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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
—— helicascolide C 1393544-23-4 C12H18O3
helicascolide C
—— Artenolide 113807-34-4 C30H40O8
Artenolide
—— tetrahydro-3-(3-methylbut-2-enyl)pyran-2-one 412026-41-6 C10H16O2
tetrahydro-3-(3-methylbut-2-enyl)pyran-2-one
—— 7-(2-Phenylethyl)-3-phenylselanyloxepan-2-one 199797-20-1 C20H22O2Se
7-(2-Phenylethyl)-3-phenylselanyloxepan-2-one
—— (3RS,5S)-3-phenylseleno-5-methyldihydro-2(3H)-furanone 112775-67-4 C11H12O2Se
(3RS,5S)-3-phenylseleno-5-methyldihydro-2(3H)-furanone
—— (R)-6-<<(tert-butyldiphenylsilyl)oxy>methyl>-3,4,5,6-tetrahydro-2H-pyran-2-one 175398-33-1 C22H28O3Si
(R)-6-<<(tert-butyldiphenylsilyl)oxy>methyl>-3,4,5,6-tetrahydro-2H-pyran-2-one
—— 7-(2-phenethyl)-2-oxepanone 199797-18-7 C14H18O2
7-(2-phenethyl)-2-oxepanone
—— (5S)-5-(3-Iodo-2-methylprop-2-en-1-yl)oxolan-2-one 404356-75-8 C8H11IO2
(5S)-5-(3-Iodo-2-methylprop-2-en-1-yl)oxolan-2-one
—— (+/-)-4-(tert-butyldiphenylsilyloxymethyl)-4H,5H-dihydrofuran-2-one 328386-16-9 C21H26O3Si
(+/-)-4-(tert-butyldiphenylsilyloxymethyl)-4H,5H-dihydrofuran-2-one
—— 6-[2'-(tert-butyldimethylsilanyloxy)-1,1'-dimethyl-ethyl]-4-triisopropylsilanyloxy-tetrahydropyran-2-one 611236-91-0 C24H50O4Si2
6-[2'-(tert-butyldimethylsilanyloxy)-1,1'-dimethyl-ethyl]-4-triisopropylsilanyloxy-tetrahydropyran-2-one
—— (1S,2R,6R,7R,8S)-2-but-3-enyl-7-[tert-butyl(dimethyl)silyl]oxy-1,8-dimethyl-3,10-dioxatricyclo[6.3.0.02,6]undecane-4,9-dione 902768-23-4 C21H34O5Si
(1S,2R,6R,7R,8S)-2-but-3-enyl-7-[tert-butyl(dimethyl)silyl]oxy-1,8-dimethyl-3,10-dioxatricyclo[6.3.0.02,6]undecane-4,9-dione
—— 6-oxaspiro[3.4]octan-5-one 84565-26-4 C7H10O2
6-oxaspiro[3.4]octan-5-one
—— α-Methylen-β-pentyl-γ-butyrolacton 137669-66-0 C10H16O2
α-Methylen-β-pentyl-γ-butyrolacton
—— 2-ethyl-4-hydroxy-4-methyl-5-oxo-tetrahydro-furan-2-carbonitrile 122693-57-6 C8H11NO3
2-ethyl-4-hydroxy-4-methyl-5-oxo-tetrahydro-furan-2-carbonitrile
—— (1R,3S,5R,8S,11S)-3,5-dimethyl-7-oxo-2,6-dioxatricyclo[9.2.2.01,8]pentadeca-9,14-diene-12,12,13,13-tetracarbonitrile 201848-53-5 C19H16N4O3
(1R,3S,5R,8S,11S)-3,5-dimethyl-7-oxo-2,6-dioxatricyclo[9.2.2.01,8]pentadeca-9,14-diene-12,12,13,13-tetracarbonitrile
—— 5-propoxymethyl-dihydro-furan-2-one 105273-65-2 C8H14O3
5-propoxymethyl-dihydro-furan-2-one
—— γ-Isopentenyl-butyrolacton 22908-68-5 C10H18O2
γ-Isopentenyl-butyrolacton
—— 5-isopentyl-dihydro-furan-2-one 2429-94-9 C9H16O2
5-isopentyl-dihydro-furan-2-one
—— Ethyl 5-chloromethyl-2-oxo-tetrahydrofuran-3-carboxylate 5406-65-5 C8H11ClO4
Ethyl 5-chloromethyl-2-oxo-tetrahydrofuran-3-carboxylate
—— cis,trans-3-carboxy-4-phenyl-tetrahydrofuran-2-on 1016-01-9 C11H10O4
cis,trans-3-carboxy-4-phenyl-tetrahydrofuran-2-on
—— 7-cyclohexyl-oxepan-2-one 34680-84-7 C12H20O2
7-cyclohexyl-oxepan-2-one
—— 2-Carboxy-4-phenylbutyrolacton 6005-95-4 C11H10O4
2-Carboxy-4-phenylbutyrolacton
—— (3Z)-8a-hydroxy-8,8-dimethyl-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylidene]-5,6,7,8b-tetrahydro-3aH-indeno[1,2-b]furan-2-one 143572-84-3 C19H22O6
(3Z)-8a-hydroxy-8,8-dimethyl-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylidene]-5,6,7,8b-tetrahydro-3aH-indeno[1,2-b]furan-2-one
—— α-(Diisopropoxyphosphinyl)-δ-valerolactone 151746-93-9 C11H21O5P
α-(Diisopropoxyphosphinyl)-δ-valerolactone
