Molecules 2010, 15
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[C(3), C(6)]; 50.3 [C(1′), C(1′′)]; 28.0 [C(2′), C(2′′)]; 20.5 [C(3′), C(4′), C(3′′), C(4′′)]; MS, m/z (%):
250 (84) [M+], 235 (13), 207 (100), 193 (40), 165 (28), 164 (31), 151 (60), 138 (23), 123 (20), 67 (21),
53 (46); HRMS (ESI TOF-MS): Calcd. for C14H23N2O2 251.1754; found: 251.1756.
2,5-Bis-(pentylamino)-1,4-benzoquinone (16). Red crystals. Purified by column chromatography,
eluent hexane/dichloromethane 1:2 (v/v). Mp 134.6–137.1 ºC; IR: 3,263 (NH), 2,957, 2,927, 2,857,
1,644, 1,553, 1,497, 1,463, 1,369, 1271, and 812 cm-1; 1H-NMR (* indicates assignments that could be
reversed) δ: 6.62 (br. s, NH), 5.28 [s, H-C(3), H-C(6)]; 3.12 [q, J = 6.8 Hz, 2 H-C(1′); 2 H-C(1′′)];
1.59-1.68 [m, 2 H-C(2′), 2 H-C(2′′)]; 1.21-1.38 [m, 2 H-C(3′), 2 H-C(4′), 2 H-C(3′′), 2 H-C(4′′)];
0.86-0.91 [m, 3 H-C(5′), 3 H-C(5′′)]; 13C-NMR δ: 177.1 [C(1), C(4)]; 150.4 [C(2), C(5)]; 91.6 [C(3),
C(6)]; 41.6 [C(1′), C(1′′)]; 28.1 [C(3′), C(3′′)]*; 27.0 [C(2′), C(2′′)]; 21.3 [C(4′), C(4′′)]*; 13.0
[C(5′), C(5′′)]; MS, m/z (%): 278 (100) [M+], 235 (73), 223 (30), 207 (40), 193 (46), 179 (28), 165
(62), 164 (19), 151 (45), 138 (23), 137 (23), 110 (23), 67 (54), 54 (56); HRMS (ESI TOF-MS): Calcd.
for C16H27N2O2 279.2067; found: 279.2070.
2,5-Bis-(decylamino)-1,4-benzoquinone (19): Red crystals. Purified by column chromatography, eluent
hexane/diethylether 2:1 (v/v). Mp 126.4–127.3 ºC; IR: 3,256 (NH), 2,954, 2,917, 2,848, 1,644, 1,554,
1,503, 1,456, 1,365, 1,291, and 683 cm-1; 1H-NMR δ: 6.62 (br. s, NH); 5.30 [s, H-C(3), H-C(6)]; 3.13
[q, J = 6.6 Hz, 2 H-C(1′), 2 H-C(1′′)]; 1.50-1.70 [m, 2 H-C(2′), 2 H-C(2′′)]; 1.15-1.40 [m, 14 H-C(3′-
13
9′), 14 H-C(3′′-9′′)]; 0.88 [t, J = 6.6 Hz, 3 H-C(10′), 3 H-C(10′′)]; C-NMR (* indicates assignments
that could be reversed) δ: 178.3 [C(1), C(4)]; 151.6 (C(2), C(5)]; 92.8 [C(3), C(6)]; 42.8 (C(1′), C(1′′)];
32.1 [C(2′), C(2′′)]*; 29.7 [C(8′), C(8′′)]*; 29.7 [C(3′), C(3′′)]*; 29.5 [C(4′), C(4′′)]*; 29.4 [C(5′),
C(5′′)]*; 28.5 [C(6′), C(6′′)]*; 27.2 [C(7′), C(7′′)]*; 22.9 [C(9′), C(9′′)]*; 14.4 [C(10′), C(10′′)]; MS, m/z
(%): 418 (100) [M+], 362 (35), 333 (11), 305 (31), 165 (25), 162 (27), 151 (17), 138 (17), 68 (20), 54
(30). HRMS (ESI TOF-MS): Calcd. for C26H47N2O2 419.3632; found: 419.3637.
2,5-Bis-(1-(2-aminoethyl)piperidino)-1,4-benzoquinone (20). Red crystals. Purified by column
chromatography, eluent hexane/methanol 1:3 (v/v). Mp 164.2–165.5 ºC; IR: 3,291 (NH), 3,251 (NH),
1
2,935, 2,849, 1,641, 1,551, 1,493, 1,462, 1,364, 1,289, 1,223, 1,126, 993, and 693 cm-1; H-NMR δ:
7.04 (br. s, NH); 5.30 [s, H-C(3), H-C(6)]; 3.19 [q, J = 6.0 Hz, 2 H-C(1′), 2 H-C(1′′)]; 2.58 [t,
J = 6.0 Hz, 2 H-C(2′), 2 H-C(2′′)]; 2.34-2.42 [m, 2 H-C(3′), 2 H-C(7′), 2 H-C(3′′), 2 H-C(7′′)]; 1.59
[quint., J = 5.5 Hz, 2 H-C(4′), 2 H-C(6′), 2 H-C(4′′), 2 H-C(6′′)]; 1.40-1.44 [m, 2 H-C(5′), 2 H-C(5′′)];
13C-NMR δ: 178.5 [C(1), C(4)]; 151.6 [C(2), C(5)]; 93.3 [C(3), C(6)]; 56.11 [C(2′), C(2′′)]; 54.5
[C(3′), C(7′), C(3′′), C(7′′)]; 39.3 (C(1′), C(1′′)]; 26.1 [C(4′), C(6′), C(4′′), C(6′′)]; 24.5 [C(5′), C(5′′)];
MS, m/z (%): 360 (2) [M+], 99 (11), 98 (100), 70 (6), 55 (14). HRMS (ESI TOF-MS): Calcd. for
C20H33N4O2 361.2598; found: 361.2599.
2,5-Bis-(4-(2-aminoethyl)morfoline)-1,4-benzoquinone (21). Red crystals. Purified by column
chromatography, eluent hexane/ethanol 1:4 (v/v). Mp 186.8–188.0 ºC; IR: 3,354 (NH), 2,869, 2,811,
1,645, 1,613, 1,495, 1,455, 1,354, 1,293, 1,115, 1,026, and 809 cm-1; 1H-NMR δ: 7.00 (br. s, NH); 5.28
[s, H-C(3), H-C(6)]; 3.72 [t, J = 4.5 Hz, 2 H-C(4′), 2 H-C(5′), 2 H-C(4′′), 2 H-C(5′′)]; 3.20 [q,
J = 6.0 Hz, 2 H-C(1′), 2 H-C(1′′)]; 2.64 [t, J = 6.0 Hz, 2 H-C(2′), 2 H-C(2′′)]; 2.47 [t, J = 4.5 Hz, 2 H-