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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
—— (E)-4,5-dihydro-3-methyl-3-[4,4-di(methylthio)-buta-1,3-dien-1-yl]-2(3H)-furanone —— C11H16O2S2
(E)-4,5-dihydro-3-methyl-3-[4,4-di(methylthio)-buta-1,3-dien-1-yl]-2(3H)-furanone
—— (E)-(3-adamantan-2-yl-2-methylallyl)-3-methyldihydrofuran-2(3H)-one —— C19H28O2
(E)-(3-adamantan-2-yl-2-methylallyl)-3-methyldihydrofuran-2(3H)-one
—— (Z,Z)-4,5-dihydro-3-methyl-3-[4-(methylthio)-2-nitrobuta-1,3-dien-1-yl]-2(3H)-furanone —— C10H13NO4S
(Z,Z)-4,5-dihydro-3-methyl-3-[4-(methylthio)-2-nitrobuta-1,3-dien-1-yl]-2(3H)-furanone
—— (1E,3Z)-4,5-dihydro-3-methyl-3-[4-(methylthio)-2-nitrobuta-1,3-dien-1-yl]-2(3H)-furanone —— C10H13NO4S
(1E,3Z)-4,5-dihydro-3-methyl-3-[4-(methylthio)-2-nitrobuta-1,3-dien-1-yl]-2(3H)-furanone
—— (S)-5-isopropyloxepan-2-one —— C9H16O2
(S)-5-isopropyloxepan-2-one
—— 5-isopropyloxepan-2-one —— C9H16O2
5-isopropyloxepan-2-one
—— 5,9-dioxabicyclo<5.3.0>dec-1-en-3-methyliden-6,8-dione —— C9H8O4
5,9-dioxabicyclo<5.3.0>dec-1-en-3-methyliden-6,8-dione
—— (E)-2-trimethylsilylmethylene-4-methyl-γ-butyrolactone —— C9H16O2Si
(E)-2-trimethylsilylmethylene-4-methyl-γ-butyrolactone
—— 1-methyl-2-phenyl-11-oxadispiro[2.1.5.2]dodecane-4,12-dione —— C18H20O3
1-methyl-2-phenyl-11-oxadispiro[2.1.5.2]dodecane-4,12-dione
—— (3aS,9R,9aS,9bS)-6,9-dimethyl-3-methylene-2-oxo-2,3,3a,4,5,7,8,9,9a,9b-decahydroazuleno[4,5-b]furan-9-yl 2-bromoacetate —— C17H21BrO4
(3aS,9R,9aS,9bS)-6,9-dimethyl-3-methylene-2-oxo-2,3,3a,4,5,7,8,9,9a,9b-decahydroazuleno[4,5-b]furan-9-yl 2-bromoacetate
—— 7-oxa-6,6-pentamethylene-2-thia-3-(thien-2-yl)bicyclo[3.3.0]octa-3-en-8-one —— C15H16O2S2
7-oxa-6,6-pentamethylene-2-thia-3-(thien-2-yl)bicyclo[3.3.0]octa-3-en-8-one
—— (E)-3-(4-oxooxetan-2-yl)prop-2-enal —— C6H6O3
(E)-3-(4-oxooxetan-2-yl)prop-2-enal
—— (3aR,4S,7R,9aR)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>-3a,4,7,9a-tetrahydro-7-methylcycloocta<c>furan-1,5(3H,6H)-dione —— C32H42O4Si
(3aR,4S,7R,9aR)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>-3a,4,7,9a-tetrahydro-7-methylcycloocta<c>furan-1,5(3H,6H)-dione
—— (R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl propiolate —— C9H10O4
(R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl propiolate
—— (E)-5,7-octadien-5-olide —— C8H10O2
