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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
—— (2aα,2bα,5aα,5bα)-2,2a,2b,5,5a,5b-Hexahydro-2-oxo-2a-phenylcyclopenta<1,2>cyclobuta<3,4-b>oxet-5b-carbonsaeure-methylester 140695-40-5 C16H14O4
—— (E)-6-(4-chlorobut-2-en-1-yl)-6-methyltetrahydro-2H-pyran-2-one 1267665-13-3 C10H15ClO2
—— α-Dimethylaminomethyl-δ-valerolacton 56783-31-4 C8H15NO2
—— (+/-)-9ξ-Brom-8c-hydroxy-4-oxo-(1rC<sup>8</sup>)-bicyclo<3.2.2>nonan-dicarbonsaeure-(6c,7c)-methylester-(6)-lacton-(7,8) 100118-98-7 C12H13BrO5
—— Xeniolide-B 9-Acetate 74175-97-6 C22H30O5
—— 5-methyl (S)-3-oximino-2-oxotetrahydrofuran-5-carboxylate 239125-35-0 C6H7NO5
—— (3R,4R,5S)-5-[(1R,2E)-3-cyclopentyl-1-hydroxyprop-2-en-1-yl]-4-hydroxy-3-methoxydihydrofuran-2(3H)-one 958075-67-7 C13H20O5
—— 141397-04-8 C34H42O6
—— 5-methyl (S)-3-dimethylaminomethylene-2-oxotetrahydrofuran-5-carboxylate 219813-99-7 C9H13NO4
—— (2RS, 5SR)-2,5-dimethyl-8-oxabicyclo<4.3.0>nona-1(6),3-dien-7-one 86739-67-5 C10H12O2
—— rac-1-((3aR,4R,5S,6aS)-5-hydroxy-2-oxohexahydro-2H-cyclopenta[b]furan-4-yl)-N-methylenemethanaminium chloride 75283-77-1 C9H14NO3*Cl
—— (5S,6R,9S)-6-methyl-9-(2-methyl-4-oxopentan-2-yl)-2-oxaspiro[4.4]nonane-1,4-dione 1262789-46-7 C15H22O4
—— 13-oxa-dispiro[5.0.5.2]tetradecan-14-one 51175-27-0 C13H20O2
—— tetraoxispirophosphorane 35375-90-7 C8H13O6P
—— 158199-31-6 C9H11BrO2
—— bi(5,5-bis(acetoxymethyl)-3-methyl-2-oxomorpholin-3-yl) 86527-90-4 C22H32N2O12
—— α-(1,2-Epoxy-2-hydroxymethyl-cyclopentyl)-isobuttersaeurelacton 90926-78-6 C10H14O3
—— 4-phenyl-2-hydroxy-2-(trifluoromethyl)butan-4-olide 404576-89-2 C11H9F3O3
—— (<i>R</i>)-2-isopropyl-glutaric acid-anhydride 57280-77-0 C8H12O3
—— 2-Hydroxy-2-methyl-4-carboxy-4,5-methylen-adipinsaeure-δ-Lacton-dimethylester 104217-14-3 C11H14O6
—— (3S,3aR,7aS)-7a-bromo-3-butyl-3,3a,4,5,6,7-hexahydro-2-benzofuran-1-one 124549-66-2 C12H19BrO2
—— endo-6-(dimethyl-t-butylsilyloxy)-anti-8-(E)-<3-(dimethyl-t-butylsilyloxy)oct-1-enyl>-2-oxabicyclo<3.2.1>octan-3-one 64767-22-2 C27H52O4Si2
—— (2S,3S,5R)-2-allyl-3-(tert-butyldimethylsilyloxy)-5-(tert-butyldiphenylsilyloxy)-2-(2-methoxyethoxymethoxy)cyclohexanone 631900-14-6 C35H54O6Si2
—— (6R)-6-[(2R)-2-hydroxyhexyl]tetrahydro-2H-2-pyranone 1073160-40-3 C11H20O3
—— 89470-35-9 C19H26O6
