Synthesis, Molecular and Crystal Structure of Ethyl 5-Cyano-2-(Dicyanomethyl)-2-Methyl-4-Oxo-6-Phenyl-3-Azabicyclo[3.1.0]Hexane-1-Carboxylate

被引:6
作者
Ismiyev, A. I. [1 ]
Potekhin, K. A. [2 ]
Maleev, A. V. [2 ]
Askerov, R. K. [1 ]
Maharramov, A. M. [1 ]
机构
[1] Baku State Univ, Baku, Azerbaijan
[2] Vladimir State Univ, Vladimir, Russia
关键词
multicomponent cascade condensation; malonodinitrile; 3-azabicyclo[3; 1; 0]hexane; atom-atom potentials; molecular agglomerates; molecular salts; hydrogen bond; ONE-POT SYNTHESIS; MALONATE; MALONONITRILE; ALDEHYDE;
D O I
10.1134/S0022476619030181
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
As a result of triple condensation of malonodinitrile with benzaldehyde and ethyl 2-chloro-3-oxobutanoate a compound with 3-azabicyclo[3.1.0]hexane framework is formed whose crystal structure is determined by X-ray crystallography. In the crystal structure a layered character of the molecular packing is found. Molecules are linked in the layer by H bonds of N-H...O=C and C-H...O=C types and also a large number of atom-atom contacts whose energy corresponds to potential wells.
引用
收藏
页码:485 / 493
页数:9
相关论文
共 20 条
[1]  
[Anonymous], CAMBR STRUCT DAT VER
[2]   Structure, synthesis, and chemical reactions of fluorinated cyclopropanes and cyclopropenes [J].
Dolbier, WR ;
Battiste, MA .
CHEMICAL REVIEWS, 2003, 103 (04) :1071-1098
[3]   Synthesis of cyclopropane containing natural products [J].
Donaldson, WA .
TETRAHEDRON, 2001, 57 (41) :8589-8627
[4]   Cyclopropanation Strategies in Recent Total Syntheses [J].
Ebner, Christian ;
Carreira, Erick M. .
CHEMICAL REVIEWS, 2017, 117 (18) :11651-11679
[5]   Electrochemical synthesis of cyclopropanes [J].
Elinson, M. N. ;
Dorofeeva, E. O. ;
Vereshchagin, A. N. ;
Nikishin, G. I. .
RUSSIAN CHEMICAL REVIEWS, 2015, 84 (05) :485-497
[6]   Electrocatalytic multicomponent cyclization of an aldehyde, malononitrile and a malonate into 3-substituted-2,2-dicyanocyclopropane-1,1-dicarboxylate - the first one-pot synthesis of a cyclopropane ring from three different molecules [J].
Elinson, Michail N. ;
Feducovich, Sergey K. ;
Vereshchagin, Anatolii N. ;
Gorbunov, Sergey V. ;
Belyakov, Pavel A. ;
Nikishin, Gennady I. .
TETRAHEDRON LETTERS, 2006, 47 (51) :9129-9133
[7]   Stereoselective electrocatalytic transformation of arylidene- or alkylidenemalononitriles and malonate into alkyl (1R,5R,6R)*6-substituted 5-cyano-4,4-dialkoxy-2-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylates [J].
Elinson, MN ;
Feducovich, SK ;
Starikova, ZA ;
Vereshchagin, AN ;
Gorbunov, SV ;
Nikishin, GI .
TETRAHEDRON LETTERS, 2005, 46 (37) :6389-6393
[8]   Methods of assembling 3-azabicyclo[3.1.0]hexane skeleton (microreview) [J].
Ershov, Oleg V. ;
Bardasov, Ivan N. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (07) :447-449
[9]   GEOMETRY OF THE INTERMOLECULAR X-H...Y (X, Y=N, O) HYDROGEN-BOND AND THE CALIBRATION OF EMPIRICAL HYDROGEN-BOND POTENTIALS [J].
GAVEZZOTTI, A ;
FILIPPINI, G .
JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (18) :4831-4837
[10]   ARE CRYSTAL-STRUCTURES PREDICTABLE [J].
GAVEZZOTTI, A .
ACCOUNTS OF CHEMICAL RESEARCH, 1994, 27 (10) :309-314