M. Gucma et al.
1410, 1330, 1257, 1150, 1120, 1112, 1072, 1018, 968, 920,
870, 846, 830, 750, 695 cm-1 1H NMR (CDCl3,
H15), 3.16 (s, 3H, H12), 1.8–1.5 (m, 6H, H6, H7, H8), 1.46
(s, 3H, H13), 1.14 (s, 3H), 1.13 (s, 3H) ppm; 13C NMR
(CDCl3, 125.8 MHz): d = 168.3 (C14), 153.4 (C3), 132.9
(C1’), 131.6 (q, J = 32.7 Hz C4’), 126.6 (C2’, C6’), 125.6
(q, J = 3.9 Hz, C3’, C5’), 91.1 (C5), 74.4 (C9), 52.7
(C12), 50.9 (C15), 41.9 (C4), 40.2 (C8), 37.6 (C6), 24.9
(C10), 24.8 (C11), 20.4 (C13), 18.0 (C7) ppm.
;
200 MHz): d = 7.85 (dm, J = 8.1 Hz, 2H, H2’, H6’),
7.67 (dm, J = 8.1 Hz, 2H, H3’, H5’), 7.43–7.27 (m, 5H),
6.77 (d, J = 15.8 Hz, 1H, H7), 6.26 (dd, J = 15.8, 7.5 Hz,
1H, H6), 5.64 (ddd, J = 7.5, 6.5, 1.0 Hz, 1H, H5), 4.39 (d,
J = 7.5 Hz, 1H, H4), 3.76 (s, 3H, H9) ppm; 13C NMR
(CDCl3, 125.8 MHz): d = 169.1 (C8), 152.9 (C3), 135.4
(C1’’), 134.4 (C7), 132.1 (C1’), 131.9 (q, J = 32.7 Hz,
C4’), 128.7 (C2’, C6’), 128.6 (C3’’, C5’’), 127.2 (C4’’),
126.9 (C2’’, C6’’), 125.8 (q, J = 3.9 Hz, C3’, C5’), 124.7
(C6), 123.8 (q, J = 272.2 Hz, F3C), 87.0 (C5), 58.9 (C4),
53.3 (C9) ppm; 19F NMR (CDCl3, 471 MHz): d = -63.33
(s, 3F, F3CAr) ppm; MS (EI): m/z = 374 ([M - H]?, 3),
356 ([M - F]?, 25), 316 ([M - O=COCH3]?, 52), 212
(22), 144 (63), 145 (C6H4CF3, 56), 129 (100), 115 27), 104
(48), 77 (C6H5, 18); MS (ESI): m/z = 376 ([M?H]?).
Methyl (2E)-5-[5,5-dimethyl-3-[4-(trifluoromethyl)
phenyl]-4,5-dihydro-1,2-oxazol-4-yl]-3-methylpent-2-eno-
ate (22, C20H26F3NO4)
A brown liquid, yield: 10 %; 1H NMR (CDCl3, 500 MHz):
d = 7.76 (d, J = 8.3 Hz, 2H, H2’, H6’), 7.67 (d,
J = 8.3 Hz, 2H, H3’, H5’), 5.59 (q, J = 1.0 Hz, 1H,
H12), 3.67 (s, 3H, H14), 3.17 (dd, J = 8.0, 3.5 Hz, 1H,
H4), 2.17 (s, 3H, H11), 2.16–2.08 (m, 2H, H9), 1.86–1.78
(m, 2H, H8), 1.53 (s, 3H, H6), 1.37 (s, 3H, H7) ppm; 13C
NMR (CDCl3, 125.8 MHz): d = 166.8 (C=O), 159.5 (C3),
158.2 (C10), 131.9 (q, J = 32.7 Hz, C4’), 130.8 (C1’),
127.3 (C2’, C6’), 126.2 (q, J = 3.8 Hz, C3’, C5’), 124.1
(q, J = 272.1 Hz, F3C), 116.3 (C12), 87.6 (C5), 53.4 (C4),
51.2 (C14), 38.2 (C9), 28.7 (C8), 25.8 (C6), 20.9 (C7) ppm.
Benzyl (2E)-[3-[4-(trifluoromethyl)phenyl]-1,2-oxazol-
5(4H)-ylidene]ethanoate (19, C19H14F3NO3)
A brown liquid, yield: 50 %; 1H NMR (CDCl3, 300 MHz):
d = 7.90 (dd, J = 8.2, 0.6 Hz, 2H, H2’, H6’), 7.69 (d,
J = 8.2 Hz, 2H, H3’, H5’), 7.37 (m, 5H), 6.62 (s, 1H, H6),
5.22 (s, 2H, H8), 3.93 (s, 2H, H4) ppm; 13C NMR (CDCl3,
75.5 MHz): d = 167.2 (C5), 166.1 (C7), 161.4 (C3), 135.0
(C1’’), 132.3 (C1’), 131.7 (q, J = 32.5 Hz, C4’), 128.6
(C3’’, C5’’), 128.6 (C4’’), 128.4 (C2’’, C6’’), 127.1 (C2’,
C6’), 125.8 (q, J = 3.8 Hz, C3’, C5’), 123.8 (q,
J = 270.7 Hz, F3C), 101.6 (C6), 67.5 (C8), 32.7 (C4)
ppm; MS (ESI): m/z = 361 (M?, 20), 360 ([M - H]?, 95),
189 (70), 145 (20).
