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    首页 分子通 按物质功能分类 吡喃类化合物

    吡喃类化合物

    吡喃类化合物是一种含有一个氧原子的六元杂环体系，主要分为α-吡喃和γ-吡喃两种异构体。尽管无取代基的α-吡喃和γ-吡喃尚未被发现，但其衍生物广泛存在于自然界中，尤其是植物中常见的α-及γ-吡喃酮。

    这些化合物包括苯并吡喃（色烯）、色酮、香豆素、黄酮、异黄酮以及花青素等。从电子结构上看，吡喃类似苯系化合物，环中的氧原子具有极强的碱性，在成盐后被稳定下来。许多重要的天然产物如色素、糖类、抗生素及生物碱都含有吡喃或其盐形式的环系。例如，五碳糖或六碳糖形式的半缩醛结构被称为吡喃糖。

    吡喃酮是通过将吡喃的次甲基部分氧化为羰基而形成的衍生物。α-吡喃酮为5-羟基-2,4-戊二烯酸的内酯，在酸碱催化下可以发生水解反应，也可以在催化氢化条件下转化为5-羟基戊酸内酯；此外，该化合物还能参与双烯合成反应。相比之下，γ-吡喃酮具有显著的芳香性特点，即使是一个不饱和酮，也不与苯肼形成腙，并且其羰基不易被还原。

