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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
—— D-Idonic acid-1,4-lactone —— C6H10O6
D-Idonic acid-1,4-lactone
—— [(1S,3R,7S,8S,8aR)-8-[3-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]propyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate —— C25H38O5
[(1S,3R,7S,8S,8aR)-8-[3-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]propyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate
—— 5-Oxo-2-(trichloromethyl)tetrahydrofuran-3-carboxylate —— C6H4Cl3O4-
5-Oxo-2-(trichloromethyl)tetrahydrofuran-3-carboxylate
—— 2-(4-Butyl-2-methyl-5-oxooxolan-2-yl)prop-1-enylthiourea —— C13H22N2O2S
2-(4-Butyl-2-methyl-5-oxooxolan-2-yl)prop-1-enylthiourea
—— 3-Acetyl-5-ethoxy-3,4-dimethyloxolan-2-one —— C10H16O4
3-Acetyl-5-ethoxy-3,4-dimethyloxolan-2-one
—— [4-(2-Oxo-5-pentyloxolan-3-yl)butan-2-ylideneamino]urea —— C14H25N3O3
[4-(2-Oxo-5-pentyloxolan-3-yl)butan-2-ylideneamino]urea
—— N-[1-(2-hydroxyphenyl)ethylideneamino]-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C18H22N2O4
N-[1-(2-hydroxyphenyl)ethylideneamino]-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— 5,9,9,12-Tetramethyl-2-oxatricyclo[6.3.1.04,12]dodeca-5,7-dien-3-one —— C15H20O2
5,9,9,12-Tetramethyl-2-oxatricyclo[6.3.1.04,12]dodeca-5,7-dien-3-one
—— N-[(4-hydroxyphenyl)methylideneamino]-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C17H20N2O4
N-[(4-hydroxyphenyl)methylideneamino]-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— [1-(5-Oxo-4-pentyloxolan-2-yl)ethylideneamino]urea —— C12H21N3O3
[1-(5-Oxo-4-pentyloxolan-2-yl)ethylideneamino]urea
—— N',N',4,7,7-pentamethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbohydrazide 536718-24-8 C12H20N2O3
N',N',4,7,7-pentamethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbohydrazide
—— 5-[4-(Diethylamino)but-2-ynoxymethyl]oxolan-2-one —— C13H21NO3
5-[4-(Diethylamino)but-2-ynoxymethyl]oxolan-2-one
—— 2,4-Ditert-butyl-4-hydroxy-5-oxooxolane-2-carboxylic acid —— C13H22O5
2,4-Ditert-butyl-4-hydroxy-5-oxooxolane-2-carboxylic acid
—— 2-Oxabicyclo[2.2.1]heptane-1-carboxylic acid, 4,7,7-trimethyl-3-oxo-, 2-(nitromethylene)-3-piperidinyl ester —— C16H22N2O6
2-Oxabicyclo[2.2.1]heptane-1-carboxylic acid, 4,7,7-trimethyl-3-oxo-, 2-(nitromethylene)-3-piperidinyl ester
—— (4-Heptyl-5-oxotetrahydrofuran-2-yl)methyl carbamimidothioate (non-preferred name) —— C13H24N2O2S
(4-Heptyl-5-oxotetrahydrofuran-2-yl)methyl carbamimidothioate (non-preferred name)
—— 5-pentyl-3-[(5-sulfanyl-4H-1,2,4-triazol-3-yl)methyl]dihydrofuran-2(3H)-one —— C12H19N3O2S
