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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
—— (5aR,9S,9aS)-6-propan-2-ylspiro[3,5a,6,7,8,9a-hexahydro-2-benzoxepine-9,2'-oxirane]-1-one —— C14H20O3
(5aR,9S,9aS)-6-propan-2-ylspiro[3,5a,6,7,8,9a-hexahydro-2-benzoxepine-9,2'-oxirane]-1-one
—— (5R)-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,3,4-trione;zinc —— C6H6O6Zn
(5R)-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,3,4-trione;zinc
—— 2-Methyl-3-(4-methyl-2-oxooxan-4-yl)propanal —— C10H16O3
2-Methyl-3-(4-methyl-2-oxooxan-4-yl)propanal
—— (4R)-4-methyl-3-propan-2-yloxetan-2-one —— C7H12O2
(4R)-4-methyl-3-propan-2-yloxetan-2-one
—— 3,4,4,5,5-Pentamethyl-2-oxooxolane-3-sulfonic acid —— C9H16O5S
3,4,4,5,5-Pentamethyl-2-oxooxolane-3-sulfonic acid
—— [(2R)-2-[(2R,3R)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyethoxy]-trihydroxyphosphanium —— C6H12O9P+
[(2R)-2-[(2R,3R)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyethoxy]-trihydroxyphosphanium
—— (2-Oxooxolan-3-yl) 2-(1-hydroxy-2,2-dimethylbutoxy)-2-methylpropanoate —— C14H24O6
(2-Oxooxolan-3-yl) 2-(1-hydroxy-2,2-dimethylbutoxy)-2-methylpropanoate
—— Bicyclo[3.1.0]hexa-1(6),2,4-triene;3-ethynyl-1-oxa-2-azaspiro[4.5]dec-2-en-8-imine;3-hydroxyoxolan-2-one —— C20H22N2O4
Bicyclo[3.1.0]hexa-1(6),2,4-triene;3-ethynyl-1-oxa-2-azaspiro[4.5]dec-2-en-8-imine;3-hydroxyoxolan-2-one
—— 2-Methylidenepent-4-enoic acid;oxepan-2-one;prop-2-enoic acid —— C15H22O6
2-Methylidenepent-4-enoic acid;oxepan-2-one;prop-2-enoic acid
—— (5R)-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,3,4-trione;hydrate —— C6H8O7
(5R)-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,3,4-trione;hydrate
—— (1S)-1-(hydroxymethyl)-3-oxabicyclo[3.1.0]hexan-2-one —— C6H8O3
(1S)-1-(hydroxymethyl)-3-oxabicyclo[3.1.0]hexan-2-one
—— 2-Ethyl-2-(hydroxymethyl)propane-1,3-diol;oxepan-2-one —— C18H38O8
2-Ethyl-2-(hydroxymethyl)propane-1,3-diol;oxepan-2-one
—— 2-[2,2-Bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol;oxepan-2-one —— C18H36O7
2-[2,2-Bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol;oxepan-2-one
—— 2,2-Bis(hydroxymethyl)propane-1,3-diol;oxepan-2-one —— C11H22O6
2,2-Bis(hydroxymethyl)propane-1,3-diol;oxepan-2-one
—— 10-Ethyloxecan-2-one —— C11H20O2
10-Ethyloxecan-2-one
—— 11-Butyl-oxacycloundecan-2-one —— C14H26O2
11-Butyl-oxacycloundecan-2-one
—— 11-Pentyl-oxacycloundecan-2-one —— C15H28O2
11-Pentyl-oxacycloundecan-2-one
—— 4-Dodecyloxetan-2-one —— C15H28O2
4-Dodecyloxetan-2-one
—— 10-Heptyloxecan-2-one —— C16H30O2
10-Heptyloxecan-2-one
