物质信息
ID:717756
名称和标识
IUPAC标准名
1,3-diethyl propanedioate
IUPAC传统名
diethyl malonate
别名
丙二酸二乙酯Malonic acid diethyl esterDiethyl malonatePropanedioic acid diethyl ester
化合物性质
产品相关信息
纯度
99%
理化性质
沸点
198-200°C
折射率
1.4140
熔点
-50°C
密度
1.055
闪点
90°C(194°F)
安全信息
GHS危险声明
H227
RTECS编号
OO0700000
TSCA收录
是
描述信息
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分子图谱
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参考文献
• Arylation occurs with aryl bromides in the presence of CuI: Gazz. Chim. Ital., 122, 511 (1992).
• Compare also Dimethyl malonate, A11007, Di-tert-butyl malonate, A12774, Dibenzyl malonate, A10844, and Isopropylidene malonate, A15603.
• For phase-transfer monoalkylation of the active methylene group see, e.g. (18-crown-6): Synthesis, 37 (1977); and (BTEAC): Org. Prep. Proced. Int., 26, 469 (1994). Solid-liquid phase transfer alkylation has been promoted by microwave irradiation: Synth. Commun., 25,1761 (1995). Dialkylation can also occur in the presence of BTEAC: Synthesis, 54 (1985); Org. Synth. Coll., 7, 411 (1990), to give cyclopropane derivatives. Stereoselective alkylation has been achieved under particularly mild conditions with secondary alkyl mesylates in the presence of Cesium fluoride, 12885 in DMF; complete inversion occurs at the secondary alkyl carbon: J. Org. Chem., 60, 2627 (1995); see also: Synlett, 499 (1998).
• Substituents can also be introduced by Michael addition; see e.g.: Org. Synth. Coll., 8, 467 (1993).
• A number of procedures have been devised for the direct conversion of malonic esters to acetic esters (decarboalkoxylation), in a single step of which heating in wet DMSO is perhaps the simplest: J. Org. Chem., 43, 138 (1978). See also 1,4-Diazabicyclo[2.2.2]octane, A14003.
• C-Acylation of malonic esters is normally carried out by reaction of the Mg derivative with an acid chloride. A convenient method using a combination of MgCl2 and triethylamine was introduced by Rathke: J. Org. Chem., 50, 2622 (1985); see also Triethylamine, A12646 for discussion of this system:
