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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
—— (1R,2R,5R,6R,8R)-5-ethoxy-1,8,12,12-tetramethyl-4-oxatricyclo[6.4.0.0]dodecan-3-one 467227-85-6 C17H28O3
(1R,2R,5R,6R,8R)-5-ethoxy-1,8,12,12-tetramethyl-4-oxatricyclo[6.4.0.0]dodecan-3-one
—— α-Bromo-α(α-bromobenzyl)-γ-butyrolacton 5461-04-1 C11H10Br2O2
α-Bromo-α(α-bromobenzyl)-γ-butyrolacton
—— cis-3-oxa-bicyclo[4.1.0]heptan-2-one 21251-52-5 C6H8O2
cis-3-oxa-bicyclo[4.1.0]heptan-2-one
—— 3-phenyl-4-oxo-6-ethoxy-3a,4,6,6a-tetrahydrofuro<3,4-d>-isoxazole 113003-50-2 C13H13NO4
3-phenyl-4-oxo-6-ethoxy-3a,4,6,6a-tetrahydrofuro<3,4-d>-isoxazole
—— α-tert-butoxycarbonyl-α-(4-fluorophenyl)-γ-methylidene-δ-valerolactone 1401354-80-0 C17H19FO4
α-tert-butoxycarbonyl-α-(4-fluorophenyl)-γ-methylidene-δ-valerolactone
—— 3-methoxyoxetan-2-one-4-spirocyclohexane 131436-03-8 C9H14O3
3-methoxyoxetan-2-one-4-spirocyclohexane
—— 6-Propyl-dihydro-pyran-2,4-dione 89269-61-4 C8H12O3
6-Propyl-dihydro-pyran-2,4-dione
—— (5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-1-oxa-spiro[4.4]nonan-2-one 341032-16-4 C14H26O3Si
(5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-1-oxa-spiro[4.4]nonan-2-one
—— 3,4-Dihydroxy-3,5-diphenyldihydrofuran-2(3h)-one 6267-04-5 C16H14O4
3,4-Dihydroxy-3,5-diphenyldihydrofuran-2(3h)-one
—— 4-Methylmevalolactone 109655-89-2 C7H12O3
4-Methylmevalolactone
—— (-)-(3R,4R,5S)-3-methyl-4-(tris(methylthio)methyl)-5-tridecyldihydrofuran-2(3H)-one 1265896-04-5 C22H42O2S3
(-)-(3R,4R,5S)-3-methyl-4-(tris(methylthio)methyl)-5-tridecyldihydrofuran-2(3H)-one
—— (4R,5S)-5-tridecyl-4-[tris(methylsulfanyl)methyl]-4,5-dihydro-3H-furan-2-one 897657-67-9 C21H40O2S3
(4R,5S)-5-tridecyl-4-[tris(methylsulfanyl)methyl]-4,5-dihydro-3H-furan-2-one
—— (1S,2S)-2-((R)-6-Oxo-tetrahydro-pyran-2-yl)-cyclopropanecarboxylic acid 625455-54-1 C9H12O4
(1S,2S)-2-((R)-6-Oxo-tetrahydro-pyran-2-yl)-cyclopropanecarboxylic acid
—— (R)-6-{(1S,2S)-2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-cyclopropyl}-tetrahydro-pyran-2-one 284662-65-3 C17H32O3Si
(R)-6-{(1S,2S)-2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-cyclopropyl}-tetrahydro-pyran-2-one
—— (5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-1-oxa-spiro[4.4]nonan-2-one —— C14H26O3Si
(5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-1-oxa-spiro[4.4]nonan-2-one
—— (4S,5R)-4-(4-chlorophenyl)-5-nitro-1-oxaspiro[5.5]undecan-2-one 1430853-23-8 C16H18ClNO4
(4S,5R)-4-(4-chlorophenyl)-5-nitro-1-oxaspiro[5.5]undecan-2-one
—— (4S,5R)-4-(4-methylphenyl)-5-nitro-1-oxaspiro[5.5]undecan-2-one 1430853-27-2 C17H21NO4
(4S,5R)-4-(4-methylphenyl)-5-nitro-1-oxaspiro[5.5]undecan-2-one
