Med Chem Res
4-(2-Methoxy-2-oxoethyl)phenyl oleate (16) IR (KBr)
νmax: 3005, 2925, 2854, 1743,1609, 1508, 1460, 1018, 916,
848, 723 cm−1; 1H NMR (CDCl3, 400 MHz): δ = 0.88 (3H,
t, J = 6.8 Hz, CH3), 1.27–1.34 (20H, m, H-4–7, 12–17),
1.71–1.78 (2H, m, H-3), 2.03 (4H, m, H-8, 11), 2.54 (2H, t,
J = 7.4 Hz, H-2), 3.61 (2H, s, ph–CH2), 3.69 (3H, s,
OCH3), 5.34–5.37 (2H, m, H-9, 10), 7.02–7.05 (2H, m, H-
2', 6'), 7.27–7.31 (2H, m, H-3', 5'); 13C NMR (CDCl3, 100
MHz): δ = 14.22 (CH3, C-20), 22.79 (CH2, C-18), 25.04
(CH2, C-8), 27.34 (CH2, C-3), 27.36 (CH2, C-12), 29.20
(CH2, C-7), 29.27 (CH2, C-16), 29.43 (CH2, C-6), 29.64
(CH2, C-15), 29.70 (CH2, C-5), 29.79 (CH2, C-14), 29.88
(CH2, C-4), 29.90 (CH2, C-13), 32.02 (CH2, C-17), 34.49
(CH2, COCH2), 40.65 (CH2, ph–CH2), 52.17 (CH3,
O–CH3), 121.78 (CH, C-22), 128.01 (CH, C-26), 128.19
(CH, C-25), 129.82 (CH, C-23), 130.14 (CH, CH=CH),
130.36 (CH, CH=CH), 131.48 (C, C-24), 149.97 (C, O–C),
171.85 (C, ph–O–C=O), 172.34 (C, CH3O–C=O); EIMS
m/z 430.3 [M + H]+, 453.3 [M + Na]+.
171.69 (C, O–C = O); EIMS m/z 472.4 [M + H]+, 495.5
[M + Na]+.
Ethyl
(Z)-4-(docos-13-enamido)benzoate
(19) M.p.
77.2–77.4 °C; 1H NMR (CDCl3, 400 MHz): δ = 0.89 (3H, t,
J = 6.8 Hz, CH3), 1.27–1.42 (28H, m, H4–11, H16–21),
1.40 (3H, t, J = 7.2 Hz, O–CH2CH3), 1.71–1.77 (2H, m, H-
3), 2.00–2.05 (4H, m, H-12, -15), 2.39 (2H, t, J = 7.2 Hz,
H-2), 4.37 (2H, q, J = 7.2 Hz, O–CH2CH3), 5.32–5.40(2H,
m, H-13,-14), 7.63 (2H, d, J = 8.4 Hz, H-3', -5'), 7.62 (1H,
brs, NH), 8.00 (2H, d, J = 8.4 Hz, H-2', 6'); 13C NMR
(CDCl3, 100 MHz): δ 14.31 (2CH3, C-11, 35), 22.80 (CH2,
C-26), 25.57 (CH2, C-15), 27.31 (CH2, C-21), 27.45 (CH2,
C-16), 29.26 (CH2, C-14), 29.32 (CH2, C-24), 29.37 (CH2,
C-30), 29.47 (3CH2, C-25, 27, 28), 29.52 (2CH2, C-23, 32),
29.55 (2CH2, C-22, 31), 29.61 (2CH2, C-19, 20), 29.77
(CH2, C-29), 31.90 (CH2, COCH2), 52.00 (CH2, O–CH2),
118.75 (2CH, C-3, 7), 125.42 (CH, C-5), 129.87 (CH, C-6),
129.92 (CH, C-4), 130.82 (CH=CH, C-17, 18), 142.27 (C,
NH–C), 166.66 (C, ph–C = O), 171.79 (C, CONH); EIMS
m/z 486.6 [M + H]+.
Methyl (Z)-4-(docos-13-enamido)benzoate (17) M.p.
81.3–81.5 °C; 1H NMR (CDCl3, 400 MHz): δ = 0.90 (3H, t,
J = 6.8 Hz, CH3), 1.28–1.33 (28H, m, H4–11, H16–22),
1.70–1.77 (2H, m, H-3), 2.00–2.05 (4H, m, H-12, -15), 2.39
(2H, t, J = 7.6 Hz, H-2), 3.91 (3H, s, O–CH3), 5.35–5.40
(2H, m, H-13,-14), 7.63 (2H, d, J = 8.4 Hz, H-3',-5'), 7.62
(1H, brs, NH), 7.98 (2H, d, J = 8.4 Hz, H-2', -6'); 13C NMR
(CDCl3, 100 MHz): δ = 14.31 (CH3, C-22), 22.80 (CH2, C-
15), 25.57 (CH2, C-18), 27.31 (CH2, C-6), 27.45 (CH2, C-
3), 29.26 (CH2, C-19), 29.32 (CH2, C-16), 29.37 (CH2, C-
11), 29.47 (3CH2, C-13, 14, 17), 29.52 (2CH2, C-8, 9),
29.55 (2CH2, C-7,10), 29.61 (2CH2, C-4, 5), 29.77 (CH2,
C-12), 31.90 (CH2, COCH2), 52.00 (CH3, O–CH3), 118.75
(C, C-30), 125.42 (C, C-26), 129.87 (C, CO–C), 129.92
(2CH, C-27, 29), 130.82 (CH=CH, C-1, 2), 142.27 (C,
NH–C), 166.66 (C, ph–C = O), 171.79 (C, CONH); EIMS
m/z 472.5 [M + H]+.
