SHAKHMAEV et al.
912
1061. 1H NMR spectrum, δ, ppm: 0.88 t (3H, CH3, J =
7 Hz), 1.21–1.46 m (10H, CH2), 2.15 q (2H, 6-H, J =
6.9 Hz), 3.00 s and 3.07 s (3H each, CH3N), 6.06 d.t
(1H, 5-H, J = 15.3, 6.9 Hz), 6.19 d.d (1H, 4-H, J =
15.3, 10.6 Hz), 6.25 d (1H, 2-H, J = 15 Hz), 7.25 d.d
(1H, 3-H, J = 15, 10.6 Hz). 13C NMR spectrum, δC,
ppm: 13.82 (C12), 22.36 (C11), 28.56 (C7), 28.86 (CH2),
31.52 (C10), 32.69 (C6), 35.42 and 36.98 (CH3N),
118.10 (C2), 128.53 (C4), 142.58 and 142.64 (C3, C5),
166.78 (C1). Mass spectrum, m/z (Irel, %): 223 (16)
[M]+, 179 (15), 125 (10), 124 (100), 95 (19), 91 (10),
87 (17), 81 (55), 79 (14), 72 (29), 67 (11), 55 (15), 44
(16), 43 (10), 41 (13).
2857, 1719, 1649, 1624, 1603, 1439, 1254, 1138,
1
1018, 999. H NMR spectrum, δ, ppm: 0.88 t (3H,
CH3, J = 6.9 Hz), 1.20–1.46 m (6H, CH2), 1.50–1.69 m
(6H, CH2), 2.14 q (2H, 6-H, J = 6.9 Hz), 3.49 br.s and
3.59 br.s (2H each, CH2N), 6.04 d.t (1H, 5-H, J = 15.1,
6.9 Hz), 6.18 d.d (1H, 4-H, J = 15.1, 10.7 Hz), 6.26 d
(1H, 2-H, J = 14.9 Hz), 7.23 d.d (1H, 3-H, J = 14.9,
10.7 Hz). 13C NMR spectrum, δC, ppm: 13.81 (C10),
22.29 (C9), 24.48 (C4′), 25.35 and 26.58 (C3′, C5′),
28.34 (C7), 31.19 (C8), 32.72 (C6), 42.96 and 46.68
(CH2N), 118.41 (C2), 128.71 (C4), 142.28 and 142.61
(C3, C5), 165.50 (C1). Mass spectrum, m/z (Irel, %): 235
(29) [M]+, 192 (100), 178 (29), 176 (20), 164 (51), 151
(25), 138 (34), 84 (42), 83 (28), 81 (33), 78 (21), 69
(28), 41 (29).
(2E,4E)-N-(2-Methylpropyl)deca-2,4-dienamide
(IIIc, pellitorine) was synthesized from Ia and IIb.
Yield 0.190 g (85%), mp 88–89°C. IR spectrum, ν,
cm–1: 3296, 2955, 2926, 2868, 1655, 1628, 1551, 1466,
(2E,4E)-1-(Piperidin-1-yl)dodeca-2,4-dien-1-one
(IIIf) was synthesized from Ib and IId. Yield 0.214 g
(81%), oily substance. IR spectrum, ν, cm–1: 2924,
2855, 1718, 1651, 1618, 1603, 1439, 1254, 1136,
1
1256, 995. H NMR spectrum, δ, ppm: 0.86–0.95 m
(9H, CH3), 1.22–1.46 m (6H, CH2), 1.74–1.87 m [1H,
CH(CH3)2], 2.13 q (2H, 6-H, J = 7 Hz), 3.14 t (2H,
CH2N, J = 6.4 Hz), 5.93 d (1H, 3-H, J = 15 Hz), 5.99–
6.17 m (2H, 4-H, 5-H), 6.64 br.s (1H, NH), 7.17 d.d
(1H, 3-H, J = 15, 10.3 Hz). 13C NMR spectrum, δC,
ppm: 13.82 (C10), 20.02 [CH(CH3)2], 22.30 (C9), 28.35
(C7), 28.44 [CH(CH3)2], 31.20 (C8), 32.72 (C6), 46.86
(CH2N), 122.15 (C2), 128.26 (C4), 140.69 (C3), 142.55
(C5), 166.63 (C1). Mass spectrum, m/z (Irel, %): 223
(19) [M]+, 152 (36), 151 (100), 113 (24), 110 (21), 96
(87), 95 (31), 81 (86), 79 (20), 69 (32), 67 (33), 66
(22), 57 (21), 55 (25), 53 (27), 44 (27), 41 (40).
