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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
    —— 2-carboxymethyl-4-pentanolide 1126-33-6 C7H10O4
    2-carboxymethyl-4-pentanolide
    —— (-)(2S,3S,4R)-2-methyl-3-hydroxy-4-pentanolide 79386-78-0 C6H10O3
    (-)(2S,3S,4R)-2-methyl-3-hydroxy-4-pentanolide
    —— (3RS,4SR,5SR)-3-Phenylseleno-4-hydroxy-5-methyldihydro-2(3H)-furanone —— C11H12O3Se
    (3RS,4SR,5SR)-3-Phenylseleno-4-hydroxy-5-methyldihydro-2(3H)-furanone
    —— (+)-blastmycinolactol 37676-49-6 C9H16O3
    (+)-blastmycinolactol
    —— 3-phenyl-6-methylidenetetrahydro-2-pyranone 122019-81-2 C12H12O2
    3-phenyl-6-methylidenetetrahydro-2-pyranone
    —— 3-phenyl-6(E)-(bromomethylidene)tetrahydro-2-pyranone 88070-96-6 C12H11BrO2
    3-phenyl-6(E)-(bromomethylidene)tetrahydro-2-pyranone
    —— 3-phenyl-6(Z)-(bromomethylidene)tetrahydro-2-pyranone 136457-92-6 C12H11BrO2
    3-phenyl-6(Z)-(bromomethylidene)tetrahydro-2-pyranone
    —— (1β,2α,6α,8β)-1,8,12,12-Tetramethyl-4-oxatricyclo<6.4.0.0<sup>2,6</sup>>undecan-3-one 102358-27-0 C15H24O2
    (1β,2α,6α,8β)-1,8,12,12-Tetramethyl-4-oxatricyclo<6.4.0.0<sup>2,6</sup>>undecan-3-one
    —— 6(E)-(iodomethylene)tetrahydro-2-pyrone 120205-38-1 C6H7IO2
    6(E)-(iodomethylene)tetrahydro-2-pyrone
    —— 3-benzyl-6(E)-<3-(trimethylsilyl)prop-2-ynylidene>tetrahydro-2-pyrone 103437-81-6 C18H22O2Si
    3-benzyl-6(E)-<3-(trimethylsilyl)prop-2-ynylidene>tetrahydro-2-pyrone
    —— (3R,4S)-3-Dodecyl-4-((R)-2-hydroxy-nonyl)-3-trimethylsilanyl-oxetan-2-one 206359-80-0 C27H54O3Si
    (3R,4S)-3-Dodecyl-4-((R)-2-hydroxy-nonyl)-3-trimethylsilanyl-oxetan-2-one
    —— 5-O-methoxymethoxybacillariolide I 313218-82-5 C22H32O4
    5-O-methoxymethoxybacillariolide I
    —— (1S,5S,6R)-5-(N-(tert-Butoxycarbonyl)amino)-3-oxabicyclo<4.1.0>heptan-2-one 117747-69-0 C11H17NO4
    (1S,5S,6R)-5-(N-(tert-Butoxycarbonyl)amino)-3-oxabicyclo<4.1.0>heptan-2-one
    —— 5-methoxy-dihydro-furan-2-one 21963-36-0 C5H8O3
    5-methoxy-dihydro-furan-2-one
    —— (3R,5R)-dihydro-3-hydroxy-5-phenylfuran-2-one —— C10H10O3
    (3R,5R)-dihydro-3-hydroxy-5-phenylfuran-2-one
    —— (3R,5R)-dihydro-3-hydroxy-5-phenylfuran-2-one —— C10H10O3
    (3R,5R)-dihydro-3-hydroxy-5-phenylfuran-2-one
    —— (1S,2S,6S,7R,8S)-7-[tert-butyl(dimethyl)silyl]oxy-2,6-dimethyl-14-methylidene-4,11-dioxatetracyclo[6.3.3.01,8.02,6]tetradecane-5,10-dione 902768-27-8 C21H32O5Si
    (1S,2S,6S,7R,8S)-7-[tert-butyl(dimethyl)silyl]oxy-2,6-dimethyl-14-methylidene-4,11-dioxatetracyclo[6.3.3.01,8.02,6]tetradecane-5,10-dione
    —— 5-chloro-4-ethyl-4-hydroxypentanoic acid 1,4 lactone 80642-09-7 C7H11ClO2
    5-chloro-4-ethyl-4-hydroxypentanoic acid 1,4 lactone
    —— 5,6-dimethyldihydropyran-2,4-dione 338386-56-4 C7H10O3
