VASILYEVA
1640
(2Н, СН2, J 7.5 Hz), 2.82 t (2Н, СН2, J 7.5 Hz), 2.95 t
(2Н, СН2, J 8.0 Hz), 2.96 d.d (1Н, СН, J 16.5, 8.0 Hz),
3.40 d.d (1Н, СН, J 16.5, 10.5 Hz), 4.12–4.32 m (1Н,
СН), 4.63–4.83 m (1Н, ОН), 6.56 br.s (1Н, NH), 7.39
t (3Н, Нarom, J 7.0 Hz), 7.67 d (2Н, Нarom, J 7.0 Hz),
12.26 br.s (1Н, NH). 13С NMR spectrum, δ, ppm: 15.1,
25.1, 28.9, 29.6, 29.7, 29.9, 31.3, 37.3, 38.8, 48.8,
66.8, 110.5, 128.6, 128.8, 133.1, 136.7, 171.0, 194.4,
196.2. Found, %: С 72.14; Н 8.33; N 3.52. С24Н33NО4.
Calculated, %: С 72.15; Н 8.33; N 3.51.
128.6, 128.8, 133.1, 136.7, 194.4, 196.2, 194.4, 196.3,
205.4. Found, %: С 71.94; Н 8.04. С24Н32О5.
Calculated, %: С 71.97; Н 8.05.
2-(10-Hydroxy-12-oxo-12-phenyldodecanoyl)-5,5-
dimethylcyclohexane-1,3-dione (6b) was obtained
similarly from 0.640 g (1.5 mmol) of enamine 5b.
Yield 0.434 g (71%). IR spectrum (film), ν, cm–1: 3300
br (С–Нarom), 1670 s (С=О), 1520 s (С=Оchelate), 1465 s
(С–Сarom), 1370 s (СН3 gem-dimethyl). 1Н NMR
spectrum, δ, ppm: 1.08 s (6Н, 2СН3), 1.16–1.36 m (12Н,
6СН2), 1.51–1.71 m (2Н, СН2), 2.35 s (2Н, СН2), 2.53
s (2Н, СН2), 2.96 d.d (1Н, СН, J 16.5, 8.0 Hz), 3.01 t
(2Н, СН2, J 8.0 Hz), 3.39 d.d (1Н, СН, J 16.5, 10.5 Hz),
4.62–4.82 m (1Н, СН), 5.24–5.44 m (1Н, ОН), 7.39 t
(3Н, Нarom, J 7.0 Hz), 7.67 d (2Н, Нarom, J 7.0 Hz),
18.26 s (1Н, ОН). 13С NMR spectrum, δ, ppm: 25.1,
25.2, 27.5, 29.1, 29.3, 29.6, 29.9, 30.6, 37.3, 40.2,
45.8, 48.8, 51.7, 66.8, 112.2, 128.6, 128.8, 133.1,
136.7, 196.2, 197.8, 200.1, 205.4. Found, %: С 72.81;
Н 8.43. С26Н36О5. Calculated, %: С 72.87; Н 8.47.
2-(1-Amino-10-hydroxy-12-oxo-12-phenyldode-
cylidene)-5,5-dimethylcyclohexane-1,3-dione (5b)
was obtained similarly from 0.427 g (1 mmol) of iso-
xazolone 4b. Yield 0.393 g (92%), mp 87–89°С (ethyl
ether). IR spectrum (KBr), ν, cm–1: 3300 br (С–Нarom),
1700–1600 s (С=О, С=N), 1465 s (С–Сarom), 1370 s
1
(СН3 gem-dimethyl). Н NMR spectrum, δ, ppm: 1.03
s (6Н, 2СН3), 1.24–1.44 m (10Н, 5СН2), 1.61–1.81 m
(4Н, 2СН2), 2.35 s (2Н, СН2), 2.41 s (2Н, СН2), 2.91 t
(2Н, СН2, J 8.0 Hz), 2.96 d.d (1Н, СН, J 16.5, 8.0 Hz),
3.40 d.d (1Н, СН, J 16.5, 10.5 Hz), 4.12–4.32 m (1Н,
СН), 4.63–4.83 m (1Н, ОН), 6.56 br.s (1Н, NH), 7.39
t (3Н, Нarom, J 7.0 Hz), 7.67 d (2Н, Нarom, J 7.0 Hz),
12.26 br.s (1Н, NH). 13С NMR spectrum, δ, ppm: 25.1,
26.6, 28.9, 29.6, 29.7, 29.9, 30.4, 31.3, 37.3, 48.8,
51.6, 66.8, 110.5, 128.6, 128.8, 133.1, 136.7, 171.0,
194.4, 196.2. Found, %: С 73.04; Н 8.71; N 3.28.