    一些重要药物如红霉素和双氢链霉素含有四氢吡喃环结构，而许多碳水化合物也具有四氢吡喃环。

    中文名称 英文名称 CAS号 化学式 结构式图片
    —— 3-O-acetyl-1,2-O-isopropylidene-6-O-trityl-β-L-arabino-hexofuranos-5-ulose 109680-98-0 C30H30O7
    3-O-acetyl-1,2-O-isopropylidene-6-O-trityl-β-L-arabino-hexofuranos-5-ulose
    —— Methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 162678-87-7 C21H23N3O5
    Methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
    —— 2-(2-(tert-butyl)-6-methyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione 251359-13-4 C19H18O3
    2-(2-(tert-butyl)-6-methyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione
    —— 2,2-dimethyl-7-((tetrahydro-2H-pyran-2-yl)oxy)-2H-chromen-3-carbaldehyde 1298093-47-6 C17H20O4
    2,2-dimethyl-7-((tetrahydro-2H-pyran-2-yl)oxy)-2H-chromen-3-carbaldehyde
    —— (2S,4R)-4-chloro-2-methyloxane 92826-98-7 C6H11ClO
    (2S,4R)-4-chloro-2-methyloxane
    —— 1-Borneol-beta-apisyl-beta-glucopyranoside 88700-35-0 C21H36O10
    1-Borneol-beta-apisyl-beta-glucopyranoside
    —— [(E)-[(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-ylidene]amino] N-(2,3,4,5,6-pentadeuteriophenyl)carbamate 1331383-16-4 C15H19N3O7
    [(E)-[(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-ylidene]amino] N-(2,3,4,5,6-pentadeuteriophenyl)carbamate
    —— 3,4,6-tri-O-benzyl-2-O-acetyl-α-D-glucosyl trichloroimidate 108869-64-3 C31H32Cl3NO7
    3,4,6-tri-O-benzyl-2-O-acetyl-α-D-glucosyl trichloroimidate
    —— 2,3,4-tri-O-acetyl-D-xylopyranosyl trichloroacetimidate 197144-02-8 C13H16Cl3NO8
    2,3,4-tri-O-acetyl-D-xylopyranosyl trichloroacetimidate
    —— 1,2:3,4-Di-O-isopropylidene-6-deoxy-6-tosyl-alpha-D-galactopyranose 4478-43-7 C19H26O8S
    1,2:3,4-Di-O-isopropylidene-6-deoxy-6-tosyl-alpha-D-galactopyranose
    —— 3,3-dimethyltetrahydro-2H-pyran-4-amine 1357396-54-3 C7H15NO
    3,3-dimethyltetrahydro-2H-pyran-4-amine
    —— 2,3,4,6-tetra-O-benzyl-1-C-(dichloromethyl)-D-glucopyranose 140658-50-0 C35H36Cl2O6
    2,3,4,6-tetra-O-benzyl-1-C-(dichloromethyl)-D-glucopyranose
    —— (2R,3S,4R,5R,6S)-5-amino-6-[(2R,4R,5R)-5-amino-6-[(2R,3S,4R,5R,6R)-5-amino-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-2-(hydroxymethyl)oxane-3,4-diol 78341-33-0 C18H35N3O13
    (2R,3S,4R,5R,6S)-5-amino-6-[(2R,4R,5R)-5-amino-6-[(2R,3S,4R,5R,6R)-5-amino-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-2-(hydroxymethyl)oxane-3,4-diol
    —— 2,3,4,6-tetra-O-benzyl-L-idopyranose 4132-28-9 C34H36O6
    2,3,4,6-tetra-O-benzyl-L-idopyranose
    —— Tetra-O-benzyl-D-galactopyranose 4132-28-9 C34H36O6
    Tetra-O-benzyl-D-galactopyranose
    —— 7-Methylamino-4-trifluoromethyl-chromen-2-one 53518-14-2 C11H8F3NO2
    7-Methylamino-4-trifluoromethyl-chromen-2-one
    —— 3-(2-bromo-1-hydroxyethyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one 1378391-38-8 C19H17BrO3
    3-(2-bromo-1-hydroxyethyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one
    —— 9-Ethylidene-3-oxatricyclo(6.2.1.02,7)undecane-4-one 69486-14-2 C12H16O2
    9-Ethylidene-3-oxatricyclo(6.2.1.02,7)undecane-4-one
    —— trans-2-methyltetrahydropyran-4-ol 55230-32-5 C6H12O2
    trans-2-methyltetrahydropyran-4-ol
    —— cis-2-methyl-4-pyranol 33747-08-9 C6H12O2
    cis-2-methyl-4-pyranol
    —— methyl 3,5-di-O-benzyl-D-xylofuranoside 102339-30-0 C20H24O5
    methyl 3,5-di-O-benzyl-D-xylofuranoside
    —— benzyl N-[6-oxo-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]hexyl]carbamate 38822-58-1 C20H30N2O8
    benzyl N-[6-oxo-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]hexyl]carbamate
    —— GlcNPhth[36Bn,4Ac]-beta-MP 140615-77-6 C37H35NO9
    GlcNPhth[36Bn,4Ac]-beta-MP
    —— [(2S,3S,4R,5S,6S)-3,4-diacetyloxy-6-phenylsulfanyl-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl acetate 187022-49-7 C21H24Cl3NO9S
    [(2S,3S,4R,5S,6S)-3,4-diacetyloxy-6-phenylsulfanyl-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl acetate
    —— (2R,4aS,6S,6aS,9aR)-7-Benzyl-2-phenyl-6-(phenylsulfanyl)hexahydro-2H-[1,3]dioxino[4',5':5,6]pyrano[3,4-d][1,3]oxazol-8(6H)-one 910805-49-1 C27H25NO5S
