PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Tytuł artykułu

Tert-butyl esters of 2,3-diaryl-3-arylaminopropanoic acids – stereoselective synthesis, isolation, spectroscopic and structural elucidation

Treść / Zawartość
Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
A series of seven substituted tert-butyl esters of 2,3-diaryl-3-arylaminopropanoic acids has been synthesized, isolated, spectroscopically and structurally elucidated. An influence of the substituents on the spectroscopic characteristics and conformations is discussed using the data of the linear-polarized IR- (IR-LD), UV-spectroscopy and 1H-NMR. Theoretical quantum chemical calculations are carried out, with a view to explaining and supporting the experimental optical properties and the electronic structure. The stereoselective synthesis of the corresponding diastereoisomers is optimized, thus giving good yields (62–72%) and purity of the compounds.
Rocznik
Strony
12--17
Opis fizyczny
Bibliogr. 28 poz., rys., tab.
Twórcy
autor
Bibliografia
  • 1. Drey, C.N. (1985). In Barret G. S. (Ed.), Chemistry and Biochemistry of the Amino Acids (1 st ed.), London, Chapman & Hall.
  • 2. Liu, M. & Sibi, M. (2002). Recent advances in the stereoselective synthesis of ß-amino acids. Tetrahedron 58(40), 7991–8035. DOI: 10.1016/S0040-4020(02)00991-2.
  • 3. Periasamy, M., Suresh, S. & Ganesan, S. (2005). Stereoselective synthesis of syn-ß-amino esters using the TiCl4/R3N reagent system. Tetrahedron Lett. 46(33), 5521–5524. DOI:10.1016/j.tetlet.2005.06.048.
  • 4. Krauthauser, S., Christianson, L., Powell, D. & Gellman, S. (1997). Antiparallel sheet formation in ß-peptide foldamers: Effects of ß-amino acid substitution on conformational preference. J. Am. Chem. Soc. 119(48), 11719–11720. DOI: 10.1021/ja9730627.
  • 5. Kise, N., Ueda, N. (1999). A new method for the synthesis of ß-amino acid derivatives and ß-lactams. Reaction of N-alkoxycarbonyl-1-methoxyamines with esters. J. Org. Chem. 64(20), 7511–7514. DOI: 10.1021/jo990821q.
  • 6. Escalante, J., Guanzales-Tototzin, M., Avina, J., Minoz-Miniz, O. & Juaristi, E. (2001). Synthesis of ß-lactams and cyclo-ß-dipeptides from ß-amino acids: experimental observations and theoretical analysis. Tetrahedron, 57(10), 1883–1890. DOI:10.1016/S0040-4020(00)01169-8.
  • 7. Taggi, A., Havez, A. & Lectka, T. (2003). 7-Imino esters: Versatile substrates for the catalytic, asymmetric synthesis of e- and ß-amino acids and ß-lactams. Acc. Chem. Res. 36(1), 10–19. DOI: 10.1021/ar020137p.
  • 8. Rosenblum, S., Huynh, T., Afonso, A., Davis, H., Yumibe, N., Clader, J. & Burnett, D. (1998). Discovery of 1-(4-Fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)-hydroxypropyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone (SCH 58235): A Designed, Designed,Potent, Orally Active Inhibitor of Cholesterol Absorption.J. Med. Chem. 41(6), 973–980. DOI: 10.1021/jm970701f.
  • 9. Koleva, B., Kolev, T., Seidel, R., Spiteller, M., Mayer-Figge, H. & Sheldrick, W. (2009). Self-assembly of hydrogensquarates: Crystal structures and properties. J. Phys. Chem. A 113(13), 3088–3095. DOI: 10.1021/jp8106233.
  • 10. Koleva, B., Kolev, T., Seidel, R., Mayer-Figge, H., Spiteller, M. & Sheldrick, W. (2008). On the origin of the color in the solid state. Crystal structure and optical and magnetic properties of 4-Cyanopyridinium hydrogensquarate monohydrate. J. Phys. Chem. A. 112(13), 2899–2905. DOI: 10.1021/jp710765v.
  • 11. Koleva, B.B, Kolev, T.M., Simeonov, V., Spassov, T. & Spiteller, M. (2008) Linearly polarized IR-spectroscopy of partially oriented solids as a colloid suspension in nematic host: A tool for spectroscopic and structural elucidation of the embedded chemicals. J. Incl. Phen. Macro. 61, 319–333. DOI: 10.1007/s10847-008-9425-5.
  • 12. Koleva, B.B., Kolev, T., Mayer-Figge, H., Seidel, R.W., Spiteller, M. & Sheldrick, W.S. (2008) Are there preferable conformations of the tryptammonium cation in the solid state? Crystal structure and solid-state linear polarized IRspectroscopic study of tryptammonium hydrogentartarate Struct. Chem. 19, 147–154. DOI: 10.1007/s11224-007-9265-8.