—— 9-Hexyloxonan-2-one —— C14H26O2
9-Hexyloxonan-2-one
—— 9-Heptyloxonan-2-one —— C15H28O2
9-Heptyloxonan-2-one
—— 7-Palmitolactone —— C16H30O2
7-Palmitolactone
—— 8-Octyloxocan-2-one —— C15H28O2
8-Octyloxocan-2-one
—— 8-Heptyloxocan-2-one —— C14H26O2
8-Heptyloxocan-2-one
—— (1R,4S)-N,N-bis(2-cyanoethyl)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C16H21N3O3
(1R,4S)-N,N-bis(2-cyanoethyl)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1S,4R)-N,N-bis(2-cyanoethyl)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C16H21N3O3
(1S,4R)-N,N-bis(2-cyanoethyl)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— 6-[(2R)-4-hydroxy-3,3-dimethyl-5-oxooxolan-2-yl]oxan-2-one —— C11H16O5
6-[(2R)-4-hydroxy-3,3-dimethyl-5-oxooxolan-2-yl]oxan-2-one
—— (3Z)-3-(3,3,3-trifluoro-1-hydroxypropylidene)oxolane-2,4-dione —— C7H5F3O4
(3Z)-3-(3,3,3-trifluoro-1-hydroxypropylidene)oxolane-2,4-dione
—— (1S,5S,10R,13R,14S,17S)-5,9,9,13,14,17,20,20-octamethyl-23-oxapentacyclo[15.5.2.01,14.04,13.05,10]tetracos-3-ene-2,8,24-trione —— C31H46O4
(1S,5S,10R,13R,14S,17S)-5,9,9,13,14,17,20,20-octamethyl-23-oxapentacyclo[15.5.2.01,14.04,13.05,10]tetracos-3-ene-2,8,24-trione
—— (1S,5S,13R,16R,17S,20S)-5,12,12,16,17,23,23-heptamethyl-10,26-dioxa-9-azaheptacyclo[18.5.2.01,17.04,16.05,13.07,11.020,25]heptacosa-3,7(11),8-triene-2,27-dione —— C31H41NO4
(1S,5S,13R,16R,17S,20S)-5,12,12,16,17,23,23-heptamethyl-10,26-dioxa-9-azaheptacyclo[18.5.2.01,17.04,16.05,13.07,11.020,25]heptacosa-3,7(11),8-triene-2,27-dione
—— (E)-3-[(3aR,5R,6aS)-2-oxo-5-phosphanyloxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-yl]prop-2-enal —— C10H13O4P
(E)-3-[(3aR,5R,6aS)-2-oxo-5-phosphanyloxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-yl]prop-2-enal
—— (3aR,5R,6aS)-4-(3,8-dihydroxyoctyl)-5-phosphanyloxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one —— C15H27O5P
(3aR,5R,6aS)-4-(3,8-dihydroxyoctyl)-5-phosphanyloxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
—— 4,4a,5,7,8,9,10,11,12,12a-decahydro-3H-cyclodeca[c]pyran-1,6-dione;methyl 2,2,3,3,4-pentamethylpentanoate —— C24H42O5
4,4a,5,7,8,9,10,11,12,12a-decahydro-3H-cyclodeca[c]pyran-1,6-dione;methyl 2,2,3,3,4-pentamethylpentanoate
—— (3R,4R)-4-phenyl-3-(3,3,3-trifluoropropyl)oxolan-2-one —— C13H13F3O2
(3R,4R)-4-phenyl-3-(3,3,3-trifluoropropyl)oxolan-2-one
—— (3E)-3-(2,3,3-trifluoro-1-hydroxypropylidene)oxolane-2,4-dione —— C7H5F3O4
(3E)-3-(2,3,3-trifluoro-1-hydroxypropylidene)oxolane-2,4-dione
—— 2-(4-Ethyl-6-oxooxan-3-yl)acetaldehyde —— C9H14O3
2-(4-Ethyl-6-oxooxan-3-yl)acetaldehyde