(E)-5,7-octadien-5-olide
—— 8,8-di-tert-butyl-3-(3-chloropropyl)-4a,5a,6,9a,9b,9c-hexahydro-2aH-1,5,7,9-tetraoxa-4-aza-8-silapentaleno[1,6-ab]naphthalen-2-one —— C20H32ClNO5Si
8,8-di-tert-butyl-3-(3-chloropropyl)-4a,5a,6,9a,9b,9c-hexahydro-2aH-1,5,7,9-tetraoxa-4-aza-8-silapentaleno[1,6-ab]naphthalen-2-one
—— (S)-4-n-heptyl-oxetan-2-one —— C10H18O2
(S)-4-n-heptyl-oxetan-2-one
—— (R)-4-(but-1-ynyl)oxetan-2-one —— C7H8O2
(R)-4-(but-1-ynyl)oxetan-2-one
—— 3-(1-ethyl-1-hydroxypropyl)-dihydrofuran-2-one —— C9H16O3
3-(1-ethyl-1-hydroxypropyl)-dihydrofuran-2-one
—— (-)-teubrevin G —— C22H22O8
(-)-teubrevin G
—— teubrevin H —— C22H22O8
teubrevin H
—— 3(R)-hydroxy-4(S)-ethyl-4-methyldihydrofuran-2-one —— C7H12O3
3(R)-hydroxy-4(S)-ethyl-4-methyldihydrofuran-2-one
—— (3R,4S,5R,1'R,2'R)-4-hydroxy-5-(1-hydroxy-2-methylbutyl)-3,5-dimethyl-4,5-dihydrofuran-2(3H)-one —— C11H20O4
(3R,4S,5R,1'R,2'R)-4-hydroxy-5-(1-hydroxy-2-methylbutyl)-3,5-dimethyl-4,5-dihydrofuran-2(3H)-one
—— (3R,4S,5R,1'R,2'S)-4-hydroxy-5-(1-hydroxy-2-methylbutyl)-3,5-dimethyl-4,5-dihydrofuran-2(3H)-one —— C11H20O4
(3R,4S,5R,1'R,2'S)-4-hydroxy-5-(1-hydroxy-2-methylbutyl)-3,5-dimethyl-4,5-dihydrofuran-2(3H)-one
—— 5-ethyl-5-methyl-2-oxepanone —— C9H16O2
5-ethyl-5-methyl-2-oxepanone
—— (3aS,4R,6aR)-4-[(S,E)-3-(tert-butyldimethylsilyloxy)oct-1-en-5-ynyl]-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one 1554688-79-7 C21H32O3Si
(3aS,4R,6aR)-4-[(S,E)-3-(tert-butyldimethylsilyloxy)oct-1-en-5-ynyl]-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one
—— (Z)-3-benzylidene-5-phenyldihydrofuran-2(3H)-one —— C17H14O2
(Z)-3-benzylidene-5-phenyldihydrofuran-2(3H)-one
—— 4-(chlorodifluoromethyl)-4-(dichlorofluoromethyl)-2-oxetanone —— C5H2Cl3F3O2
4-(chlorodifluoromethyl)-4-(dichlorofluoromethyl)-2-oxetanone
—— 6-methyl-5-phenyl-3-oxabicyclo[3.1.0]hexan-2-one —— C12H12O2
6-methyl-5-phenyl-3-oxabicyclo[3.1.0]hexan-2-one
—— γ-lactone 2,2-difluorobutyric acid —— C4H4F2O2
γ-lactone 2,2-difluorobutyric acid
—— (R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl methacrylate —— C10H14O4
(R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl methacrylate
—— 3-(2,2,2-trifluoroacetyl)oxepan-2-one —— C8H9F3O3
3-(2,2,2-trifluoroacetyl)oxepan-2-one
—— 5-phenyl-3-(2,2,2-trifluoroacetyl)tetrahydro-2-furanone —— C12H9F3O3
