消旋3-氨基-1,3,4,5-四氢-2H-1-苯并氮杂卓-2-酮的合成及其催化结晶诱导法手性拆分  

Synthesis of Racemic 3-Amino-1,3,4,5-tetrahydro-1H-1-benzazepin-2-one and Chiral Resolution through Catalyed Crystallization-induced Method

作　　者：蒋薇薇[1] 张雄[1] 王莉[1] 

机构地区：[1]浙江外国语学院理工学院,浙江杭州310012

出　　处：《浙江外国语学院学报》2011年第5期107-112,共6页Journal of Zhejiang International Studies University

基　　金：浙江省大学生科技创新项目(2008R40G1120002)

摘　　要：合成了3-氨基-1,3,4,5-四氢-2H-1-苯并氮杂卓-2-酮的消旋体,对所合成到的消旋体化合物进行了手性拆分实验研究,找到了以焦谷氨酸为手性拆分结晶试剂,5-硝基水杨醛为不对称结晶诱导催化剂,乙醇-水溶液为溶剂的实验条件.反应条件温和,所得手性化合物的光学纯度高,其中R(+)-3-氨基-1,3,4,5-四氢-2H-1-苯并氮杂卓-2-酮的拆分收率为74%,[!]D+446"(c=1.0,CH3OH);S(-)-3-氨基-1,3,4,5-四氢-2H-1-苯并氮杂卓-2-酮的拆分收率为71%,[!]D-443"(c=1.0,CH3OH).The racemic 3-amino-1,3,4,5-tetrahydro-1H-1-benzazepin-2-one was synthesized.The chiral resolution of the racemic had been studied.The experimental conditions were found： D/L-Pyroglutamic acid as the chiral crystallization reagent,5-nitro-salicylaldehyde as the crystallization-induced catalyst and the ethanol-water solution as the solvent.The reaction conditions were mild.The optical purified products were obtained.The resolution yield for the 3（R）-amino-1,3,4,5-tetrahydro-1H-1-benzazepin-2-one was 78% with [ɑ]D＋449°（c=1.0,CH3OH） and 3（S）-amino-1,3,4,5-tetrahydro-1H-1-benzazepin-2-one was 71% with [ɑ]D-444°（c=1.0,CH3OH）.

关 键 词：3-氨基-1 3 4 5-四氢-2H-1-苯并氮杂卓-2-酮 催化 结晶诱导 手性拆分 

分 类 号：TQ463.55[化学工程—制药化工]