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4.05 (1H, m, –CH(CH3)2), 2.57 (2H, t, J = 7.2 Hz, H-7), 2.27 (4H, m,
H-2, H-11), 1.58 (4H, m, H-3, H-6), 1.46 (2H, m, H-12), 1.35–1.25
(14H, m, CH2), 1.13 (6H, d, J = 6.8 Hz, –CH(CH3)2), 0.89 (3H, t,
J = 6.8 Hz, H-18); FABMS m/z 360 [M+Na]+.
3.55 (1H, m, –CH(CH3)CHaOH), 2.60 (2H, t, J = 7.5 Hz, H-8), 2.27
(4H, m, H-2, H-12), 1.59 (4H, m, H-3, H-7), 1.49 (2H, m, H-13),
1.35–1.28 (14H, m, CH2), 1.15 (3H, d, J = 6.8 Hz, –CH(CH3)CH2OH),
0.90 (3H, t, J = 7.0 Hz, H-18); FABMS m/z 376 [M+Na]+.
5.2.5. (E)-N-Hydroxyethyl-11-oxo-octadec-9-enamide (5)
Colorless oil; 1H NMR (CDCl3, 400 MHz) d 6.93 (1H, dt, J = 16.4,
7.2 Hz, H-9), 6.12 (1H, dt, J = 16.4, 1.2 Hz, H-10), 5.93 (1H, br s, NH),
3.73 (2H, t, J = 5.6 Hz, –CH2CH2OH), 3.44 (2H, quint, J = 6.0 Hz, –
CH2OH), 2.57 (2H, t, J = 7.6 Hz, H-12), 2.25 (4H, m, H-2, H-8), 1.59
(4H, m, H-3, H-13), 1.49 (2H, m, H-7), 1.37–1.26 (14H, m, CH2),
0.89 (3H, t, J = 6.8 Hz, H-18); FABMS m/z 362 [M+Na]+.
5.2.12. (E)-N-[(1R)-2-Hydroxy-1-methylethyl]-8-oxo-octadec-9-
enamide (12)
Colorless oil; 1H NMR (CDCl3, 400 MHz) d 6.93 (1H, dt, J = 16.0,
7.6 Hz, H-10), 6.12 (1H, dt, J = 16.0, 1.4 Hz, H-9), 5.61 (1H, br s, NH),
4.08 (1H, m, –CH(CH3)CH2OH), 3.66 (1H, m, –CH(CH3)CHbOH), 3.55
(1H, m, –CH(CH3)CHaOH), 2.59 (2H, t, J = 7.2 Hz, H-7), 2.25 (4H, m,
H-2, H-11), 1.57 (4H, m, H-3, H-6), 1.47 (2H, m, H-12), 1.37–1.21
(14H, m, CH2), 1.16 (3H, d, J = 6.8 Hz, –CH(CH3)CH2OH), 0.91 (3H,
t, J = 6.8 Hz, H-18); FABMS m/z 376 [M+Na]+.
5.2.6. (E)-N-Hydroxyethyl-10-oxo-octadec-8-enamide (6)
Colorless oil; 1H NMR (CDCl3, 400 MHz) d 6.91 (1H, dt, J = 16.0,
6.5 Hz, H-8), 6.12 (1H, dt, J = 16.0, 1.5 Hz, H-9), 5.92 (1H, br s, NH),
3.74 (2H, t, J = 5.6 Hz, –CH2CH2OH), 3.46 (2H, quint, J = 6.0 Hz, –
CH2OH), 2.59 (2H, t, J = 7.5 Hz, H-11), 2.28 (4H, m, H-2, H-7), 1.62
(4H, m, H-3, H-12), 1.51 (2H, m, H-6), 1.36–1.25 (14H, m, CH2),
0.91 (3H, t, J = 6.5 Hz, H-18); FABMS m/z 362 [M+Na]+.
5.2.13. (E)-N-Chloroethyl-11-oxo-octadec-9-enamide (13)
Colorless oil; 1H NMR (CDCl3, 400 MHz) d 6.92 (1H, dt, J = 16.4,
7.2 Hz, H-9), 6.13 (1H, dt, J = 16.4, 1.2 Hz, H-10), 5.83 (1H, br s, NH),
3.62 (4H, m, –(CH2)2Cl), 2.59 (2H, t, J = 7.6 Hz, H-12), 2.28 (4H, m,
H-2, H-8), 1.57 (4H, m, H-3, H-13), 1.49 (2H, m, H-7), 1.36–1.30
(14H, m, CH2), 0.91 (3H, t, J = 6.8 Hz, H-18); FABMS m/z 380
[M+Na]+.
