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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
—— methyl 2-[(3R)-3-hydroxy-5-(2-methylprop-1-enyl)-2-oxooxolan-3-yl]acetate 910237-11-5 C11H16O5
methyl 2-[(3R)-3-hydroxy-5-(2-methylprop-1-enyl)-2-oxooxolan-3-yl]acetate
—— 1-oxo-3β-(4-methyl-3-pentenyl)-6β-methyl-6aα-carbomethoxy-1,3,3aα,6a-tetrahydrocyclopenta<c>furan 97673-28-4 C16H22O4
1-oxo-3β-(4-methyl-3-pentenyl)-6β-methyl-6aα-carbomethoxy-1,3,3aα,6a-tetrahydrocyclopenta<c>furan
—— 1-oxo-3β-(4-methyl-3-pentenyl)-6α-methyl-6aα-carbomethoxy-1,3,3aα,6a-tetrahydrocyclopenta<c>furan 97673-29-5 C16H22O4
1-oxo-3β-(4-methyl-3-pentenyl)-6α-methyl-6aα-carbomethoxy-1,3,3aα,6a-tetrahydrocyclopenta<c>furan
—— 1-oxo-3α-(4-methyl-3-pentenyl)-6β-methyl-6aα-carbomethoxy-1,3,3aα,6a-tetrahydrocyclopenta<c>furan 97673-26-2 C16H22O4
1-oxo-3α-(4-methyl-3-pentenyl)-6β-methyl-6aα-carbomethoxy-1,3,3aα,6a-tetrahydrocyclopenta<c>furan
—— 1-oxo-3α-(4-methyl-3-pentenyl)-6α-methyl-6aα-carbomethoxy-1,3,3aα,6a-tetrahydrocyclopenta<c>furan 97635-13-7 C16H22O4
1-oxo-3α-(4-methyl-3-pentenyl)-6α-methyl-6aα-carbomethoxy-1,3,3aα,6a-tetrahydrocyclopenta<c>furan
—— (R)-(+)-2-Oxo-4,5-dihydro-3H-furan-2-carbonsaeureamid 166765-04-4 C5H7NO3
(R)-(+)-2-Oxo-4,5-dihydro-3H-furan-2-carbonsaeureamid
—— 6-[(2R)-5-oxooxolan-2-yl]hex-4-ynal 1258196-36-9 C10H12O3
6-[(2R)-5-oxooxolan-2-yl]hex-4-ynal
—— 3,7-dimethyl-3-(4-methylpent-4-enyl)-2-oxa-spiro[3.5]non-6-en-1-one 622793-12-8 C16H24O2
3,7-dimethyl-3-(4-methylpent-4-enyl)-2-oxa-spiro[3.5]non-6-en-1-one
—— (3S,5R)-5-(tert-butyldiphenylsilyloxymethyl)-3-methyl-dihydrofuran-2(3H)-one 147200-08-6 C22H28O3Si
(3S,5R)-5-(tert-butyldiphenylsilyloxymethyl)-3-methyl-dihydrofuran-2(3H)-one
—— 3S,5R-5-azidomethyl-3-methyl-4,5-dihydro-2(3H)-furanone 147093-44-5 C6H9N3O2
3S,5R-5-azidomethyl-3-methyl-4,5-dihydro-2(3H)-furanone
—— (5S)-5-methyl-3-prop-2-enyloxolan-2-one 3926-76-9 C8H12O2
(5S)-5-methyl-3-prop-2-enyloxolan-2-one
—— (3S,5R)-5-(aminomethyl)-3-methyloxolan-2-one 785019-69-4 C6H11NO2
(3S,5R)-5-(aminomethyl)-3-methyloxolan-2-one
—— tert-butyl (R)-5-oxotetrahydrofuran-2-carboxylate 176237-48-2 C9H14O4
tert-butyl (R)-5-oxotetrahydrofuran-2-carboxylate
—— 4,5-Dihydro-4,4,5-trimethyl-3-methylen-2(3H)-furanon 102870-18-8 C8H12O2
4,5-Dihydro-4,4,5-trimethyl-3-methylen-2(3H)-furanon
—— 4-(4-guanidinophenyl)-6-(E)-(iodomethylidene)tetrahydro-2-pyranone 149577-66-2 C13H14IN3O2
4-(4-guanidinophenyl)-6-(E)-(iodomethylidene)tetrahydro-2-pyranone
—— 4-(4-guanidinophenyl)-6-methylidenetetrahydro-2-pyranone 149577-65-1 C13H15N3O2