—— 6-but-3-ynyl-3-chloro-6-cyclopentyl-dihydro-pyran-2,4-dione 612062-76-7 C14H17ClO3
6-but-3-ynyl-3-chloro-6-cyclopentyl-dihydro-pyran-2,4-dione
—— α-phenylmethylene-δ-lactone 40541-35-3 C12H12O2
α-phenylmethylene-δ-lactone
—— (S)-4-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 1056676-01-7 C17H29NO5
(S)-4-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
—— (4S,2'S)-2,2-dimethyl-4-(5-oxotetrahydrofuran-2-yl)oxazolidine-3-carboxylic acid tert-butyl ester 906662-77-9 C14H23NO5
(4S,2'S)-2,2-dimethyl-4-(5-oxotetrahydrofuran-2-yl)oxazolidine-3-carboxylic acid tert-butyl ester
—— 5-benzyl-4-phenyl-dihydro-furan-2,3-dione 6362-70-5 C17H14O3
5-benzyl-4-phenyl-dihydro-furan-2,3-dione
—— (3R,5S)-dihydro-5-(methoxymethyl)-3-(octadec-17-en-9-ynyl)furan-2(3H)-one 1333896-66-4 C24H40O3
(3R,5S)-dihydro-5-(methoxymethyl)-3-(octadec-17-en-9-ynyl)furan-2(3H)-one
—— (3R,5S)-dihydro-5-(hydroxymethyl)-3-(octadec-17-en-9-ynyl)furan-2(3H)-one 1333896-65-3 C23H38O3
(3R,5S)-dihydro-5-(hydroxymethyl)-3-(octadec-17-en-9-ynyl)furan-2(3H)-one
—— (3R,5S)-dihydro-5-(methoxymethyl)-3-(octadeca-9,11-diynyl)furan-2(3H)-one 1333896-63-1 C24H38O3
(3R,5S)-dihydro-5-(methoxymethyl)-3-(octadeca-9,11-diynyl)furan-2(3H)-one
—— (3S,5S,1'S,3'S)-5-(1'-amino-3'-hydroxymethyl-4'-methylpentyl)-3-isopropyl-dihydrofuran-2-one 179993-29-4 C14H27NO3
(3S,5S,1'S,3'S)-5-(1'-amino-3'-hydroxymethyl-4'-methylpentyl)-3-isopropyl-dihydrofuran-2-one
—— Coriamyrtin 2571-86-0 C15H18O5
Coriamyrtin
—— propoxy-6 octanolide-4 93676-80-3 C11H20O3
propoxy-6 octanolide-4
—— 5-(2-chloroethyl)dihydrofuran-2(3H)-one 5864-77-7 C6H9ClO2
5-(2-chloroethyl)dihydrofuran-2(3H)-one
—— 5-(2 (benzylthio)ethyl)dihydrofuran-2(3H)-one 6725-60-6 C13H16O2S
5-(2 (benzylthio)ethyl)dihydrofuran-2(3H)-one
—— (3aR,6R)-6-methyl-8-[tri(isopropyl)-silanyloxy]-3,3a,6,7-tetrahydrocyclohepta[c]furan-1-one 860480-94-0 C19H32O3Si
(3aR,6R)-6-methyl-8-[tri(isopropyl)-silanyloxy]-3,3a,6,7-tetrahydrocyclohepta[c]furan-1-one
—— 4,4-dimethyl-tetrahydro-pyran-2-one 22791-80-6 C7H12O2
4,4-dimethyl-tetrahydro-pyran-2-one
—— 3,3-Dichloro-4-(chloro-phenylmethyl)oxolan-2-one 87223-95-8 C11H9Cl3O2
3,3-Dichloro-4-(chloro-phenylmethyl)oxolan-2-one
—— (4,4-dichloro-5-oxo-2-phenyltetrahydrofuran-3-yl)methyl acetate 957470-75-6 C13H12Cl2O4
(4,4-dichloro-5-oxo-2-phenyltetrahydrofuran-3-yl)methyl acetate
—— 3-methylene-tetrahydro-pyran-2-one 42023-19-8 C6H8O2
3-methylene-tetrahydro-pyran-2-one
—— 4-(Dimethoxyphosphinothioylmethyl)oxetan-2-one 80986-68-1 C6H11O4PS
4-(Dimethoxyphosphinothioylmethyl)oxetan-2-one
—— Ethyl 2-butyl-4,5-dioxooxolane-3-carboxylate 921894-22-6 C11H16O5
Ethyl 2-butyl-4,5-dioxooxolane-3-carboxylate
—— 8,8-dimethyl-3-oxabicyclo<3.2.1>octane-2,4-dione 5763-51-9 C9H12O3
8,8-dimethyl-3-oxabicyclo<3.2.1>octane-2,4-dione
—— (5S)-5-methyl-5-phenyldihydrofuran-2(3H)-one 7210-42-6 C11H12O2
(5S)-5-methyl-5-phenyldihydrofuran-2(3H)-one
—— (R)-5-methyl-5-phenyl-3,4-dihydro(5H)-furan-2-one 88314-79-8 C11H12O2
(R)-5-methyl-5-phenyl-3,4-dihydro(5H)-furan-2-one
—— 5-butoxymethyl-3-chlorooxolan-2-one 78508-82-4 C9H15ClO3
5-butoxymethyl-3-chlorooxolan-2-one
—— (R)-5-(iodomethyl)-5-phenyldihydrofuran-2(3H)-one 398142-09-1 C11H11IO2
(R)-5-(iodomethyl)-5-phenyldihydrofuran-2(3H)-one
—— ε-(2-chloroethyl)-ε-caprolactone 120476-62-2 C8H13ClO2
ε-(2-chloroethyl)-ε-caprolactone