—— (3R,5R)-5-[4-[(2R)-2-[(1R)-1-hydroxyprop-2-enyl]pyrrolidin-1-yl]butyl]-3-methyloxolan-2-one 1231765-71-1 C16H27NO3
(3R,5R)-5-[4-[(2R)-2-[(1R)-1-hydroxyprop-2-enyl]pyrrolidin-1-yl]butyl]-3-methyloxolan-2-one
—— (4R,5R)-4-propyl-5-nitro-1-oxaspiro[5.5]undecan-2-one 1430853-31-8 C13H21NO4
(4R,5R)-4-propyl-5-nitro-1-oxaspiro[5.5]undecan-2-one
—— [(1R)-1-[(2R)-1-[4-[(2R,4R)-4-methyl-5-oxooxolan-2-yl]butyl]pyrrolidin-2-yl]prop-2-enyl] 2-methylprop-2-enoate 1231765-72-2 C20H31NO4
[(1R)-1-[(2R)-1-[4-[(2R,4R)-4-methyl-5-oxooxolan-2-yl]butyl]pyrrolidin-2-yl]prop-2-enyl] 2-methylprop-2-enoate
—— (4R,5R)-4-(2-furanyl)-5-nitro-1-oxaspiro[5.5]undecan-2-one 1430853-29-4 C14H17NO5
(4R,5R)-4-(2-furanyl)-5-nitro-1-oxaspiro[5.5]undecan-2-one
—— (4S,5R)-4-(3-chlorophenyl)-5-nitro-1-oxaspiro[5.5]undecan-2-one 1430853-22-7 C16H18ClNO4
(4S,5R)-4-(3-chlorophenyl)-5-nitro-1-oxaspiro[5.5]undecan-2-one
—— (4S,5R)-4-phenyl-5-nitro-1-oxaspiro[5.4]decan-2-one 1430853-32-9 C15H16ClNO4
(4S,5R)-4-phenyl-5-nitro-1-oxaspiro[5.4]decan-2-one
—— (4S,5R)-4-phenyl-5-nitro-1-oxaspiro[5.5]undecan-2-one 1430853-20-5 C16H19NO4
(4S,5R)-4-phenyl-5-nitro-1-oxaspiro[5.5]undecan-2-one
—— (4R,5R)-4-methyl-5-nitro-1-oxaspiro[5.5]undecan-2-one 1430853-30-7 C11H17NO4
(4R,5R)-4-methyl-5-nitro-1-oxaspiro[5.5]undecan-2-one
—— 2-[2-azido-2-(4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-ethyl]-3-methyl-butyraldehyde 173154-02-4 C14H23N3O3
2-[2-azido-2-(4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-ethyl]-3-methyl-butyraldehyde
—— (2R,3S,4R)-3-Hydroxy-4-(hydroxymethyl)-2-methyldihydro-1(2H)-furanone 35786-19-7 C6H10O4
(2R,3S,4R)-3-Hydroxy-4-(hydroxymethyl)-2-methyldihydro-1(2H)-furanone
—— 5,5-dinitro-tetrahydro-pyran-2-one 5029-19-6 C5H6N2O6
5,5-dinitro-tetrahydro-pyran-2-one
—— 3-[2-((1R,3R,4aS,8aS)-3-Hydroxy-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-eth-(E)-ylidene]-dihydro-furan-2-one 882032-99-7 C20H30O3
3-[2-((1R,3R,4aS,8aS)-3-Hydroxy-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-eth-(E)-ylidene]-dihydro-furan-2-one
—— hedychilactone A 361483-29-6 C20H30O3
hedychilactone A
—— 3-[2-((1R,3R,4aS,8aS)-3-Hydroxy-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-eth-(Z)-ylidene]-dihydro-furan-2-one 882033-01-4 C20H30O3
3-[2-((1R,3R,4aS,8aS)-3-Hydroxy-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-eth-(Z)-ylidene]-dihydro-furan-2-one
—— 3-[2-((1R,4aS,8aS)-5,5,8a-Trimethyl-2-methylene-3-oxo-decahydro-naphthalen-1-yl)-eth-(E)-ylidene]-dihydro-furan-2-one 882033-00-3 C20H28O3
3-[2-((1R,4aS,8aS)-5,5,8a-Trimethyl-2-methylene-3-oxo-decahydro-naphthalen-1-yl)-eth-(E)-ylidene]-dihydro-furan-2-one