—— 2-(4-Ethyl-2-oxooxan-4-yl)acetaldehyde —— C9H14O3
2-(4-Ethyl-2-oxooxan-4-yl)acetaldehyde
—— (3aR,4R,5R,6aS)-4-[(E,3R)-3-amino-3-hydroxyprop-1-enyl]-5-phosphanyloxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one —— C10H16NO4P
(3aR,4R,5R,6aS)-4-[(E,3R)-3-amino-3-hydroxyprop-1-enyl]-5-phosphanyloxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
—— (3aR,4R,5R,6aS)-4-[(E)-4-hexa-1,3,5-triynoxy-3-oxobut-1-enyl]-5-(phosphanylidyne-lambda5-phosphanylidene)boranyloxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one —— C17H13BO5P2
(3aR,4R,5R,6aS)-4-[(E)-4-hexa-1,3,5-triynoxy-3-oxobut-1-enyl]-5-(phosphanylidyne-lambda5-phosphanylidene)boranyloxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
—— (3aR,4R,5R,6aS)-4-[(3R)-3-amino-3-hydroxypropyl]-5-phosphanyloxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one —— C10H18NO4P
(3aR,4R,5R,6aS)-4-[(3R)-3-amino-3-hydroxypropyl]-5-phosphanyloxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
—— (5S)-5-[[(2S,6R)-4-hydroxy-9-thia-3-azatricyclo[6.3.0.02,6]undec-1(8)-en-5-yl]methoxy]-3-methyloxolan-2-one —— C15H21NO4S
(5S)-5-[[(2S,6R)-4-hydroxy-9-thia-3-azatricyclo[6.3.0.02,6]undec-1(8)-en-5-yl]methoxy]-3-methyloxolan-2-one
—— 5-[[4-hydroxy-3-[(1R)-1-hydroxyethyl]-9-thia-3-azatricyclo[6.3.0.02,6]undec-1(8)-en-5-yl]methoxy]-3-methyloxolan-2-one —— C17H25NO5S
5-[[4-hydroxy-3-[(1R)-1-hydroxyethyl]-9-thia-3-azatricyclo[6.3.0.02,6]undec-1(8)-en-5-yl]methoxy]-3-methyloxolan-2-one
—— 5-(Ethoxymethyl)oxepan-2-one —— C9H16O3
5-(Ethoxymethyl)oxepan-2-one
—— (3S,4S)-4-hydroxy-5-(hydroxymethyl)-3-methyl-2-oxooxolane-3-carbonitrile —— C7H9NO4
(3S,4S)-4-hydroxy-5-(hydroxymethyl)-3-methyl-2-oxooxolane-3-carbonitrile
—— (3R,4S)-4-hydroxy-5-(hydroxymethyl)-3-methyl-2-oxooxolane-3-carbonitrile —— C7H9NO4
(3R,4S)-4-hydroxy-5-(hydroxymethyl)-3-methyl-2-oxooxolane-3-carbonitrile
—— (3S,4R)-3-chloro-4-hydroxy-3-methyloxolan-2-one —— C5H7ClO3
(3S,4R)-3-chloro-4-hydroxy-3-methyloxolan-2-one
—— (3S,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methyl-2-oxooxolane-3-carbonitrile —— C7H9NO4
(3S,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methyl-2-oxooxolane-3-carbonitrile
—— (5R)-4-hydroxy-5-(hydroxymethyl)-3-methyl-2-oxooxolane-3-carbonitrile —— C7H9NO4
(5R)-4-hydroxy-5-(hydroxymethyl)-3-methyl-2-oxooxolane-3-carbonitrile
—— N-benzyl-2-[(3S,5S)-2-oxo-5-pentyloxolan-3-yl]acetamide —— C18H25NO3
N-benzyl-2-[(3S,5S)-2-oxo-5-pentyloxolan-3-yl]acetamide
—— N-benzyl-2-[(3S,5R)-2-oxo-5-pentyloxolan-3-yl]acetamide —— C18H25NO3
N-benzyl-2-[(3S,5R)-2-oxo-5-pentyloxolan-3-yl]acetamide