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1.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Korolyova M. A., Vigorov A. Yu., Krasnov V. P.
Заглавие : Theoretical study of the stereoselectivity in the reaction of 4-haloglutamic acid derivatives with arylamines
Место публикации : Russian chemical bulletin. - 2022. - Vol. 71, № 6. - С. 1135-1142
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Diastereoselective nucleophilic substitution reaction of halogen in dimethyl (2S,4RS)-4-bromo- and 4-iodo-N-phthaloylglutamates with arylamines was studied within the framework of the electron density functional theory. According to calculations, the stereoselectivity of the substitution reaction with respect to (2S,4S)-isomers of 4-arylamino derivatives is determined not only by the steric hindrances in the transition state leading to minor (2S,4R)-diastereomers, but also by the stabilization of the corresponding initial reagents complex due to stacking interactions of the aromatic fragments of reagents.
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2.

Вид документа :
Шифр издания :
Автор(ы) : Goryaeva M. V., Kushch S. O., Burgart Y. V., Saloutin V. I.
Заглавие : Synthesis of heterocycles on the base of trifluoroacetoacetate, methyl ketones and diamines
Место публикации : AIP conference proceedings. - 2022. - Vol. 2390. - Ст.020021
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): trifluoroacetoacetate--methyl ketones--diamines
Аннотация: The three-component cyclization of ethyl trifluoroacetoacetate and 2-aminoethanol with 3-methyl-2-butanone in hexahydrooxazolo[3,2-a]pyridin-5-ones was studied. The reaction leads to a mixture of cis- and trans- diastereomers, the structures of which were investigated using 1H, 19F, 13C NMR spectroscopy.
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3.

Вид документа : Статья из журнала
Шифр издания : 54/S 98
Автор(ы) : Krasnov V. P., Vigorov A. Yu., Nizova I. A., Matveeva T. V., Grishakov A. N., Bazhov I. V., Tumashov A. A., Ezhikova M. A., Kodess M. I.
Заглавие : Synthesis of 4-amino derivatives of 5-oxoproline
Место публикации : European Journal of Organic Chemistry. - 2007. - № 25. - С. 4257-4266
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The possibility of obtaining the stereoisomeric derivatives of 5-oxoproline and glutamic acid with a tertiary amino group at C-4, using the nucleophilic substitution of bromine in dimethyl (2S,4RS)-4-bromo-N-phthaloylglutamate with secondary amines followed by resolution of diastereomers and removal of protecting groups has been studied. We have shown that the reaction with arylamines results in optically pure 5-oxoproline derivatives in high yields. In the case of more basic amines, the reaction is accompanied by racemization, and the target products can be isolated only as diastereomeric racemates.
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4.

Вид документа : Статья из журнала
Шифр издания : Г/S 83
Автор(ы) : Musiyak V. V. , Nizova I. A., Chulakov E. N., Sadretdinova L. S., Tumashov A. A., Levit G. L., Krasnov V. P.
Заглавие : Stereochemical aspects in the synthesis of novel N-(purin-6-yl)dipeptides as potential antimycobacterial agents
Место публикации : Amino Acids. - 2021. - Vol. 53, № 3. - С. 407-415
ББК : Г
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): dipeptides--racemization--purine--coupling--nucleophilic substitution--antimycobacterial activity
Аннотация: The synthesis of purine conjugates with natural amino acids is one of the promising directions in search for novel therapeutic agents, including antimycobacterial agents. The purpose of this study was to synthesize N-(purin-6-yl)dipeptides containing the terminal fragment of (S)-glutamic acid. To obtain the target compounds, two synthetic routes were tested. The first of them is based on coupling of N-(purin-6-yl)-(S)-amino acids to dimethyl (S)-glutamate in the presence of carbodiimide coupling agent followed by the removal of ester groups. However, it turned out that this coupling process was accompanied by racemization of the chiral center of N-(purin-6-yl)-α-amino acids and in all cases led to mixtures of (S,S)- and (R,S)diastereomers (6:4). Individual (S,S)-diastereomers were obtained using an alternative approach based on the nucleophilic substitution of chlorine in 6-chloropurine or 2-amino-6-chloropurine with corresponding dipeptides as nucleophiles. The enantiomeric purity of the target compounds was confirmed by chiral HPLC. To test the assumption that racemization of the chiral center of N-(purin-6-yl)-α-amino acids occurs with the participation of nitrogen atoms of the imidazole ring via the stage of formation of a chirally labile intermediate, we obtained such structural analogs of N-(purin-6-yl)-(S)-alanine as N-(9-benzylpurin-6-yl)-(S)-alanine and N-(7-deazapurin-6-yl)-(S)-alanine. It was found that coupling of these compounds to dimethyl (S)-glutamate was also accompanied by racemization. This indicates that the imidazole fragment does not play a crucial role in this process. When testing the antimycobacterial activity of some of the obtained compounds, conjugates with moderate activity against the laboratory Mycobacterium tuberculosis H37Rv strain (MIC 3.1–6.25 μg/mL) were identified.
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5.

