Mechanism of One-Pot Stereoselective Assembly of Spiroketal Derivatives from Cyclohexanone and Phenylacetylene in KOH/DMSO: a Quantum Chemical Study

V. B. Orel; Орел В. Б.; A. A. Manzhueva; Манжуева А. А.

doi:10.31857/S0207401X23070154

Mechanism of One-Pot Stereoselective Assembly of Spiroketal Derivatives from Cyclohexanone and Phenylacetylene in KOH/DMSO: a Quantum Chemical Study

Autores: Orel V.B.¹, Manzhueva A.A.¹
Afiliações:
1. Irkutsk State University
Edição: Volume 42, Nº 7 (2023)
Páginas: 59-69
Seção: XXXIV СИМПОЗИУМ “СОВРЕМЕННАЯ ХИМИЧЕСКАЯ ФИЗИКА” (СЕНТЯБРЬ 2022 г., ТУАПСЕ)
URL: https://rjmseer.com/0207-401X/article/view/674853
DOI: https://doi.org/10.31857/S0207401X23070154
EDN: https://elibrary.ru/YFNJBE
ID: 674853

Citar

Texto integral

Acesso aberto
Acesso é fechado

Acesso está concedido
Acesso é fechado

Acesso é pago ou somente para assinantes

Resumo

The formation mechanisms of 15-[(Z)-phenylmethylidene]-7,14-dioxadispiro[5.1.5.2]pentadecane and the competitive formation of unsaturated ketones from cyclohexanone and phenylacetylene are studied using the B2PLYP-D2/6-311+G**//B3LYP/6-31+G* quantum chemical approach, taking into account solvation effects within the IEFPCM model. All stages of the assembly of dispiroketal and the stability of various conformers and isomers of the intermediates and the product are considered using the anionic model (ANIONGAS). Within the more detailed MONOPCM model, the activation barriers of the assembly of dispiroketal and the competing reaction of C-vinylation are evaluated. The obtained results of the quantum chemical calculations are in close agreement with the experimental data.

