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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
—— (3S,4S)-3-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>dihydro-4-<(E)-3-(octahydro-1,3-dimethyl-2H-1,3,2-benzodiazaphosphol-2-yl)allyl>-2(3H)furanone 162789-33-5 C36H53N2O4PSi
(3S,4S)-3-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>dihydro-4-<(E)-3-(octahydro-1,3-dimethyl-2H-1,3,2-benzodiazaphosphol-2-yl)allyl>-2(3H)furanone
—— 6-cyclopentyl-6-[2-(3-ethyl-4-hydroxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione 749927-90-0 C20H26O4
6-cyclopentyl-6-[2-(3-ethyl-4-hydroxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione
—— 5-[3-(3-Hexyl-4,5-dihydro-1,2-oxazol-5-yl)propyl]oxolan-2-one 1082071-01-9 C16H27NO3
5-[3-(3-Hexyl-4,5-dihydro-1,2-oxazol-5-yl)propyl]oxolan-2-one
—— 5-[4-(3-hexyl-4,5-dihydro-5-isoxazolyl)butyl]dihydro-2(3H)-furanone 1082070-86-7 C17H29NO3
5-[4-(3-hexyl-4,5-dihydro-5-isoxazolyl)butyl]dihydro-2(3H)-furanone
—— Acetic acid 2-hydroxymethyl-4-octadec-9-enylidene-5-oxo-tetrahydro-furan-2-ylmethyl ester 172926-98-6 C26H44O5
Acetic acid 2-hydroxymethyl-4-octadec-9-enylidene-5-oxo-tetrahydro-furan-2-ylmethyl ester
—— 7a-phenyl-3,3a,7,7a-tetrahydro-3,6-methanobenzofuran-2(6H)-one 1627214-42-9 C15H14O2
7a-phenyl-3,3a,7,7a-tetrahydro-3,6-methanobenzofuran-2(6H)-one
—— Dihydro-3-methylene-2,4-furandione 129178-41-2 C5H4O3
Dihydro-3-methylene-2,4-furandione
—— (R)-5-(2-hydroxyethyl)dihydrofuran-2(3H)-one 134386-07-5 C6H10O3
(R)-5-(2-hydroxyethyl)dihydrofuran-2(3H)-one
—— 3-Methyl-4-(prop-1-en-2-yl)oxolan-2-one 633315-80-7 C8H12O2
3-Methyl-4-(prop-1-en-2-yl)oxolan-2-one
—— (1R,5R)-1,8,8-trimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione —— C10H14O3
(1R,5R)-1,8,8-trimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione
—— (2S,3S,4R)-2-Hexyl-3-hydroxy-4-pentanolide 137171-30-3 C11H20O3
(2S,3S,4R)-2-Hexyl-3-hydroxy-4-pentanolide
—— methyl (1R,2S,3R,7R,8R,11R)-4,12-dimethylidene-5-oxo-7-(3-oxopropyl)-6-oxatetracyclo[9.2.1.01,8.03,7]tetradecane-2-carboxylate 307345-03-5 C20H24O5
methyl (1R,2S,3R,7R,8R,11R)-4,12-dimethylidene-5-oxo-7-(3-oxopropyl)-6-oxatetracyclo[9.2.1.01,8.03,7]tetradecane-2-carboxylate
—— methyl (1R,2S,3S,4R,7R,8R,11R)-4-bromo-7-(3-hydroxypropyl)-4-methyl-12-methylidene-5-oxo-6-oxatetracyclo[9.2.1.01,8.03,7]tetradecane-2-carboxylate 307345-08-0 C20H27BrO5
methyl (1R,2S,3S,4R,7R,8R,11R)-4-bromo-7-(3-hydroxypropyl)-4-methyl-12-methylidene-5-oxo-6-oxatetracyclo[9.2.1.01,8.03,7]tetradecane-2-carboxylate
—— methyl (1R,2S,3S,4S,7S,8R,11R)-7-[3-[tert-butyl(dimethyl)silyl]oxypropyl]-4-methyl-12-methylidene-5-oxo-6-oxatetracyclo[9.2.1.01,8.03,7]tetradecane-2-carboxylate 307345-05-7 C26H42O5Si
