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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-(4-chlorophenyl)-5,5-dimethyl-4,6-dioxotetrahydro-2H-pyran-3-yl]acetate —— C16H17ClO5
methyl [2-(4-chlorophenyl)-5,5-dimethyl-4,6-dioxotetrahydro-2H-pyran-3-yl]acetate
—— methyl (5,5-dimethyl-4,6-dioxo-2-phenyltetrahydro-2H-pyran-3-yl)acetate —— C16H18O5
methyl (5,5-dimethyl-4,6-dioxo-2-phenyltetrahydro-2H-pyran-3-yl)acetate
—— 2-Oxo-1-oxaspiro[4.4]nonane-4-carboxamide —— C9H13NO3
2-Oxo-1-oxaspiro[4.4]nonane-4-carboxamide
—— 6-[(Z)-1-Bromo-2-phenylethenyl]-3,3,5,5-tetramethyldihydro-2H-pyran-2,4(3H)-dione —— C17H19BrO3
6-[(Z)-1-Bromo-2-phenylethenyl]-3,3,5,5-tetramethyldihydro-2H-pyran-2,4(3H)-dione
—— 4,4-dimethyl-3-[(1E)-prop-1-en-1-yl]-2-oxaspiro[5.5]undecane-1,5-dione —— C15H22O3
4,4-dimethyl-3-[(1E)-prop-1-en-1-yl]-2-oxaspiro[5.5]undecane-1,5-dione
—— ethyl (3R,5S)-5-(4-ethylphenyl)-2-oxooxolane-3-carboxylate —— C15H18O4
ethyl (3R,5S)-5-(4-ethylphenyl)-2-oxooxolane-3-carboxylate
—— ethyl (3R,5R)-5-(4-ethylphenyl)-2-oxooxolane-3-carboxylate —— C15H18O4
ethyl (3R,5R)-5-(4-ethylphenyl)-2-oxooxolane-3-carboxylate
—— ethyl (3S,5S)-5-(4-ethylphenyl)-2-oxooxolane-3-carboxylate —— C15H18O4
ethyl (3S,5S)-5-(4-ethylphenyl)-2-oxooxolane-3-carboxylate
—— ethyl (3S,5R)-2-oxo-5-thiophen-2-yloxolane-3-carboxylate —— C11H12O4S
ethyl (3S,5R)-2-oxo-5-thiophen-2-yloxolane-3-carboxylate
—— ethyl (3R,5R)-2-oxo-5-thiophen-2-yloxolane-3-carboxylate —— C11H12O4S
ethyl (3R,5R)-2-oxo-5-thiophen-2-yloxolane-3-carboxylate
—— (3S,5S)-3-acetyl-5-(4-ethylphenyl)oxolan-2-one —— C14H16O3
(3S,5S)-3-acetyl-5-(4-ethylphenyl)oxolan-2-one
—— (3R,5R)-3-acetyl-5-(4-ethylphenyl)oxolan-2-one —— C14H16O3
(3R,5R)-3-acetyl-5-(4-ethylphenyl)oxolan-2-one
—— (3R,5S)-3-acetyl-5-(4-ethylphenyl)oxolan-2-one —— C14H16O3
(3R,5S)-3-acetyl-5-(4-ethylphenyl)oxolan-2-one
—— (3S,5S)-5-(4-ethylphenyl)-2-oxooxolane-3-carbonitrile —— C13H13NO2
(3S,5S)-5-(4-ethylphenyl)-2-oxooxolane-3-carbonitrile
—— (3R,5S)-5-(4-ethylphenyl)-2-oxooxolane-3-carbonitrile —— C13H13NO2
(3R,5S)-5-(4-ethylphenyl)-2-oxooxolane-3-carbonitrile
—— (3R,5S)-3-acetyl-5-thiophen-2-yloxolan-2-one —— C10H10O3S
(3R,5S)-3-acetyl-5-thiophen-2-yloxolan-2-one
—— (3S,5S)-3-acetyl-5-thiophen-2-yloxolan-2-one —— C10H10O3S
(3S,5S)-3-acetyl-5-thiophen-2-yloxolan-2-one
—— (3R,5R)-3-acetyl-5-thiophen-2-yloxolan-2-one —— C10H10O3S
(3R,5R)-3-acetyl-5-thiophen-2-yloxolan-2-one
—— (3E)-3-(aminomethylidene)oxane-2,4-dione —— C6H7NO3
(3E)-3-(aminomethylidene)oxane-2,4-dione
—— Enicoflavine —— C10H13NO4
Enicoflavine
—— Vernolide 27428-86-0 C19H22O7
Vernolide
—— Alectrol —— C19H22O6
Alectrol
—— (3S,5S)-3-acetyl-5-(furan-2-yl)oxolan-2-one —— C10H10O4
(3S,5S)-3-acetyl-5-(furan-2-yl)oxolan-2-one
—— (3R,5R)-2-oxo-5-thiophen-2-yloxolane-3-carbonitrile —— C9H7NO2S
(3R,5R)-2-oxo-5-thiophen-2-yloxolane-3-carbonitrile
—— (3S,5S)-2-oxo-5-thiophen-2-yloxolane-3-carbonitrile —— C9H7NO2S
(3S,5S)-2-oxo-5-thiophen-2-yloxolane-3-carbonitrile
—— 5,8,8-Trimethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide —— C11H15NO4
5,8,8-Trimethyl-2,4-dioxo-3-oxabicyclo[3.2.1]octane-1-carboxamide
—— (10-Oxo-9-oxatricyclo[6.3.1.01,5]dodec-4-en-11-yl) 2-bromoacetate —— C13H15BrO4
(10-Oxo-9-oxatricyclo[6.3.1.01,5]dodec-4-en-11-yl) 2-bromoacetate
—— 7a-Methylspiro[2,3,3a,4,6,7-hexahydroindene-5,4'-oxolane]-1,2'-dione —— C13H18O3
7a-Methylspiro[2,3,3a,4,6,7-hexahydroindene-5,4'-oxolane]-1,2'-dione
—— 9-Tert-butyl-1-oxaspiro[5.5]undecan-2-one —— C14H24O2
9-Tert-butyl-1-oxaspiro[5.5]undecan-2-one
—— 14,14-Dimethyl-12-oxatricyclo[9.2.1.03,8]tetradeca-3,5,7-trien-13-one —— C15H18O2