Palavras-chave

spiroketals, cycloaliphatic ketones, superbase, quantum chemical calculations

Sobre autores

V. Orel

Irkutsk State University

Email: orelv@isu.ru
Irkutsk, Russia

A. Manzhueva

Irkutsk State University

Autor responsável pela correspondência
Email: orelv@isu.ru
Irkutsk, Russia

Bibliografia

Brimble M., Furkert D. // Curr. Org. Chem. 2003. V. 7. № 14. P. 1461; https://doi.org/10.2174/1385272033486404
Perron F., Albizati K.F. // Chem. Rev. 1989. V. 89. № 7. P. 1617; https://doi.org/10.1021/cr00097a015
Koshino H., Takahashi H., Osada H. et al. // J. Antibiot. (Tokyo). 1992. V. 45. № 9. P. 1420; https://doi.org/10.7164/antibiotics.45.1420
Shimizu T., Usui T., Machida K. et al. // Bioorg. Med. Chem. Lett. 2002. V. 12. № 23. P. 3363; https://doi.org/10.1016/S0960-894X(02)00782-5
Cullen W.P., Celmer W.D., Chappel L.R. et al. // J. Ind. Microbiol. 1988. V. 2. № 6. P. 349; https://doi.org/10.1007/BF01569573
Kotecha N.R., Ley S.V., Mantegani S. // Synlett. 1992. № 05. P. 395; https://doi.org/10.1055/s-1992-21357
Tachibana K., Scheuer P.J., Tsukitani Y. et al. // J. Amer. Chem. Soc. 1981. V. 103. № 9. P. 2469; https://doi.org/10.1021/ja00399a082
Singh S.B., Zink D.L., Heimbach B. et al. // Org. Lett. 2002. V. 4. № 7. P. 1123; https://doi.org/10.1021/ol025539b
Pettit G.R., Chicacz Z.A., Gao F. et al. // J. Org. Chem. 1993. V. 58. № 6. P. 1302; https://doi.org/10.1021/jo00058a004
Ueno T., Takahashi H., Oda M. et al. // Biochemistry 2000. V. 39. № 20. P. 5995; https://doi.org/10.1021/bi992661i
Li A., Piel J. // Chem. Biol. 2002. V. 9. № 9. P. 1017; https://doi.org/10.1016/S1074-5521(02)00223-5
Francke W., Kitching W. // Curr. Org. Chem. 2001. V. 5. № 2. P. 233; https://doi.org/10.2174/1385272013375652
Lenci E. // Small Molecule Drug Discovery. Elsevier, 2020. P. 225–245; https://doi.org/10.1016/B978-0-12-818349-6.00008-X
Sun P., Zhao Q., Zhang H. et al. // ChemBioChem 2014. V. 15. № 5. P. 660; https://doi.org/10.1002/cbic.201300616
Zarganes-Tzitzikas T., Dömling A. // Org. Chem. Front. 2014. V. 1. № 7. P. 834; https://doi.org/10.1039/C4QO00088A
Ramachary D.B., Mondal R., Venkaiah C. // Org. Biomol. Chem. 2010. V. 8. № 2. P. 321; https://doi.org/10.1039/B920152A
Sydnes M.O. // Curr. Green Chem. 2014. V. 1. P. 216; https://doi.org/10.2174/2213346101666140221225404
Mead K.T., Brewer B.N. // Curr. Org. Chem. 2003. V. 7. № 3. P. 227; https://doi.org/10.2174/1385272033372969
Palmes J.A., Aponick A. // Synthesis (Stuttg). 2012. V. 44. № 24. P. 3699; https://doi.org/10.1055/s-0032-1317489
Raju B.R., Saikia A.K. // Molecules. 2008. V. 13. № 8. P. 1942; https://doi.org/10.3390/molecules13081942
Yadav J.S., Raghavendra Rao K.V., Ravindar K. et al. // Synlett. 2010. № 1. P. 51; https://doi.org/10.1055/s-0029-1218546
Trofimov B.A., Schmidt E.Y. // Acc. Chem. Res. 2018. V. 51. № 5. P. 1117; https://doi.org/10.1021/acs.accounts.7b00618
Schmidt E.Y., Zorina N.V., Skitaltseva E.V. et al. // Tetrahedron Lett. 2011. V. 52. № 29. P. 3772; https://doi.org/10.1016/j.tetlet.2011.05.056
Schmidt E.Y., Zorina N.V., Skitaltseva E.V. et al. // Tetrahedron Lett. 2011. V. 52. № 29. P. 3772; https://doi.org/10.1016/j.tetlet.2011.05.056
Trofimov B.A., Schmidt E.Y., Skitaltseva E.V. et al. // Ibid. 2011. V. 52. № 33. P. 4285; https://doi.org/10.1016/j.tetlet.2011.06.019
Siyamak Shahab, Masoome Sheikhi // Russ. J. Phys. Chem. B. 2020. V. 14. № 1. P. 15–18. https://doi.org/10.1134/S1990793120010145
Zhiyan Wu, Zhang L., Liao Y. // Russ. J. Phys. Chem. B. 2021. V. 15. № S1. P. S81–S91. https://doi.org/10.1134/S1990793121090153