methyl (1R,2S,3S,4S,7S,8R,11R)-7-[3-[tert-butyl(dimethyl)silyl]oxypropyl]-4-methyl-12-methylidene-5-oxo-6-oxatetracyclo[9.2.1.01,8.03,7]tetradecane-2-carboxylate
—— methyl (1R,2S,3R,7R,8R,11R)-7-(3-hydroxypropyl)-4,12-dimethylidene-5-oxo-6-oxatetracyclo[9.2.1.01,8.03,7]tetradecane-2-carboxylate 307345-07-9 C20H26O5
methyl (1R,2S,3R,7R,8R,11R)-7-(3-hydroxypropyl)-4,12-dimethylidene-5-oxo-6-oxatetracyclo[9.2.1.01,8.03,7]tetradecane-2-carboxylate
—— 3-Dodecyldihydro-2(3H)-furanone, (S)- 127126-75-4 C16H30O2
3-Dodecyldihydro-2(3H)-furanone, (S)-
—— methyl (1R,2S,3S,4R,7R,8R,11R)-4-bromo-7-[3-[tert-butyl(dimethyl)silyl]oxypropyl]-4-methyl-12-methylidene-5-oxo-6-oxatetracyclo[9.2.1.01,8.03,7]tetradecane-2-carboxylate 307345-06-8 C26H41BrO5Si
methyl (1R,2S,3S,4R,7R,8R,11R)-4-bromo-7-[3-[tert-butyl(dimethyl)silyl]oxypropyl]-4-methyl-12-methylidene-5-oxo-6-oxatetracyclo[9.2.1.01,8.03,7]tetradecane-2-carboxylate
—— methyl (1R,2S,3S,4S,7S,8R,11R)-7-(3-hydroxypropyl)-4-methyl-12-methylidene-5-oxo-6-oxatetracyclo[9.2.1.01,8.03,7]tetradecane-2-carboxylate 307345-04-6 C20H28O5
methyl (1R,2S,3S,4S,7S,8R,11R)-7-(3-hydroxypropyl)-4-methyl-12-methylidene-5-oxo-6-oxatetracyclo[9.2.1.01,8.03,7]tetradecane-2-carboxylate
—— Trimethyladipic anhydride 29011-65-2 C9H14O3
Trimethyladipic anhydride
—— (+)-(R)-4-(3-methylbut-3-en-1-yl)tetrahydro-2H-pyran-2-one 1612797-06-4 C10H16O2
(+)-(R)-4-(3-methylbut-3-en-1-yl)tetrahydro-2H-pyran-2-one
—— α-Ethoxalyl-γ-methyl-γ-butyrolacton 90674-04-7 C9H12O5
α-Ethoxalyl-γ-methyl-γ-butyrolacton
—— (-)-(R)-7-methyl-4,4a,5,6-tetrahydrocyclopenta[c]pyran-1(3H)-one 1612797-40-6 C9H12O2
(-)-(R)-7-methyl-4,4a,5,6-tetrahydrocyclopenta[c]pyran-1(3H)-one
—— (5S)-9,9-dimethyl-8-methylidene-2-oxaspiro[4.4]nonan-1-one 182164-20-1 C11H16O2
(5S)-9,9-dimethyl-8-methylidene-2-oxaspiro[4.4]nonan-1-one
—— (1S,5E,6R)-7,7-dimethyl-3-oxabicyclo[4.1.0]heptane-4,5-dione 5-oxime 1207861-81-1 C8H11NO3
(1S,5E,6R)-7,7-dimethyl-3-oxabicyclo[4.1.0]heptane-4,5-dione 5-oxime
—— 1,5-dimethyl-6-oxabicyclo<3.2.1>octan-7-one 13747-98-3 C9H14O2
1,5-dimethyl-6-oxabicyclo<3.2.1>octan-7-one
—— 1,4-dimethyl-2-oxa-3-oxobicyclo<2.2.2>octane 28886-59-1 C9H14O2
1,4-dimethyl-2-oxa-3-oxobicyclo<2.2.2>octane
—— 3-Dodecyldihydro-2(3H)-furanone, (R)- 127126-76-5 C16H30O2
3-Dodecyldihydro-2(3H)-furanone, (R)-
—— 3,5-dideoxy-5-nitromethyl-D-xylono-1,4-lactone 1220627-38-2 C6H9NO5
3,5-dideoxy-5-nitromethyl-D-xylono-1,4-lactone
—— 3-(5-oxo-tetrahydro-[2]furyl)-propionyl chloride 124468-90-2 C7H9ClO3
3-(5-oxo-tetrahydro-[2]furyl)-propionyl chloride
—— N-[2-Phenylethyl]-2,3,4,5-tetrahydro-5-oxo-2-furanpropanamide 119627-09-7 C15H19NO3
N-[2-Phenylethyl]-2,3,4,5-tetrahydro-5-oxo-2-furanpropanamide
—— (E)-5-(3-Hexenyl)dihydrofuran-2(3H)-one 97416-87-0 C10H16O2
(E)-5-(3-Hexenyl)dihydrofuran-2(3H)-one
