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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
    —— (5S,8R,9S)-8-benzyl-2-[(1S,2S,3Z)-1,2-bis(methoxymethoxy)-3-hexenyl]-9-methoxymethoxy-3-methyl-1,7-dioxaspiro[4.4]non-2-ene-4,6-dione 660842-18-2 C27H36O10
    (5S,8R,9S)-8-benzyl-2-[(1S,2S,3Z)-1,2-bis(methoxymethoxy)-3-hexenyl]-9-methoxymethoxy-3-methyl-1,7-dioxaspiro[4.4]non-2-ene-4,6-dione
    —— (5S,8R,9S)-8-benzyl-2-[(1S,2S,3Z)-1,2-bis(methoxymethoxy)-3-hexenyl]-3-methyl-9-triethylsiloxy-1,7-dioxaspiro[4.4]non-2-ene-4,6-dione 499120-89-7 C31H46O9Si
    (5S,8R,9S)-8-benzyl-2-[(1S,2S,3Z)-1,2-bis(methoxymethoxy)-3-hexenyl]-3-methyl-9-triethylsiloxy-1,7-dioxaspiro[4.4]non-2-ene-4,6-dione
    —— (3R,4S,5S,6R)-3-fluoro-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-one 286378-21-0 C6H9FO5
    (3R,4S,5S,6R)-3-fluoro-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-one
    —— D-pantolactone 176374-84-8 C7H12O2
    D-pantolactone
    —— (+/-)-3-Ethyl-1-oxaspiro<3.5>nonan-2-one 125382-72-1 C10H16O2
    (+/-)-3-Ethyl-1-oxaspiro<3.5>nonan-2-one
    —— 2-(5-oxo-4-oxa-5-homoadamantane-1-yl)oxy-2-oxoethylchloride 1338917-15-9 C12H15ClO4
    2-(5-oxo-4-oxa-5-homoadamantane-1-yl)oxy-2-oxoethylchloride
    —— (6R,7R,8R,8aS)-(-)-6,7-O-isopropylidene-6,7,8-trihydroxyhexahydrooxazolo[3,4-a]pyridin-3-one 8-(1S)-(-)-camphanic ester 1380112-76-4 C20H27NO8
    (6R,7R,8R,8aS)-(-)-6,7-O-isopropylidene-6,7,8-trihydroxyhexahydrooxazolo[3,4-a]pyridin-3-one 8-(1S)-(-)-camphanic ester
    —— (6S,7S,8S,8aR)-(-)-6,7-O-isopropylidene-6,7,8-trihydroxyhexahydrooxazolo[3,4-a]pyridin-3-one 8-(1S)-(-)-camphanic ester 1380112-75-3 C20H27NO8
    (6S,7S,8S,8aR)-(-)-6,7-O-isopropylidene-6,7,8-trihydroxyhexahydrooxazolo[3,4-a]pyridin-3-one 8-(1S)-(-)-camphanic ester
    —— 2,6-Dibromo-2,6-dideoxy-D-glucono-1,4-lactone 78138-23-5 C6H8Br2O4
    2,6-Dibromo-2,6-dideoxy-D-glucono-1,4-lactone
    —— α-chloromethylthio-γ-butyrolactone 106241-39-8 C5H7ClO2S
    α-chloromethylthio-γ-butyrolactone
    —— (3aR,4R,5R,6aS)-5-(1-Ethoxyethoxy)-4-[(3R)-3-(1-ethoxyethoxy)-5-phenylpentyl]hexahydro-2H-cyclopenta[b]furan-2-one 374674-51-8 C26H40O6
    (3aR,4R,5R,6aS)-5-(1-Ethoxyethoxy)-4-[(3R)-3-(1-ethoxyethoxy)-5-phenylpentyl]hexahydro-2H-cyclopenta[b]furan-2-one
    —— 2,2-dichloro-3,4-dimethyl-4-ethyl-γ-butyrolactone 89345-09-5 C8H12Cl2O2
    2,2-dichloro-3,4-dimethyl-4-ethyl-γ-butyrolactone
    —— (2S,4S)-4-amino-4-[(2S,4S)-5-oxo-4-propan-2-yloxolan-2-yl]-2-propan-2-ylbutanoyl chloride;hydrochloride 1413281-93-2 C14H24ClNO3*ClH
    (2S,4S)-4-amino-4-[(2S,4S)-5-oxo-4-propan-2-yloxolan-2-yl]-2-propan-2-ylbutanoyl chloride;hydrochloride
