Synthetic approaches to physiologically active polycyclic compounds: IV. X-ray diffraction study of isomeric amino acid derivatives of adamantane

被引：4

作者：

Zefirova, ON

Nurieva, EV

Chekhlov, AN

Aldoshin, SM

Nesterenko, PN

Zyk, NV

Zefirov, NS

机构：

[1] Moscow MV Lomonosov State Univ, Fac Chem, Moscow 119992, Russia

[2] Russian Acad Sci, Inst Chem Phys Problems, Moscow, Russia

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 40卷 / 04期

基金：

俄罗斯基础研究基金会;

关键词：

D O I：

10.1023/B:RUJO.0000036070.38148.e7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

According to the X-ray diffraction data, the major isomer of 1-(N-benzoyl-beta-alanyloxy)-4-benzoyl-oxyadamantane obtained by esterification of beta-alanine with 5-hydroxyadamantan-2-one and subsequent benzoylation has trans configuration. The trans-cis isomer ratio is 2:1. A similar isomer ratio was found for 1-(N-benzoylphenylisoseryloxy)-4-benzoyloxyadamantane synthesized by an analogous method.

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页码：502 / 505

页数：4

相关论文

共 10 条

[1] Synthetic approaches to physiologically active polycyclic compounds: III. Ritter reaction with ketones of the adamantane and oxahomoadamantane series [J].

Averina, NV ;

Borisova, GS ;

Zefirova, ON ;

Selyunina, EV ;

Zyk, NV ;

Zefirov, NS .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (04) :497-501

[2] FACE SELECTIVITY IN THE PATERNO-BUCHI REACTIONS OF METHACRYLONITRILE TO 5-SUBSTITUTED ADAMANTAN-2-ONES [J].

CHUNG, WS ;

LIU, YD ;

WANG, NJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1995, (03) :581-586

[3] C-13 NUCLEAR MAGNETIC-RESONANCE SPECTRA .1. MONOSUBSTITUTED ADAMANTANES AND ADAMANTANONES [J].

DUDDECK, H .

ORGANIC MAGNETIC RESONANCE, 1975, 7 (04) :151-153

[4] PI ROUTE TO SUBSTITUTED ADAMANTANES .1. [J].

FAULKNER, D ;

MCKERVEY, MA .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (23) :3906-+

[5]

HENKEL JG, 1983, J ORG CHEM, V48, P3657, DOI 10.1021/jo00169a008

[6]

NESTERENKO PN, 1991, ZH FIZ KHIM+, V65, P2671

[7]

Sheldrick G.M., 1997, SHELX 97 MANUAL

[8] DEFINITIVE IDENTIFICATION OF THE C-5 AND C-7 NMR SIGNALS OF ADAMANTAN-2-OL [J].

SRIVASTAVA, S ;

CHEUNG, CK ;

LENOBLE, WJ .

MAGNETIC RESONANCE IN CHEMISTRY, 1985, 23 (04) :232-235

[9] Synthetic approach to preparation of polycyclic compounds possessing physiological activity: I. Synthesis of 1,4-disubstituted adamantanes with amino acid fragment [J].

Zefirova, ON ;

Selyunina, EV ;

Averina, NV ;

Zyk, NV ;

Zefirov, NS .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 38 (08) :1125-1129

[10] Synthetic approach to the synthesis of physiologically active compounds:: II.: Synthesis of disubstituted adamantanes containing an N-benzoylphenylisoserine fragment [J].

Zefirova, ON ;

Selyunina, EV ;

Nuriev, VN ;

Zyk, NV ;

Zefirov, NS .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 39 (06) :831-833