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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
—— 5-(2-Iodoethyl)-5-pentanolide 152667-82-8 C7H11IO2
5-(2-Iodoethyl)-5-pentanolide
—— (1R,5S,7R)-7-(1-ethoxyethoxy)-1-methyl-2-oxabicyclo<3.2.1>nonan-3-one 148679-94-1 C13H22O4
(1R,5S,7R)-7-(1-ethoxyethoxy)-1-methyl-2-oxabicyclo<3.2.1>nonan-3-one
—— (1R,5R,8S)-8-(1',3'-dithianyl-2')methyl-2-oxabicyclo[3,2,1]octan-3-one 163748-47-8 C12H18O2S2
(1R,5R,8S)-8-(1',3'-dithianyl-2')methyl-2-oxabicyclo[3,2,1]octan-3-one
—— (4R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-4-hydroxy-3,3-dimethyl-tetrahydro-pyran-2-one 476005-13-7 C14H28O4Si
(4R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-4-hydroxy-3,3-dimethyl-tetrahydro-pyran-2-one
—— (1S,4R,5S,9S,13R)-4,7,7,13-Tetramethyl-10-oxa-tricyclo[7.2.2.0<sup>1,5</sup>]tridecan-11-one 299915-64-3 C16H26O2
(1S,4R,5S,9S,13R)-4,7,7,13-Tetramethyl-10-oxa-tricyclo[7.2.2.0<sup>1,5</sup>]tridecan-11-one
—— tert-butyl N-[(1'S,2'S,4S,6'S,8'R,11'S,12'R)-12'-ethenyl-11'-hydroxy-2,2,4',4'-tetramethyl-10'-oxospiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-1'-yl]carbamate 616225-52-6 C22H33NO9
tert-butyl N-[(1'S,2'S,4S,6'S,8'R,11'S,12'R)-12'-ethenyl-11'-hydroxy-2,2,4',4'-tetramethyl-10'-oxospiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-1'-yl]carbamate
—— 6-[4,5-bis(tert-butyldimethylsilanyloxy)-2-methylpent-1-enyl]-4-hydroxytetrahydropyran-2-one 857026-63-2 C23H46O5Si2
6-[4,5-bis(tert-butyldimethylsilanyloxy)-2-methylpent-1-enyl]-4-hydroxytetrahydropyran-2-one
—— 2(3H)-Furanone, 3,4,4-trifluorodihydro-5,5-dimethyl- 60375-64-6 C6H7F3O2
2(3H)-Furanone, 3,4,4-trifluorodihydro-5,5-dimethyl-
—— alpha-(2-Trifluoromethyl-2-propenoyloxy)-gamma-butyrolactone 357294-11-2 C8H7F3O4
alpha-(2-Trifluoromethyl-2-propenoyloxy)-gamma-butyrolactone
—— 4-Triisopropylsilanyloxy-tetrahydro-pyran-2-one 859844-14-7 C14H28O3Si
4-Triisopropylsilanyloxy-tetrahydro-pyran-2-one
—— 5-epi-14-oxo-ent-haliman-18,10β-olide 732306-51-3 C20H32O3
5-epi-14-oxo-ent-haliman-18,10β-olide
—— (+)-latifolic acid 50460-94-1 C7H10O5
(+)-latifolic acid
—— (3aR,5S,5aR,8S,9aS)-5,8-dimethyl-9-methylidene-1,3a,4,5,5a,6,7,8-octahydroindeno[1,7a-c]furan-3-one 478314-56-6 C14H20O2
(3aR,5S,5aR,8S,9aS)-5,8-dimethyl-9-methylidene-1,3a,4,5,5a,6,7,8-octahydroindeno[1,7a-c]furan-3-one
—— (4aR,5S,7R,7aR)-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-4,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyran-3-one 159812-82-5 C20H40O4Si2
(4aR,5S,7R,7aR)-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-4,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyran-3-one
—— (1R,5R,6S)-4,4-dimethyl-11-(tributylstannylmethyl)-3-oxatricyclo[4.3.2.01,5]undec-7-en-2-one 332182-69-1 C25H44O2Sn
(1R,5R,6S)-4,4-dimethyl-11-(tributylstannylmethyl)-3-oxatricyclo[4.3.2.01,5]undec-7-en-2-one
—— (1R,4S,5S,6R)-5,6-bis-(tert-butyldimethylsilanyloxy)-6-methyl-2-oxabicyclo[2.2.1]heptan-3-one 594853-85-7 C19H38O4Si2
(1R,4S,5S,6R)-5,6-bis-(tert-butyldimethylsilanyloxy)-6-methyl-2-oxabicyclo[2.2.1]heptan-3-one
—— (4R,5S,6R)-4-(3,3-Dibromo-allyl)-5-methoxy-6-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-tetrahydro-pyran-2-one 323181-89-1 C15H22Br2O5
