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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
    —— (3R,5S)-5-[(2R)-2-[(1R,3aR,7aR)-7a-methyl-4-oxo-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-methyl-3-trimethylsilyloxyoxolan-2-one 83685-54-5 C21H36O4Si
    (3R,5S)-5-[(2R)-2-[(1R,3aR,7aR)-7a-methyl-4-oxo-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-methyl-3-trimethylsilyloxyoxolan-2-one
    —— 7-hydroxy-6-oxaspiro<3.4>octan-7-one 111728-63-3 C7H10O3
    7-hydroxy-6-oxaspiro<3.4>octan-7-one
    —— (3R,5S)-5-[(2R)-2-[(1R,3aR,7aR)-7a-methyl-4-oxo-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-hydroxy-3-methyloxolan-2-one 95667-89-3 C18H28O4
    (3R,5S)-5-[(2R)-2-[(1R,3aR,7aR)-7a-methyl-4-oxo-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-hydroxy-3-methyloxolan-2-one
    —— 3-[(1,3-Thiazol-2-ylamino)methylidene]oxolan-2-one 380631-70-9 C8H8N2O2S
    3-[(1,3-Thiazol-2-ylamino)methylidene]oxolan-2-one
    —— (2S,3S)-2,3,4,5-tetrahydro-5-oxo-2-pentylfuran-3-carboxylic acid 203514-28-7 C10H16O4
    (2S,3S)-2,3,4,5-tetrahydro-5-oxo-2-pentylfuran-3-carboxylic acid
    —— (4R,5R)-4-vinyl-5-[(R)-1-hydroxypentyl]-4,5-dihydro-2(3H)-furanone 1132793-44-2 C11H18O3
    (4R,5R)-4-vinyl-5-[(R)-1-hydroxypentyl]-4,5-dihydro-2(3H)-furanone
    —— (4R,5S)-4-ethenyl-2,3,4,5-tetrahydro-5-pentylfuran-2-one 501666-56-4 C11H18O2
    (4R,5S)-4-ethenyl-2,3,4,5-tetrahydro-5-pentylfuran-2-one
    —— (2S,3R)-(-)-3-formyl-5-oxo-2-pentyltetrahydrofuran 503605-23-0 C10H16O3
    (2S,3R)-(-)-3-formyl-5-oxo-2-pentyltetrahydrofuran
    —— (4S,5R)-4-vinyl-5-[(R)-1-hydroxypentyl]-4,5-dihydro-2(3H)-furanone 1132793-39-5 C11H18O3
    (4S,5R)-4-vinyl-5-[(R)-1-hydroxypentyl]-4,5-dihydro-2(3H)-furanone
    —— 5-epidihydromevinolin 101834-06-4 C24H38O5
    5-epidihydromevinolin
    —— 2H-Pyran-2,4(3H)-dione, dihydro-6-methyl-6-(phenylmethyl)- 626244-91-5 C13H14O3
    2H-Pyran-2,4(3H)-dione, dihydro-6-methyl-6-(phenylmethyl)-
    —— 6-Benzyl-3-[bis(methylsulfanyl)methylidene]-6-methyloxane-2,4-dione 626244-81-3 C16H18O3S2
    6-Benzyl-3-[bis(methylsulfanyl)methylidene]-6-methyloxane-2,4-dione
    —— (R)-5-(chloromethyl)-5-phenyldihydrofuran-2(3H)-one 1217263-85-8 C11H11ClO2
    (R)-5-(chloromethyl)-5-phenyldihydrofuran-2(3H)-one
    —— 5-(chloromethyl)-5-phenyldihydrofuran-2(3H)-one 1354037-29-8 C11H11ClO2
    5-(chloromethyl)-5-phenyldihydrofuran-2(3H)-one
    —— (2S,3S,4R,5R)-4-amino-2,5-dimethyl-6-oxooxane-3-carboxylic acid 116501-96-3 C8H13NO4
    (2S,3S,4R,5R)-4-amino-2,5-dimethyl-6-oxooxane-3-carboxylic acid
    —— (3R,5R)-5-(1-(tert-butyldiphenylsilyloxy)-2-methylpropan-2-yl)-3-methyldihydrofuran-2(3H)-one 215317-64-9 C25H34O3Si
    (3R,5R)-5-(1-(tert-butyldiphenylsilyloxy)-2-methylpropan-2-yl)-3-methyldihydrofuran-2(3H)-one
    —— (3R,5S)-3-hydroxy-5-hexyldihydrofuran-2-one 1383977-45-4 C10H18O3
    (3R,5S)-3-hydroxy-5-hexyldihydrofuran-2-one
    —— 4-Hydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one 91199-00-7 C6H10O4