    —— Dihydro-3-hydroxy-5,5-dimethyl-2(3H)-furanone 13416-69-8 C6H10O3
    Dihydro-3-hydroxy-5,5-dimethyl-2(3H)-furanone
    —— 2-oxa-3-oxo-6-syn-formyl-7-anti-acetoxy-cis-bicyclo[3,3,0]-octane 51705-35-2 C10H12O5
    2-oxa-3-oxo-6-syn-formyl-7-anti-acetoxy-cis-bicyclo[3,3,0]-octane
    —— 2-oxa-3-oxo-6-syn-hydroxymethyl-7-anti-acetoxy-cis-bicyclo[3,3,0]octane 51705-34-1 C10H14O5
    2-oxa-3-oxo-6-syn-hydroxymethyl-7-anti-acetoxy-cis-bicyclo[3,3,0]octane
    —— (5R)-5-[2-[(2S,5S)-5-(3-hydroxypropyl)-3-methylideneoxolan-2-yl]ethyl]oxolan-2-one 871360-01-9 C14H22O4
    (5R)-5-[2-[(2S,5S)-5-(3-hydroxypropyl)-3-methylideneoxolan-2-yl]ethyl]oxolan-2-one
    —— 2-(2-Methyl-6-oxooxan-4-yl)acetic acid 1460272-24-5 C8H12O4
    2-(2-Methyl-6-oxooxan-4-yl)acetic acid
    —— 3-Benzylidene-5-phenyloxolan-2-one 190448-97-6 C17H14O2
    3-Benzylidene-5-phenyloxolan-2-one
    —— 5-Heptyl-2-oxo-tetrahydro-furan-3-carboxylic acid methylester 99373-11-2 C13H22O4
    5-Heptyl-2-oxo-tetrahydro-furan-3-carboxylic acid methylester
    —— 2-oxaspiro[4.5]decan-1-one 4420-11-5 C9H14O2
    2-oxaspiro[4.5]decan-1-one
    —— 3-(2-hydroxy-ethyl)-dihydro-furan-2-one 78344-32-8 C6H10O3
    3-(2-hydroxy-ethyl)-dihydro-furan-2-one
    —— 3-(4-fluorophenyl)glutaric anhydride 4926-12-9 C11H9FO3
    3-(4-fluorophenyl)glutaric anhydride
    —— 3-chloro-5-chloromethyl-dihydro-furan-2-one 2584-72-7 C5H6Cl2O2
    3-chloro-5-chloromethyl-dihydro-furan-2-one
    —— 5-[(methylthio)methyl]dihydrofuran-2(3H)-one 37552-56-0 C6H10O2S
    5-[(methylthio)methyl]dihydrofuran-2(3H)-one
    —— (1S,3R,5R)-3-((tert-butyldimethylsilyl)oxy)-6-oxabicyclo[3.2.1]octane-7-one 163217-19-4 C13H24O3Si
    (1S,3R,5R)-3-((tert-butyldimethylsilyl)oxy)-6-oxabicyclo[3.2.1]octane-7-one
    —— 7-hydroxy-2,2-dimethyl-tetrahydro-4,7-methano-[1,3]dioxolo[4,5-<i>c</i>]oxepin-6-one 202527-54-6 C10H14O5
    7-hydroxy-2,2-dimethyl-tetrahydro-4,7-methano-[1,3]dioxolo[4,5-<i>c</i>]oxepin-6-one
    —— 1,5-quinide 665-27-0 C7H10O5
    1,5-quinide
    —— (5R,8S,9R)-3-[tert-butyl(diphenyl)silyl]oxy-8,9-dihydroxy-1-oxaspiro[4.5]dec-6-en-2-one 934389-43-2 C25H30O5Si
    (5R,8S,9R)-3-[tert-butyl(diphenyl)silyl]oxy-8,9-dihydroxy-1-oxaspiro[4.5]dec-6-en-2-one
    —— 3,4-O-ethylpropylidenequinic acid-1,5-lactone 374687-78-2 C12H18O5
    3,4-O-ethylpropylidenequinic acid-1,5-lactone
    —— (-)-4,5-cyclohexylidenequinic acid lactone 35949-53-2 C13H18O5
    (-)-4,5-cyclohexylidenequinic acid lactone
    —— (1R,4S,5R)-1,4-dimethoxy-6-oxabicyclo[3.2.1]octane-3,7-dione 185810-86-0 C9H12O5
    (1R,4S,5R)-1,4-dimethoxy-6-oxabicyclo[3.2.1]octane-3,7-dione
