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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
—— 3-benzyldihydrofuran-2(3H)-one 68975-07-5 C11H12O2
3-benzyldihydrofuran-2(3H)-one
—— (2'R,3R,5S)-3-(2'-tert-butyldimethylsilyloxy-7'-trimethylsilyl-6'-heptynyl)-5-methyl-3-(methylsulfenyl)tetrahydrofuran-2-one 251998-71-7 C22H42O3SSi2
(2'R,3R,5S)-3-(2'-tert-butyldimethylsilyloxy-7'-trimethylsilyl-6'-heptynyl)-5-methyl-3-(methylsulfenyl)tetrahydrofuran-2-one
—— (2'R,3S,5S)-3-(2'-tert-butyldimethylsilyloxy-7'-trimethylsilyl-6'-heptynyl)-5-methyl-3-(methylsulfenyl)tetrahydrofuran-2-one 251998-73-9 C22H42O3SSi2
(2'R,3S,5S)-3-(2'-tert-butyldimethylsilyloxy-7'-trimethylsilyl-6'-heptynyl)-5-methyl-3-(methylsulfenyl)tetrahydrofuran-2-one
—— Isobutyric acid (2S,4R,8S,9R,11R)-13-bromo-2,11-dimethyl-7-methylene-6,12-dioxo-5,14-dioxa-tricyclo[9.2.1.0<sup>4,8</sup>]tetradec-1(13)-en-9-yl ester 75197-65-8 C19H23BrO6
Isobutyric acid (2S,4R,8S,9R,11R)-13-bromo-2,11-dimethyl-7-methylene-6,12-dioxo-5,14-dioxa-tricyclo[9.2.1.0<sup>4,8</sup>]tetradec-1(13)-en-9-yl ester
—— Isobutyric acid (2S,4R,8S,9R,11R)-13-hydroxy-2,11-dimethyl-7-methylene-6,12-dioxo-5,14-dioxa-tricyclo[9.2.1.0<sup>4,8</sup>]tetradec-1(13)-en-9-yl ester 75197-66-9 C19H24O7
Isobutyric acid (2S,4R,8S,9R,11R)-13-hydroxy-2,11-dimethyl-7-methylene-6,12-dioxo-5,14-dioxa-tricyclo[9.2.1.0<sup>4,8</sup>]tetradec-1(13)-en-9-yl ester
—— Isobutyric acid (2S,4R,8R,9R,11R)-8-hydroxy-2,11-dimethyl-7-methylene-6,12-dioxo-5,14-dioxa-tricyclo[9.2.1.0<sup>4,8</sup>]tetradec-1(13)-en-9-yl ester 75197-64-7 C19H24O7
Isobutyric acid (2S,4R,8R,9R,11R)-8-hydroxy-2,11-dimethyl-7-methylene-6,12-dioxo-5,14-dioxa-tricyclo[9.2.1.0<sup>4,8</sup>]tetradec-1(13)-en-9-yl ester
—— 3-Butyl-3-methyl-oxetan-2-one 16230-69-6 C8H14O2
3-Butyl-3-methyl-oxetan-2-one
—— (E)-9-octadecen-4-olide 366468-89-5 C18H32O2
(E)-9-octadecen-4-olide
—— methyl [(3R)-3-hydroxy-5-isopropenyl-2-oxotetrahydro-3-furanyl]acetate 910237-07-9 C10H14O5
methyl [(3R)-3-hydroxy-5-isopropenyl-2-oxotetrahydro-3-furanyl]acetate
—— 4-methylene-2-oxa-bicyclo[3.3.1]nonan-3-one 57428-15-6 C9H12O2
4-methylene-2-oxa-bicyclo[3.3.1]nonan-3-one
—— (1S,6S,8S)-10-oxatricyclo[6.3.0.0<sup>1,6</sup>]undeca-5,11-dione 188556-54-9 C10H12O3
(1S,6S,8S)-10-oxatricyclo[6.3.0.0<sup>1,6</sup>]undeca-5,11-dione
—— α-methoxycarbonyl-α-methyl-γ-valerolactone 74002-72-5 C8H12O4