    4-Hydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one
    —— (3S,5R)-3-hydroxy-5-hexyldihydrofuran-2-one 1383977-17-0 C10H18O3
    (3S,5R)-3-hydroxy-5-hexyldihydrofuran-2-one
    —— (3S,5S)-3-hydroxy-5-hexyldihydrofuran-2-one 1383977-28-3 C10H18O3
    (3S,5S)-3-hydroxy-5-hexyldihydrofuran-2-one
    —— 4,5-dimethyltetrahydro-2-pyrone 78094-66-3 C7H12O2
    4,5-dimethyltetrahydro-2-pyrone
    —— (3S,4S,5R)-3-methyl-5-undecyl-4-vinyltetrahydro-2-furanone 1219612-94-8 C18H32O2
    (3S,4S,5R)-3-methyl-5-undecyl-4-vinyltetrahydro-2-furanone
    —— 1-Oxa-8,11-dithiaspiro[5.6]dodeca-2,4-dione 116583-67-6 C9H12O3S2
    1-Oxa-8,11-dithiaspiro[5.6]dodeca-2,4-dione
    —— 2-oxo-6-phenyl-3-oxabicyclo[3.1.0]hexane-1-carbonitrile 910226-22-1 C12H9NO2
    2-oxo-6-phenyl-3-oxabicyclo[3.1.0]hexane-1-carbonitrile
    —— (3S,5S)-3-bromo-5-methyloxolan-2-one 25966-39-6 C5H7BrO2
    (3S,5S)-3-bromo-5-methyloxolan-2-one
    —— (+/-)-2-allyl-4-methyl-threo-1,4-butanolide 3926-76-9 C8H12O2
    (+/-)-2-allyl-4-methyl-threo-1,4-butanolide
    —— 4-methyl-2-(methylthio)-γ-butyrolactone 75938-43-1 C6H10O2S
    4-methyl-2-(methylthio)-γ-butyrolactone
    —— (3R,5R)-5-methyl-3-prop-2-enyloxolan-2-one 135820-07-4 C8H12O2
    (3R,5R)-5-methyl-3-prop-2-enyloxolan-2-one
    —— 3-[Hydroxy(phenyl)methyl]-5-methyloxolan-2-one 72806-83-8 C12H14O3
    3-[Hydroxy(phenyl)methyl]-5-methyloxolan-2-one
    —— 3-(1-Hydroxy-1-phenylethyl)-5-methyloxolan-2-one 113426-33-8 C13H16O3
    3-(1-Hydroxy-1-phenylethyl)-5-methyloxolan-2-one
    —— (3R,5S)-3-bromo-5-methyloxolan-2-one 25966-39-6 C5H7BrO2
    (3R,5S)-3-bromo-5-methyloxolan-2-one
    —— 3-[Bis(methylsulfanyl)methylidene]-6-methyloxane-2,4-dione 626244-80-2 C9H12O3S2
    3-[Bis(methylsulfanyl)methylidene]-6-methyloxane-2,4-dione
    —— (3a'R,4'R,7'R,8a'R)-tetrahydrospiro[cyclohexane-1,2'-[1,3,5]trioxa[4,7]methano[1,3]dioxolo[4,5-c]oxepin]-6'(4'H)-one 185900-33-8 C13H18O4
    (3a'R,4'R,7'R,8a'R)-tetrahydrospiro[cyclohexane-1,2'-[1,3,5]trioxa[4,7]methano[1,3]dioxolo[4,5-c]oxepin]-6'(4'H)-one
    —— (+)-(1S,2S,4aR,6S,8S,8aS)-1-(ethoxycarbonyl)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6,8-naphthalenecarbolactone 116097-23-5 C15H20O4
    (+)-(1S,2S,4aR,6S,8S,8aS)-1-(ethoxycarbonyl)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6,8-naphthalenecarbolactone
    —— (5aS,9aS)-1,3,5a,6,7,8,9,9a-octahydro-4-hydroxymethyl-9-methylen-2-benzoxepin-1-one 443646-89-7 C12H16O3
    (5aS,9aS)-1,3,5a,6,7,8,9,9a-octahydro-4-hydroxymethyl-9-methylen-2-benzoxepin-1-one
    —— 1-Bromo-4'-(diethylamino)-4,5'-dimethoxyspiro[3-oxabicyclo[3.1.0]hexane-6,3'-oxolane]-2,2'-dione 106874-89-9 C14H20BrNO6
    1-Bromo-4'-(diethylamino)-4,5'-dimethoxyspiro[3-oxabicyclo[3.1.0]hexane-6,3'-oxolane]-2,2'-dione
    —— (5aS,9aS)-1,3,5a,6,7,8,9,9a-octahydro-9-methylen-2-benzoxepin-4-carbaldehyde 443646-90-0 C12H14O3
    (5aS,9aS)-1,3,5a,6,7,8,9,9a-octahydro-9-methylen-2-benzoxepin-4-carbaldehyde