5-pentyl-3-[(5-sulfanyl-4H-1,2,4-triazol-3-yl)methyl]dihydrofuran-2(3H)-one
—— 3-(Bromomethyl)-3-methyloxolan-2-one —— C6H9BrO2
3-(Bromomethyl)-3-methyloxolan-2-one
—— 12'-(2-Ethoxyethenyl)-12'-hydroxy-3'-methyl-13'-propylspiro[1,3-dioxolane-2,6'-15-oxatetracyclo[11.2.1.02,11.03,8]hexadec-8-ene]-14'-one —— C25H36O6
12'-(2-Ethoxyethenyl)-12'-hydroxy-3'-methyl-13'-propylspiro[1,3-dioxolane-2,6'-15-oxatetracyclo[11.2.1.02,11.03,8]hexadec-8-ene]-14'-one
—— 4,7,7-Trimethyl-1-[2-[[5-(trifluoromethyl)pyridin-2-yl]oxymethyl]morpholine-4-carbonyl]-2-oxabicyclo[2.2.1]heptan-3-one —— C21H25F3N2O5
4,7,7-Trimethyl-1-[2-[[5-(trifluoromethyl)pyridin-2-yl]oxymethyl]morpholine-4-carbonyl]-2-oxabicyclo[2.2.1]heptan-3-one
—— (3S,3aR,4R,8aS,8bR)-4-hydroxy-3,5,8-trimethyl-3a,4,8a,8b-tetrahydro-3H-cyclopenta[g][1]benzofuran-2,6-dione —— C14H16O4
(3S,3aR,4R,8aS,8bR)-4-hydroxy-3,5,8-trimethyl-3a,4,8a,8b-tetrahydro-3H-cyclopenta[g][1]benzofuran-2,6-dione
—— (3S,4R,5R)-3,4,5,6-tetrahydroxyoxan-2-one —— C5H8O6
(3S,4R,5R)-3,4,5,6-tetrahydroxyoxan-2-one
—— N-[[17-(cyclohexanecarbonyl)-5,13-dihydroxy-6,10-dimethyl-5-pentacyclo[13.2.2.01,9.02,6.010,15]nonadeca-16,18-dienyl]methyl]-4,7,7-trimethyl-3-oxo-N-propyl-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C42H61NO6
N-[[17-(cyclohexanecarbonyl)-5,13-dihydroxy-6,10-dimethyl-5-pentacyclo[13.2.2.01,9.02,6.010,15]nonadeca-16,18-dienyl]methyl]-4,7,7-trimethyl-3-oxo-N-propyl-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— 6-[(1Z,3z,6z,9z)-1,3,6,9-pentadecatetraen-1-yl]tetrahydro-2H-pyran-2-one —— C20H30O2
6-[(1Z,3z,6z,9z)-1,3,6,9-pentadecatetraen-1-yl]tetrahydro-2H-pyran-2-one
—— 5-[(1E,3E)-5-oxohexa-1,3-dienyl]oxolan-2-one —— C10H12O3
5-[(1E,3E)-5-oxohexa-1,3-dienyl]oxolan-2-one
—— 5-[(E)-2-methoxyhex-1-enyl]-3-oxabicyclo[3.1.0]hexan-2-one —— C12H18O3
5-[(E)-2-methoxyhex-1-enyl]-3-oxabicyclo[3.1.0]hexan-2-one
—— 5-tetradec-1-enyloxolan-2-one —— C18H32O2
5-tetradec-1-enyloxolan-2-one
—— 4-nonadec-1-enylidene-3-octadec-1-enyloxetan-2-one —— C40H72O2
4-nonadec-1-enylidene-3-octadec-1-enyloxetan-2-one
—— 4-[(Z)-nonadec-10-enylidene]-3-[(Z)-octadec-9-enyl]oxetan-2-one —— C40H72O2
4-[(Z)-nonadec-10-enylidene]-3-[(Z)-octadec-9-enyl]oxetan-2-one
—— 3-Hex-1-enyloxolan-2-one —— C10H16O2
3-Hex-1-enyloxolan-2-one
—— (5S)-5-tetradec-1-enyloxolan-2-one —— C18H32O2
(5S)-5-tetradec-1-enyloxolan-2-one
—— (4E)-4-(2H-1,3-oxazol-5-ylidene)oxolane-2,3-dione —— C7H5NO4
(4E)-4-(2H-1,3-oxazol-5-ylidene)oxolane-2,3-dione
—— (6E)-6-(iodomethylidene)-3-phenyloxan-2-one —— C12H11IO2
(6E)-6-(iodomethylidene)-3-phenyloxan-2-one
—— 6-Ethyl-7-methyl-3-phenyl-3a,6,7,7a-tetrahydropyrano[3,4-d][1,2]oxazol-4-one —— C15H17NO3