(4R,5S,6R)-4-(3,3-Dibromo-allyl)-5-methoxy-6-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-tetrahydro-pyran-2-one
—— (1S,5S,6R)-2-Oxo-3-oxa-bicyclo[3.1.0]hexane-6-carbaldehyde 201553-39-1 C6H6O3
(1S,5S,6R)-2-Oxo-3-oxa-bicyclo[3.1.0]hexane-6-carbaldehyde
—— (3R,4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-1-oxa-spiro[4.4]nonan-2-one 797801-26-4 C14H26O5Si
(3R,4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-1-oxa-spiro[4.4]nonan-2-one
—— 5-epi-14,15-di-nor-13-oxo-ent-haliman-18,10β-olide 732306-54-6 C18H28O3
5-epi-14,15-di-nor-13-oxo-ent-haliman-18,10β-olide
—— (4S,5R,6S)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-1-oxa-spiro[4.4]nonan-2-one 797801-29-7 C20H40O4Si2
(4S,5R,6S)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-1-oxa-spiro[4.4]nonan-2-one
—— (3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(3-trimethylsilanyl-prop-2-ynyl)-dihydro-furan-2-one 374680-87-2 C16H30O3Si2
(3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(3-trimethylsilanyl-prop-2-ynyl)-dihydro-furan-2-one
—— [4S,(2R,3R)]-4-(3-hydroxy-5-oxo-tetrahydro-furan-2-yl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 1053271-27-4 C14H23NO6
[4S,(2R,3R)]-4-(3-hydroxy-5-oxo-tetrahydro-furan-2-yl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
—— (R)-dihydro-5-[(R)-1-(tert-butyldimethylsilyloxy)tridecyl]furan-2(3H)-one 171087-68-6 C23H46O3Si
(R)-dihydro-5-[(R)-1-(tert-butyldimethylsilyloxy)tridecyl]furan-2(3H)-one
—— (3R,4S,5S,6S)-4-[tert-butyl(dimethyl)silyl]oxy-6-[(2S)-2-hydroxy-4-methylpent-3-enyl]-3,5-dimethyloxan-2-one 256920-77-1 C19H36O4Si
(3R,4S,5S,6S)-4-[tert-butyl(dimethyl)silyl]oxy-6-[(2S)-2-hydroxy-4-methylpent-3-enyl]-3,5-dimethyloxan-2-one
—— 4,4-dimethyl-7-(triisopropylsilyloxy)-2-oxabicyclo[3.3.0]octan-3-one 611236-94-3 C18H34O3Si
4,4-dimethyl-7-(triisopropylsilyloxy)-2-oxabicyclo[3.3.0]octan-3-one
—— 2(3H)-Furanone, 4-(3-butenyl)dihydro-5,5-dimethyl- 502760-22-7 C10H16O2
2(3H)-Furanone, 4-(3-butenyl)dihydro-5,5-dimethyl-
—— 2(3H)-Furanone, 3-ethyldihydro-4-hydroxy-4-(hydroxymethyl)-(9CI) 549545-97-3 C7H12O4
2(3H)-Furanone, 3-ethyldihydro-4-hydroxy-4-(hydroxymethyl)-(9CI)
—— (R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-tetrahydro-pyran-2-one 285570-89-0 C13H26O3Si
(R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-tetrahydro-pyran-2-one
—— (3R,4S,5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-1-oxa-spiro[4.4]nonan-2-one 797801-35-5 C14H26O5Si
(3R,4S,5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-1-oxa-spiro[4.4]nonan-2-one
—— (1R,2R,5S,8S,9S,13R,14S,15S,16R,20S,21S,24S)-3,8,21,25-tetramethyl-6,23-dioxaheptacyclo[13.9.2.01,16.02,14.04,13.05,9.020,24]hexacosa-3,25-diene-7,12,17,22-tetrone 832135-42-9 C28H32O6
(1R,2R,5S,8S,9S,13R,14S,15S,16R,20S,21S,24S)-3,8,21,25-tetramethyl-6,23-dioxaheptacyclo[13.9.2.01,16.02,14.04,13.05,9.020,24]hexacosa-3,25-diene-7,12,17,22-tetrone
—— (5R)-5-allyl-5-methyldihydrofuran-2-one 654676-04-7 C8H12O2
(5R)-5-allyl-5-methyldihydrofuran-2-one
—— (4S,5R,6R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-1-oxa-spiro[4.4]nonan-2-one 797801-37-7 C20H40O4Si2
(4S,5R,6R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-1-oxa-spiro[4.4]nonan-2-one