Ethyl (Z)-4-(docos-13-enoyloxy)benzoate (20) 1H NMR
(CDCl3, 400 MHz): δ = 0.90 (3H, t, J = 6.8 Hz, CH3),
1.28–1.31 (28H, m, H4–11, H16–21), 1.40 (3H, t, J = 7.2
Hz, O–CH2CH3), 1.74–1.81 (2H, m, H-3), 1.99–2.06 (4H,
m, H-12, -15), 2.59 (2H, t, J = 7.2 Hz, H-3), 4.93 (2H, t, J
= 7.2 Hz, O–CH2CH3), 5.36–5.38 (2H, m, H-13, -14), 7.17
(2H, d, J = 8.8 Hz, H-3', -5'), 8.09 (2H, d, J = 8.8 Hz, H-2',
-6'); 13C NMR (CDCl3, 100 MHz): δ = 14.11 (CH3, C-22),
14.32 (CH3, C-35), 22.69 (CH2, C-8), 24.85 (CH2, C-18),
27.22 (2CH2, C-11, 14), 29.09 (CH2, C-19), 29.25 (CH2, C-
9), 29.32 (CH2, C-4), 29.45 (3CH2, C-6, 7, 17), 29.53
(2CH2, C-1, 2), 29.59 (2CH2, C-3, 10), 29.78 (2CH2, C-12,
13), 31.92 (CH2, C-5), 34.40 (CH2, COCH2), 61.03 (CH2,
O–CH2), 121.53 (2CH, C-26, 30), 127.95 (C, C-28), 129,87
(CH, C-29), 129.91 (CH, C-27), 131.07 (CH=CH, C-15,
16), 154.36 (C, O–C), 165.83 (C, ph–C=O), 171.76 (C,
O–C=O); EIMS m/z 509.6 [M + Na]+.
Methyl (Z)-4-(docos-13-enoyloxy)benzoate (18) M.p.
37.0–37.8 °C; 1H NMR (CDCl3, 400 MHz): δ = 0.90 (3H, t,
J = 6.8 Hz, CH3), 1.28–1.30 (m, 28H, H4–11, H16–21),
1.74–1.81 (m, 2H, H-3), 2.02–2.06 (m, 4H, H-12, -15), 2.59
(t, J = 7.6 Hz, 2H, H-2), 3.93 (s, 3H, OCH3), 5.33–5.41 (m,
2H, H-13, -14), 7.18 (d, J = 8.8 Hz, 2H, H-3', -5'), 8.08 (d,
J = 8.8 Hz, 2H, H-2', -6'); 13C NMR (CDCl3, 100 MHz): δ
= 14.16 (CH3, C-22), 22.68 (CH2, C-15), 24.85 (CH2, C-
18), 27.21 (2CH2, C-3, 6), 29.09 (CH2, C-19), 29.24 (CH2,
C-16), 29.32 (CH2, C-11), 29.45 (CH2, C-17), 29.53 (2CH2,
C-13, 14), 29.59 (2CH2, C-8, 9), 29.59 (2CH2, C-7, 10),
29.78 (2CH2, C-4, 5), 31.91 (CH2, C-12), 34.40 (CH2,
COCH2), 52.14 (CH3, O–CH3), 121.59 (2CH, C-26, 30),
127.60 (C, C-28), 129.87 (2CH, C-27, 29), 131.12
(CH=CH, C-1, 2), 154.45 (C, O–C), 166.31 (C, ph–C = O),
Ethyl (Z)-2-(4-(docos-13-enamido)phenyl)acetate (21) M.
p. 91.3–92.0 °C; 1H NMR (CDCl3, 400 MHz): δ = 0.88
(3H, t, J = 6.8 Hz, CH3), 1.23 (2H, t, J = 7.6 Hz,
O–CH2CH3) 1.24–1.31 (28H, m, H4–11, H16–21),
1.68–1.75 (2H, m, H-3), 1.98–2.03 (4H, m, H-12, -15), 2.32
(2H, t, J = 7.2 Hz, H-32), 3.56 (2H, s, CH2CO), 4.13 (2H,
q, J = 7.6 Hz, O–CH2CH3), 5.30–5.38 (2H, m, H-13, -14),
7.20 (2H, d, J = 8.4 Hz, H-3', -5'), 7.44 (1H, brs, NH), 7.45
(2H, d, J = 8.4 Hz, H-2', -6'); 13C NMR (CDCl3, 100 MHz):
δ = 14.09 (CH3, C-33), 14.16 (CH3, C-36), 22.67 (CH2, C-
26), 25.56 (CH2, C-29), 27.22 (2CH2, C-14, 17), 29.32
(CH2, C-30), 29.40 (CH2, C-27), 29.52 (CH2, C-22), 29.56
(3CH2, C-24, 25, 28), 29.62 (4CH2, C-18–21), 29.77