    —— (5aS,9S,9aS)-1,3,5a,6,7,8,9,9a-octahydro-1-oxo-spiro-(2-benzoxepin-9,2'-oxirane)-4-carbaldehyde 443646-92-2 C12H14O4
    (5aS,9S,9aS)-1,3,5a,6,7,8,9,9a-octahydro-1-oxo-spiro-(2-benzoxepin-9,2'-oxirane)-4-carbaldehyde
    —— γ-Fluoro-γ-butyrolactone 2343-90-0 C4H5FO2
    γ-Fluoro-γ-butyrolactone
    —— 4-Isopropenyl-7-methyloxepan-2-one 99181-17-6 C10H16O2
    4-Isopropenyl-7-methyloxepan-2-one
    —— 1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one —— C12H12O2
    1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one
    —— 4-hydroxy-5-phenyl-dihydro-furan-2-one 154993-32-5 C10H10O3
    4-hydroxy-5-phenyl-dihydro-furan-2-one
    —— harzialactone A 321868-49-9 C11H12O3
    harzialactone A
    —— 2(3H)-Furanone, 4-butyl-4-ethyldihydro- 72230-89-8 C10H18O2
    2(3H)-Furanone, 4-butyl-4-ethyldihydro-
    —— simvastatin 79902-39-9 C24H36O5
    simvastatin
    —— (4R,6R)-6-[2-[(1S,2S,6S,7S,8aR)-7-[(1R)-1-hydroxyethyl]-2,6-dimethyl-8-oxo-2,6,7,8a-tetrahydro-1H-naphthalen-1-yl]ethyl]-4-[tert-butyl(dimethyl)silyl]oxyoxan-2-one 136521-50-1 C27H44O5Si
    (4R,6R)-6-[2-[(1S,2S,6S,7S,8aR)-7-[(1R)-1-hydroxyethyl]-2,6-dimethyl-8-oxo-2,6,7,8a-tetrahydro-1H-naphthalen-1-yl]ethyl]-4-[tert-butyl(dimethyl)silyl]oxyoxan-2-one
    —— 6(R)-<2-<8(S)-<(2-methylbutyryl)oxy>-2(S),6(S)-dimethyl-1,2,4a(R),5,6,7,8,8a(S)-octahydronaphth-1(S)-yl>ethyl>-4(R)-(tert-butyldimethylsiloxy)-3,4,5,6-tetrahydro-2H-pyran-2-one 85648-17-5 C30H52O5Si
    6(R)-<2-<8(S)-<(2-methylbutyryl)oxy>-2(S),6(S)-dimethyl-1,2,4a(R),5,6,7,8,8a(S)-octahydronaphth-1(S)-yl>ethyl>-4(R)-(tert-butyldimethylsiloxy)-3,4,5,6-tetrahydro-2H-pyran-2-one
    —— 6(R)-<2-<8-hydroxy-2(S),6(S)-dimethyl-7(S)-<1(S)-hydroxybenzyl>-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)>ethyl>-4(R)-<(tert-butyldimethylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyran-2-one 143746-98-9 C32H48O5Si
    6(R)-<2-<8-hydroxy-2(S),6(S)-dimethyl-7(S)-<1(S)-hydroxybenzyl>-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)>ethyl>-4(R)-<(tert-butyldimethylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyran-2-one
    —— 6(R)-[2-[8(S)-[3-(Diethylamino)-2,2-dimethyl-3-oxopropionyloxy]2(S),6(R)-dimethyl-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)]ethyl]-4(R)-(dimethyl-tert-butylsilyloxy)-3,4,5,6-tetrahydro-2H-pyran-2-one 109233-90-1 C34H57NO6Si
    6(R)-[2-[8(S)-[3-(Diethylamino)-2,2-dimethyl-3-oxopropionyloxy]2(S),6(R)-dimethyl-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)]ethyl]-4(R)-(dimethyl-tert-butylsilyloxy)-3,4,5,6-tetrahydro-2H-pyran-2-one
    —— 6(R)-<2-<7(S),8(R)-(isopropylidenedioxy)-2(S),6(S)-dimethyl-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)>ethyl>-4(R)-<(tert-butyldimethylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyran-2-one 143746-94-5 C28H46O5Si
    6(R)-<2-<7(S),8(R)-(isopropylidenedioxy)-2(S),6(S)-dimethyl-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)>ethyl>-4(R)-<(tert-butyldimethylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyran-2-one