Abstract
The nucleophilic addition reactions of tertiary phosphines and unsaturated carboxylic acids have led to the formation of mono- and dicarboxylate phosphabetaines containing an asymmetric carbon atom. The data of 1D and 2D NMR spectroscopy have revealed the presence of diastereotopic geminal protons of the CH2 group adjacent to the chiral center in the obtained compounds. The values of spin-spin coupling constants of the vicinal hydrogen atoms have coincided with the dihedral angles values (X-ray diffraction analysis data).
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REFERENCES
Cooney, C.A., Dave, A.A., and Wolff, G.L., J. Nutr., 2002, vol. 132, no. 8, p. 2393S. https://doi.org/10.1093/jn/132.8.2393s
Waterland, R.A. and Jirtle, R.L., Mol. Cell. Biol., 2003, vol. 23, no. 15, p. 5293. https://doi.org/10.1128/mcb.23.15.5293-5300.2003
Irfan, M. and Idris, A., Mater. Sci. Eng., 2015, vol. 56, p. 574. https://doi.org/10.1016/j.msec.2015.06.035
Mollahosseini, A., Abdelrasoulab, A., and Shoker, A., Mater. Today Chem., 2020, vol. 15, p. 1. https://doi.org/10.1016/j.mtchem.2019.100227
He, M., Gao, K., Zhou, L., Jiao, Z., Wu, M., Cao, J., You, X., Cai, Z., Su, Y., and Jiang, Z., Acta Biomater., 2016, vol. 40, p. 142. https://doi.org/10.1016/j.actbio.2016.03.038
Galkina, I., Tufatullin, A., Krivolapov, D., Bakhtiyarova, Y., Chubukaeva, D., Stakheev, V., Galkin, V., Cherkasov, R., Büchnerc, B., and Kataeva, O., CrystEngComm., 2014, vol. 16. P. 9010. https://doi.org/10.1039/c4ce01361a
Galkina, I., Romanov, S., Gerasimov, A., Bakhtiyarova, Yu., and Galkin, V., J. Organomet. Chem., 2020, vol. 910, p. 121131. https://doi.org/10.1016/j.jorganchem.2020.121131
Xu, D., Wei, H., Zhen, Y., Gao, Y., Li, R., Li, X., He, Y., Zhang, Z., and Xie, W., Org. Chem. Front., 2019, vol. 6, p. 1681. https://doi.org/10.1039/C9QO00304E
Il’in, A.V., Gubaev, A.F., Islamov, D.R. Islamov, K.R., and Galkin, V.I., Chem. Heterocycl. Compd., 2020, vol. 57, p. 175. https://doi.org/10.1007/s10593-021-02890-x
Il’in, A., Gubaev, A., Antonova, A., Khannanov, A., and Galkin, V., Synth. Commun., 2020, vol. 50, no. 21, p. 3287. https://doi.org/10.1080/00397911.2020.1799015
Tian, P., Xiao, H., Wang, L., Yu, Y., and Huang, Y., Tetrahedron Lett., 2019, vol. 60, p. 1015. https://doi.org/10.1016/j.tetlet.2019.03.015
Nedopekina, D.A., Gubaidullin, R.R., Odinokov, V.N., Maximchik, P.V., Zhivotovsky, B., Bel’skii, Y.P., Khazanov, V.A., Manuylova, A.V., Gogvadze, V., and Spivak, A.Yu., MedChemComm., 2017, vol. 8, no. 10, p. 1934. https://doi.org/10.1039/c7md00248c
Tsepaeva, O.V., Nemtarev, A.V., Salikhova, T.I., Abdullin, T.I., Grigor’eva, L.R., Khozyainova, S.A., and Mironov, V.F., Anti-Cancer Agents Med. Chem., 2020, vol. 20, p. 286. https://doi.org/10.2174/1871520619666191014153554
Galkina, I.V., Bakhtiyarova, Yu.V., Shulaeva, M.P., Pozdeev, O.K., Egorova, S.N., Cherkasov, R.A., and Galkin, V.I., J. Chem., 2013, vol. 2013, p. 1. https://doi.org/10.1155/2013/302937
Bakhtiyarova, Yu.V., Minnullin, R.R., Galkina, I.V., Cherkasov, R.A., and Galkin, V.I., Russ. J. Gen. Chem., 2015, vol. 85, no. 9, p. 2037. https://doi.org/10.1134/S1070363215090042
Bakhtiyarova, Y.V., Aksunova, A.F., Minnullin, R.R., Galkina, I.V., and Galkin, V.I., Russ. Chem. Bull., 2016, vol. 65, p. 1308. https://doi.org/10.1007/s11172-016-1453-5
Bakhtiyarova, Yu.V., Minnullin, R.R., Morozov, M.V., Bakhtiyarov, D.I., Islamov, D.R., Dobrynin, A.B., Kataeva, O.N., Cherkasov, R.A., Galkina, I.V., and Galkin, V.I., Phosphorus, Sulfur, Silicon, Relat. Elem., 2016, vol. 191, p. 1633. https://doi.org/10.1080/10426507.2016.1223660
Romanov, S., Aksunova, A., Bakhtiyarova, Y., Shulaeva, M., Pozdeev, O., Egorova, S., Galkina, I., and Galkin, V., J. Organomet. Chem., 2020, vol. 910, p. 121130. https://doi.org/10.1016/j.jorganchem.2020.121130
Karplus, M., J. Chem. Phys., 1960, vol. 33, p. 1842.
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Translated from Zhurnal Obshchei Khimii, 2021, Vol. 91, No. 7, pp. 1068–1077 https://doi.org/10.31857/S0044460X21070118.
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Romanov, S.R., Bakhtiyarova, Y.V., Morozov, M.V. et al. Carboxylate Phosphabetaines Containing Chiral Carbon Atom: Synthesis and NMR Spectroscopy Data. Russ J Gen Chem 91, 1333–1341 (2021). https://doi.org/10.1134/S1070363221070112
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DOI: https://doi.org/10.1134/S1070363221070112