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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
—— (6R)-6-[(E)-hex-3-enyl]oxan-2-one —— C11H18O2
(6R)-6-[(E)-hex-3-enyl]oxan-2-one
—— (3R)-3-ethyloxolane-2,4-dione —— C6H8O3
(3R)-3-ethyloxolane-2,4-dione
—— [1-(4-Hexyl-2-methyl-5-oxooxolan-2-yl)ethylideneamino]urea —— C14H25N3O3
[1-(4-Hexyl-2-methyl-5-oxooxolan-2-yl)ethylideneamino]urea
—— propyl (2S)-2-methyl-5-oxooxolane-2-carboxylate —— C9H14O4
propyl (2S)-2-methyl-5-oxooxolane-2-carboxylate
—— (7S)-7-cyclohexyloxepan-2-one —— C12H20O2
(7S)-7-cyclohexyloxepan-2-one
—— (4S)-5,5-dimethyl-3-methylidene-4-phenyloxolan-2-one —— C13H14O2
(4S)-5,5-dimethyl-3-methylidene-4-phenyloxolan-2-one
—— ethyl (3R)-2-oxo-3-phenyloxolane-3-carboxylate —— C13H14O4
ethyl (3R)-2-oxo-3-phenyloxolane-3-carboxylate
—— (7aR)-4-phenyl-7a,8-dihydro-7H-thieno[2,3-f][2]benzofuran-5-one —— C16H12O2S
(7aR)-4-phenyl-7a,8-dihydro-7H-thieno[2,3-f][2]benzofuran-5-one
—— (5R)-3-methylidene-5-phenyl-5-thiophen-2-yloxolan-2-one —— C15H12O2S
(5R)-3-methylidene-5-phenyl-5-thiophen-2-yloxolan-2-one
—— ethyl (3S)-4-methylidene-5-oxooxolane-3-carboxylate —— C8H10O4
ethyl (3S)-4-methylidene-5-oxooxolane-3-carboxylate
—— (3S,5S)-3-benzyl-5-(prop-2-ynoxymethyl)oxolan-2-one —— C15H16O3
(3S,5S)-3-benzyl-5-(prop-2-ynoxymethyl)oxolan-2-one
—— (3S,5R)-3-benzyl-5-(prop-2-ynoxymethyl)oxolan-2-one —— C15H16O3
(3S,5R)-3-benzyl-5-(prop-2-ynoxymethyl)oxolan-2-one
—— 4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate —— C10H13O4-
4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
—— ethyl (3R)-4-methylidene-5-oxooxolane-3-carboxylate —— C8H10O4
ethyl (3R)-4-methylidene-5-oxooxolane-3-carboxylate
—— ethyl 2-[(3S,5R)-2-oxo-5-(prop-2-ynoxymethyl)oxolan-3-yl]acetate —— C12H16O5
ethyl 2-[(3S,5R)-2-oxo-5-(prop-2-ynoxymethyl)oxolan-3-yl]acetate
—— ethyl 2-[(3R,5S)-2-oxo-5-(prop-2-ynoxymethyl)oxolan-3-yl]acetate —— C12H16O5
ethyl 2-[(3R,5S)-2-oxo-5-(prop-2-ynoxymethyl)oxolan-3-yl]acetate
—— (3R,5R)-3-hydroxy-3,5-bis(hydroxymethyl)oxolan-2-one —— C6H10O5
(3R,5R)-3-hydroxy-3,5-bis(hydroxymethyl)oxolan-2-one
—— ethyl (3S)-2-oxo-3-phenyloxolane-3-carboxylate —— C13H14O4
ethyl (3S)-2-oxo-3-phenyloxolane-3-carboxylate
—— (4S,5R)-5-benzyl-4-phenyloxolane-2,3-dione —— C17H14O3
(4S,5R)-5-benzyl-4-phenyloxolane-2,3-dione
—— (7aS)-4-phenyl-7a,8-dihydro-7H-thieno[2,3-f][2]benzofuran-5-one —— C16H12O2S
(7aS)-4-phenyl-7a,8-dihydro-7H-thieno[2,3-f][2]benzofuran-5-one
—— (4R,5S)-5-benzyl-4-phenyloxolane-2,3-dione —— C17H14O3
(4R,5S)-5-benzyl-4-phenyloxolane-2,3-dione
—— diethyl-methyl-[[(3R,5R)-5-methyl-2-oxooxolan-3-yl]methyl]azanium —— C11H22NO2+
diethyl-methyl-[[(3R,5R)-5-methyl-2-oxooxolan-3-yl]methyl]azanium
—— (2R,4R)-5-oxo-4-phenyloxolane-2-carboxylic acid —— C11H10O4
(2R,4R)-5-oxo-4-phenyloxolane-2-carboxylic acid
—— (4R,5R)-5-benzyl-4-phenyloxolane-2,3-dione —— C17H14O3
(4R,5R)-5-benzyl-4-phenyloxolane-2,3-dione
—— (2R,4S)-5-oxo-4-phenyloxolane-2-carboxylic acid —— C11H10O4
(2R,4S)-5-oxo-4-phenyloxolane-2-carboxylic acid
—— (5S)-3-methylidene-5-phenyl-5-thiophen-2-yloxolan-2-one —— C15H12O2S
(5S)-3-methylidene-5-phenyl-5-thiophen-2-yloxolan-2-one