(5,6)-Anti (5Z)-6,10-dimethyl-2-[3-[4-(trifluoromethyl)
phenyl]-4,5-dihydro-1,2-oxazol-5-yl]undeca-5,9-dien-2-yl
acetate (23) and (5,6)-syn (5Z)-6,10-dimethyl-2-[3-[4-(tri-
fluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]undeca-
5,9-dien-2-yl acetate (24)
ꢀ
IR (neat): m = 2970, 2929, 2860, 1735, 1620, 1600, 1450,
1410, 1326, 1248, 1169, 1129, 1070, 1016, 916, 843,
770 cm-1; MS (ESI): m/z = 474 ([M ? Na]?, 100), 178
(12); HRMS (ESI): m/z calcd for C25H32F3NO3Na
474.2232, found 474.2217.
Methyl 3-[4-(trifluoromethyl)phenyl]-5-(4-methoxy-4-
methylpentyl)-5-methyl-4,5-dihydro-1,2-oxazole-4-car-
boxylate (20, C20H26F3NO4)
1
23 (C25H32F3NO3): A brown liquid, yield: 40 %; H NMR
(CDCl3, 200 MHz): d = 7.79 (d, J = 8.4 Hz, 2H, H2’,
H6’), 7.67 (d, J = 8.4 Hz, 2H, H3’, H5’), 5.28 (dd,
J = 10.0, 9.0 Hz, 1H, H5), 5.16–5.08 (m, 2H, H9, H13),
3.34 (d, J = 10.0 Hz, 1H, H4a), 3.33 (d, J = 9.0 Hz, 1H,
H4b), 2.20–1.80 (m, 8H, H7, H8, H11, H12), 2.02 (s, 3H,
H20), 1.69 (s, 9H, H17, H16, H15), 1.41 (s, 3H, H18) ppm;
13C NMR (CDCl3, 125.8 MHz): d = 170.0 (C19), 155.4
(C3), 136.0 (C10), 132.8 (q, J = 1.0 Hz, C1’), 131.9
(C14), 131.7 (C4’), 126.9 (C2’, C6’), 125.7 (q, J = 3.9 Hz,
C3’, C5’), 124.2 (C9), 124.1 (C13), 123.8 (q,
J = 272.16 Hz, F3C), 84.2 (C6), 84.7 (C5), 35.6 (C7), 35.5
(C4), 31.9 (C11), 25.7 (C12), 23.4 (C16), 22.2, 22.1, 21.9,
18.5 (C20), 17.7 (C15) ppm.
A brown liquid, yield: 30 %; 1H NMR (CDCl3, 500 MHz):
d = 7.77 (d, J = 8.0 Hz, 2H, H2’, H6’), 7.66 (d,
J = 8.0 Hz, 2H, H3’, H5’), 3.67 (s, 1H, H4), 3.68 (s, 3H,
H15), 3.16 (s, 3H, H12), 1.82 (m, 2H, H6), 1.58–1.42 (m,
4H, H7, H8), 1.48 (s, 3H, H13), 1.14 (s, 3H), 1.13 (s, 3H)
ppm; 13C NMR (CDCl3, 125.8 MHz): d = 170.5 (C14),
155.6 (C3), 133.2 (d, J = 1.3 Hz, C1’), 131.6 (q,
J = 32.6 Hz, C4’), 127.0 (C2’, C6’), 125.7 (q,
J = 3.8 Hz, C3’, C5’), 123.8 (q, J = 271.4 Hz, CF3),
87.8 (C5), 74.4 (C9), 60.4 (C4), 51.9 (C15), 49.1 (C12),
40.0 (C8), 39.0 (C6), 24.9 (C10), 24.8 (C11), 24.8 (C13),
18.0 (C7) ppm.
1
24 (C25H32F3NO3): A brown liquid, yield: 35 %; H NMR
Methyl 3-[4-(trifluoromethyl)phenyl]-4-(4-methoxy-4-
methylpentyl)-4-methyl-4,5-dihydro-1,2-oxazole-5-car-
boxylate (21, C20H26F3NO4)
A brown liquid, yield: 20 %; 1H NMR (CDCl3, 500 MHz):
d = 7.71 (d, J = 8.3 Hz, 2H, H2’, H6’), 7.65 (d,
J = 8.3 Hz, 2H, H3’, H5’), 4.13 (s, 1H, H5), 3.72 (s, 3H,
(CDCl3, 200 MHz): d = 7.79 (d, J = 8.4 Hz, 2H, H2’,
H6’), 7.67 (d, J = 8.4 Hz, 2H, H3’, H5’), 5.25 (dd,
J = 11.0, 8.8 Hz, 1H, H5), 5.11 (m, 2H, H9, H13), 3.32 (d,
J = 11.0 Hz, 1H, H4a), 3.27 (d, J = 8.8 Hz, H4b),
2.20–1.80 (m, 8H, H7, H8, H11, H12), 2.01 (s, 3H, H20),
123