Вид документа : Статья из журнала
Шифр издания : 54/R 35
Автор(ы) : Platonova A.Yu., Deeva E. V., Zimovets O. A., Shatunova D. V., Eltsov O. S., Slepukhin P. A., Gluchareva T.V., Morzherin Yu. Yu.
Заглавие : Regioselective reaction of ortho-piperidinobenzaldehydes with pyrazolone
Место публикации : Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №5. - С. 961-964
Примечания : Bibliogr. : p. 964 (20 ref.)
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): tert-amino effect--pyrazolone--diastereomers
Аннотация: Cyclization of 2 (4 R piperidino)benzaldehydes with 5 methyl 2 phenyl 2,4 dihydro 3H pyrazol 3 one proceeding via tert amino effect mechanism is stereoselective. Relative configu ration of (3R*,4aS*,5R*) 2,3,4,4a,5,6 hexahydro 1H benzo[c]quinolizine was established on the base of NMR spectroscopy data and X ray analysis
\\\\expert2\\NBO\\Russian Chemical Bulletin\\2011, 60 (5), 961-964.pdf
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6.

Вид документа : Статья из журнала
Шифр издания : 54/R 30
Автор(ы) : Korotaev V.Yu., Sosnovskikh V. Ya., Kutyashev I. B., Kodess M. I.
Заглавие : Reactions of 3-nitro-2-trihalomethyl-2H-chromenes with S-and N-nucleophiles. Synthesis and stereochemistry of 2,3,4-trisubstituted chromanes [Electronic resource]
Место публикации : Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2006. - Vol. 55, № 2. - С. 317-330
Систем. требования: http://www.springerlink.com/content/x633528n25154252/fulltext.pdf
Примечания : 26.10.2011 г.
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The reactions of 3-nitro-2-trifluoromethyl-and 3-nitro-2-trichloromethyl-2H-chromenes with thiols and aromatic amines proceed via the nucleophilic addition type to the activated double bond to form 2,3,4-trisubstituted chromanes in high yields. The stereoisomeric compositions and structures of the diastereomers were determined by 1H, 19F NMR and 2D NOESY spectroscopies and X-ray diffraction analysis
\\\\Expert2\\nbo\\Russian Chemical Bulletin\\2006, 55 (2), 317.pdf
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7.