14,14-Dimethyl-12-oxatricyclo[9.2.1.03,8]tetradeca-3,5,7-trien-13-one
—— 2-Iodo-5-oxo-4-oxatricyclo[4.3.1.03,7]decane-10-carboxylic acid —— C10H11IO4
2-Iodo-5-oxo-4-oxatricyclo[4.3.1.03,7]decane-10-carboxylic acid
—— 8-[(6,6-Dimethyl-4-oxo-3-oxabicyclo[3.1.0]hexan-2-yl)oxy]-2,2,6-trimethyl-3-oxabicyclo[4.2.0]octan-4-one —— C17H24O5
8-[(6,6-Dimethyl-4-oxo-3-oxabicyclo[3.1.0]hexan-2-yl)oxy]-2,2,6-trimethyl-3-oxabicyclo[4.2.0]octan-4-one
—— (2,3-Dimethyl-2,3-dinitrobutyl) 4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate —— C16H24N2O8
(2,3-Dimethyl-2,3-dinitrobutyl) 4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
—— 4-hydroxy-8,8-dimethyl-3a,4,5,6,7,8b-hexahydro-3H-indeno[1,2-b]furan-2-one —— C13H18O3
4-hydroxy-8,8-dimethyl-3a,4,5,6,7,8b-hexahydro-3H-indeno[1,2-b]furan-2-one
—— 11-Methyl-2-oxaspiro[5.5]undec-10-ene-1,9-dione —— C11H14O3
11-Methyl-2-oxaspiro[5.5]undec-10-ene-1,9-dione
—— 5-hydroxy-8,8-dimethyl-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylidene]-3a,5,6,7,8a,8b-hexahydroindeno[1,2-b]furan-2-one —— C19H22O6
5-hydroxy-8,8-dimethyl-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylidene]-3a,5,6,7,8a,8b-hexahydroindeno[1,2-b]furan-2-one
—— 3-Methyl-8-oxaspiro[5.6]dodec-3-ene-5,7-dione —— C12H16O3
3-Methyl-8-oxaspiro[5.6]dodec-3-ene-5,7-dione
—— 4-bromo-1,8-dimethyl-7-oxo-N-(1-phenylethyl)-6-oxabicyclo[3.2.1]octane-2-carboxamide —— C18H22BrNO3
4-bromo-1,8-dimethyl-7-oxo-N-(1-phenylethyl)-6-oxabicyclo[3.2.1]octane-2-carboxamide
—— S-(4,4-dimethoxythian-2-yl) 4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbothioate —— C17H26O5S2
S-(4,4-dimethoxythian-2-yl) 4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbothioate
—— (6,7-Dimethyl-5-oxo-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-yl) 2-methylprop-2-enoate —— C15H18O4
(6,7-Dimethyl-5-oxo-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-yl) 2-methylprop-2-enoate
—— (1-Chloro-10-methyl-5-oxo-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-yl) but-2-enoate —— C14H15ClO4
(1-Chloro-10-methyl-5-oxo-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-yl) but-2-enoate
—— (7-Chloro-6-methyl-5-oxo-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-yl) 2-methylprop-2-enoate —— C14H15ClO4
(7-Chloro-6-methyl-5-oxo-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-yl) 2-methylprop-2-enoate
—— (10-Methyl-5-oxo-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-yl) but-2-enoate —— C14H16O4
(10-Methyl-5-oxo-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-yl) but-2-enoate
—— (7-Bromo-10-methyl-5-oxo-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-yl) but-2-enoate —— C14H15BrO4
(7-Bromo-10-methyl-5-oxo-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-yl) but-2-enoate
—— 5-Ethyl-6-hydroxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one —— C9H14O3
5-Ethyl-6-hydroxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
—— 12-Phenyl-3-oxapentacyclo[11.2.1.02,6.07,15.09,14]hexadecan-4-one —— C21H24O2
12-Phenyl-3-oxapentacyclo[11.2.1.02,6.07,15.09,14]hexadecan-4-one
—— 3,5,9,11-Tetramethyl-1,7-dioxaspiro[5.5]undecane-2,8-dione —— C13H20O4
3,5,9,11-Tetramethyl-1,7-dioxaspiro[5.5]undecane-2,8-dione
—— 4-hydroxy-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one —— C12H16O3
4-hydroxy-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
—— 4-Hydroxy-3,3a,4,5,7,8,8a,8b-octahydrocyclopenta[g][1]benzofuran-2-one —— C11H14O3
4-Hydroxy-3,3a,4,5,7,8,8a,8b-octahydrocyclopenta[g][1]benzofuran-2-one
—— 4-(Iodomethyl)-3-propan-2-yloxan-2-one —— C9H15IO2
4-(Iodomethyl)-3-propan-2-yloxan-2-one