5-phenyl-3-(2,2,2-trifluoroacetyl)tetrahydro-2-furanone
—— 2-oxooxolan-3-yl methanesulfonate —— C5H8O5S
2-oxooxolan-3-yl methanesulfonate
—— (4R,5R)-4-methyl-5-pentyldihydrofuran-2(3H)-one —— C10H18O2
(4R,5R)-4-methyl-5-pentyldihydrofuran-2(3H)-one
—— S-[(6-oxotetrahydro-2H-pyran-2-yl)methyl] ethanethioate —— C8H12O3S
S-[(6-oxotetrahydro-2H-pyran-2-yl)methyl] ethanethioate
—— 6-(bromomethyl)tetrahydro-2H-pyran-2-one —— C6H9BrO2
6-(bromomethyl)tetrahydro-2H-pyran-2-one
—— (Z)-5-[(2,2-dimethylpropoxy)methyl]-5-(hydroxymethyl)-3-[5-methyl-3-(2-methylpropyl)hexylidene]-4,5-dihydrofuran-2-one —— C22H40O4
(Z)-5-[(2,2-dimethylpropoxy)methyl]-5-(hydroxymethyl)-3-[5-methyl-3-(2-methylpropyl)hexylidene]-4,5-dihydrofuran-2-one
—— (1RS,5SR,6SR,7RS)-6,7-bis(chloromethyl)-3-oxabicyclo[3.2.0]-heptan-2-one —— C8H10Cl2O2
(1RS,5SR,6SR,7RS)-6,7-bis(chloromethyl)-3-oxabicyclo[3.2.0]-heptan-2-one
—— (1RS,5SR,6SR,7SR)-6,7-bis(chloromethyl)-3-oxabicyclo[3.2.0]-heptan-2,4-dione —— C8H8Cl2O3
(1RS,5SR,6SR,7SR)-6,7-bis(chloromethyl)-3-oxabicyclo[3.2.0]-heptan-2,4-dione
—— (1RS,5SR,6RS,7RS)-6,7-bis(chloromethyl)-3-oxabicyclo[3.2.0]heptan-2,4-dione —— C8H8Cl2O3
(1RS,5SR,6RS,7RS)-6,7-bis(chloromethyl)-3-oxabicyclo[3.2.0]heptan-2,4-dione
—— (1RS,5SR,6SR,7RS)-6,7-bis(chloromethyl)-3-oxabicyclo[3.2.0]heptan-2,4-dione —— C8H8Cl2O3
(1RS,5SR,6SR,7RS)-6,7-bis(chloromethyl)-3-oxabicyclo[3.2.0]heptan-2,4-dione
—— (1RS,5SR,6RS,7SR)-6,7-bis(chloromethyl)-3-oxabicyclo[3.2.0]heptan-2-one —— C8H10Cl2O2
(1RS,5SR,6RS,7SR)-6,7-bis(chloromethyl)-3-oxabicyclo[3.2.0]heptan-2-one
—— cis-tetrahydro-3-methylene-2-oxo-5-n-octyl-4-furancarboxylic acid —— C14H22O4
cis-tetrahydro-3-methylene-2-oxo-5-n-octyl-4-furancarboxylic acid
—— C75 191282-48-1 C14H22O4
C75
—— 4-(methoxymethyl)-2-propiolactone —— C5H8O3
4-(methoxymethyl)-2-propiolactone
—— trans-3-methyldihydro-4-nitromethyl-2(3H)-furanone —— C6H9NO4
trans-3-methyldihydro-4-nitromethyl-2(3H)-furanone
—— 3,4-dibromo-3-methyldihydrofuran-2-one —— C5H6Br2O2
3,4-dibromo-3-methyldihydrofuran-2-one
—— 4,5-dihydro-3-chloro-3-methyl-2(3H)-furanone —— C5H7ClO2
4,5-dihydro-3-chloro-3-methyl-2(3H)-furanone
—— exo/endo-Z-2-carboxy-3-(hydroxymethylene)bicyclo[2.2.2]oct-5-ene γ-lactone —— C10H12O2
exo/endo-Z-2-carboxy-3-(hydroxymethylene)bicyclo[2.2.2]oct-5-ene γ-lactone