グルタルイミド 化学特性,用途語,生産方法
外観
白色～うすい黄色、結晶～結晶性粉末
溶解性
水に可溶:エーテルに不溶。
解説
グルタルイミド，2,6-piperidinedione．C5H7NO2(113.12)．グルタル酸イミドともいう．グルタル酸と尿素を反応させることによって得られる．"白色の結晶．融点152～154 ℃．密度1.393 g cm－3．一般に，グルタルイミド骨格を有する化合物は抗真菌，抗ウイルス活性などの薬理活性を示すので，誘導体が医薬品として用いられる．[CAS 1121-89-7]
森北出版「化学辞典（第2版）
用途
有機合成原料。
化学的特性
white crystalline powder
使用
Glutarimide acts as an inhibitor of protein synthesis. Further, it is used as a reactant for thionations and biocatalytic asymmetric synthesis of sitagliptin production. It is also employed in the generation of beta-adrenoceptor ligands, enantioselective synthesis of securinega alkaloids and alfa-fluoro-alfa amino amides. In addition to this, it is used in intramolecular amidocyclopropanation reactions.
製造方法
To a flask containing 70 gm (0.53 mole) of glutaric acid is added 150 ml (2.2 mole) of 28% aqueous ammonia. The mixture is set for distillation and heated for 7 hr as the temperature of the mixture rises from 90° to 180°C. The temperature is held at 170-180°C for \\ hr or until the evolution of ammonia ceases. The reaction mixture solidifies on cooling and the product is recrystallized from acetone to afford 37.4 gm (63%), m.p. 145-146°C.
t may be advantageous to preform the ammonium salt of dicarboxylic acids prior to the application of enough heat to form the imide. The preparation of succinimide is a case in point.
定義
ChEBI: A dicarboximide that is piperidine which is substituted by oxo groups at positions 2 and 6.
一般的な説明
A glutarimide antibiotic, 9-methylstreptimidone, shows antiviral, antitumor and antifungal activities.
純化方法
Purify it by dissolving 75g in 200mL of H2O, boil for 30minutes with 2g of charcoal, filter, evaporate to dryness and recystallise the residue from 125mL of 95% EtOH to give 70g of white crystals, m 152-154o. It also crystallises from Me2CO (m 163-165o) or EtOH (m 153-154o). The N-bromo derivative (a brominating agent) crystallises from H2O with m 180-185o. [Paris et al. Org Synth Coll Vol IV 496 1963, Beilstein 21 H 382, 21 I 331, 21 II 307, 21 III/IV 4582.]
グルタルイミド 上流と下流の製品情報
原材料
準備製品