α-methoxycarbonyl-α-methyl-γ-valerolactone
—— 3-bromo-3,5-dimethyloxolan-2-one 74002-74-7 C6H9BrO2
3-bromo-3,5-dimethyloxolan-2-one
—— 5,5-Dimethyl-3-methylen-6-phenyltetrahydro-2-pyranon 54312-55-9 C14H16O2
5,5-Dimethyl-3-methylen-6-phenyltetrahydro-2-pyranon
—— 6,6-dimethyl-3-methylene-2,7-dioxo-1-oxaspiro(4.5)decane 65461-27-0 C12H16O3
6,6-dimethyl-3-methylene-2,7-dioxo-1-oxaspiro(4.5)decane
—— α-hydroxy-γ-octyl-γ-butyrolactone 117339-16-9 C12H22O3
α-hydroxy-γ-octyl-γ-butyrolactone
—— 3,9-dimethylene-1,7-dioxa-dispiro[4.0.4.2]dodecane-2,8-dione 904215-47-0 C12H12O4
3,9-dimethylene-1,7-dioxa-dispiro[4.0.4.2]dodecane-2,8-dione
—— 1,5,6,7-tetramethyl-4-methylene-2-oxa-bicyclo[3.2.0]hept-6-en-3-one 56745-76-7 C11H14O2
1,5,6,7-tetramethyl-4-methylene-2-oxa-bicyclo[3.2.0]hept-6-en-3-one
—— 3R-dihydroxy-caryophyllan-[5,8]-6,7-olide 1254952-98-1 C15H24O4
3R-dihydroxy-caryophyllan-[5,8]-6,7-olide
—— ent-seco-plakortolide I 1403494-54-1 C24H38O4
ent-seco-plakortolide I
—— (S)-5-((1S,2R)-1-Hydroxy-2-methyl-butyl)-dihydro-furan-2-one 182370-47-4 C9H16O3
(S)-5-((1S,2R)-1-Hydroxy-2-methyl-butyl)-dihydro-furan-2-one
—— seco-plakortolide K 1267675-67-1 C26H42O4
seco-plakortolide K
—— seco-plakortolide L 1267675-91-1 C26H42O4
seco-plakortolide L
—— seco-plakortolide V 1346557-27-4 C23H44O4
seco-plakortolide V
—— (3R,4S,5R)-3-hydroxy-4-methyl-5-phenyl-dihydrofuran-2-one 1215021-52-5 C11H12O3
(3R,4S,5R)-3-hydroxy-4-methyl-5-phenyl-dihydrofuran-2-one
—— 3,4-dihydroxy-5-methyl-3-phenyl-dihydro-furan-2-one 99865-82-4 C11H12O4
3,4-dihydroxy-5-methyl-3-phenyl-dihydro-furan-2-one
—— (1'S,2'S,4S,6'S,8'R,11'S,12'R)-1'-amino-12'-ethenyl-11'-hydroxy-2,2,4',4'-tetramethylspiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-10'-one 616225-53-7 C17H25NO7
(1'S,2'S,4S,6'S,8'R,11'S,12'R)-1'-amino-12'-ethenyl-11'-hydroxy-2,2,4',4'-tetramethylspiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-10'-one
—— 5-Chlorpentan-4-olid-4-carbonsaeure 53856-91-0 C6H7ClO4
5-Chlorpentan-4-olid-4-carbonsaeure
—— 2-Chloromethyl-5-oxo-tetrahydro-furan-2-carboxylic acid propyl ester 60947-40-2 C9H13ClO4
2-Chloromethyl-5-oxo-tetrahydro-furan-2-carboxylic acid propyl ester
—— 5-Brompentan-4-olid-4-carbonsaeure 53856-92-1 C6H7BrO4
5-Brompentan-4-olid-4-carbonsaeure
—— 7-Octyl-oxepan-2-one 3041-18-7 C14H26O2
7-Octyl-oxepan-2-one