5.2.7. (E)-N-Hydroxyethyl-9-oxo-octadec-10-enamide (7)
Colorless oil; 1H NMR (CDCl3, 400 MHz) d 6.93 (1H, dt, J = 14.0,
7.0 Hz, H-11), 6.10 (1H, dt, J = 14.0, 1.5 Hz, H-10), 5.91 (1H, br s,
NH), 3.71 (2H, t, J = 5.6 Hz, –CH2CH2OH), 3.42 (2H, quint,
J = 6.0 Hz, –CH2OH), 2.56 (2H, t, J = 7.5 Hz, H-8), 2.26 (4H, m, H-2,
H-12), 1.58 (4H, m, H-3, H-7), 1.48 (2H, m, H-13), 1.37–1.28
(14H, m, CH2), 0.92 (3H, t, J = 7.0 Hz, H-18); FABMS m/z 362
[M+Na]+.
5.2.14. (E)-N-Chloroethyl-10-oxo-octadec-8-enamide (14)
Colorless oil; 1H NMR (CDCl3, 400 MHz) d 6.93 (1H, dt, J = 16.0,
6.5 Hz, H-8), 6.13 (1H, dt, J = 16.0, 1.5 Hz, H-9), 5.81 (1H, br s, NH),
3.63 (4H, m, –(CH2)2Cl), 2.56 (2H, t, J = 7.5 Hz, H-11), 2.29 (4H, m,
H-2, H-7), 1.64 (4H, m, H-3, H-12), 1.53 (2H, m, H-6), 1.37–1.33
(14H, m, CH2), 0.93 (3H, t, J = 6.5 Hz, H-18); FABMS m/z 380
[M+Na]+.
5.2.8. (E)-N-Hydroxyethyl-8-oxo-octadec-9-enamide (8)
Colorless oil; 1H NMR (CDCl3, 400 MHz) d 6.92 (1H, dt, J = 16.0,
7.6 Hz, H-10), 6.11 (1H, dt, J = 16.0, 1.4 Hz, H-9), 5.93 (1H, br s,
NH), 3.75 (2H, t, J = 5.6 Hz, –CH2CH2OH), 3.41 (2H, quint, J =
6.0 Hz, –CH2OH), 2.60 (2H, t, J = 7.2 Hz, H-7), 2.28 (4H, m, H-2,
H-11), 1.59 (4H, m, H-3, H-6), 1.46 (2H, m, H-12), 1.35–1.22
(14H, m, CH2), 0.91 (3H, t, J = 6.8 Hz, H-18); FABMS m/z 362
[M+Na]+.
5.2.15. (E)-N-Chloroethyl-9-oxo-octadec-10-enamide (15)
Colorless oil; 1H NMR (CDCl3, 400 MHz) d 6.91 (1H, dt, J = 14.0,
7.0 Hz, H-11), 6.12 (1H, dt, J = 14.0, 1.5 Hz, H-10), 5.80 (1H, br s,
NH), 3.65 (4H, m, –(CH2)2Cl), 2.61 (2H, t, J = 7.5 Hz, H-8), 2.28
(4H, m, H-2, H-12), 1.58 (4H, m, H-3, H-7), 1.48 (2H, m, H-13),
1.37–1.28 (14H, m, CH2), 0.90 (3H, t, J = 7.0 Hz, H-18); FABMS m/
z 380 [M+Na]+.
5.2.16. (E)-N-Chloroethyl-8-oxo-octadec-9-enamide (16)
Colorless oil; 1H NMR (CDCl3, 400 MHz) d 6.94 (1H, dt, J = 16.0,
7.6 Hz, H-10), 6.10 (1H, dt, J = 16.0, 1.4 Hz, H-9), 5.84 (1H, br s, NH),
3.62 (4H, m, –(CH2)2Cl), 2.58 (2H, t, J = 7.2 Hz, H-7), 1.59 (4H, m, H-
3, H-6), 1.48 (2H, m, H-12), 1.35–1.24 (14H, m, CH2), 0.89 (3H, t,
J = 6.8 Hz, H-18); FABMS m/z 380 [M+Na]+.