4-(4-guanidinophenyl)-6-methylidenetetrahydro-2-pyranone
—— 2-[2-(2-Iodo-ethyl)-phenyl]-5-oxo-tetrahydro-furan-3-carboxylic acid methyl ester 112471-40-6 C14H15IO4
2-[2-(2-Iodo-ethyl)-phenyl]-5-oxo-tetrahydro-furan-3-carboxylic acid methyl ester
—— (3aR,4R,7aR)-4-Methyl-2-trichloromethyl-3a,4,7,7a-tetrahydro-pyrano[4,3-d]oxazol-6-one 110079-94-2 C8H8Cl3NO3
(3aR,4R,7aR)-4-Methyl-2-trichloromethyl-3a,4,7,7a-tetrahydro-pyrano[4,3-d]oxazol-6-one
—— 3,4-Diethyl-oxetan-2-one 115367-78-7 C7H12O2
3,4-Diethyl-oxetan-2-one
—— 2',6'-endo-spiro<cyclohexane-1,5'-<4>oxatricyclo<5.2.1.0<sup>2,6</sup>>dec-8'-ena3'-one> 82639-62-1 C14H18O2
2',6'-endo-spiro<cyclohexane-1,5'-<4>oxatricyclo<5.2.1.0<sup>2,6</sup>>dec-8'-ena3'-one>
—— 2',6'-endo-spiro<cyclopentane-1,5'-<4>oxatricyclo<5.2.1.0<sup>2,6</sup>>dec-8'-en-3'-one> 82639-61-0 C13H16O2
2',6'-endo-spiro<cyclopentane-1,5'-<4>oxatricyclo<5.2.1.0<sup>2,6</sup>>dec-8'-en-3'-one>
—— dihexyl-5,5 oxa-4,10 endo-tricyclo<5.2.1.0<sup>2.6</sup>>decene-8 one-3 —— C21H34O2
dihexyl-5,5 oxa-4,10 endo-tricyclo<5.2.1.0<sup>2.6</sup>>decene-8 one-3
—— dibenzyl-5,5 oxa-4,10 endo-tricyclo<5.2.1.0<sup>2.6</sup>>decene-8 one-3 —— C23H22O2
dibenzyl-5,5 oxa-4,10 endo-tricyclo<5.2.1.0<sup>2.6</sup>>decene-8 one-3
—— dipentyl-5,5 oxa-4,10 endo-tricyclo<5.2.1.0<sup>2.6</sup>>decene-8 one-3 94192-07-1 C19H30O2
dipentyl-5,5 oxa-4,10 endo-tricyclo<5.2.1.0<sup>2.6</sup>>decene-8 one-3
—— diethyl-5,5 oxa-4,10 endo-tricyclo<5.2.1.0<sup>2.6</sup>>decene-8 one-3 —— C13H18O2
diethyl-5,5 oxa-4,10 endo-tricyclo<5.2.1.0<sup>2.6</sup>>decene-8 one-3
—— (3S,4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-methyl-tetrahydro-pyran-2-one 132958-25-9 C23H30O4Si
(3S,4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-methyl-tetrahydro-pyran-2-one
—— 6,7-dimethyl-2-thia-bicyclo[3.2.0]hept-3-ene-6,7-dicarboxylic acid anhydride 78306-48-6 C10H10O3S
6,7-dimethyl-2-thia-bicyclo[3.2.0]hept-3-ene-6,7-dicarboxylic acid anhydride
—— 5-tert-butyl-6-<(phenylseleno)methyl>tetrahydropyran-2-one 116733-41-6 C16H22O2Se
5-tert-butyl-6-<(phenylseleno)methyl>tetrahydropyran-2-one
—— 9,13-Dimethyl-11-oxa-3,7-diselenatetracyclo[6.5.0.02,6.09,13]trideca-2(6),4-diene-10,12-dione 89480-97-7 C12H10O3Se2
9,13-Dimethyl-11-oxa-3,7-diselenatetracyclo[6.5.0.02,6.09,13]trideca-2(6),4-diene-10,12-dione
—— 9,13-Dimethyl-11-oxa-5,7-diselenatetracyclo[6.5.0.02,6.09,13]trideca-2(6),3-diene-10,12-dione 89480-96-6 C12H10O3Se2
9,13-Dimethyl-11-oxa-5,7-diselenatetracyclo[6.5.0.02,6.09,13]trideca-2(6),3-diene-10,12-dione
