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酰胺类化合物

酰胺类化合物是指氨或胺的氮原子上的氢被酰基取代后生成的化合物。这类化合物也可视为羧酸分子中的羟基被氨基或胺苯基取代后的产物。常见的酰胺包括甲酰胺(HCO-NH₂)、乙酰胺(CH₃-CO-NH₂)和碳酰胺(CO-(NH₂)₂)等。

在常温条件下,除了甲酰胺为液体外,其余多为晶体;低级酰胺易溶于水。这类化合物通常呈中性,在加热煮沸时会与水发生水解反应生成羧酸和氨:RCONH₂ + H₂O → RCOOH + NH₃(加热条件下)。若在水解过程中加入碱,生成的酸将变成盐,并且氨气逸出。例如,当使用氢氧化钠作为碱时,反应方程式为 RCONH₂ + NaOH → RCOONa + NH₃↑(加热条件下)。

多肽、蛋白质及尼龙6、尼龙66和尼龙1010等合成纤维均含有酰胺键。生物体内的常见酰胺有谷氨酰胺(简写为GLn或Q)和天冬酰胺(简写为Asn或N),以及它们的衍生物,这些化合物不仅是蛋白质的重要组成成分,还具有贮氮、供氮的作用,在合成嘌呤和嘧啶核苷酸中提供一部分氮。此外,它们还可以作为糖蛋白中连接蛋白质与碳水化合物的关键桥梁。

氨分子中的两个氢原子被酰基取代后形成的是酰亚胺。在酰亚胺分子中,与氮原子相连的氢可以以质子形式离去,因此该类化合物具有微弱的酸性特性。

许多酰胺类化合物在工业上有着广泛的应用价值。例如,乙酰胺(CH₃CONH₂)和二甲基甲酰胺(HCON(CH₃)₂)作为重要溶剂;乙酰苯胺作为一种合成磺胺药物的重要中间体;尿素不仅用作重要的氮肥,还是合成树脂的原料。此外,环状结构的酰胺类化合物被称为内酰胺,其中最为重要的是己内酰胺,它是合成尼龙6的关键单体之一。通过使用环己酮为原料可制备得到己内酰胺。