  • 13. Ivanova, B. & Spiteller, M. (2010). Noncentrosymmetric crystals with marked nonlinear optical properties. J. Phys. Chem. A. 114(15), 5099–5103. DOI: 10.1021/jp1002758.
  • 14. Ivanova, B. & Spiteller, M. (2010). Possible application of the organic barbiturates as NLO materials. Cryst. Growth Des. 10(6), 2470–2474. DOI: 10.1021/cg100284r.
  • 15. Kolev, T., Koleva, B., Seidel, R., Spiteller, M. & Sheldrick, W. (2009). New aspects on the origin of color in the solid state. Coherently shifting of the protons in violurate crystals. Cryst. Growth Des. 9(8), 3348–3352. DOI: 10.1021/cg900188k.
  • 16. Ivanova, B. & Spiteller, M. (2010). Conformations and properties of the L-tryptophyl-containing peptides in solution, depending on the pH-theoretical study vs. experiments. Biopolymers 93(8), 727–734. DOI: 10.1002/bip.21437.
  • 17. Ivanova, B. & Spiteller, M. (2010). Organic mandelates as promising materials with non-linear optical application. Struct. Chem. 21(5), 989–993. DOI 10.1007/s11224-010-9635-5.
  • 18. Frisch, M.J. Trucks, G.W. Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Montgomery Jr., J.A., Stratmann, R.E., Burant, J.C., Dapprich, S., Millam, J.M.; Daniels, A.D., Kudin, K.N., Strain, M.C., Farkas, Ö.,Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B.,Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G. A., Ayala, P.Y., Cui, Q., Morokuma, K., Salvador, P.,Dannenberg, J.J., Malick, D. K., Rabuck, A. D., Raghavachari,K., Foresman, J. B., Cioslowski, J., Ortiz, J.V., Baboul, A. G., Stefanov, B.B., Liu, G.; Liashenko, A., Piskorz, P., Komáromi,I., Gomperts, R., Martin, R.L., Fox, D.J., Keith, T., Al-Laham,M.A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill,P.M.W., Johnson, B., Chen, W., Wong, M.W., Andres, J.L.,Gonzalez, C., Head-Gordon, M., Replogle, E. S. & Pople, J.A. Gaussian 98, Gaussian, Inc., Pittsburgh, PA, 1998.
  • 19. Dalton 2.0 Program Package, http://www.kjemi.uio.no/software/dalton/dalton.html.
  • 20. Becke, A.D. (1993). Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98(7), 5648-5652. DOI: 10.1063/1.464913.
  • 21. Becke, A.D. (1996). Density-functional thermochemistry. IV. A new dynamical correlation functional and implications for exact-exchange mixing. J. Chem. Phys. 104(3), 1040–1046. DOI:10.1063/1.470829.
  • 22. Lee, C., Yang, W. & Parr, R.G. (1988). Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 37(2), 785–789. DOI: 10.1103/PhysRevB.37.785.
  • 23. Scott, P. & Radom, L. (1996). Harmonic Vibrational Frequencies: An Evaluation of Hartree-Fock, Moller-Plesset, Quadratic Configuration Interaction, Density Functional Theory, and Semiempirical Scale Factors. J. Phys. Chem. 100(41), 16502–16513. DOI: 10.1021/jp960976r.
  • 24. DeFrees D.J. & McLean, A.D. (1985). Molecular orbital predictions of the vibrational frequencies of some molecular ions. J. Chem. Phys. 82(1), 333–341. DOI:10.1063/1.448805.
  • 25. Dryanska, V.D., Tasheva, D.N. & Ivanov, Ch.Ch. (1992). Phase transfer catalyzed additions IX. Influence of the reaction conditions on the reaction of tert-butyl phenylacetate with benzylideneaniline. Bulg. Chem. Commun. 26(1), 66–73.
  • 26. Spassov, S.L. (1971). Nuclear magnetic resonance spectra, configuration and conformation of diastereomers-II: Ethyl esters of 3-substituted 2,3-diphenylpropanoic acids: Magnetic nonequivalence induced by two asymmetric centres. Tetrahedron 27(6), 1323–1329. DOI:10.1016/S0040-4020(01)90883-X.
  • 27. Kolev, T., Preut, H., Bleckmann, P. & Juchnovski, I. (1995). (+/-)-Threo-3-Hydroxy-2,3-diphenylpropanoic acid methyl ester Acta Crystallogr. C. 51, 1350–1352. DOI:10.1107/S0108270194014277.
  • 28. Kolev, T., Preut, H., Bleckmann, P. & Juchnovski, I. (1995). (+/-)-Threo-3-Hydroxy-2,3-diphenylpropanoic acid dimethylamide. Acta Crystallogr. C. 51, 1169–1170. DOI:10.1107/S0108270194014666.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BPS3-0020-0037
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.