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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
—— Adamantane-1-carboxylic acid (1S,3R,7S,8S,8aR)-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester 79902-44-6 C30H42O5
—— 1,9-dioxa-2,10-dioxo-3,11-dimethylene cyclohexadecane 132891-38-4 C16H24O4
—— 4-metoxi-3-oxabiciclo<3.1.0>hexan-2-ona 157826-47-6 C6H8O3
—— 3-Acetyl-2-oxo-5-(1-chlor-vinyl)-tetrahydrofuran 3132-79-4 C8H9ClO3
—— (5S)-[(3’S, 3'aS, 7’S, 7’aR)-octahydro-7’-(tert-butyldimethylsilyloxy)-3'a-methyl-1H-inden-3’a-methyl-1H-inden-3'-yl-(1"S)-ethyl]-3H,5H-furan-2-one 1443043-79-5 C22H40O3Si
—— (3aS,4S,6aR)-4-(1-Phenylselanyl-octyl)-dihydro-furo[3,4-b]furan-2,6-dione 94859-63-9 C20H26O4Se
—— 5-(1-hydroxy-1-methyl-ethyl)-3-(3-methyl-butyl)-dihydro-furan-2-one 6723-01-9 C12H22O3
—— 4-Cyclopropyl-4-hydroxy-9-oxa-dispiro[2.1.2.3]decane-8,10-dione 74824-37-6 C12H14O4
—— 8α-tert-butyldimethylsilyloxy-4,5α-epoxy-6β7αH-eudesm-11-en-12,6-olide 108653-91-4 C21H34O4Si
—— 1055288-99-7 C8H10Cl2O3
—— (3S,3aS,5aR,9aS,9bS)-5a-(2-Hydroxy-ethyl)-2-methoxy-3,9-dimethyl-decahydro-furo[2,3-f]isochromen-8-one 73719-40-1 C16H26O5
—— 1346154-67-3 C22H25ClO4
—— (3S,5R)-3-Hydroxy-3-hydroxymethyl-5-methyl-dihydro-furan-2-one 78687-62-4 C6H10O4
—— [4,4-Dimethyl-2-(2-oxo-2,5-dihydro-furan-3-ylmethyl)-cyclopent-(Z)-ylidene]-acetonitrile 128593-84-0 C14H17NO2
—— (3aS,6S,6aR)-6-benzyltetrahydrofuro[3,4-b]furan-2,4-dione 1197132-94-7 C13H12O4
—— (R)-3-((S)-2-oxocyclopentyl)-5,5-diphenylmorpholin-2-one 1114967-81-5 C21H21NO3
—— (3R,4R)-trans-3-methyl-4-(9-decenyl)oxetan-2-one 1057557-63-7 C14H24O2
—— 5-Ethyl-3,3-dimethyl-5-phenyl-dihydro-furan-2-one 66687-65-8 C14H18O2
—— Lacton 4.5-Dimethyl-2-hydroxymethyl-cyclohexan-carbonsaeure-(1) 13702-79-9 C10H16O2
—— 2-((2R,3S,4R)-4-Diphenylphosphanyl-2-methoxy-5-oxo-tetrahydro-furan-3-yl)-2-methyl-propionic acid ethyl ester 132990-36-4 C23H27O5P
—— D-<i>lyxo</i>-3-deoxy-hexonic acid-4-lactone 55658-88-3 C6H10O5
—— (6Z,9S)-6-ethylidene-9-hydroxy-10-decanolide 138253-41-5 C12H20O3
—— S-(2-oxooxolan-3-yl) 2-bromoethanethioate 118534-93-3 C6H7BrO3S
—— rac-γ-Methyl-α-trimethylsilyl-γ-butyrolactone 57025-70-4 C8H16O2Si