С26Н37NО4. Calculated, %: С 73.03; Н 8.72; N 3.28.
REFERENCES
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Chem. Nat. Compd., 1995, vol. 31, p. 537. doi 10.1007/
BF01164877
2. Lakhvich, F.A. and Khlebnikov, T.S., Izv. Akad. Nauk
Belarus., Ser. Khim., 1996, p. 101.
3. Li, X.-C., Ferreira, D., Jacob, M.R., Zhang, Q.,
Khan, S.I., ElSohly, H.N., Nagle, D.G., Smillie, T.J.,
Khan, I.A., Walker, L.A., and Clark, A.M., J. Am.
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ja048081c
2-(10-Hydroxy-12-oxo-12-phenyldodecanoyl)-
cyclohexane-1,3-dione (6a). To a solution of 0.599 g
(1.5 mmol) of enamine 5a in 20 mL of ethanol was
added 0.072 g (1.8 mmol) of sodium hydroxide
dissolved in 5 mL of water. The reaction mixture was
boiled for ~2 h, cooled, acidified with a solution of
hydrochloric acid (1 : 5) to рН 3, diluted with 100 mL
of water, and extracted with ethyl ether (3 × 75 mL).
The extract was dried with magnesium sulfate. The
residue after evaporation of the solvent was subjected
to column chromatography. Yield 0.40 g (70%). IR
spectrum (film), ν, cm–1: 3300 br (С–Нarom), 1670 s
4. Ciochina, R. and Grossman, R.B., Chem. Rev., 2006,
vol. 106, p. 3963.
5. Andersen, Ø.M. and Markham, K.R., Flavonoids:
Chemistry, Biochemistry and Application. Boca Raton:
CRS Press, 2006.
6. Modern Crop Protection Compounds, Kramer, W.,
Schirmer, U., Jeschke, P., and Witschel, M., Eds.,
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J. Pediatr., 2010, vol. 169, p. 689.
1
(С=О), 1520 s (С=Оchelate), 1465 s (С–Сarom). Н NMR
spectrum, δ, ppm: 1.24–1.44 m (12Н, 6СН2), 1.61–
1.81 m (2Н, СН2), 2.14–2.34 m (2Н, СН2), 2.56 t (2Н,
СН2, J 7.5 Hz), 2.92 t (2Н, СН2, J 7.5 Hz), 2.96 d.d
(1Н, СН, J 16.5, 8.0 Hz), 3.05 t (2Н, СН2, J 8.0 Hz),
3.40 d.d (1Н, СН, J 16.5, 10.5 Hz), 4.22 m (1Н, СН),
4.63–4.83 m (1Н, ОН), 7.39 t (3Н, Нarom, J 7.0 Hz),
7.67 d (2Н, Нarom, J 7.0 Hz), 18.24 s (1Н, ОН). 13С
NMR spectrum, δ, ppm: 20.4, 25.1, 25.2, 29.1, 29.3,
29.6, 29.9, 33.3, 37.3, 38.0, 40.2, 48.8, 66.8, 112.2,
9. Rubinov, D.B., Rubinova, I.L., and Akhrem, A.A.,
Chem. Rev., 1999, vol. 99, p. 1047.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 53 No. 11 2017