—— 5-Butylsulfanylmethyl-2-oxo-tetrahydro-furan-3-carboxylic acid methyl ester 139022-63-2 C11H18O4S
—— 1402922-05-7 C12H16O2
—— 5-(acetoxyimino)-3-methylene-4,5-dihydrofuran-2(3H)-one 75834-39-8 C7H7NO4
—— (3S,4S,5R)-5-Acetyl-3-isopropenyl-3,4-dimethyl-dihydro-furan-2-one 155224-34-3 C11H16O3
—— 5-hydroxymethyl-3-phenyl-dihydro-furan-2-one 99865-55-1 C11H12O3
—— 366492-18-4 C25H42O5Si
—— 2-Oxo-3-methyl-4-<3-oxo-butyl>-tetrahydrofuran-carbonsaeure-(5)-methylester 99862-13-2 C11H16O5
—— 2,4-Benzyliden-D-glucuron-dimethylmercaptal 108884-60-2 C15H18O5S2
—— (3aR,4R,5R,6aS)-4-(3,8-bis((tert-butyldimethylsilyl)oxy)octyl)-5-((tert-butyldimethylsilyl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one 1352751-75-7 C33H68O5Si3
—— 2-(trimethylsilyl)ethyl (2S,3S,4R)-4-methyl-5-oxo-2-(9-oxononyl)tetrahydrofuran-3-carboxylate 1446490-29-4 C20H36O5Si
—— methyl (1S,4S,5S,6S)-4-hydroxymethyl-2-oxo-3-oxabicyclo[3.1.0]hexane-6-carboxylate 1030901-12-2 C8H10O5
—— (1R,2S,5S)-2-methyl-4-oxo-5-(2-methyloxiran-2-yl)-4-oxo-2-vinylcyclohexyl pivalate 1416545-98-6 C17H26O4
—— 3-butyl-5,5-diphenyl-6,7-dihydrooxepin-2(5H)-one 1427003-07-3 C22H24O2
—— 7-(4-bromophenyl)oxepan-2-one 1402080-84-5 C12H13BrO2
—— 6-endo-(t-butyldimethylsilyloxy)-2-oxabicyclo[3.3.0]oct-7-en-3-one 43209-31-0 C13H22O3Si
—— (3aR,4S,5aR,6R,8aS,8bR)-4,6,8a-Trihydroxy-3,3,5a-trimethyl-decahydro-indeno[4,5-c]furan-1-one 88558-61-6 C14H22O5
—— Acetic acid (1S,5R,6R,7S)-6-ethoxycarbonylamino-3-oxo-2,8-dioxa-bicyclo[3.2.1]oct-7-yl ester 120262-39-7 C11H15NO7
—— (4S,5S)-5-((S)-1-Bromo-2-hydroxy-ethyl)-4-(tert-butyl-diphenyl-silanyloxy)-dihydro-furan-2-one 204328-23-4 C22H27BrO4Si
—— α-Acetyl-α,γ-dimethyl-γ-vinyl-γ-butyrolacton 3154-71-0 C10H14O3
—— (5R)-5-<(1S)-1-tert-butoxycarbonylamino-2-cyclohexylethyl>-4,4-dimethyl-tetrahydrofuran-2-one 133956-93-1 C19H33NO4
—— (4R,6R)-cis-4-<t-butyl(dimethyl)silyloxy>-6-iodomethyltetrahydropyran-2-one 121772-45-0 C12H23IO3Si
—— terebic acid propyl ester 77666-62-7 C10H16O4
—— (4aS,8aR)-(-)-3,4,7,8-tetrahydro-4a-allyl-2H,5H-thiopyrano<4,3-b>pyran-2-one 139027-64-8 C11H16O2S
—— (3bS,6S,10aR)-3b-Hydroxymethyl-6,10a-dimethyl-9-oxo-3b,4,5,5a,6,7,9,10,10a,10b,11,12-dodecahydro-2,8-dioxa-cyclohepta[a]cyclopenta[f]naphthalene-6-carboxylic acid 130574-80-0 C20H26O6
—— 1-Hydroxy-1,5,7-trimethyl-3-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-5-carboxylic acid 37568-95-9 C12H16O5