相关化合物

中文名称 英文名称 CAS号 化学式 结构式图片
—— (1R)-(+)-2,10-camphorsultam 94594-90-8 C10H17NO2S
(1R)-(+)-2,10-camphorsultam
—— N-(4-Bromo-2-trifluoromethyl-phenyl)-3,3-dimethylbutanamide 1009344-77-7 C13H15BrF3NO
N-(4-Bromo-2-trifluoromethyl-phenyl)-3,3-dimethylbutanamide
—— N,N-dimethylpyridine-4-carbothioamide 51444-32-7 C8H10N2S
N,N-dimethylpyridine-4-carbothioamide
—— 5-amino-6-bromo-N-{[1-(tetrahydro-2H-pyran-4-ylmethyl)-4-piperidinyl]methyl}-3,3-dihydro-2H-chromene-8-carboxamide 947373-34-4 C22H32BrN3O3
5-amino-6-bromo-N-{[1-(tetrahydro-2H-pyran-4-ylmethyl)-4-piperidinyl]methyl}-3,3-dihydro-2H-chromene-8-carboxamide
—— N,N'-Dibutylglycinamid 97474-13-0 C10H22N2O
N,N'-Dibutylglycinamid
—— N-(1-Hydroxymethyl-1-methyl-2-stearoyloxyethyl)stearamide 60209-70-3 C40H79NO4
N-(1-Hydroxymethyl-1-methyl-2-stearoyloxyethyl)stearamide
—— N-(2-fluoro-4-nitrophenyl)methanesulfonamide 57164-96-2 C7H7FN2O4S
N-(2-fluoro-4-nitrophenyl)methanesulfonamide
—— [1-carbamoyl-2-(3-indolyl)-2-oxoethyl]carbamic acid benzyl ester 255371-72-3 C19H17N3O4
[1-carbamoyl-2-(3-indolyl)-2-oxoethyl]carbamic acid benzyl ester
—— <i>N</i>-(<i>N</i>-L-prolyl-L-leucyl)-glycin-amide 2002-44-0 C13H24N4O3
<i>N</i>-(<i>N</i>-L-prolyl-L-leucyl)-glycin-amide
—— (2S)-2-amino-2-methylbutanamide 59209-90-4 C5H12N2O
(2S)-2-amino-2-methylbutanamide
—— N-formyl-L-aspartic anhydride 33605-73-1 C5H5NO4
N-formyl-L-aspartic anhydride
—— N-(6-chloro-4-morpholin-4-yl-pteridin-2-yl)-acetamide 1003844-56-1 C12H13ClN6O2
N-(6-chloro-4-morpholin-4-yl-pteridin-2-yl)-acetamide
—— (1R,2R)-1-amino-N-(cyclopropylsulfonyl)-2-ethylcyclopropanecarboxamide hydrochloride 923591-24-6 C9H16N2O3S*ClH
(1R,2R)-1-amino-N-(cyclopropylsulfonyl)-2-ethylcyclopropanecarboxamide hydrochloride
—— (2S)-5-[bis[2-(tert-butoxycarbonylamino)ethyl]amino]-2-(tert-butoxycarbonylamino)-5-oxo-pentanoic acid 1083175-00-1 C24H44N4O9
(2S)-5-[bis[2-(tert-butoxycarbonylamino)ethyl]amino]-2-(tert-butoxycarbonylamino)-5-oxo-pentanoic acid
—— (1S)-(-)-2,10-camphorsultam 94594-90-8 C10H17NO2S
(1S)-(-)-2,10-camphorsultam
—— 2-(2-Methoxy-benzamino)-5-nitro-thiazol 69818-97-9 C11H9N3O4S
2-(2-Methoxy-benzamino)-5-nitro-thiazol
—— 3-aminopropyltriethoxysilane 908595-77-7 C13H28BrNO4Si
3-aminopropyltriethoxysilane
—— N-allyl-N-ethyl-4-methyl-benzenesulfonamide 863418-78-4 C12H17NO2S
N-allyl-N-ethyl-4-methyl-benzenesulfonamide
—— (RS)-2-amino-2-methylbutanamide 59209-90-4 C5H12N2O
(RS)-2-amino-2-methylbutanamide
—— DL-N-acetyl-3-aminopropane-1,2-diol 16527-24-5 C5H11NO3
DL-N-acetyl-3-aminopropane-1,2-diol
—— N-(2-(perfluorooctyl)ethyl)methacrylamide 117068-30-1 C14H10F17NO
N-(2-(perfluorooctyl)ethyl)methacrylamide
—— N-(2,2-dimethoxyethyl)-1H-imidazole-1-carboxamide 183660-46-0 C8H13N3O3
N-(2,2-dimethoxyethyl)-1H-imidazole-1-carboxamide
—— Tert-butyl 4-benzyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate 142955-51-9 C15H17NO5
Tert-butyl 4-benzyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate
—— 2-acetylamino-N-methoxy-N-methylacetamide 329983-97-3 C6H12N2O3
