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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
—— 2H-Pyran-2-one, 6-(3-buten-1-yl)tetrahydro-4-hydroxy- 1823642-96-1 C9H14O3
2H-Pyran-2-one, 6-(3-buten-1-yl)tetrahydro-4-hydroxy-
—— 5-benzyl-2-oxo-tetrahydro-furan-3-carboxylic acid 861330-75-8 C12H12O4
5-benzyl-2-oxo-tetrahydro-furan-3-carboxylic acid
—— trans-1-hydroxymethylcyclopropane-1,2-dicarboxylic acid γ-lactone 114644-49-4 C6H6O4
trans-1-hydroxymethylcyclopropane-1,2-dicarboxylic acid γ-lactone
—— (-)-(1S,5R)-3-oxabicyclo<3.2.0>heptan-2-one 88335-95-9 C6H8O2
(-)-(1S,5R)-3-oxabicyclo<3.2.0>heptan-2-one
—— α-methoxycarbonyl-α-(3-methylphenyl)-γ-methylidene-δ-valerolactone 1095991-71-1 C15H16O4
α-methoxycarbonyl-α-(3-methylphenyl)-γ-methylidene-δ-valerolactone
—— 3,5-di-<i>tert</i>-butyl-dihydro-furan-2-one 856347-81-4 C12H22O2
3,5-di-<i>tert</i>-butyl-dihydro-furan-2-one
—— 6(R)-[2-[8(S)-(2,2-dimethylbutyryloxy)-2(S)-methyl-5(R)-dibenzylaminocarbonyloxy-6(R)-methyl-1,2,3,4,4a(R),5,6, 7,8,8a(R)-decahydronaphthyl-1(S)]ethyl]-4(R) tert-butyldiphenylsilyloxy-3,4,5,6-tetrahydro-2H-pyran-2-one 127343-22-0 C56H73NO7Si
6(R)-[2-[8(S)-(2,2-dimethylbutyryloxy)-2(S)-methyl-5(R)-dibenzylaminocarbonyloxy-6(R)-methyl-1,2,3,4,4a(R),5,6, 7,8,8a(R)-decahydronaphthyl-1(S)]ethyl]-4(R) tert-butyldiphenylsilyloxy-3,4,5,6-tetrahydro-2H-pyran-2-one
—— adamantane-2-spiro-3'-9'-oxo-1',2',4',8'-tetraoxaspiro[4.6]undecane 476373-07-6 C16H22O5
adamantane-2-spiro-3'-9'-oxo-1',2',4',8'-tetraoxaspiro[4.6]undecane
—— α-tert-butoxycarbonyl-α-(4-methylphenyl)-γ-methylidene-δ-valerolactone 1086018-40-7 C18H22O4
α-tert-butoxycarbonyl-α-(4-methylphenyl)-γ-methylidene-δ-valerolactone
—— α-tert-butoxycarbonyl-α-(3-thienyl)-γ-methylidene-δ-valerolactone 1086018-46-3 C15H18O4S
α-tert-butoxycarbonyl-α-(3-thienyl)-γ-methylidene-δ-valerolactone
—— γ-methylidene-δ-valerolactone 1086018-34-9 C17H20O4
γ-methylidene-δ-valerolactone
—— α-tert-butoxycarbonyl-α-(3-furyl)-γ-methylidene-δ-valerolactone 1086018-48-5 C15H18O5
α-tert-butoxycarbonyl-α-(3-furyl)-γ-methylidene-δ-valerolactone
—— (1R,5S)-(+)-4,4,6,6-tetramethyl-3-oxabicyclo[3.1.1]heptan-2-one 827610-64-0 C10H16O2
(1R,5S)-(+)-4,4,6,6-tetramethyl-3-oxabicyclo[3.1.1]heptan-2-one
—— 3,11-dimethylene-1,9-dioxa-dispiro[4.2.4.2]tetradecane-2,10-dione 74513-12-5 C14H16O4
3,11-dimethylene-1,9-dioxa-dispiro[4.2.4.2]tetradecane-2,10-dione
—— 3-methylene-1-oxaspiro[4.5]decan-2,8-dione 65461-25-8 C10H12O3
3-methylene-1-oxaspiro[4.5]decan-2,8-dione
—— 4-Methyl-5-(trifluoromethyl)oxolan-2-one 606489-76-3 C6H7F3O2
4-Methyl-5-(trifluoromethyl)oxolan-2-one
—— (S)-6-hydroxymethyltetrahydropyran-2-one 89408-86-6 C6H10O3
(S)-6-hydroxymethyltetrahydropyran-2-one
—— (R)-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one 160226-44-8 C6H10O3
(R)-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one
—— 6-(Diphenylphosphinoylpentadecyl)tetrahydro-2H-pyran-2-one 97509-79-0 C32H47O3P
6-(Diphenylphosphinoylpentadecyl)tetrahydro-2H-pyran-2-one
—— 5-(3-oxobutyl)-5-(2-oxopropyl)-2(3H)-dihydrofuranone 157641-00-4 C11H16O4
5-(3-oxobutyl)-5-(2-oxopropyl)-2(3H)-dihydrofuranone
—— (+)-(S)-4-hydroxytetrahydro-2H-pyran-2-one 61892-56-6 C5H8O3
(+)-(S)-4-hydroxytetrahydro-2H-pyran-2-one
—— (R)-4-hydroxytetrahydro-2H-pyran-2-one 61892-56-6 C5H8O3
