Synthesis and Properties of (+)-Ketopinic and (–)-Camphanic Acids Esters Bearing a Nitrogen-Containing Heterocycle

Synthesis and Properties of (+)-Ketopinic and (–)-Camphanic Acids Esters Bearing a Nitrogen-Containing Heterocycle Научная публикация

Журнал

Russian Journal of General Chemistry
ISSN: 1070-3632 , E-ISSN: 1608-3350

Вых. Данные

Год: 2023, Том: 93, Номер: 12, Страницы: 3062-3073 Страниц : 12 DOI: 10.1134/s1070363223120058

Авторы

Sokolova A.S. ¹ , Yarovaya O.I. ¹ , Kuzminykh L.V. ¹ , Ilyina M.G. ² , Borisevich S.S. ² , Esaulkova Ya.L. ³ , Zarubaev V.V. ³ , Salakhutdinov N.F. ¹

Организации

1	Новосибирский институт органической химии им. Н.Н. Ворожцова СО РАН
2	Уфимский Институт химии Российской академии наук
3	Федеральное бюджетное учреждение науки Санкт-Петербургский научно-исследовательский институт эпидемиологии и микробиологии им. Пастера

Информация о финансировании (1)

Российский Научный Фонд

22-23-00618

A three-stage method was proposed for the synthesis of (1S)-(+)-camphor-10-sulfonic acid, (+)-ketopinic and (–)-camphanic acids esters containing a saturated nitrogen-containing heterocycle. It was found that (1S)-(+)-camphor-10-sulfonic acid esters undergo destruction with elimination of the sulfonic acid group in substitution reactions involving nitrogen-containing heterocycles. Esters of (+)-ketopinic and (–)-camphanic acids were formed during the proposed synthetic route, but undergo transesterification under column chromatography conditions. Quantum chemical calculations showed that the destruction of the ester bond in the case of (+)-ketopinic and (–)-camphanic acids requires less energy than the breaking of a similar bond in (–)-borneol esters. It was revealed that the internal bond strength index (IBSI) for the alkyl C–O bond in (–)-borneol esters is higher than in (+)-ketopinic and (–)-camphanic acid esters. Antiviral properties against the H1N1 influenza virus were studied for derivatives of (+)-ketopinic and (–)-camphanic acids.

Sokolova A.S. , Yarovaya O.I. , Kuzminykh L.V. , Ilyina M.G. , Borisevich S.S. , Esaulkova Y.L. , Zarubaev V.V. , Salakhutdinov N.F.
Synthesis and Properties of (+)-Ketopinic and (–)-Camphanic Acids Esters Bearing a Nitrogen-Containing Heterocycle
Russian Journal of General Chemistry. 2023. V.93. N12. P.3062-3073. DOI: 10.1134/s1070363223120058 WOS Scopus РИНЦ

Соколова А.С. , Яровая О.И. , Кузьминых Л.В. , Ильина М.Г. , Борисевич С.С. , Есаулкова Я.Л. , Зарубаев В.В. , Салахутдинов Н.Ф.
Синтез и свойства сложных эфиров (+)-кетопиновой и (-)-камфановой кислот, включающих азотсодержащий гетероцикл
Журнал общей химии (RUSS J GEN CHEM+). 2023. Т.93. №12. С.1854-1866. DOI: 10.31857/S0044460X23120053 РИНЦ

Поступила в редакцию:	12 нояб. 2023 г.
Принята к публикации:	15 нояб. 2023 г.
Опубликована online:	26 янв. 2024 г.

Web of science	WOS:001151114800014
Scopus	2-s2.0-85183407609
РИНЦ	64552454
OpenAlex	W4391266037