    5,6-dimethyldihydropyran-2,4-dione
    —— (2<i>R</i>)-2,3<i>c</i>,4<i>c</i>-trimethyl-5-oxo-tetrahydro-furan-2<i>r</i>-carboxylic acid 52437-29-3 C8H12O4
    (2<i>R</i>)-2,3<i>c</i>,4<i>c</i>-trimethyl-5-oxo-tetrahydro-furan-2<i>r</i>-carboxylic acid
    —— (1R)-1-chloromethyl-4,7syn,8anti-trimethyl-2,5-dioxa-bicyclo[2.2.2]octane-3,6-dione 6882-50-4 C10H13ClO4
    (1R)-1-chloromethyl-4,7syn,8anti-trimethyl-2,5-dioxa-bicyclo[2.2.2]octane-3,6-dione
    —— (3S,5S,4'S,5'R)-5-<3'-<(tert-butyloxy)carbonyl>-4'-(cyclohexylmethyl)-2',2'-dimethyloxazolidin-5'-yl>-3-methyldihydrofuran-2(3H)-one 122226-03-3 C22H37NO5
    (3S,5S,4'S,5'R)-5-<3'-<(tert-butyloxy)carbonyl>-4'-(cyclohexylmethyl)-2',2'-dimethyloxazolidin-5'-yl>-3-methyldihydrofuran-2(3H)-one
    —— (2S,4S)-trans-2,4-dimethyl-γ-butyrolactone 5145-01-7 C6H10O2
    (2S,4S)-trans-2,4-dimethyl-γ-butyrolactone
    —— (3S,5R)-3,5-dimethyl-γ-butyrolactone 130930-17-5 C6H10O2
    (3S,5R)-3,5-dimethyl-γ-butyrolactone
    —— 3,3-diallyldihydrofuran-2,4-dione 124706-41-8 C10H12O3
    3,3-diallyldihydrofuran-2,4-dione
    —— 4-Ethyl-3-methyloxetan-2-one 115367-79-8 C6H10O2
    4-Ethyl-3-methyloxetan-2-one
    —— 2-<1-hydroxy-3-phenylprop-2-ynyl>pentan-5-olide 129205-84-1 C14H14O3
    2-<1-hydroxy-3-phenylprop-2-ynyl>pentan-5-olide
    —— 2-<1-hydroxy-3-phenylprop-2-ynyl>hexan-6-olide 129205-86-3 C15H16O3
    2-<1-hydroxy-3-phenylprop-2-ynyl>hexan-6-olide
    —— (1R,4R,5R,8R,9R,11R)-9,11-Bis-methoxymethoxy-4,9-dimethyl-3-oxa-tricyclo[6.2.1.0<sup>1,5</sup>]undecan-2-one 1026585-61-4 C16H26O6
    (1R,4R,5R,8R,9R,11R)-9,11-Bis-methoxymethoxy-4,9-dimethyl-3-oxa-tricyclo[6.2.1.0<sup>1,5</sup>]undecan-2-one
    —— 1-chloromethyl-2-oxo-3-oxabicyclo[3.1.0]hexane 172154-40-4 C6H7ClO2
    1-chloromethyl-2-oxo-3-oxabicyclo[3.1.0]hexane
    —— 1-hydroxymethyl-2-oxo-3-oxabicyclo[3.1.0]hexane 172154-27-7 C6H8O3
    1-hydroxymethyl-2-oxo-3-oxabicyclo[3.1.0]hexane
    —— 3-oxa-2-oxobicyclo[3,1,0]hexan-1-carbonyl chloride 172154-37-9 C6H5ClO3
    3-oxa-2-oxobicyclo[3,1,0]hexan-1-carbonyl chloride
    —— (3R,5aS)-3-bromo-2a,3,4,5,5a,6,7,8-octahydroazuleno[5,4-b]oxet-1-one 90933-09-8 C11H13BrO2
    (3R,5aS)-3-bromo-2a,3,4,5,5a,6,7,8-octahydroazuleno[5,4-b]oxet-1-one
    —— (1S,2S,6S,8S,11R,13R,17R)-6,15,15-trimethyl-3,12,14,16-tetraoxatetracyclo[9.6.0.02,8.013,17]heptadecan-4-one 142186-71-8 C16H24O5
    (1S,2S,6S,8S,11R,13R,17R)-6,15,15-trimethyl-3,12,14,16-tetraoxatetracyclo[9.6.0.02,8.013,17]heptadecan-4-one
    —— <R-(4S<sup>*</sup>-cis)>-2-(tert-butyldimethylsilyl)-5-oxo-2-azaspiro<3.4>octane-1,6-dione 144373-50-2 C15H25NO3Si
    <R-(4S<sup>*</sup>-cis)>-2-(tert-butyldimethylsilyl)-5-oxo-2-azaspiro<3.4>octane-1,6-dione