Breslavskaya N.N., Wasserman L.A., Barashkova I.I., Buchachenko A.L. // Russ. J. Phys. Chem. B. 2019. V. 13. № 4. P. 569; https://doi.org/10.1134/S199079311904002X
Ramakrishnan R., Dral P.O., Rupp M. et al. // Sci. Data. 2014. V. 1. P. 1; https://doi.org/10.1038/sdata.2014.22
Забалов М.В., Левина М.А., Тигер Р.П. // Хим. физика 2019. Т. 38. № 9. С. 3; https://doi.org/10.1134/S0207401X19090127
Grambow C.A., Pattanaik L., Green W.H. // Sci. Data. 2020. V. 7. № 1. P. 1–8. https://doi.org/10.1038/s41597-020-0460-4
Frisch M., Trucks G., Schlegel H., Scuseria G.E., Robb M.A., Cheeseman J.R., Scalmani G., Barone V., Petersson G.A., Nakatsuji H., Li X., Caricato M., Marenich A.V., Bloino J., Janesko B.G., Gomperts R., Mennucci B., Hratchian H.P., Ortiz J.V., Izmaylov A.F., Sonnenberg J.L., Williams-Young D., Ding F., Lipparini F., Egidi F., Goings J., Peng B., Petrone A., Henderson T., Ranasinghe D., Zakrzewski V.G., Gao J., Rega N., Zheng G., Liang W., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Throssell K., Montgomery J.A., Jr., Peralta J.E., Ogliaro F., Bearpark M.J., Heyd J.J., Brothers E.N., Kudin K.N., Staroverov V.N., Keith T.A., Kobayashi R., Normand J., Raghavachari K., Rendell A.P., Burant J.C., Iyengar S.S., Tomasi J., Cossi M., Millam J.M., Klene M., Adamo C., Cammi R., Ochterski J.W., Martin R.L., Morokuma K., Farkas O., Foresman J.B., Fox D.J. Gaussian 16. Wallingford CT: Gaussian Inc., 2019.
Becke A.D. // Phys. Rev. A. 1988. V. 38. № 6. P. 3098; https://doi.org/10.1103/PhysRevA.38.3098
Lee C., Yang W., Parr R.G. // Phys. Rev. B. 1988. V. 37. № 2. P. 785; https://doi.org/10.1103/PhysRevB.37.785
Page M., Doubleday C., McIver J.W. // J. Chem. Phys. 1990. V. 93. № 8. P. 5634; https://doi.org/10.1063/1.459634
Grimme S. // Ibid. 2006. V. 124. № 3. P. 034108; https://doi.org/10.1063/1.2148954
Grimme S., Ehrlich S., Goerigk L. // J. Comput. Chem. 2011. V. 32. № 7. P. 1456; https://doi.org/10.1002/jcc.21759
Tomasi J., Mennucci B., Cancès E. // J. Mol. Struct: THEOCHEM. 1999. V. 464. № 1–3. P. 211; https://doi.org/10.1016/S0166-1280(98)00553-3
Pascual-ahuir J.L., Silla E., Tuñon I. // J. Comput. Chem. 1994. V. 15. № 10. P. 1127; https://doi.org/10.1002/jcc.540151009
Bondi A. // J. Phys. Chem. 1964. V. 68. № 3. P. 441; https://doi.org/10.1021/j100785a001
Wertz D.H. // J. Amer. Chem. Soc. 1980. V. 102. № 16. P. 5316; https://doi.org/10.1021/ja00536a033
Vitkovskaya N.M., Kobychev V.B., Bobkov A.S. et al. // J. Org. Chem. 2017. V. 82. № 23. P. 12467; https://doi.org/10.1021/acs.joc.7b02263
Allinger N.L. // J. Amer. Chem. Soc. 1959. V. 81. № 21. P. 5727; https://doi.org/10.1021/ja01530a049
Stortz C.A. // J. Phys. Org. Chem. 2010. V. 23. № 12. P. 1173; https://doi.org/10.1002/poc.1689
Vitkovskaya N.M., Orel V.B., Kobychev V.B. et al. // Intern. J. Quantum Chem. 2020. V. 120. № 9. P. 1; https://doi.org/10.1002/qua.26158
Abramenkov A.V. Kinet for Windows. 2012. Ver. 0.8.
Ларионова Е.Ю., Витковская Н.М., Кобычев В.Б. и др. // Журн. структур. химии 2007. Т. 48. № S7. С. 101.
Ларионова Е.Ю., Витковская Н.М., Кобычев В.Б. и др. // Докл. РАН 2011. Т. 438. № 6. С. 765.
Bordwell F.G., Fried H.E. // J. Org. Chem. 1991. V. 56. № 13. P. 4218; https://doi.org/10.1021/jo00013a027
Matthews W.S., Bares J.E., Bartmess J.E. et al. // J. Amer. Chem. Soc. 1975. V. 97. № 24. P. 7006; https://doi.org/10.1021/ja00857a010
Trofimov B.A., Schmidt E.Y., Zorina N.V. et al. // Adv. Synth. Catal. 2012. V. 354. № 9. P. 1813; https://doi.org/10.1002/adsc.201200210