CLEAVAGE AND OLIGOMERIZATION OF MALONDIALDEHYDE

被引:46
作者
GOMEZSANCHEZ, A [1 ]
HERMOSIN, I [1 ]
LASSALETTA, JM [1 ]
MAYA, I [1 ]
机构
[1] UNIV SEVILLA,DEPT QUIM ORGAN,E-41012 SEVILLE,SPAIN
关键词
QUASI-DIMERIC MALONDIALDEHYDE; QUASI-TRIMERIC MALONDIALDEHYDE; 3-SUBSTITUTED 2,4-DIHYDROXYMETHYLENEGLUTARALDEHYDES, 1,4-DIHYDROPYRANE-3,5-DICARBALDEHYDES; 1,4-DIHYDROPYRIDINE-3,5-DICARBALDEHYDES;
D O I
10.1016/S0040-4020(01)85814-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Malondialdehyde (MDA) slowly self-condensates in aqueous solution at pH 4.5-6 and room temperature yielding (E)-(3'-oxo-1'-propenyl)malondialdehyde and 2,4-dihydroxymethylene-3-(2'-oxoethyl)glutaraldehyde. The latter compound exists in solution in equilibrium with 4-(1,3-dioxopropan-2-yl)-5-formyl-2-hydroxy-3,4-dihydro-2H-pyran, the trans-form of which can be readily isolated as a crystalline hemipotassium salt. Cleavage of MDA also occurs under these conditions leading to acetaldehyde, which further reacts with the excess of MDA to form 2,4-dihydroxymethylene-3-methylglutaraldehyde.
引用
收藏
页码:1237 / 1250
页数:14
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