    —— 3-methyl-3-propyl-glutaric acid-anhydride 57758-23-3 C9H14O3
    3-methyl-3-propyl-glutaric acid-anhydride
    —— 2-Oxaspiro<4.4>nonan-3-one 5724-62-9 C8H12O2
    2-Oxaspiro<4.4>nonan-3-one
    —— (5S,6R)-5-methyl-6-phenyloxan-2-one 91496-12-7 C12H14O2
    (5S,6R)-5-methyl-6-phenyloxan-2-one
    —— (S)-α-methoxy-γ-butyrolactone 159216-42-9 C5H8O3
    (S)-α-methoxy-γ-butyrolactone
    —— (4aR,5S,6R,7R,7aS,7bR)-4a,7-Dihydroxy-6-isopropenyl-7b-methyl-2-oxo-2,4,4a,5,6,7,7a,7b-octahydro-indeno[7,1-bc]furan-5-carboxylic acid methyl ester 211799-88-1 C16H20O6
    (4aR,5S,6R,7R,7aS,7bR)-4a,7-Dihydroxy-6-isopropenyl-7b-methyl-2-oxo-2,4,4a,5,6,7,7a,7b-octahydro-indeno[7,1-bc]furan-5-carboxylic acid methyl ester
    —— (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide 252664-54-3 C10H15NO3
    (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
    —— (±)-5-(iodomethyl)-3-phenyldihydrofuran-2(3H)-one 1729-26-6 C11H11IO2
    (±)-5-(iodomethyl)-3-phenyldihydrofuran-2(3H)-one
    —— (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonitrile 252664-23-6 C10H13NO2
    (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonitrile
    —— (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid ((R)-1-phenyl-ethyl)-amide 41158-09-2 C18H23NO3
    (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid ((R)-1-phenyl-ethyl)-amide
    —— (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (4S,5R)-4-furan-2-yl-3-methyl-2-oxo-oxazolidin-5-ylmethyl ester 574758-03-5 C19H23NO7
    (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (4S,5R)-4-furan-2-yl-3-methyl-2-oxo-oxazolidin-5-ylmethyl ester
    —— but-3-en-1-yl (1S,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate 1138300-40-9 C14H20O4
    but-3-en-1-yl (1S,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
    —— (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (4R,5S)-4-furan-2-yl-3-methyl-2-oxo-oxazolidin-5-ylmethyl ester 574758-00-2 C19H23NO7
    (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (4R,5S)-4-furan-2-yl-3-methyl-2-oxo-oxazolidin-5-ylmethyl ester
    —— S-[(1S)-1-(2-methoxyethyl)butyl] (1S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbothioate 449174-44-1 C17H28O4S
    S-[(1S)-1-(2-methoxyethyl)butyl] (1S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbothioate
    —— [(2R,4R,6R)-11-oxo-4-tridecyl-5,7-dioxadispiro[5.1.58.26]pentadeca-9,12-dien-2-yl] (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate 1012339-64-8 C36H54O7
    [(2R,4R,6R)-11-oxo-4-tridecyl-5,7-dioxadispiro[5.1.58.26]pentadeca-9,12-dien-2-yl] (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
    —— (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl ester 197522-61-5 C25H38O4
    (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl ester