Reduction of 1-methyl-2-phenyldecahydroquinolin-4-one

  • Oral Zhilkibayev al-Farabi Kazakh National University

Abstract

Stereochemistry of the reduction of 1-methyl-2е-phenyl-trans-decahydroquinoline-4-one has been studied under different conditions: the reduction by sodium in ethanol in accordance with the mechanism of this reaction gives mainly an equatorial alcohol; with sodium boron hydride – there forms a mixture of aminoalcohols with the predominance of an equatorial epimer; the reduction of aminoketone by aluminum isopropylate proceeds with the direction, usual for this method, and results in the predominant formation of axial alcohol.

References

1. Жилкибаев О.Т., Пралиев К.Д., Рожнов В.Б., Соколов Д.В. Стереохимия азотистых гетероциклов. VI. Стереоизомерия 2-фенилдекагидрохинолона-4// Изв. АН КазССР. Сер.хим. – 1985. – № 1. – С. 55–59.

2. Жилкибаев О.Т., Пралиев К.Д.,Клепикова С.Г. Пространственное строение стереоизомеров 2-фенилдекагидрохинолин-4-она // Труды Межд. конф. «Состояние и перспективы развития органической химии в РК». – Алматы, 2002 г. – С. 113 – 115.

3. Жылқыбаев О.Т., Пірəлиев Қ.Ж. 3-Фенил-2-азабицикло[4.4.0]-декан-5-онды тотықсыздандыру// Изв. НАН РК. Сер. хим. – 2007. – № 1. – С. 92 – 94.

4. Demarco P.V., Parcas E., Dollerell D. Pyridine indused solvent shifts in the nuclear magnetic resonance spectra of hydroxylic compaunds // J.Am. Chem. Soc. – 1968. – Vol. 90. – P. 5480 – 5486.

5. Luts E.T.G., van der Maas I.H. Structural informftion from OH stretching frequencies. VII. Prefential OH rotamers in saturated tertiary alcohols // Spectrochim. Acta. – 1982. – Vol. 37A. – N 8. – p. 693 – 697.

6. Van der Maas I.H., Luts E.T.G. Structural informftion from OH stretching frequencies. X. OH rotamer in tertiary cyclohexanols // Spectrochim. Acta. – 1982. – Vol. 38A. – N 8. – p. 927 – 931.

7. Илиел Э., Аллинжер Н., Энжиал С., Моррисон Г. Конформационный анализ. М.: Мир. 1969. 592 с.

Published
2012-03-31
How to Cite
Zhilkibayev, O. (2012). Reduction of 1-methyl-2-phenyldecahydroquinolin-4-one. Chemical Bulletin of Kazakh National University, 65(1), 250-252. https://doi.org/https://doi.org/10.15328/chemb_2012_1250-252