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目的获得1-[(苯甲酰氨基)甲基]-1,2,3,4-四氢异喹啉(BTIQ)的2种旋光异构体。方法以(±)BTIQ为原料,光学纯樟脑磺酸为拆分剂,在丙酮中对其进行反复拆分,比旋光度检测拆分产物。对BTIQ拆分所得产物进行水解,将水解所得产物1,2,3,4-四氢异喹啉(ATIQ)的比旋光度与文献报道值进行比较。结果经2次反复拆分后产物比旋光度不再发生变化,证明所得产物旋光纯度较高,所得到的(-)BTIQ异构体收率27.52%(按最高收率50%计算),比旋光度为-35.65°(CH2Cl2,C=0.5);(+)BTIQ收率31.55%(按最高收率50%计算),比旋光度为+35.17°(CH2Cl2,C=0.5)。BTIQ拆分后水解产物ATIQ的比旋光度与文献报道值一致。结论通过拆分法成功同时获得了(-)BTIQ和(+)BTIQ对映异构体,所得产物收率和光学纯度均较高,为一步开发高效低毒的手性抗血吸虫药吡喹酮及其他含有四氢异喹啉结构的手性药物奠定了基础。
Aim To obtain two optical isomers of 1 - [(benzoylamino) methyl] -1,2,3,4-tetrahydroisoquinoline (BTIQ). Methods (±) BTIQ as raw material, optical pure camphor sulfonic acid as a resolving agent, repeated resolution in acetone, the specific optical resolution of the product was resolved. The products obtained by the BTIQ resolution were hydrolyzed and the specific rotation of 1,2,3,4-tetrahydroisoquinoline (ATIQ) obtained from the hydrolysis was compared with that reported in the literature. The results showed that the specific rotation of the product after 2 times of repeated resolution did not change any more. The optical purity of the obtained product was proved to be high. The yield of (-) BTIQ isomer was 27.52% (calculated in the highest yield of 50%), The optical rotation was -35.65 ° (CH2Cl2, C = 0.5); (+) The BTIQ yield was 31.55% (calculated in the highest yield of 50%) and the specific rotation was + 35.17 ° (CH2Cl2, C = 0.5). The specific rotation of the ATIQ after the hydrolysis of BTIQ was consistent with that reported in the literature. Conclusion The enantiomers of (-) BTIQ and (+) BTIQ were successfully obtained simultaneously by the resolution method. The yield and optical purity of the obtained products were high. It is a good way to develop potent chiral anti-schistosome praziquantel And other containing tetrahydro-isoquinoline structure of chiral drugs laid the foundation.