波 谱 学 杂 志 第 17 卷第 1 期 2000 年 2 月 Chinese Journal of Magnetic Resonance Vol. 17 No. 1 Feb. 2000 文章编号 :1000 4556 ( 2000) 01217222 NMR STUDY ON THE REACTION OF REARRANGEMENT OF 17 β 2H YD R OX Y 2 7 α 2METHYL 2 19 2N OR 2 17 2 α 2PREGN 2 5( 10 ) 2EN 2 20Y N 2 3 2 ONE XU Hao 2 , L IU Xuehui 1 and CUI Yuxin 1 3( 1 National Laboratory of Natural and Biomimetic Drugs , Medical and Healthy Analysis Center , Beijing Medical University , Beijing 100083 ) ( 2 C olleg e of Chem istr y an d Molecu lar Eng ineering , Peking U niv ersity , Beijing 100871 ) ZHAO Min and S HEN Jiaxiang (Be ijing Jica i Med ica l Institute , Be ijing 100083 ) Abstract When being put into CDCl 3 ( s lightly acidic condition ), t he doub le b ond of ster oid dru g ( L IVIA L ) wi ll rearrange 24 h ours. This paper shows that t he 2D NM R techniq ues were succ ess ful 2 ly performed to determine t he struc tures of c ompound 1 and compound 2 . All of the 1 H and 13 C NN R chemic al shi ft s were ass igned by 1D and 2D N MR . Their stere ochemis t ry was discuss ed , to o. The struc tures of c omp ound 1 and compound 2 were s imulated by compute r m ole cul ar m odel ing. Their results agree with those of 2D NMR. K ey w ords Steroid , Rea cti on of Rearrangement , NMR 4 3 O 2 1 10 5 A 6 9 8 7 Me 22 B 11 12 C 18 13 D 17 OH C ≡CH 20 21 14 15 16 O Me O H C ≡CH 1 2 1 INTRODUCTION The compound 1 [1 ] , 172 β 2hydroxy 27 α 2methyl 219 2n o r 217 α 2 pregn 25 ( 10) 2en220yn 23 2 one is t he e ffective ingred ient of ster oid drug L IV I AL(or ca lled Tibol o ne ) , which can stabilize the