1
1018, 999. H NMR spectrum, δ, ppm: 0.88 t (3H,
CH3, J = 6.9 Hz), 1.21–1.46 m (10H, CH2), 1.51–
1.69 m (6H, CH2), 2.14 q (2H, 6-H, J = 6.9 Hz),
3.49 br.s and 3.60 br.s (2H each, CH2N), 6.05 d.t (1H,
5-H, J = 15.1, 6.9 Hz), 6.18 d.d (1H, 4-H, J = 15.1,
10.6 Hz), 6.26 d (1H, 2-H, J = 14.8 Hz), 7.23 d.d (1H,
3-H, J = 14.8, 10.6 Hz). 13C NMR spectrum, δC, ppm:
13.96 (C12), 22.51 (C11), 24.54 (C4′), 25.46 and 26.59
(C3′, C5′), 28.70 (C7), 28.99 (CH2), 31.64 (C10), 32.80
(C6), 43.05 (CH2N), 46.75 (CH2N), 118.40 (C2),
128.71 (C4), 142.44 and 142.70 (C3, C5), 165.58
(C1). Mass spectrum, m/z (Irel, %): 263 (19) [M]+, 192
(59), 178 (25), 164 (57), 138 (48), 95 (22), 84 (100),
81 (59), 69 (21), 67 (23), 55 (38), 53 (20), 43 (20),
41 (34).
(2E,4E)-1-(Pyrrolidin-1-yl)deca-2,4-dien-1-one
(IIId, sarmentine) was synthesized from Ia and IIc.
Yield 0.201 g (91%), oily substance. IR spectrum, ν,
cm–1: 2955, 2926, 2870, 1653, 1624, 1600, 1425, 999.
1H NMR spectrum, δ, ppm: 0.89 t (3H, CH3, J =
6.9 Hz), 1.26–1.47 m (6H, CH2), 1.81–2.03 m (4H,
3′-H, 4′-H), 2.14 q (2H, 6-H, J = 7 Hz), 3.46–3.58 m
(4H, CH2N), 6.02–6.23 m (2H, 4-H, 5-H), 6.10 d
(inside multiplet, 1H, 2-H, J = 14.7 Hz), 7.26 d.d (1H,
3-H, J = 14.7, 10.6 Hz ). 13C NMR spectrum, δC, ppm:
13.76 (C10), 22.24 (C9), 24.10 and 25.86 (C3′, C4′),
28.23 (C7), 31.11 (C8), 32.69 (C6), 45.57 and 46.17
(CH2N), 119.66 (C2), 128.50 (C4), 141.86 and 142.79
(C3, C5), 164.89 (C1). Mass spectrum, m/z (Irel, %): 221
(22) [M]+, 178 (13), 164 (15), 151 (29), 150 (100), 113
(17), 98 (27), 95 (26), 81 (76), 79 (17), 70 (46), 69
(30), 67 (27), 66 (18), 55 (36), 53 (23), 41 (28).
(2E,4E)-1-(Morpholin-4-yl)deca-2,4-dien-1-one
(IIIg) was synthesized from Ia and IIe. Yield 0.189 g
(80%), oily substance. IR spectrum, ν, cm–1: 2957,
2926, 2853, 1653, 1624, 1601, 1431, 1267, 1244,
1
1117, 1042, 999. H NMR spectrum, δ, ppm: 0.89 t
(3H, CH3, J = 7 Hz), 1.20–1.48 m (6H, CH2), 2.15 q
(2H, 6-H, J = 6.9 Hz), 3.50–3.72 m (8H, NCH2CH2O),
6.04–6.16 m (2H, 4-H, 5-H), 6.20 d (1H, 2-H, J =
14.8 Hz), 7.28 d.d (1H, 3-H, J = 14.8, 10 Hz).
13C NMR spectrum, δC, ppm: 13.79 (C10), 22.27 (C9),
28.23 (C7), 31.14 (C8), 32.72 (C6), 42.40 and 45.87
(CH2N), 66.63 (CH2O), 117.17 (C2), 128.44 (C4),
143.33 and 143.57 (C3, C5), 165.73 (C1). Mass spec-
trum, m/z (Irel, %): 237 (35) [M]+, 194 (23), 166 (100),
151 (77), 95 (35), 86 (30), 81 (93), 79 (23), 69 (24), 67
(30), 66 (40), 56 (32), 55 (22), 53 (23), 41 (51).
(2E,4E)-1-(Piperidin-1-yl)deca-2,4-dien-1-one
(IIIe) was synthesized from Ia and IId. Yield 0.198 g
(84%), oily substance. IR spectrum, ν, cm–1: 2930,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 48 No. 7 2012