摘要
2-烯丙基-4-羟基-2-环戊烯酮是合成前列腺素PGI1的关键中间体,具有重要的药用价值。该文用改进的方法合成了(±)-2-烯丙基-4-羟基-2-环戊烯酮,总收率27%,用脂肪酶对其进行动力学拆分,得到光学纯的(S)-环戊烯酮醇。结果表明,猪胰脂肪酶具有最佳的拆分效果。以乙酸乙烯酯同时作为溶剂和酰化供体,在25℃,m(酶)∶m(醇)=1.5∶1条件下,环戊烯酮醇的转化率为50.2%,(S)-醇的ee值为58.9%。采用同样条件进行二次酶动力学拆分,得到ee值>98%的手性烯酮醇,总拆分收率23%。
2-Allyl-4-hydroxy-2-eyelopentenone is a key intermediate for the synthesis of prostaglandin PGI1. The racemic 2-allyl-4-hydroxy-2-cyclopentenone was synthesized by an improved method in total yield of 27%. Optical pure （S）- cyclopentenone was obtained by kinetic resolution with lipase. The best resolution performance was shown with porcine pancreas lipase. The enantiomer excess of the cyclopentenone was 58.9% with vinyl acetate as solvent and acyl donator at 25℃ and m（ lipase）/m （cyclopentenone） 1.5, while the conversion of cyclopentenone was 50. 2%. The chiral cyclopentenone of 〉 98% enantiomer excess was obtained by a second time enzymic kinetic resolution under the same conditions,and the total yield of the enzymic resolution was 23%.
出处
《精细化工》
EI
CAS
CSCD
北大核心
2007年第3期290-292,303,共4页
Fine Chemicals
关键词
脂肪酶
拆分
环戊烯酮
前列腺素
lipase
resolution
cyclopentenone
prostaglandin