—— 5-Hydroxy-decen-(8t)-saeure-(1)-lacton 75253-68-8 C10H16O2
5-Hydroxy-decen-(8t)-saeure-(1)-lacton
—— δ,δ-Diallyl-δ-valerolactone 87998-07-0 C11H16O2
δ,δ-Diallyl-δ-valerolactone
—— (S)-5-allyl-5-methyldihydrofuran-2(3H)-one 168254-15-7 C8H12O2
(S)-5-allyl-5-methyldihydrofuran-2(3H)-one
—— (4-Methylidene-5-oxo-2-pentyloxolan-3-yl) acetate 76299-63-3 C12H18O4
(4-Methylidene-5-oxo-2-pentyloxolan-3-yl) acetate
—— vernolide 27428-86-0 C19H22O7
vernolide
—— α-Ureidomethylen-γ-butyrolacton 89532-90-1 C6H8N2O3
α-Ureidomethylen-γ-butyrolacton
—— (-)-(3S,6R)-3,6-dimethyltetrahydro-2H-pyran-2-one 65451-94-7 C7H12O2
(-)-(3S,6R)-3,6-dimethyltetrahydro-2H-pyran-2-one
—— 2-O-methyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-D-ribono-1,4-lactone 172932-43-3 C18H36O6Si2
2-O-methyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-D-ribono-1,4-lactone
—— 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-D-ribono-1,4-lactone 190908-03-3 C17H34O6Si2
3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-D-ribono-1,4-lactone
—— (-)-2,3-O-<(R)-Benzyliden>-D-ribonsaeure-γ-lacton 102850-43-1 C12H12O5
(-)-2,3-O-<(R)-Benzyliden>-D-ribonsaeure-γ-lacton
—— (4S,5S)-5-(hydroxymethyl)-4-methyldihydrofuran-2(3H)-one 81474-44-4 C6H10O3
(4S,5S)-5-(hydroxymethyl)-4-methyldihydrofuran-2(3H)-one
—— (5R,6R)-6-ethyl-5-[(2S)-2-methylbutyl]oxan-2-one 345915-39-1 C12H22O2
(5R,6R)-6-ethyl-5-[(2S)-2-methylbutyl]oxan-2-one
—— (3S,4R)-2-methylene-3-hydroxy-4-(hydroxymethyl)-γ-butyrolactone 74948-84-8 C6H8O4
(3S,4R)-2-methylene-3-hydroxy-4-(hydroxymethyl)-γ-butyrolactone
—— 3,3-ethanediyldioxy-11β-hydroxy-14-oxo-14,15-seco-androsta-5,15-dien-18-oic acid-lactone 119974-56-0 C21H26O5
3,3-ethanediyldioxy-11β-hydroxy-14-oxo-14,15-seco-androsta-5,15-dien-18-oic acid-lactone
—— 4,5-dioxo-2-trichloromethyl-tetrahydro-furan-3-carboxylic acid ethyl ester 855390-00-0 C8H7Cl3O5
4,5-dioxo-2-trichloromethyl-tetrahydro-furan-3-carboxylic acid ethyl ester
—— (S)-4-allyldihydrofuran-2(3H)-one 301535-29-5 C7H10O2
(S)-4-allyldihydrofuran-2(3H)-one
—— α-Methylen-β-propyl-γ-butyrolacton 137669-64-8 C8H12O2
α-Methylen-β-propyl-γ-butyrolacton
—— (1S,2R,6R,8S,9S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-9-hydroxy-4,10-dioxatricyclo[6.3.0.02,6]undecan-5-one 168008-04-6 C26H32O5Si
(1S,2R,6R,8S,9S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-9-hydroxy-4,10-dioxatricyclo[6.3.0.02,6]undecan-5-one
—— (3aR,5R,6S,6aR)-6a-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-(hydroxymethyl)-3-oxo-3a,4,5,6-tetrahydro-1H-cyclopenta[c]furan-5-carbaldehyde 168008-03-5 C26H32O5Si
(3aR,5R,6S,6aR)-6a-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-(hydroxymethyl)-3-oxo-3a,4,5,6-tetrahydro-1H-cyclopenta[c]furan-5-carbaldehyde