—— (3S,4R)-4-Hydroxy-3-(3-trimethylsilanyl-prop-2-ynyl)-dihydro-furan-2-one 374680-86-1 C10H16O3Si
(3S,4R)-4-Hydroxy-3-(3-trimethylsilanyl-prop-2-ynyl)-dihydro-furan-2-one
—— (4S,5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-1-oxa-spiro[4.4]nonan-2-one 797801-36-6 C14H26O4Si
(4S,5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-1-oxa-spiro[4.4]nonan-2-one
—— 5,5-dimethyl-4-propyltetrahydrofuran-2-one 60468-93-1 C9H16O2
5,5-dimethyl-4-propyltetrahydrofuran-2-one
—— 4R-(1S,2-dimethylpropyl)dihydrofuran-2-one 850080-21-6 C9H16O2
4R-(1S,2-dimethylpropyl)dihydrofuran-2-one
—— ((S)-3-Ethyl-6-oxo-tetrahydro-pyran-3-yl)-acetaldehyde 403511-50-2 C9H14O3
((S)-3-Ethyl-6-oxo-tetrahydro-pyran-3-yl)-acetaldehyde
—— 5-epi-ent-haliman-14-en-18,10β-olide 732306-50-2 C20H32O2
5-epi-ent-haliman-14-en-18,10β-olide
—— 3-(2-Chloro-allyl)-5-pentyloxymethyl-dihydro-furan-2-one 354530-17-9 C13H21ClO3
3-(2-Chloro-allyl)-5-pentyloxymethyl-dihydro-furan-2-one
—— [(1'S,2'S,4S,6'S,8'R,11'S,12'R)-12'-(2-chloroethyl)-2,2,4',4'-tetramethyl-10'-oxospiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-11'-yl] carbamate 616225-50-4 C18H26ClNO8
[(1'S,2'S,4S,6'S,8'R,11'S,12'R)-12'-(2-chloroethyl)-2,2,4',4'-tetramethyl-10'-oxospiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-11'-yl] carbamate
—— (3R,3aS,6aR)-3-(hydroxymethyl)-N-(tert-butyloxycarbonyl)tetrahydrofuro-[2,3-d]isoxazol-5-one 420846-39-5 C11H17NO6
(3R,3aS,6aR)-3-(hydroxymethyl)-N-(tert-butyloxycarbonyl)tetrahydrofuro-[2,3-d]isoxazol-5-one
—— 3-{2-Oxo-5-[2-(tetrahydro-pyran-2-yloxy)-eth-(Z)-ylidene]-tetrahydro-pyran-3-yl}-propionic acid methyl ester 606942-82-9 C16H24O6
3-{2-Oxo-5-[2-(tetrahydro-pyran-2-yloxy)-eth-(Z)-ylidene]-tetrahydro-pyran-3-yl}-propionic acid methyl ester
—— 5-epi-14,15-di-nor-13-trimethylsilyloxy-ent-halim-13(16)-en-18,10β-olide 732306-55-7 C21H36O3Si
5-epi-14,15-di-nor-13-trimethylsilyloxy-ent-halim-13(16)-en-18,10β-olide
—— (1R,5S,6R)-2-Oxo-3-oxa-bicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester 320725-08-4 C10H14O4
(1R,5S,6R)-2-Oxo-3-oxa-bicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester
—— 3-allyl-3-methyl-4-(1-phenyl-allyl)-dihydro-furan-2-one 332940-49-5 C17H20O2
3-allyl-3-methyl-4-(1-phenyl-allyl)-dihydro-furan-2-one
—— 1,1-Dimethylethyl<2R-<2α(R<sup>*</sup>),3β,4β>>-2,2-dimethyl-4-(tetrahydro-3,4-dihydroxy-5-oxo-2-furanyl)-3-oxazolidinecarboxylate 127257-26-5 C14H23NO7
1,1-Dimethylethyl<2R-<2α(R<sup>*</sup>),3β,4β>>-2,2-dimethyl-4-(tetrahydro-3,4-dihydroxy-5-oxo-2-furanyl)-3-oxazolidinecarboxylate
—— (1R,5S,9R,10S)-10-triisopropylsilyloxy-3-oxatricyclo[7.3.0.0<sup>1,5</sup>]dodec-7-ene-4-one 608534-73-2 C20H34O3Si
(1R,5S,9R,10S)-10-triisopropylsilyloxy-3-oxatricyclo[7.3.0.0<sup>1,5</sup>]dodec-7-ene-4-one
—— (2aS,4aR,10aS,10bS)-2a,3,4,4a,7,8,10a,10b-octahydro-1,5-dioxacyclonona[cd]pentalene-2,6-dione 669000-27-5 C12H14O4
(2aS,4aR,10aS,10bS)-2a,3,4,4a,7,8,10a,10b-octahydro-1,5-dioxacyclonona[cd]pentalene-2,6-dione
—— (3R,6S,7aS)-3-phenylspiro[1,3,7,7a-tetrahydropyrrolo[1,2-c][1,3]oxazole-6,5'-oxolane]-2',5-dione 502698-23-9 C15H15NO4
(3R,6S,7aS)-3-phenylspiro[1,3,7,7a-tetrahydropyrrolo[1,2-c][1,3]oxazole-6,5'-oxolane]-2',5-dione