    —— (3aR,4R,7S,8aR)-2,2-dimethyl-6-oxotetrahydro-4,7-methano[1,3]dioxolo[4,5-c]oxepin-7(6H)-yl methanesulfonate 42411-62-1 C11H16O7S
    (3aR,4R,7S,8aR)-2,2-dimethyl-6-oxotetrahydro-4,7-methano[1,3]dioxolo[4,5-c]oxepin-7(6H)-yl methanesulfonate
    —— (1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one 216662-57-6 C14H14O5
    (1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one
    —— 4,4-dimethyl-3-oxabicyclo<3.2.1>octan-2-one 66471-65-6 C9H14O2
    4,4-dimethyl-3-oxabicyclo<3.2.1>octan-2-one
    —— (3aR,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-vinylhexahydro-2H-cyclopenta[b]furan-2-one 906000-82-6 C15H26O3Si
    (3aR,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-vinylhexahydro-2H-cyclopenta[b]furan-2-one
    —— 2-deoxy-2,2-difluoro-1-oxoribose 95058-77-8 C5H6F2O4
    2-deoxy-2,2-difluoro-1-oxoribose
    —— 2-deoxy-2,2-difluoro-D-threo-pentofuranose-1-ulose 122111-12-0 C5H6F2O4
    2-deoxy-2,2-difluoro-D-threo-pentofuranose-1-ulose
    —— isomentholactone 68330-68-7 C10H18O2
    isomentholactone
    —— (1R,4S,5R,6S)-6-tert-butyldiphenylsilyloxy-4-pivaloyloxymethyl-3-oxabicyclo[3.2.0]heptan-2-one 946392-51-4 C28H36O5Si
    (1R,4S,5R,6S)-6-tert-butyldiphenylsilyloxy-4-pivaloyloxymethyl-3-oxabicyclo[3.2.0]heptan-2-one
    —— 1-oxaspiro<5.5>undeca-2,4-dione 1658-06-6 C10H14O3
    1-oxaspiro<5.5>undeca-2,4-dione
    —— (4S,5R)-4-[2,6-bis[(2S)-oxolan-2-yl]phenyl]selanyl-5-phenyloxolan-2-one 193812-96-3 C24H26O4Se
    (4S,5R)-4-[2,6-bis[(2S)-oxolan-2-yl]phenyl]selanyl-5-phenyloxolan-2-one
    —— syn-3-hydroxy-5-methyltetrahydrofuran-2-one —— C5H8O3
    syn-3-hydroxy-5-methyltetrahydrofuran-2-one
    —— (3R,5S)-5-methyl-2-oxotetrahydro furan-3-yl acetate —— C7H10O4
    (3R,5S)-5-methyl-2-oxotetrahydro furan-3-yl acetate
    —— (3R,4S,5S,1'S)-3-hydroxy-4-(N-tert-butoxycarbonylamino)-5-(1'-hydroxyethyl)dihydrofuran-2(3H)-one 1294444-89-5 C11H19NO6
    (3R,4S,5S,1'S)-3-hydroxy-4-(N-tert-butoxycarbonylamino)-5-(1'-hydroxyethyl)dihydrofuran-2(3H)-one
    —— tert-butyl N-[(2S,3R,4S)-3-hydroxy-2-methyl-6-oxooxan-4-yl]carbamate 1300575-47-6 C11H19NO5
    tert-butyl N-[(2S,3R,4S)-3-hydroxy-2-methyl-6-oxooxan-4-yl]carbamate
    —— tert-butyl N-[(2R,3S)-2-[(1S)-1-hydroxyethyl]-5-oxooxolan-3-yl]carbamate 1300575-48-7 C11H19NO5
    tert-butyl N-[(2R,3S)-2-[(1S)-1-hydroxyethyl]-5-oxooxolan-3-yl]carbamate
    —— 4-(6-METHOXYPYRIDIN-3-YL)dihydropyran-2,6(3H)-dione 721920-98-5 C11H11NO4
    4-(6-METHOXYPYRIDIN-3-YL)dihydropyran-2,6(3H)-dione
    —— (+)-prelactone V 202072-83-1 C7H12O3
    (+)-prelactone V
    —— 5,5-dimethyl-3-phenyldihydrofuran-2(3H)-one 20215-56-9 C12H14O2
    5,5-dimethyl-3-phenyldihydrofuran-2(3H)-one