6-Ethyl-7-methyl-3-phenyl-3a,6,7,7a-tetrahydropyrano[3,4-d][1,2]oxazol-4-one
—— 2-methoxymethyl-2,4-dimethyl-pentanedioic acid anhydride —— C9H14O4
2-methoxymethyl-2,4-dimethyl-pentanedioic acid anhydride
—— methyl 3-methylidene-2-oxo-1-oxaspiro[4.5]decane-4-carboxylate —— C12H16O4
methyl 3-methylidene-2-oxo-1-oxaspiro[4.5]decane-4-carboxylate
—— methyl 3,4-dioxo-3a,5,6,6a-tetrahydro-1H-cyclopenta[c]furan-6-carboxylate —— C9H10O5
methyl 3,4-dioxo-3a,5,6,6a-tetrahydro-1H-cyclopenta[c]furan-6-carboxylate
—— (2R,3R,4R)-2,4-Dimethyl-5-oxo-tetrahydro-furan-3-carboxylic acid methyl ester —— C8H12O4
(2R,3R,4R)-2,4-Dimethyl-5-oxo-tetrahydro-furan-3-carboxylic acid methyl ester
—— N-hydroxy-N'-methyl-7-oxo-6-oxabicyclo[3.2.2]non-8-ene-2-carboximidamide —— C10H14N2O3
N-hydroxy-N'-methyl-7-oxo-6-oxabicyclo[3.2.2]non-8-ene-2-carboximidamide
—— [(5Z)-6-methyl-11-(6-methylhept-5-en-2-yl)-10-oxo-9-oxabicyclo[6.2.1]undeca-1,5-dien-2-yl]methyl acetate —— C22H32O4
[(5Z)-6-methyl-11-(6-methylhept-5-en-2-yl)-10-oxo-9-oxabicyclo[6.2.1]undeca-1,5-dien-2-yl]methyl acetate
—— sodium;(3Z)-3-(hydroxymethylidene)oxolan-2-one —— C5H6NaO3+
sodium;(3Z)-3-(hydroxymethylidene)oxolan-2-one
—— 5-bromo-3,3-dimethyl-5-ethyl-6-(4-chlorophenyl)-2,3,5,6-tetrahydro-2,4-pyrandione —— C15H16BrClO3
5-bromo-3,3-dimethyl-5-ethyl-6-(4-chlorophenyl)-2,3,5,6-tetrahydro-2,4-pyrandione
—— (2-Oxooxolan-3-yl) 2,5-dioxopyrrolidine-1-carbodithioate —— C9H9NO4S2
(2-Oxooxolan-3-yl) 2,5-dioxopyrrolidine-1-carbodithioate
—— (+)-Sodium L-ascorbate crystalline —— C6H7NaO6
(+)-Sodium L-ascorbate crystalline
—— spiro[3-oxabicyclo[3.1.1]heptane-6,1'-cycloheptane]-2,4-dione 23174-68-7 C12H16O3
spiro[3-oxabicyclo[3.1.1]heptane-6,1'-cycloheptane]-2,4-dione
—— 1-(4,4-dimethyl-2-oxooxolan-3-yl)oxy-1-hydroxyprop-1-ene-2-diazonium —— C9H13N2O4+
1-(4,4-dimethyl-2-oxooxolan-3-yl)oxy-1-hydroxyprop-1-ene-2-diazonium
—— 2-diazonio-1-(4,4-dimethyl-2-oxooxolan-3-yl)oxyprop-1-en-1-olate —— C9H12N2O4
2-diazonio-1-(4,4-dimethyl-2-oxooxolan-3-yl)oxyprop-1-en-1-olate
—— N,N-diisobutyl-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C18H31NO3
N,N-diisobutyl-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— formaldehyde;5-(hydroxymethyl)-4,4-dimethyloxolan-2-one —— C8H14O4
formaldehyde;5-(hydroxymethyl)-4,4-dimethyloxolan-2-one
—— methyl N-[5-[5-(2,5-dimethyloctyl)-4-hydroxy-6-oxooxan-2-yl]hexyl]carbamate —— C23H43NO5
methyl N-[5-[5-(2,5-dimethyloctyl)-4-hydroxy-6-oxooxan-2-yl]hexyl]carbamate
—— tert-butyl N-[3-(2-oxooxetan-3-yl)prop-2-enyl]carbamate —— C11H17NO4
tert-butyl N-[3-(2-oxooxetan-3-yl)prop-2-enyl]carbamate