert-butyl)dimethylsilyl]-2,3-dideoxy-2-fluoro-3-{[(tert-butyl)dimethylsilyl]oxy(methyl)amino}arabino-1,4-lactone
    —— ((S)-4-Methyl-2-oxo-tetrahydro-pyran-4-yl)-acetaldehyde 200204-50-8 C8H12O3
    ((S)-4-Methyl-2-oxo-tetrahydro-pyran-4-yl)-acetaldehyde
    —— (+/-)-6,7-exo,exo-(isopropylidenedioxy)-2-oxabicyclo[3.2.1]octan-3-one —— C10H14O4
    (+/-)-6,7-exo,exo-(isopropylidenedioxy)-2-oxabicyclo[3.2.1]octan-3-one
    —— (R)-4-(2-Hydroxy-ethyl)-4-vinyl-dihydro-furan-2-one 1026352-20-4 C8H12O3
    (R)-4-(2-Hydroxy-ethyl)-4-vinyl-dihydro-furan-2-one
    —— (4S,5R)-4-[1,3]Dithian-2-ylmethyl-5-ethyl-tetrahydro-pyran-2-one 188434-51-7 C12H20O2S2
    (4S,5R)-4-[1,3]Dithian-2-ylmethyl-5-ethyl-tetrahydro-pyran-2-one
    —— (3aR,6aR)-6a-Hydroxymethyl-3-prop-2-en-(E)-ylidene-3a,6a-dihydro-3H-cyclopenta[b]furan-2,4-dione 110935-55-2 C11H10O4
    (3aR,6aR)-6a-Hydroxymethyl-3-prop-2-en-(E)-ylidene-3a,6a-dihydro-3H-cyclopenta[b]furan-2,4-dione
    —— 5-O-[(tert-butyl)dimethylsilyl]-2,3-dideoxy-2-fluoro-3-[hydroxy(methyl)amino]-D-arabino-1,4-lactone 219841-70-0 C12H24FNO4Si
    5-O-[(tert-butyl)dimethylsilyl]-2,3-dideoxy-2-fluoro-3-[hydroxy(methyl)amino]-D-arabino-1,4-lactone