    (2R,4aS,6S,6aS,9aR)-7-Benzyl-2-phenyl-6-(phenylsulfanyl)hexahydro-2H-[1,3]dioxino[4',5':5,6]pyrano[3,4-d][1,3]oxazol-8(6H)-one
    —— 4,6-O-Benzylidene-D-threo-hexopyranose 97232-16-1 C13H16O6
    4,6-O-Benzylidene-D-threo-hexopyranose
    —— Methyl 3-acetyl-2-oxo-6-(phenylsulfanyl)-4-[(1S,2R)-1,2,3-tris(acetyloxy)propyl]hexahydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate 934591-76-1 C25H29NO12S
    Methyl 3-acetyl-2-oxo-6-(phenylsulfanyl)-4-[(1S,2R)-1,2,3-tris(acetyloxy)propyl]hexahydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate
    —— isoscoparin 2''-O-glucoside 97605-25-9 C28H32O16
    isoscoparin 2''-O-glucoside
    —— phenyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside 177943-74-7 C34H34O6S
    phenyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside
    —— p-methoxyphenyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside 869107-36-8 C34H36O7
    p-methoxyphenyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside
    —— Koenigin 20186-29-2 C16H18O9
    Koenigin
    —— N-(9H-fluoren-9-ylmethoxycarbonyl)-3-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester 301843-65-2 C30H36N2O10
    N-(9H-fluoren-9-ylmethoxycarbonyl)-3-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester
    —— phenyl 2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside 868230-98-2 C15H18Cl3NO6S
    phenyl 2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside
    —— 2,3,4,6-Tetra-O-benzyl 1-O-p-nitrobenzoyl D-glucopyranoside 54423-54-0 C41H39NO9
    2,3,4,6-Tetra-O-benzyl 1-O-p-nitrobenzoyl D-glucopyranoside
    —— 2-bromoethyltetrahydropyranylether 172797-67-0 C7H13BrO2
    2-bromoethyltetrahydropyranylether
    —— 6-methyltetrahydro-2H-pyran-3-ol 1239275-09-2 C6H12O2
    6-methyltetrahydro-2H-pyran-3-ol
    —— (+)-pinoresinol 4-O-glucopyranoside 24404-49-7 C26H32O11
    (+)-pinoresinol 4-O-glucopyranoside
    —— (3a<i>S</i>)-1<i>c</i>-(4-β-D-Glucopyranosyloxy-3-methoxy-phenyl)-4<i>t</i>-(4-hydroxy-3-methoxy-phenyl)-(3a<i>r</i>,6a<i>c</i>)-tetrahydro-furo[3,4-<i>c</i>]furan 24404-49-7 C26H32O11
    (3a<i>S</i>)-1<i>c</i>-(4-β-D-Glucopyranosyloxy-3-methoxy-phenyl)-4<i>t</i>-(4-hydroxy-3-methoxy-phenyl)-(3a<i>r</i>,6a<i>c</i>)-tetrahydro-furo[3,4-<i>c</i>]furan
    —— [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aS,6bR,10S,12aR)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate 14162-53-9 C36H58O8
    [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aS,6bR,10S,12aR)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
    —— oleanolic acid 28-O-β-D-glucopyranosyl ester 14162-53-9 C36H58O8
    oleanolic acid 28-O-β-D-glucopyranosyl ester
    —— Methyl 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside 79528-48-6 C21H23NO9S
    Methyl 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside
    —— (E)-4-hydroxy-3-(3-(4-methoxyphenyl)acryloyl)-2H-chromen-2-one 1022282-99-0 C19H14O5
    (E)-4-hydroxy-3-(3-(4-methoxyphenyl)acryloyl)-2H-chromen-2-one
    —— Geranyl arabinopyranosyl-glucoside 150995-11-2 C21H36O10
    Geranyl arabinopyranosyl-glucoside
    —— (E)-Oxyresveratrol 3'-O-b-D-glucoside 144525-40-6 C20H22O9
    (E)-Oxyresveratrol 3'-O-b-D-glucoside
    —— phenyl N-benzyl-2-amino-4,6-O-benzylidene-2,3-N,O-carbonyl-2-deoxy-1-thio-β-D-glucopyranoside 910805-49-1 C27H25NO5S
    phenyl N-benzyl-2-amino-4,6-O-benzylidene-2,3-N,O-carbonyl-2-deoxy-1-thio-β-D-glucopyranoside
    —— 3,4-Dihydro-2H-1-benzopyran-4-aminium 53981-38-7 C9H12NO+
    3,4-Dihydro-2H-1-benzopyran-4-aminium
    —— [(2-Oxo-2H-1-benzopyran-7-yl)oxy]acetate 126424-85-9 C11H7O5-
    [(2-Oxo-2H-1-benzopyran-7-yl)oxy]acetate
    —— (2R,5R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol 4132-28-9 C34H36O6
    (2R,5R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol
    —— <i>meso</i>-1,4-bis-tetrahydropyran-2-yloxy-benzene 2139-44-8 C16H22O4
    <i>meso</i>-1,4-bis-tetrahydropyran-2-yloxy-benzene
    —— <i>racem.</i>-1,4-bis-tetrahydropyran-2-yloxy-benzene 2139-44-8 C16H22O4
    <i>racem.</i>-1,4-bis-tetrahydropyran-2-yloxy-benzene