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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
—— 7-((E)-3-Hydroxy-3-methyl-but-1-enyl)-oxepan-2-one 125214-68-8 C11H18O3
7-((E)-3-Hydroxy-3-methyl-but-1-enyl)-oxepan-2-one
—— 3-deoxy-d-mannoic lactone 85985-74-6 C6H10O5
3-deoxy-d-mannoic lactone
—— (1R,6S,7S,8S)-7-ethyl-8-phenyl-1-nitro-3-oxabicyclo[4.2.0]octan-4-one 1378941-92-4 C15H17NO4
(1R,6S,7S,8S)-7-ethyl-8-phenyl-1-nitro-3-oxabicyclo[4.2.0]octan-4-one
—— 3-phenethyl-pentanedioic acid anhydride 71280-36-9 C13H14O3
3-phenethyl-pentanedioic acid anhydride
—— 2,3-bis-(5,5-dimethyl-2-oxo-tetrahydro-[3]furyl)-succinic acid dimethyl ester 101887-44-9 C18H26O8
2,3-bis-(5,5-dimethyl-2-oxo-tetrahydro-[3]furyl)-succinic acid dimethyl ester
—— 9-METHYL-2-OXASPIRO[5.5]UNDECAN-3-ONE 465533-26-0 C11H18O2
9-METHYL-2-OXASPIRO[5.5]UNDECAN-3-ONE
—— 5-diethylaminomethyl-3-propyl-dihydro-furan-2-one 27846-67-9 C12H23NO2
5-diethylaminomethyl-3-propyl-dihydro-furan-2-one
—— 3-<(Dimethylamino)methyl>-4,5-dihydro-4,4,5-trimethyl-2(3H)-furanon 102870-17-7 C10H19NO2
3-<(Dimethylamino)methyl>-4,5-dihydro-4,4,5-trimethyl-2(3H)-furanon
—— 4-(4-Oxo-oxetan-2-yl)-butyraldehyde 197144-86-8 C7H10O3
4-(4-Oxo-oxetan-2-yl)-butyraldehyde
—— (2S,3R)-3-Methoxy-5-oxo-tetrahydro-furan-2-carbaldehyde 110089-31-1 C6H8O4
(2S,3R)-3-Methoxy-5-oxo-tetrahydro-furan-2-carbaldehyde
—— Tricyclo[4.4.3.01,6]-11-oxa-3,12-dioxotridecane 72542-12-2 C12H16O3
Tricyclo[4.4.3.01,6]-11-oxa-3,12-dioxotridecane
—— D-glucaric acid-1-isobutyl ester-6=>3-lactone 122360-89-8 C10H16O7
D-glucaric acid-1-isobutyl ester-6=>3-lactone
—— 5-oxatetracyclo[4.4.0.02,8.03,7]dec-9-en-4-one 77083-36-4 C9H8O2
5-oxatetracyclo[4.4.0.02,8.03,7]dec-9-en-4-one
—— 591231-25-3 C29H42O6
—— 19β,28-epoxy-4-hydroxy-3,4-seco-18α-oleanan-3-oic acid lactone 124150-16-9 C30H48O3
19β,28-epoxy-4-hydroxy-3,4-seco-18α-oleanan-3-oic acid lactone
—— ((E)-3-But-1-enyl)-dihydro-furan-2-one 90292-24-3 C8H12O2
((E)-3-But-1-enyl)-dihydro-furan-2-one
—— (E)-(2R,4S,5S,6S)-9-(1-ethoxyethoxy)-5-hydroxy-2,4,6-trimethyl-7-nonenecarboxylic acid γ-lactone 103563-59-3 C16H28O4
(E)-(2R,4S,5S,6S)-9-(1-ethoxyethoxy)-5-hydroxy-2,4,6-trimethyl-7-nonenecarboxylic acid γ-lactone
—— (3R,4S,5S)-3-methyl-4-(nitromethyl)-5-tridecyloxolan-2-one 1452900-15-0 C19H35NO4
(3R,4S,5S)-3-methyl-4-(nitromethyl)-5-tridecyloxolan-2-one
—— 6,7-bis(hydroxymethyl)-4-(pivaloyloxymethyl)-3-oxabicyclo[3.2.0]heptan-2-one 1323991-12-3 C14H22O6
6,7-bis(hydroxymethyl)-4-(pivaloyloxymethyl)-3-oxabicyclo[3.2.0]heptan-2-one
—— (4S,5R)-(+)-hydroxy-5 heptanolide-4 97101-19-4 C7H12O3
(4S,5R)-(+)-hydroxy-5 heptanolide-4
—— 80110-18-5 C22H36O7
—— α-Cyano-δ,δ-pentamethylen-δ-valerolacton 28525-68-0 C11H15NO2
α-Cyano-δ,δ-pentamethylen-δ-valerolacton
—— 3-Furancarboxylic acid, tetrahydro-5-methyl-2-oxo-, ethyl ester 14872-53-8 C8H12O4
3-Furancarboxylic acid, tetrahydro-5-methyl-2-oxo-, ethyl ester
—— methyl <3E,(4aR),4aβ,8α,8aα>-2,3,4a,5,8,8a-hexahydro-3-ethylidene-2-oxo-8-hydroxy-1,4-benzodioxin-6-carboxylate 139704-91-9 C12H14O6
methyl <3E,(4aR),4aβ,8α,8aα>-2,3,4a,5,8,8a-hexahydro-3-ethylidene-2-oxo-8-hydroxy-1,4-benzodioxin-6-carboxylate
—— 4,5-dibutyl-2-oxo-tetrahydro-furan-3-carbonitrile 36603-22-2 C13H21NO2