—— (3S,4aS,7R,7aS,10R,11aR)-3,7,10-trimethylhexahydro-4aH,6H-[1,2,4]trioxino[6,5-j]isochromen-6-one 120354-72-5 C13H20O5
—— (1S,2R,5S)-2-Phenyl-6-oxa-bicyclo[3.2.1]octan-7-one 128888-80-2 C13H14O2
—— 7-imino-1,3a,4a,5,7b-pentamethyl-2-oxo-hexahydro-3,5-cyclo-furo[3',4':4,5]furo[3,2-<i>b</i>]pyrrole-3,7a-dicarbonitrile 57825-19-1 C15H16N4O3
—— 3,4-dibromo-3-bromomethyl-4,5-dihydro-3H-furan-2-one 109765-96-0 C5H5Br3O2
—— (3aR,4aS,5S,7aS,8S,9aR)-5-Hydroxy-4a,8-dimethyl-decahydro-azuleno[6,5-b]furan-2-one 114579-29-2 C14H22O3
—— 4-methyl-2-oxo-tetrahydro-cyclopenta[<i>b</i>]furan-3a,6a-dicarboxylic acid 13382-35-9 C10H12O6
—— opt.-inakt. <2-Oxo-hexahydro-2H-cyclopenta<b>furan-3-yl>-essigsaeure-ethylester 1136-92-1 C11H16O4
—— 3-acetyl-4,6,6-trimethyl-tetrahydro-pyran-2-one 7391-54-0 C10H16O3
—— (2R,3R,4R)-4-[2-(5-benzyloxypyridyl)]-2-hydroxy-3-methyl-butano-4-lactone 909913-32-2 C17H17NO4
—— 3-Butyl-6,6-dimethyl-tetrahydro-pyran-2-one 20474-03-7 C11H20O2
—— (1S,3R)-3-(1,2-dihydroxyethyl)-2,2-dimethylcyclopropanecarboxylic acid γ-lactone 108404-48-4 C8H12O3
—— (1SR,5RS,6RS,7RS)-(+/-)-7-Hydroxy-6-<(1E,3RS)-3-hydroxy-4,4-dimethyl-6-oxa-1-octenyl>-2-oxabicyclo<3.3.0>octan-3-on 107298-11-3 C16H26O5
—— ethyl 4-(1-chloroethyl)-3-(2-propenyl)-2-oxotetrahydrofuran-3-carboxylate 133472-63-6 C12H17ClO4
—— (3R,3a'S,6a'S)-octahydro-2H,2'H-spiro[furan-3,1'-pentalen]-2-one 82517-62-2 C11H16O2
—— 2-((3S)-2-(iodomethyl)-2-methyl-5-oxotetrahydrofuran-3-yl)acetic acid 1280738-55-7 C8H11IO4
—— 3-((Ξ)-nonylidene)-dihydro-furan-2-one 98441-93-1 C13H22O2
—— 1-oxo-3α-(4-methyl-3-pentenyl)-6β-methyl-1,3,3aα,6aα-tetrahydrocyclopenta<c>furan 97673-27-3 C14H20O2
—— γ-Phenyl-tetronsaeure 14738-01-3 C10H8O3
—— (3aS,6aS)-3a,4,6,6a-tetrahydro-3H-cyclopenta[b]furan-2,5-dione 59013-17-1 C7H8O3
—— [(3aS,4R,5S,6aR)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] acetate 138875-14-6 C16H28O5Si
—— simvastatin 123049-81-0 C25H38O5
—— α,β-Dimethyl-β-aethyl-γ-butyrolacton 1679-30-7 C8H14O2
—— 3,5-Di-O-acetyl-6,7-10,11-dianhydro-erythronolid B 13118-63-3 C25H38O7
—— ((2S,3S)-5-oxo-3-triethylsilanyloxydihydrofuran-2-yl)acetaldehyde 865872-25-9 C12H22O4Si
—— 83605-38-3 C13H16O4
—— (3aRS,6aSR)-methyl-1,1-dimethyl-3-oxotetrahydro-1H-cyclopenta[c]-furan-3a-carboxylate 101046-07-5 C11H16O4