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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
—— Acetic acid (3aR,4R,5R,6aS)-4-((E)-(R)-4-methyl-3-oxo-oct-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 39850-02-7 C18H26O5
—— (3aS,5R,6aR)-5-hydroxyhexahydro-1H-cyclopenta[c]furan-1-one 122921-28-2 C7H10O3
—— (+/-)-9-Isobutyl-7-oxatricyclo<4.3.0.0<sup>2,9</sup>>nonan-8-on 58400-69-4 C12H18O2
—— L-oleandrono-1,4-lactone 94729-12-1 C7H12O4
—— 9-Acetyl-oxonane-2,5-dione 42769-24-4 C10H14O4
—— 5-[3-Chloro-4-(4-hydroxy-cyclohexyl)-phenyl]-dihydro-furan-2-one 53954-78-2 C16H19ClO3
—— 3-fluoro-3-trifluoromethyl-1,4-oxathian-2-one 75355-71-4 C5H4F4O2S
—— 6-Methyl-dihydro-pyran-2,3,4-trione 86396-22-7 C6H6O4
—— γ-(1-propenyl)-γ-butyrolactone 1130937-80-2 C7H10O2
—— <i>cis</i>-tetrahydro-thiopyran-2,6-dicarboxylic acid-anhydride 116331-08-9 C7H8O3S
—— (1R,2S,3S,6R,7R,9R)-2-Chloro-1,8,8-trimethyl-5-oxo-4-oxa-tricyclo[4.2.1.0<sup>3,7</sup>]nonane-9-carboxylic acid methyl ester 57199-66-3 C13H17ClO4
—— anisatin acetonide 130434-87-6 C18H24O8
—— 52114-35-9 C12H14O5
—— (S)-7-Methyl-4-methylene-2-oxa-spiro[4.4]nonan-1-one 51769-06-3 C10H14O2
—— 3,3-dimethyl-6-phenyltetrahydro-2H-pyran-2-one 33158-80-4 C13H16O2
—— 2-endo,3,6-endo-trimethyl-3-<(tetrahydro-2H-pyran-2-yl)oxy>-4-oxatricyclo<5.2.1.0<sup>2,6</sup>>decan-5-one 77224-24-9 C17H26O4
—— 5-[3-Chloro-4-(4-hydroxy-cyclohexyl)-phenyl]-dihydro-furan-2-one 53954-77-1 C16H19ClO3
—— 4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (Z)-(R)-cyclodec-2-enyl ester 127672-08-6 C20H30O4
—— pentalenolactone F 85416-36-0 C15H18O5
—— 1,1,3,3,6,6,8,8-Octamethyl-1,3,3b,6,8,8b-hexahydro-furo[3,4-b]furo[3',4':5,6]pyrano[3,4-d]pyran-4,9-dione 52040-24-1 C20H26O6
—— 2-Bromo-4-oxa-tricyclo[4.3.1.1<sup>3,8</sup>]undecane-5,9-dione 53036-78-5 C10H11BrO3
—— methyl (Z)-2-cyano-2-(6-methyl-2-oxomorpholin-3-ylidene)ethanoate 1372812-67-3 C9H10N2O4
—— rac-(1R,2S,6R,7R,10R,10aR,13R)-1-hydroxy-13-methyl-4-oxooctahydro-2H,4H-2,6,6a-(epimethanetriyloxymethano)benzo[d]oxocine-7,10-diyl diacetate 72844-69-0 C18H24O8
—— 5-Methyl-4-((E)-propenyl)-dihydro-furan-2-one 23636-68-2 C8H12O2
—— 6-endo-Acetoxy-2-oxabicyclo<2.2.2>octan-3-on 51608-92-5 C9H12O4
—— 52356-42-0 C13H15BrO4
—— (3aS,6aR,7S,8R,10aS)-7-(2-Furan-3-yl-ethyl)-4-methoxy-7,8-dimethyl-octahydro-2-oxa-cyclopenta[d]naphthalene-3,5-dione 52210-13-6 C21H28O5
—— 3a-methyl-cis-hexahydrocyclopenta<b>furan-2-one 39778-83-1 C8H12O2
—— (2S)-(3S)-(4S)-2-C-methyl-5-deoxyribono-1,4-lactone 116491-25-9 C6H10O4
—— 11,13-Dihydro-15-chloro-1-epiallohelenalin 42895-80-7 C15H19ClO4
—— Acetic acid 1-ethyl-1-methyl-3-((1R,5aS,9aS)-6,6,9a-trimethyl-3-oxo-decahydro-benzo[c]oxepin-1-yl)-propyl ester 52567-95-0 C21H36O4
—— Acetic acid (2R,3S,4S,5R,8R,9S,10S,11R)-5-ethyl-9,11-dihydroxy-2,4,8,10,12,14-hexamethyl-7-oxo-6,15-dioxa-bicyclo[10.2.1]pentadec-1(14)-en-3-yl ester 51021-71-7 C23H38O7
—— (3S,4S,5R)-5-Cyano-3-ethyl-4,5-dimethyl-2-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester 50676-20-5 C12H17NO4
—— 54837-70-6 C24H24O10
—— 39020-23-0 C15H18O6
—— (2R,3S)-2,3,4-Trimethyl-5-oxo-tetrahydro-furan-2,4-dicarboxylic acid diethyl ester 51486-73-8 C13H20O6
—— (3R,3aR,4S,5aS,7R,8S,9bR)-8-hydroxy-3-methoxy-3,4,7-trimethyl-2-oxo-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-5a-carbonitrile 1429194-84-2 C17H23NO4
—— 1420965-11-2 C17H26O4Si
—— trans-3-hydroxy-5-(thiophen-2-yl)dihydrofuran-2(3H)-one 1233242-09-5 C8H8O3S
—— 6-(2-phenylethyl)-3-phenylselanyloxan-2-one 172805-64-0 C19H20O2Se
—— 4-[(1R,2R,3R)-2-(2-Methoxycarbonyl-ethyl)-2-methyl-3-(5-oxo-tetrahydro-furan-2-yl)-cyclopentyl]-pentanoic acid methyl ester 63472-61-7 C20H32O6
—— α-(4-Methyl-2-oxopentyl)-γ-butyrolacton 79138-02-6 C10H16O3
—— 8-Desoxy-4,5,6,7,10,11,12,13-oktahydro-lankacidin-C-2'-ol 52557-80-9 C25H43NO6
—— (1S,2S,5R,6R,7S)-7-Acetoxy-2-[(3aS,4S,7aR)-7,7-dimethyl-1-oxo-4-(tetrahydro-pyran-2-yloxy)-hexahydro-isobenzofuran-3a-yl]-6-methyl-bicyclo[3.2.1]octane-1-carboxylic acid methyl ester 57494-41-4 C28H42O8
—— 3-allyl-3-methyl-4-(1-phenyl-but-3-enyl)-dihydro-furan-2-one 332940-65-5 C18H22O2
—— 1062629-31-5 C10H16O4
—— methyl 5-(4-bromophenyl)-8-methyl-7,9-dioxo-6-oxaspiro[4.5]decane-9-carboxylate 1240483-09-3 C18H19BrO5
—— 2-bromo-3-O-tert-butyldimethylsilyl-2-deoxy-D-ribono-1,4-lactone 142329-65-5 C11H21BrO4Si
—— (3S,4S,5R)-4-hydroxy-5-((S)-1-hydroxyethyl)-3-methyldihydrofuran-2(3H)-one 1350524-17-2 C7H12O4
—— (4R,5R)-5-Hydroxymethyl-4-((E)-propenyl)-dihydro-furan-2-one 114605-38-8 C8H12O3