—— (2S,4R)-5-oxo-4-phenyloxolane-2-carboxylic acid —— C11H10O4
(2S,4R)-5-oxo-4-phenyloxolane-2-carboxylic acid
—— (2S,4S)-5-oxo-4-phenyloxolane-2-carboxylic acid —— C11H10O4
(2S,4S)-5-oxo-4-phenyloxolane-2-carboxylic acid
—— (3R)-3-methyl-2-oxooxolane-3-carboximidamide —— C6H10N2O2
(3R)-3-methyl-2-oxooxolane-3-carboximidamide
—— (5R)-3-methylidene-5-[3-[(2R)-4-methylidene-5-oxooxolan-2-yl]propyl]oxolan-2-one —— C13H16O4
(5R)-3-methylidene-5-[3-[(2R)-4-methylidene-5-oxooxolan-2-yl]propyl]oxolan-2-one
—— (3E)-3-[9-[(2S)-oxiran-2-yl]nonylidene]oxolan-2-one —— C15H24O3
(3E)-3-[9-[(2S)-oxiran-2-yl]nonylidene]oxolan-2-one
—— (5R)-3-methylidene-5-[6-[(2R)-4-methylidene-5-oxooxolan-2-yl]hexyl]oxolan-2-one —— C16H22O4
(5R)-3-methylidene-5-[6-[(2R)-4-methylidene-5-oxooxolan-2-yl]hexyl]oxolan-2-one
—— (5S)-3-methylidene-5-[3-[(2S)-4-methylidene-5-oxooxolan-2-yl]propyl]oxolan-2-one —— C13H16O4
(5S)-3-methylidene-5-[3-[(2S)-4-methylidene-5-oxooxolan-2-yl]propyl]oxolan-2-one
—— (3E)-3-[9-[(2R)-oxiran-2-yl]nonylidene]oxolan-2-one —— C15H24O3
(3E)-3-[9-[(2R)-oxiran-2-yl]nonylidene]oxolan-2-one
—— (5R)-3-methylidene-5-[4-[(2R)-4-methylidene-5-oxooxolan-2-yl]butyl]oxolan-2-one —— C14H18O4
(5R)-3-methylidene-5-[4-[(2R)-4-methylidene-5-oxooxolan-2-yl]butyl]oxolan-2-one
—— (5S)-3-methylidene-5-[6-[(2S)-4-methylidene-5-oxooxolan-2-yl]hexyl]oxolan-2-one —— C16H22O4
(5S)-3-methylidene-5-[6-[(2S)-4-methylidene-5-oxooxolan-2-yl]hexyl]oxolan-2-one
—— (3S,5S)-3-methyl-5-(2-oxopropyl)oxolan-2-one —— C8H12O3
(3S,5S)-3-methyl-5-(2-oxopropyl)oxolan-2-one
—— (1R,4aS,6aS,7S,9aR)-7,8-dimethyl-2-oxospiro[4,4a,6a,7-tetrahydropentaleno[1,6a-c]pyran-1,2'-oxirane]-5-carboxylic acid —— C15H16O5
(1R,4aS,6aS,7S,9aR)-7,8-dimethyl-2-oxospiro[4,4a,6a,7-tetrahydropentaleno[1,6a-c]pyran-1,2'-oxirane]-5-carboxylic acid
—— (3R,5R)-3-methyl-5-(2-oxopropyl)oxolan-2-one —— C8H12O3
(3R,5R)-3-methyl-5-(2-oxopropyl)oxolan-2-one
—— (3S,5R)-2-oxo-5-phenyloxolane-3-carboxylic acid —— C11H10O4
(3S,5R)-2-oxo-5-phenyloxolane-3-carboxylic acid
—— (3S,5S)-2-oxo-5-phenyloxolane-3-carboxylic acid —— C11H10O4
(3S,5S)-2-oxo-5-phenyloxolane-3-carboxylic acid
—— (3R,5R)-2-oxo-5-phenyloxolane-3-carboxylic acid —— C11H10O4
(3R,5R)-2-oxo-5-phenyloxolane-3-carboxylic acid
—— (3R,5S)-2-oxo-5-phenyloxolane-3-carboxylic acid —— C11H10O4
(3R,5S)-2-oxo-5-phenyloxolane-3-carboxylic acid
—— (3Z)-3-(thiophen-3-ylmethylidene)oxolan-2-one —— C9H8O2S
(3Z)-3-(thiophen-3-ylmethylidene)oxolan-2-one
—— (3R)-4-methylidene-5-oxooxolane-3-carboxylic acid —— C6H6O4
(3R)-4-methylidene-5-oxooxolane-3-carboxylic acid
—— (1R,5S)-6-oxabicyclo[3.2.2]nonan-7-one —— C8H12O2
(1R,5S)-6-oxabicyclo[3.2.2]nonan-7-one
—— (1S,6S)-7-oxabicyclo[4.2.2]decan-8-one —— C9H14O2
(1S,6S)-7-oxabicyclo[4.2.2]decan-8-one
—— (1S,6R)-7-oxabicyclo[4.2.2]decan-8-one —— C9H14O2
(1S,6R)-7-oxabicyclo[4.2.2]decan-8-one
—— Lacton der cis-4-Hydroxy-cyclooctan-carbonsaeure —— C9H14O2
Lacton der cis-4-Hydroxy-cyclooctan-carbonsaeure
—— methyl (1R,6S,9R)-8-oxo-7-oxabicyclo[4.2.1]nonane-9-carboxylate —— C10H14O4
methyl (1R,6S,9R)-8-oxo-7-oxabicyclo[4.2.1]nonane-9-carboxylate