(R)-4-hydroxytetrahydro-2H-pyran-2-one
—— (R)-6-Methyl-dihydro-pyran-2,5-dione 194034-01-0 C6H8O3
(R)-6-Methyl-dihydro-pyran-2,5-dione
—— methyl (2R,3R)-2-propyl-5-oxo-tetrahydrofuran-3-carboxylate 1199942-09-0 C9H14O4
methyl (2R,3R)-2-propyl-5-oxo-tetrahydrofuran-3-carboxylate
—— methyl (2R,3S)-2-propyl-5-oxo-tetrahydrofuran-3-carboxylate 1199942-05-6 C9H14O4
methyl (2R,3S)-2-propyl-5-oxo-tetrahydrofuran-3-carboxylate
—— 4,4-dimethyl-5,6-dibromotetrahydro-alpha-pyrone 79749-57-8 C7H10Br2O2
4,4-dimethyl-5,6-dibromotetrahydro-alpha-pyrone
—— 4,5-dioxo-2-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester 408326-03-4 C13H12O5
4,5-dioxo-2-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester
—— 3-Bromo-5-methoxy-4-[(propan-2-yl)sulfanyl]oxolan-2-one 88050-99-1 C8H13BrO3S
3-Bromo-5-methoxy-4-[(propan-2-yl)sulfanyl]oxolan-2-one
—— 4-methylene-3-oxa-bicyclo[3.2.1]octan-2-one 612483-87-1 C8H10O2
4-methylene-3-oxa-bicyclo[3.2.1]octan-2-one
—— 3-hydroxy-4-pentanolide of (3S,4R)-3,4-dihydroxypentanoic acid 88400-20-8 C5H8O3
3-hydroxy-4-pentanolide of (3S,4R)-3,4-dihydroxypentanoic acid
—— 5-bromo-2,5-dideoxy-D-erythro-pentono-γ-lactone 78139-03-4 C5H7BrO3
5-bromo-2,5-dideoxy-D-erythro-pentono-γ-lactone
—— (3R,4S)-4-(2-cyclohexylethyl)-3-(cyclohexylmethyl)oxetan-2-one 898799-38-7 C18H30O2
(3R,4S)-4-(2-cyclohexylethyl)-3-(cyclohexylmethyl)oxetan-2-one
—— (Z)-4-(2-cyclohexylethylidene)-3-cyclohexylmethyl-oxetan-2-one 942516-92-9 C18H28O2
(Z)-4-(2-cyclohexylethylidene)-3-cyclohexylmethyl-oxetan-2-one
—— 4-(2-cyclohexyl-ethylidene)-3-cyclohexylmethyl-oxetan-2-one 408333-49-3 C18H28O2
4-(2-cyclohexyl-ethylidene)-3-cyclohexylmethyl-oxetan-2-one
—— (R,Z)-4-(2-cyclohexylethylidene)-3-(cyclohexylmethyl)oxetan-2-one 898799-32-1 C18H28O2
(R,Z)-4-(2-cyclohexylethylidene)-3-(cyclohexylmethyl)oxetan-2-one
—— 4-(1,3,3,3-Tetrachloropropyl)oxolan-2-one 88037-52-9 C7H8Cl4O2
4-(1,3,3,3-Tetrachloropropyl)oxolan-2-one
—— bromo-6 hexanolide-4 2018-75-9 C6H9BrO2
bromo-6 hexanolide-4
—— octahydro-2H-cyclohepta[b]furan-2-one 4401-23-4 C9H14O2
octahydro-2H-cyclohepta[b]furan-2-one
—— 5-cyclohexyldihydrofuran-2(3H)-one 15972-17-5 C10H16O2
5-cyclohexyldihydrofuran-2(3H)-one
—— 7,7-dimethyloxepan-2-one 76638-13-6 C8H14O2
7,7-dimethyloxepan-2-one
—— 3-(2-Methyl-propenyl)-dihydro-furan-2-one 90292-26-5 C8H12O2
3-(2-Methyl-propenyl)-dihydro-furan-2-one
—— α-chloro-γ-hexyl-γ-lactone 89344-89-8 C10H17ClO2
α-chloro-γ-hexyl-γ-lactone
—— 3-isopropyl-6-methyltetrahydro-2H-pyran-2-one 21722-34-9 C9H16O2
3-isopropyl-6-methyltetrahydro-2H-pyran-2-one
—— (2,4-dioxo-tetrahydro-[3]furyl)-acetic acid ethyl ester 59773-59-0 C8H10O5
(2,4-dioxo-tetrahydro-[3]furyl)-acetic acid ethyl ester
—— δ-dodecanolactone 93863-11-7 C12H22O2
δ-dodecanolactone
—— 2-<(methoxycarbonyl)methyl>-4,4-dimethyl-γ-butyrolactone 2044-46-4 C9H14O4
2-<(methoxycarbonyl)methyl>-4,4-dimethyl-γ-butyrolactone
—— 5-methylsulfanyl-dihydro-furan-2-one 137549-98-5 C5H8O2S
5-methylsulfanyl-dihydro-furan-2-one
—— 2-Methoxycarbonyl-β-methyl-butyrolacton 13353-18-9 C7H10O4
2-Methoxycarbonyl-β-methyl-butyrolacton
—— 3,3-(ethylenedioxy)-2,2-dimethyl-5-pentanolide 84752-37-4 C9H14O4
3,3-(ethylenedioxy)-2,2-dimethyl-5-pentanolide
—— 2,2-dimethyl-3-oxo-5-pentanolide 84752-36-3 C7H10O3
2,2-dimethyl-3-oxo-5-pentanolide