—— (3E)-3-[1-(propylamino)ethylidene]oxolane-2,4-dione 1248589-97-0 C9H13NO3
(3E)-3-[1-(propylamino)ethylidene]oxolane-2,4-dione
—— 2-Methyl-L-arabono-γ-lacton 89674-07-7 C6H10O5
2-Methyl-L-arabono-γ-lacton
—— Tricocin-S2 62139-17-7 C25H28O8
Tricocin-S2
—— 3-ethylidene-5-methyldihydrofuran-2-one 62527-65-5 C7H10O2
3-ethylidene-5-methyldihydrofuran-2-one
—— 4,5-dihydro-3-ethenyl-5-methyl-2(3H)-furanone 6000-81-3 C7H10O2
4,5-dihydro-3-ethenyl-5-methyl-2(3H)-furanone
—— 7,7,9,9-Tetramethyl-3-methylen-1-oxaspiro<4.5>decan-2-on 67464-49-7 C14H22O2
7,7,9,9-Tetramethyl-3-methylen-1-oxaspiro<4.5>decan-2-on
—— 2-acetyl-4-methyl-3-(2',2'-dichlorovinyl)-γ-valerolactone 70603-89-3 C10H12Cl2O3
2-acetyl-4-methyl-3-(2',2'-dichlorovinyl)-γ-valerolactone
—— 3-[(E)-but-2-enyl]oxolan-2-one 150163-14-7 C8H12O2
3-[(E)-but-2-enyl]oxolan-2-one
—— (3R,3aS,6aR)-3-(tert-butyldimethylsilanyloxymethyl)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one 909911-42-8 C14H24O3Si
(3R,3aS,6aR)-3-(tert-butyldimethylsilanyloxymethyl)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one
—— (3R,3aS,6aR)-3-(hydroxymethyl)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one 909911-30-4 C8H10O3
(3R,3aS,6aR)-3-(hydroxymethyl)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one
—— 3-hexen-6-olide 102575-06-4 C6H8O2
3-hexen-6-olide
—— Methyl 2-cyano-2-(4,4-dimethyl-2-oxo-oxolan-3-ylidene)acetate 82698-90-6 C10H11NO4
Methyl 2-cyano-2-(4,4-dimethyl-2-oxo-oxolan-3-ylidene)acetate
—— trans-5,5-dibenzyl-3,4-dimethyldihydrofuran-2(3H)-one 114090-95-8 C20H22O2
trans-5,5-dibenzyl-3,4-dimethyldihydrofuran-2(3H)-one
—— 7-(2-Diphenylphosphinoylethyl)oxepan-2-one 147263-11-4 C20H23O3P
7-(2-Diphenylphosphinoylethyl)oxepan-2-one
—— D-glycero-D-gulo-heptono-1,4-lactone 1120352-71-7 C7H12O7
D-glycero-D-gulo-heptono-1,4-lactone
—— 3,5-dihydroxy-2-methoxy-8-methylnon-6-ene 1,4-lactone 118477-07-9 C11H18O5
3,5-dihydroxy-2-methoxy-8-methylnon-6-ene 1,4-lactone
—— 3-methylene-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one 343929-44-2 C8H8O2
3-methylene-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one
—— 3-Methylene-3,3a,4,5,6,8a-hexahydro-2H-cyclohepta(b)furan-2-one 343852-61-9 C10H12O2
3-Methylene-3,3a,4,5,6,8a-hexahydro-2H-cyclohepta(b)furan-2-one
—— β-Hexyl-α-methylen-γ-butyrolacton 72277-31-7 C11H18O2
β-Hexyl-α-methylen-γ-butyrolacton