—— 5-tert-butyl-3-(methoxycarbonyl)-5-phenyl-γ-butyrolactone 134391-17-6 C16H20O4
5-tert-butyl-3-(methoxycarbonyl)-5-phenyl-γ-butyrolactone
—— (1R,2S,6S,7S)-1,7-dimethyl-9-oxa-3-selenatricyclo[5.3.0.02,6]dec-4-ene-8,10-dione 75899-41-1 C10H10O3Se
(1R,2S,6S,7S)-1,7-dimethyl-9-oxa-3-selenatricyclo[5.3.0.02,6]dec-4-ene-8,10-dione
—— 3-Bromo-4-hydroxyoxolan-2-one 87683-15-6 C4H5BrO3
3-Bromo-4-hydroxyoxolan-2-one
—— 4-chloro-dihydro-furan-2-one 16507-30-5 C4H5ClO2
4-chloro-dihydro-furan-2-one
—— 4-iodomethyl-oxetan-2-one 36598-06-8 C4H5IO2
4-iodomethyl-oxetan-2-one
—— 5-5(2-methylprop-1-en-1-yl)dihydrofuran-2(3H)-one 121224-95-1 C8H12O2
5-5(2-methylprop-1-en-1-yl)dihydrofuran-2(3H)-one
—— 5-(1-butylvinyl)dihydro-2(3H)-furanone 121224-97-3 C10H16O2
5-(1-butylvinyl)dihydro-2(3H)-furanone
—— 5-[(1E)-1-hexenyl]dihydro-2(3H)-furanone 121224-92-8 C10H16O2
5-[(1E)-1-hexenyl]dihydro-2(3H)-furanone
—— 3-bromomethyl-oxetan-2-one 1333401-25-4 C4H5BrO2
3-bromomethyl-oxetan-2-one
—— (R)-4-dodecanolide 69830-91-7 C12H22O2
(R)-4-dodecanolide
—— 5-heptyl-5-methyl-dihydro-furan-2-one 72473-99-5 C12H22O2
5-heptyl-5-methyl-dihydro-furan-2-one
—— (Z)-4-(4-(triphenylsilyl)-2-oxodihydrofuran-3(2H)-ylidene)-2,2-dimethylbutanal 1256752-72-3 C28H28O3Si
(Z)-4-(4-(triphenylsilyl)-2-oxodihydrofuran-3(2H)-ylidene)-2,2-dimethylbutanal
—— 4-hydroxy-2-oxaspiro[4.4]nonan-3-one 98558-54-4 C8H12O3
4-hydroxy-2-oxaspiro[4.4]nonan-3-one
—— (R)-4,4-diethyl-3-hydroxydihydrofuran-2(3H)-one 108100-41-0 C8H14O3
(R)-4,4-diethyl-3-hydroxydihydrofuran-2(3H)-one
—— (2S,3S,4S)-2-allyl-3-hydroxy-4-methyl-4-butanolide 861902-86-5 C8H12O3
(2S,3S,4S)-2-allyl-3-hydroxy-4-methyl-4-butanolide
—— Isobutyric acid (3S,3aR,4R,6R,9bS)-6-hydroxy-3,6,9-trimethyl-2,8-dioxo-2,3,3a,4,5,6,7,8,9,9b-decahydro-azuleno[4,5-b]furan-4-yl ester 123159-80-8 C19H26O6
Isobutyric acid (3S,3aR,4R,6R,9bS)-6-hydroxy-3,6,9-trimethyl-2,8-dioxo-2,3,3a,4,5,6,7,8,9,9b-decahydro-azuleno[4,5-b]furan-4-yl ester
—— 3-isopropyl-6(Z)-(bromomethylidene)tetrahydro-2-pyranone 136358-13-9 C9H13BrO2
3-isopropyl-6(Z)-(bromomethylidene)tetrahydro-2-pyranone
—— 3-isopropyl-6(E)-(bromomethylidene)tetrahydro-2-pyranone 136358-14-0 C9H13BrO2
3-isopropyl-6(E)-(bromomethylidene)tetrahydro-2-pyranone
—— 3-isopropyl-6(E)-(1-bromoethylidene)tetrahydro-2-pyranone 136358-17-3 C10H15BrO2
3-isopropyl-6(E)-(1-bromoethylidene)tetrahydro-2-pyranone
—— (R)-3-isopropyl-6,6-dimethyltetrahydro-2H-pyran-2-one 1435447-26-9 C10H18O2
(R)-3-isopropyl-6,6-dimethyltetrahydro-2H-pyran-2-one