5.2.9. (E)-N-[(1R)-2-Hydroxy-1-methylethyl]-11-oxo-octadec-9-
enamide (9)
Colorless oil; 1H NMR (CDCl3, 400 MHz) d 6.91 (1H, dt, J = 16.4,
7.2 Hz, H-9), 6.13 (1H, dt, J = 16.4, 1.2 Hz, H-10), 5.66 (1H, br s, NH),
4.07 (1H, m, –CH(CH3)CH2OH), 3.66 (1H, m, –CH(CH3)CHbOH), 3.53
(1H, m, –CH(CH3)CHaOH), 2.56 (2H, t, J = 7.6 Hz, H-12), 2.25 (4H, m,
H-2, H-8), 1.58 (4H, m, H-3, H-13), 1.47 (2H, m, H-7), 1.36–1.27
(14H, m, CH2), 1.15 (3H, d, J = 6.8 Hz, –CH(CH3)CH2OH), 0.89 (3H,
t, J = 6.8 Hz, H-18); FABMS m/z 376 [M+Na]+.
5.2.17. (E)-N-2,3-Dihydroxylpropyl-11-oxo-octadec-9-enamide
(17)
Colorless oil; 1H NMR (CDCl3, 400 MHz) d 6.91 (1H, dt, J = 16.4,
7.2 Hz, H-9), 6.13 (1H, dt, J = 16.4, 1.2 Hz, H-10), 5.98 (1H, br s, NH),
3.77 (1H, m, –CH2CH(OH)CH2OH), 3.53 (2H, m, –CH2CH(OH)-
CH2OH), 3.44 (2H, m, –CH2CH(OH)CH2OH), 2.59 (2H, t, J = 7.6 Hz,
H-12), 2.26 (4H, m, H-2, H-8), 1.59 (4H, m, H-3, H-13), 1.49 (2H,
m, H-7), 1.35–1.30 (14H, m, CH2), 0.89 (3H, t, J = 6.8 Hz, H-18);
FABMS m/z 392 [M+Na]+.
5.2.10. (E)-N-[(1R)-2-Hydroxy-1-methylethyl]-10-oxo-octadec-
8-enamide (10)
Colorless oil; 1H NMR (CDCl3, 400 MHz) d 6.92 (1H, dt, J = 16.0,
6.5 Hz, H-8), 6.12 (1H, dt, J = 16.0, 1.5 Hz, H-9), 5.63 (1H, br s, NH),
4.04 (1H, m, –CH(CH3)CH2OH), 3.67 (1H, m, –CH(CH3)CHbOH), 3.54
(1H, m, –CH(CH3)CHaOH), 2.57 (2H, t, J = 7.5 Hz, H-11), 2.28 (4H, m,
H-2, H-7), 1.66 (4H, m, H-3, H-12), 1.52 (2H, m, H-6), 1.37–1.31
(14H, m, CH2), 1.18 (3H, d, J = 6.8 Hz, –CH(CH3)CH2OH), 0.92 (3H,
t, J = 6.5 Hz, H-18); FABMS m/z 376 [M+Na]+.
5.2.18. (E)-N-2,3-Dihydroxylpropyl-10-oxo-octadec-8-enamide
(18)
Colorless oil; 1H NMR (CDCl3, 400 MHz) d 6.92 (1H, dt, J = 16.0,
6.5 Hz, H-8), 6.13 (1H, dt, J = 16.0, 1.5 Hz, H-9), 5.97 (1H, br s, NH),
3.75 (1H, m, –CH2CH(OH)CH2OH), 3.55 (2H, m, –CH2CH(OH)-
CH2OH), 3.42 (2H, m, –CH2CH(OH)CH2OH), 2.59 (2H, t, J = 7.5 Hz,
H-11), 2.25 (4H, m, H-2, H-7), 1.62 (4H, m, H-3, H-12), 1.51 (2H,
m, H-6), 1.36–1.27 (14H, m, CH2), 0.91 (3H, t, J = 6.5 Hz, H-18);
FABMS m/z 392 [M+Na]+.
5.2.11. (E)-N-[(1R)-2-Hydroxy-1-methylethyl]-9-oxo-octadec-
10-enamide (11)
Colorless oil; 1H NMR (CDCl3, 400 MHz) d 6.91 (1H, dt, J = 14.0,
7.0 Hz, H-11), 6.11 (1H, dt, J = 14.0, 1.5 Hz, H-10), 5.65 (1H, br s,
NH), 4.06 (1H, m, –CH(CH3)CH2OH), 3.68 (1H, m, –CH(CH3)CHbOH),