Synthesis, crystal structure, and DFT study of methyl 3-fluoro-
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate and
(2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)
(pyrrolidin-1-yl)methanone
compounds
- Received: December, 18, 2020
- Revised: February, 2, 2021
- Accepted for publication: February, 4, 2021
- DOI 10.26902/JSC_id74415
- Views: 153
1 Guizhou Engineering Laboratory for Synthetic Drugs, Guiyang, P. R. China
2 School of Chemistry and Chemical Engineering, Guizhou University, Guiyang, P. R. China
3 School of Pharmaceutical Sciences, Guizhou University, Guiyang, P. R. China
4 Department of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang, P. R. China
5 Key Laboratory of Guizhou for Fermentation Engineering and Biomedicine, Guiyang, P. R. China
Methyl 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate and (2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)(pyrrolidin-1-yl)methanone are boric acid ester intermediates with benzene rings. In this paper, the title compounds are obtained by a three-step substitution reaction. The structures of the compounds are confirmed by FTIR, 1H and 13C NMR
spectroscopy, and mass spectrometry. At the same time, single crystals of the
title compounds are measured by X-ray diffraction and subjected to
crystallographic and conformational analyses. The molecular structures are
further calculated using density functional theory (DFT) and, which were
compared with the X-ray diffraction value. The results of the conformational
analysis indicate that the molecular structures optimized by DFT are consistent
with the crystal structures determined by single crystal X-ray diffraction. In
addition, the molecular electrostatic potential and frontier molecular orbitals
of the title compounds are further investigated by DFT, and some
physicochemical properties of the compounds are revealed.
Keywords: 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl, synthesis, X-ray diffraction, DFT
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Импакт-фактор 2023 1.2 |
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Срок опубликования 4 мес |
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