4,5-dibutyl-2-oxo-tetrahydro-furan-3-carbonitrile
—— (3R,4R,5S)-3-benzyl-4-(tert-butyldimethylsilanyloxy)-5-methyldihydrofuran-2-one 215798-01-9 C18H28O3Si
(3R,4R,5S)-3-benzyl-4-(tert-butyldimethylsilanyloxy)-5-methyldihydrofuran-2-one
—— (-)-1α-Ethyl-5β-(hydroxymethyl)-3aβ,4,5,7aα-tetrahydroindan-4β-carboxylic Acid γ-Lactone 91109-68-1 C13H18O2
(-)-1α-Ethyl-5β-(hydroxymethyl)-3aβ,4,5,7aα-tetrahydroindan-4β-carboxylic Acid γ-Lactone
—— (5S)-5-[(2S,4R)-2,4-bis[[tert-butyl(dimethyl)silyl]oxy]-6-hydroxyhexyl]oxolan-2-one 1047684-68-3 C22H46O5Si2
(5S)-5-[(2S,4R)-2,4-bis[[tert-butyl(dimethyl)silyl]oxy]-6-hydroxyhexyl]oxolan-2-one
—— 3-ethyl-3-[(E)-2-nitroprop-1-enyl]oxan-2-one 114577-89-8 C10H15NO4
3-ethyl-3-[(E)-2-nitroprop-1-enyl]oxan-2-one
—— (3S,6R)-3-methyl-6-vinyltetrahydro-2H-pyran-2-one 1354401-70-9 C8H12O2
(3S,6R)-3-methyl-6-vinyltetrahydro-2H-pyran-2-one
—— 1407674-48-9 C9H15NO2
—— 5-(bromomethyl)-5-(ethyl)dihydrofuran-2(3H)-one 1402559-72-1 C7H11BrO2
5-(bromomethyl)-5-(ethyl)dihydrofuran-2(3H)-one
—— 2-propenyl <5R-(5α,8α,8aα)>-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5,6,8,8a-tetrahydro-3-oxo-5-<(trimethylsilyl)ethynyl>spiro<1H-2-benzopyran-7(3H),2'-<1,3>dioxolan>-8-yl>carbamate 225368-13-8 C26H41NO7Si2
2-propenyl <5R-(5α,8α,8aα)>-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5,6,8,8a-tetrahydro-3-oxo-5-<(trimethylsilyl)ethynyl>spiro<1H-2-benzopyran-7(3H),2'-<1,3>dioxolan>-8-yl>carbamate
—— 3-(cyclopent-1-en-1-yl)oxetanone 77192-33-7 C8H10O2
3-(cyclopent-1-en-1-yl)oxetanone
—— α-Acetyl-δ-brom-γ-valerolacton 89856-57-5 C7H9BrO3
α-Acetyl-δ-brom-γ-valerolacton
—— 5-diethylaminomethyl-3-(3-methyl-butyl)-dihydro-furan-2-one 27846-69-1 C14H27NO2
5-diethylaminomethyl-3-(3-methyl-butyl)-dihydro-furan-2-one
—— 33880-82-9 C16H24O3
—— (1R,4S,8S)-1,8-dimethyl-3-oxabicyclo[3.2.1]octan-2,4-dione 311806-81-2 C9H12O3
(1R,4S,8S)-1,8-dimethyl-3-oxabicyclo[3.2.1]octan-2,4-dione
—— 92721-14-7 C9H14O2
—— sodium bis(2-ethyl-2-hydroxybutyrato)oxochromate(V) 84622-43-5 C8H12CrO7*Na
sodium bis(2-ethyl-2-hydroxybutyrato)oxochromate(V)
—— (E)-(2S,4S,7R,11S)-2,4,7,9,11-Pentamethyl-1,5-dioxa-cyclododec-8-ene-6,12-dione 92771-00-1 C15H24O4
(E)-(2S,4S,7R,11S)-2,4,7,9,11-Pentamethyl-1,5-dioxa-cyclododec-8-ene-6,12-dione
—— (E)-(2S,4S,7R,11R)-2,4,7,9,11-Pentamethyl-1,5-dioxa-cyclododec-9-ene-6,12-dione 92771-00-1 C15H24O4
(E)-(2S,4S,7R,11R)-2,4,7,9,11-Pentamethyl-1,5-dioxa-cyclododec-9-ene-6,12-dione
—— α-Methylen-β-nonyl-γ-butyrolacton 137669-69-3 C14H24O2
α-Methylen-β-nonyl-γ-butyrolacton
—— 5-(bromo(isopropyl)methyl)dihydrofuran-2(3H)-one 1379786-24-9 C8H13BrO2
5-(bromo(isopropyl)methyl)dihydrofuran-2(3H)-one
—— 1240382-65-3 C17H30O3Si
—— (S)-5-((S)-1-Amino-pent-4-enyl)-dihydro-furan-2-one 873017-39-1 C9H15NO2
(S)-5-((S)-1-Amino-pent-4-enyl)-dihydro-furan-2-one
—— 1240382-58-4 C11H16O3
—— 5,6-Bis-O-(t-butyldimethylsilyl)-D-glucono-1,4-lacton 78283-75-7 C18H38O6Si2
5,6-Bis-O-(t-butyldimethylsilyl)-D-glucono-1,4-lacton
—— 7-oxo-5-hydroxy-4,6,8,8-tetramethylnonanoic acid δ-lactone 72658-41-4 C13H22O3
7-oxo-5-hydroxy-4,6,8,8-tetramethylnonanoic acid δ-lactone
—— 1,2-Dimethyl-1-triphenylsilylcyclopropan-2,3-dicarbonsaeureanhydrid 33168-02-4 C25H22O3Si
1,2-Dimethyl-1-triphenylsilylcyclopropan-2,3-dicarbonsaeureanhydrid