Вид документа : Статья из журнала
Шифр издания : 54/R 30
Автор(ы) : Shchepin V. V., Korzun A.E., Vakhrin M.I., Silaichev P. S., Ezhikova M. A., Kodess M. I.
Заглавие : Reaction of alkyl 5,5-dimethyl-2-oxo-2,5-dihydrofuran-3-carboxylates with zinc enolates prepared from zinc and 1-arul-2-bromo-2-phenylethanones, 2 bromoindanone, and 2-bromo-6-methyltetralone [Electronic resource]
Место публикации : Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2006. - Vol. 42, № 8. - С. 1169-1173
Систем. требования: http://www.springerlink.com/content/rq9rw6g47x119818/fulltext.pdf
Примечания : 1.11.2011 г.
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Alkyl 5,5-dimethyl-2-oxo-2,5-dihydrofuran-3-carboxylates react with zinc enolates prepared from 1-aryl-2-bromo-2-phenylethanones, 2-bromo indanone, 2-bromo-6-methyltetralone and zinc with formation of ethyl 4-(2-aryl-2-oxo-1-phenyl-ethyl)-5,5-dimethyl-2-oxotetrahydrofuran-3-carboxylates, alkyl 5,5-dimethyl-2-oxo-4-(1-oxoindan-2-yl)tetrahydrofuran-3-carboxylates, and ethyl 5,5-dimethyl-4-(6-methyl-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-2-oxotetrahydrofuran-3-carboxylates respectively, mainly as single diastereomers
\\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2006, 42 (8), 1169.pdf
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8.

Вид документа : Статья из журнала
Шифр издания : 54/N 91
Автор(ы) : Krasnov V. P., Koroleva M. A., Evstigneeva N. G., Nizova I. A.
Заглавие : Nucleophilic-substitution of halogen in 4-halogenated derivatives of glutamic-acid. 2. Structural effects of arylamine as nucleophile [Electronic resource]
Место публикации : Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1995. - Vol. 44, № 4. - С. 635-638
Систем. требования: http://www.springerlink.com/content/r47174047415j4r5/fulltext.pdf
Примечания : 27.10.2011 г.
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Kinetics of nucleophilic substitution of halogen in diastereomeric dimethyl 4-bromo- and 4-iodoglutamates with ortho-, meta-, and para-substituted anilines was studied by HPLC. The threo-diastereomers of the halogenated derivatives react 3-5 times faster than the erythro ones. The structure of the transition state is discussed.
\\\\Expert2\\nbo\\Russian Chemical Bulletin\\1995, 44 (4), 635.pdf
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9.

Вид документа : Статья из журнала
Шифр издания : 54/K 81
Автор(ы) : Krasnov V. P., Koroleva M. A.
Заглавие : Nucleophilic-substitution of halogen in 4-halogenated derivatives of glutamic-acid. 1. Solvent effect [Electronic resource]
Место публикации : Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1995. - Vol. 44, № 4. - С. 631-634
Систем. требования: http://www.springerlink.com/content/k9027577p356012q/fulltext.pdf
Примечания : 27.10.2011 г.
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The reaction of nucleophilic substitution of bromine by p-anisidine in dimethyl (2S,4S)- and (2S,4R)-N-phthaloyl-4-bromoglutamates proceeds according to the S(N)2 mechanism. The relative reactivity of diastereomers in various solvents was studied.
\\\\Expert2\\nbo\\Russian Chemical Bulletin\\1995, 44 (4), 631.pdf
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10.

Вид документа : Статья из журнала
Шифр издания : 54/K 81
Автор(ы) : Krasnov V. P., Koroleva M. A., Rusinov G. L.
Заглавие : Nucleophilic substitution of halogen in 4-halo derivatives of glutamic acid 3. High pressure effect on the stereochemical result of the reaction [Electronic resource]
Место публикации : Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1996. - Vol. 45, № 3. - С. 543-544
Систем. требования: http://www.springerlink.com/content/l4q073g857048057/fulltext.pdf
Примечания : 27.10.2011 г.
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Reactions of diastereomeric dialkyl N-phthaloyl-4-haloglutamates withpara-anisidine were studied at high pressure, and an additional confirmation of the exactS N2 mechanism of the reactions was obtained. Quantitative parameters of the relative reactivity of the diastereomers were found in various solvents, which made it possible to perform the desired synthesis of products of diastereomeric substitution. kg]Key words kw]glutamic acid kw]diastereoselectivity kw]nucleophilic substitution kw]reaction rate constant kw]high pressure.
\\\\Expert2\\nbo\\Russian Chemical Bulletin\\1996, 45 (3), 543.pdf
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