—— 3-[2-((1R,4aS,8aS)-5,5,8a-Trimethyl-2-methylene-3-oxo-decahydro-naphthalen-1-yl)-eth-(Z)-ylidene]-dihydro-furan-2-one 882033-02-5 C20H28O3
3-[2-((1R,4aS,8aS)-5,5,8a-Trimethyl-2-methylene-3-oxo-decahydro-naphthalen-1-yl)-eth-(Z)-ylidene]-dihydro-furan-2-one
—— 4-phenyl-3-(pyridine-2-sulfonyl)-tetrahydropyran-2-one 1352411-45-0 C16H15NO4S
4-phenyl-3-(pyridine-2-sulfonyl)-tetrahydropyran-2-one
—— 3-(2-Cyano-5-oxotetrahydrofuran-2-yl)propanoic acid 6307-16-0 C8H9NO4
3-(2-Cyano-5-oxotetrahydrofuran-2-yl)propanoic acid
—— 3-(1-amino-ethylidene)-furan-2,4-dione 7251-95-8 C6H7NO3
3-(1-amino-ethylidene)-furan-2,4-dione
—— (4R)-4-(difluoromethyl)-4-hydroxy-tetrahydro-2H-pyran-2-one 956398-62-2 C6H8F2O3
(4R)-4-(difluoromethyl)-4-hydroxy-tetrahydro-2H-pyran-2-one
—— (4S)-4-hydroxy-4-(trifluoromethyl)tetrahydro-2H-pyran-2-one 956398-58-6 C6H7F3O3
(4S)-4-hydroxy-4-(trifluoromethyl)tetrahydro-2H-pyran-2-one
—— (4S)-4-(difluoromethyl)-4-hydroxy-tetrahydro-2H-pyran-2-one 956398-60-0 C6H8F2O3
(4S)-4-(difluoromethyl)-4-hydroxy-tetrahydro-2H-pyran-2-one
—— (4R)-4-hydroxy-4-(trifluoromethyl)tetrahydro-2H-pyran-2-one 956398-59-7 C6H7F3O3
(4R)-4-hydroxy-4-(trifluoromethyl)tetrahydro-2H-pyran-2-one
—— (3S,4S,5S)-4-hydroxy-5-[(1S)-hydroxy(phenyl)methyl]-3-(2,2,2-trifluoroethyl)dihydrofuran-2(3H)-one 1532540-66-1 C13H13F3O4
(3S,4S,5S)-4-hydroxy-5-[(1S)-hydroxy(phenyl)methyl]-3-(2,2,2-trifluoroethyl)dihydrofuran-2(3H)-one
—— 1-p-Tolyl-3-oxa-bicyclo[3.1.0]hexan-2-one 85467-92-1 C12H12O2
1-p-Tolyl-3-oxa-bicyclo[3.1.0]hexan-2-one
—— 1-(4-chlorophenyl)-3-oxa-bicyclo[3.1.0]hexan-2-one 85467-85-2 C11H9ClO2
1-(4-chlorophenyl)-3-oxa-bicyclo[3.1.0]hexan-2-one
—— 6,7,8,9,3',4'-hexahydro-spiro[benzocycloheptene-5,2'-furan]-5'-one 27896-15-7 C14H16O2
6,7,8,9,3',4'-hexahydro-spiro[benzocycloheptene-5,2'-furan]-5'-one
—— (3aS,6R,6aS,9aR,9bR)-9b-Hydroxy-6,9-dimethyl-3-methylene-3a,4,5,6,6a,7,9a,9b-octahydro-3H-benzo[de]chromen-2-one 64439-86-7 C15H20O3
(3aS,6R,6aS,9aR,9bR)-9b-Hydroxy-6,9-dimethyl-3-methylene-3a,4,5,6,6a,7,9a,9b-octahydro-3H-benzo[de]chromen-2-one
—— 5-Fluoro-4-hydroxy-4-methyloxan-2-one 2266-57-1 C6H9FO3
5-Fluoro-4-hydroxy-4-methyloxan-2-one
—— penta-epi-compactin 109785-29-7 C23H34O5
penta-epi-compactin
—— (S)-5-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-butyl]-dihydro-furan-2-one 147461-29-8 C24H32O3Si
(S)-5-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-butyl]-dihydro-furan-2-one
—— 3-Oxo-tetrahydro-cyclopenta[c]furan-3a-carboxylic acid methyl ester 135482-22-3 C9H12O4
3-Oxo-tetrahydro-cyclopenta[c]furan-3a-carboxylic acid methyl ester
—— (3aα,6aα)-dihydro-6a-carbomethoxycyclopenta<c>furan-1(3H)-one 120790-39-8 C9H12O4
(3aα,6aα)-dihydro-6a-carbomethoxycyclopenta<c>furan-1(3H)-one