采用Chirex (S)-LEU & (S)-NEA、Chiralcel OD-H和Chiralpak AD-H手性色谱柱直接拆分了2′-羟基-1,1′-联萘-2-苯甲酸酯(HBNB)、1,1′-联萘-2,2′-二苯甲酸酯(BNDB)和2′-甲氧基-1,1′-联萘-2-苯甲酸酯(MBNB)对映体.分别考察了流动相组成、柱温和化合物结构对手性分离的影响.结果表明:3对联萘二酚苯甲酸酯对映体在Chiralpak AD-H柱上的拆分效果最好.当采用正己烷/异丙醇(40/60,v/v)为流动相时,HBNB、BNDB和MBNB对映体的分离因子(α)和分离度(R_s)分别为1.76、1.74、1.40和6.47、7.81、4.75.对比联萘二酚(BN)的分离,从联萘分子中 2-位取代基、对映体出峰顺序和热力学参数等方面探讨了相关手性分离机理.
The enantioseparations of 2′-hydroxy-1,1′-binaphthyl-2-yl benzoate (HBNB),1,1′-binaphthyl-2,2′-diyl dibenzoate (BNDB) and 2′-methoxy-1,1′-binaphthyl-2-yl benzoate (MBNB) were studied on Chirex (S)-LEU & (S)-NEA,cellulose tris(3,5-dimethylphenylcarbamate) (Chiralcel OD-H) and amylose tris(3,5-dimethylphenyl- carbamate) (Chiralpak AD-H) columns,respectively,using high performance liquid chromatography.The effects of mobile phase,column temperature and compound structures on the enantioseparations were discussed.The Chiralpak AD-H exhibited stronger capability of enantioseparation in comparison with those of Chirex (S)-LEU & (S)-NEA and Chiralcel OD-H for 1,1′-bi-2-naphthol benzoates.When using the mobile phase of n-hexane/2-propanol (40/60,v/v),the chiral selectivities of HBNB,BNDB and MBNB were 1.76,1.74,and 1.40,respectively.Moreover,in comparison with that of 1,1′-bi-2-naphthol (BN),the mechanisms of the enantioseparation of 1,1′-bi-2-naphthol benzoates,related to the substituted groups at 2-position,the elution orders and thermodynamic parameters were also discussed.
参考文献
| [1] | Brunel J M.Chem Rev,2007,107:1 |
| [2] | Cui X,Fu F M,Zhu J,et al.Chinese Journal of Analytical Chemistry (崔欣,付芳敏,朱槿,等.分析化学),2002,30(12):1494 |
| [3] | Liu X D,Ding J Y,Gao L X.Chinese Journal of Chromatography (刘旭东,丁金英,高连勋.色谱),2005,23(2):146 |
| [4] | Beer G,Rurack K,Daub J.Chem Commun,2001(12):1138 |
| [5] | Guo Q S,Lu Y N,Liu B,et al.J Organomet Chem,2006,691(6):1282 |
| [6] | Matsubara J,Otsubo K,Kawano Y,et al.Heterocycles,2000,52(1):81 |
| [7] | Ruan Y P,Ao X P,Chen A Q,et al.Journal of Xiamen University:Natural Science (阮源萍,敖小平,陈安齐,等.厦门大学学报:自然科学版),2002,41(2):217 |
| [8] | Weng W,Fan W J,Zhu Q,et al.Journal of Instrumental Analysis (翁文,范文静,朱钦,等.分析测试学报),2008,27(7):721 |
| [9] | Nakajima M,Miyoshi I,Kanayama K,et al.J Org Chem,1999,64:2264 |
| [10] | Li C P,Yang H L,Li J H,et al.Chinese Journal of Analytical Chemistry (李成平,杨会来,李景华,等.分析化学),2006,34(8):1133 |
| [11] | Loukotková L,Rambousková M,Bosáková Z,et al.Chirality,2008,20:900 |
| [12] | Meca L,(R)eha D,Havlas Z.J Org Chem,2003,68:5677 |
| [13] | Li L H,Liu L,Luo Y,et al.Chinese Journal of Chromatography (李丽虹,刘岚,罗勇,等.色谱),2006,24(6):574 |
| [14] | Mofaddel N,Krajian H,Villemin D,et al.J Chromatogr A,2008,1211:142 |
| [15] | Wang T,Chen Y W,Vailaya A.J Chromatogr A,2000,902:345 |
| [16] | Helmy R,Wang T.J Sep Sci,2005,28:189 |
| [17] | Wang F,O'Brien T,Dowling T,et al.J Chromatogr A,2002,958:69 |
| [18] | Weng W,Yao B X,Chen X Q,et al.Progress in Chemistry (翁文,姚碧霞,陈秀琴,等.化学进展),2006,18(7/8):1056 |
- 下载量()
- 访问量()
- 您的评分：
-
10%
-
20%
-
30%
-
40%
-
50%