SYNTHESIS AND MOLECULAR-STRUCTURE OF STABLE DERIVATIVES OF (E)-DEHYDROPHENYLALANINE AND (Z)-DEHYDROPHENYLALANINE

被引:17
作者
EASTON, CJ
HUTTON, CA
ROSELT, PD
TIEKINK, ERT
机构
[1] Departments of Chemistry, University of Adelaide
关键词
D O I
10.1071/CH9910687
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Bromination of the phenylalanine derivative (1) affords the bromides (2) and (3), which react by stereospecific anti-elimination to give the isomeric pair of stable dehydrophenylalanine derivatives (4) and (5). The molecular structures of (4) and (5), which have been determined by X-ray crystallographic analysis, correlate with their lack of interconversion and the unusual stability of (5).
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页码:687 / 694
页数:8
相关论文
共 27 条
[1]   STRUCTURE OF ETHYL "(Z)-N-ACETYLDEHYDROPHENYLALANINATE, C13H15NO3 [J].
AJO, D ;
BUSETTI, V ;
OTTENHEIJM, HCJ ;
PLATE, R .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1984, 40 (FEB) :324-327
[2]   CONFORMATIONAL FLEXIBILITY OF THE DEHYDROALANINE DERIVATIVES - MOLECULAR AND ELECTRONIC-STRUCTURE OF (Z)-N-ACETYLDEHYDROPHENYLALANINE [J].
AJO, D ;
CASARIN, M ;
GRANOZZI, G ;
BUSETTI, V .
TETRAHEDRON, 1981, 37 (20) :3507-3512
[3]   CONFORMATIONAL FLEXIBILITY OF DEHYDROALANINE DERIVATIVES - CRYSTAL AND MOLECULAR-STRUCTURE OF 2-N-ACETYLDEHYDROPHENYLALANYL-L-PROLINE [J].
AJO, D ;
BUSETTI, V ;
GRANOZZI, G .
TETRAHEDRON, 1982, 38 (22) :3329-3334
[4]   CRYSTAL STRUCTURE OF STABLE ISOMER OF ALPHA-BENZAMIDOCINNAMIC ACID - INFLUENCE OF CIS-TRANS-ISOMERISM ON KINETICS OF HYDROLYSIS OF PRODUCTS OF INTERACTION OF ALPHA-CHYMOTRYPSIN WITH ISOMERIC 4-BENZYLIDENE-2-PHENYL DELTA2-OXAZOLIN-5-ONES [J].
BROCKLEH.K ;
BYWATER, RP ;
PALMER, RA ;
PATRICK, R .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (12) :632-&
[5]  
BROCKLEHURST K, 1968, J CHEM SOC CHEM COMM, P884
[6]   STRUCTURE OF (Z)-N-ACETYL-ALPHA,BETA-DIDEHYDROPHENYLALANYL-L-ALANINE HYDRATE, C14H16N2O41/3H2O [J].
BUSETTI, V ;
AJO, D ;
CASARIN, M .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1984, 40 (JUL) :1245-1248
[7]   STRUCTURE OF (Z)-N-BENZOYL-ALPHA,BETA-DEHYDROLEUCINE [J].
BUSETTI, V ;
AJO, D ;
VITTADINI, A .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1986, 42 :1178-1181
[8]   ACTION OF DIAZOMETHANE ON METHYL (Z(OR E))-2-(ACYLAMINO)CINNAMATES - A NEW ROUTE TO METHYL (Z)-2-(ACYLAMINO)-3-METHYLCINNAMATES [J].
CATIVIELA, C ;
DEVILLEGAS, MDD ;
MAYORAL, JA ;
MELENDEZ, E .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (17) :3167-3169
[9]   SYNTHESIS OF NOVEL CROSS-LINKED AMINO-ACID DERIVATIVES [J].
EASTON, CJ ;
PETERS, SC .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (01) :87-97
[10]   BROMINATION OF N-PHTHALOYLAMINO ACID-DERIVATIVES [J].
EASTON, CJ ;
TAN, EW ;
HAY, MP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (07) :385-386