2-acetylamino-N-methoxy-N-methylacetamide
—— 6-amino-3-bromo-2-fluoro-N-methylbenzamide 1380305-18-9 C8H8BrFN2O
6-amino-3-bromo-2-fluoro-N-methylbenzamide
—— N-(2,4,6-Trichlorophenyl)benzenesulfonamide 351027-75-3 C12H8Cl3NO2S
N-(2,4,6-Trichlorophenyl)benzenesulfonamide
—— GSK-2982772 1622848-92-3 C20H19N5O3
GSK-2982772
—— (S)-5-benzyl-N-(5-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)-4H-1,2,4-triazole-3-carboxamide 1622848-92-3 C20H19N5O3
(S)-5-benzyl-N-(5-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)-4H-1,2,4-triazole-3-carboxamide
—— N-(3,4-dimethoxyphenyl)-4-methylbenzenesulfonamide 100956-66-9 C15H17NO4S
N-(3,4-dimethoxyphenyl)-4-methylbenzenesulfonamide
—— 2-(3-fluoro-5-(trifluoromethyl)phenyl)ethanethioamide 1318757-95-7 C9H7F4NS
2-(3-fluoro-5-(trifluoromethyl)phenyl)ethanethioamide
—— terephthalamidine dihydrochloride 14401-56-0 C8H10N4*2ClH
terephthalamidine dihydrochloride
—— 2-oxopropanethioamide 31787-50-5 C3H5NOS
2-oxopropanethioamide
—— (6S,7aS)-8,8-dimethylhexahydro-3H-3a,6-methanobenzo[c]isothiazole 2,2-dioxide 108448-77-7 C10H17NO2S
(6S,7aS)-8,8-dimethylhexahydro-3H-3a,6-methanobenzo[c]isothiazole 2,2-dioxide
—— N-3-tolyl 3,5-dinitrobenzamide 36293-08-0 C14H11N3O5
N-3-tolyl 3,5-dinitrobenzamide
—— N-benzyl-3,5-dinitrobenzamide 14401-98-0 C14H11N3O5
N-benzyl-3,5-dinitrobenzamide
—— (R)-3-hydroxy-N-phenylbutanamide 124095-27-8 C10H13NO2
(R)-3-hydroxy-N-phenylbutanamide
—— (S)-3-hydroxy-N-phenylbutanamide 61444-22-2 C10H13NO2
(S)-3-hydroxy-N-phenylbutanamide
—— 2-Hydroxy-2-[(propan-2-yl)imino]ethan-1-aminium 67863-05-2 C5H13N2O+
2-Hydroxy-2-[(propan-2-yl)imino]ethan-1-aminium
—— 2-[Hydroxy(imino)methyl]cyclopentan-1-aminium 135053-11-1 C6H13N2O+
2-[Hydroxy(imino)methyl]cyclopentan-1-aminium
—— (NZ)-N-[(4-chlorophenyl)methylidene]-4-methylbenzenesulfonamide 3157-65-1 C14H12ClNO2S
(NZ)-N-[(4-chlorophenyl)methylidene]-4-methylbenzenesulfonamide
—— N-Fmoc-Freidinger's lactam 957507-85-6 C24H26N2O5
N-Fmoc-Freidinger's lactam
—— Sulfasuccinamide sodium 93777-01-6 C10H11N2NaO5S
Sulfasuccinamide sodium
—— (7R)-10,10-dimethyl-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane 3,3-dioxide 94594-90-8 C10H17NO2S
(7R)-10,10-dimethyl-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane 3,3-dioxide
—— 2-bromo-N-(3,4-dimethoxyphenyl)acetamide 1019399-51-9 C10H12BrNO3
2-bromo-N-(3,4-dimethoxyphenyl)acetamide
—— (S)-(-)-lactamide 2043-43-8 C3H7NO2
(S)-(-)-lactamide
—— N-(5-(2-bromoacetyl)-4-methylthiazol-2-yl)-acetamide 32519-74-7 C8H9BrN2O2S
N-(5-(2-bromoacetyl)-4-methylthiazol-2-yl)-acetamide
—— 5-bromo-2-fluoro-N-methoxy-N-methylbenzamide 910912-20-8 C9H9BrFNO2
5-bromo-2-fluoro-N-methoxy-N-methylbenzamide
—— N-isobutyl-3,5-dinitrobenzamide 56808-99-2 C11H13N3O5
N-isobutyl-3,5-dinitrobenzamide
—— (Rs)-N-tert-butanesulfinyl-(3,3,3)-trifluoroacetaldimine 1219607-85-8 C6H10F3NOS
(Rs)-N-tert-butanesulfinyl-(3,3,3)-trifluoroacetaldimine
—— N,N-diallyl-3,5-dinitrobenzamide 91768-82-0 C13H13N3O5
N,N-diallyl-3,5-dinitrobenzamide