Molecules 2019, 24, 459
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4
7
2
-Phenyl-N-propylbutanamide (2b): colorless oil (97.5 mg, 95%). 1H-NMR (300 MHz, CDCl3)
δ
.33–7.23 (m, 2H), 7.23–7.13 (m, 3H), 5.49 (s, 1H),
δ
3.20 (td, J = 7.1, 6.5 Hz, 2H), 2.65 (t, J = 7.5 Hz, 2H),
.17 (t, J = 7.5 Hz, 2H), 1.97 (m, 2H), 1.51 (m, 2H), 0.91 (t, J = 7.4 Hz, 3H); 13C-NMR (75 MHz, CDCl3)
δ
1
72.7, 141.6, 128.6, 128.4, 126. 0, 41.3, 36.0, 35.3, 27.2, 23.0, 11.4.
1
2
7
3
-Phenyl-N-propylacetamide (2c) [35]: white solid (66.5 mg, 75%). H-NMR (300 MHz, CDCl )
δ
3
.40–7.23 (m, 5H), 5.41 (s, 1H), 3.57 (s, 2H),
δ
3.17 (td, J = 7.2, 6.2 Hz, 2H), 1.44 (m, 2H), 0.83 (t, J = 7.4 Hz
H); C-NMR (75 MHz, CDCl ) δ 171.0, 135.2, 129.5, 129.1, 127.4, 44.0, 41.4, 22.8, 11.3.
,
13
3
1
3
-(4-Methoxyphenyl)-N-propylpropanamide (2d) [34]: white solid (105.1 mg, 95%). H-NMR (300
MHz, CDCl3)
δ
7.11 (d, J = 8.1 Hz, 2H), 6.82 (d, J = 8.1 Hz, 2H), 5.53 (s, 1H), 3.77 (s, 3H), 3.16 (td,
J = 6.7 × 2 Hz, 2H), 2.90 (t, J = 7.5 Hz, 2H), 2.42 (t, J = 7.5 Hz, 2H), 1.45 (m, 2H), 0.85 (t, J = 7.4 Hz, 3H);
13
C-NMR (75 MHz, CDCl ) δ 172.2, 158.1, 133.0, 129.3, 114.0, 55.3, 41.2, 38.9, 31.0, 22.9, 11.3.
3
1
N-Propyl-3-(p-tolyl)propanamide (2e): white solid (100.6 mg, 98%). H-NMR (300 MHz, CDCl )
δ
3
7
2
.18–6.99 (m, 4H), 5.72 (s, 1H), 3.16 (td, J = 6.5, 6.4 Hz, 2H), 2.91 (t, J = 7.8 Hz, 2H), 2.44 (t, J = 7.8 Hz,
H), 2.30 (s, 3H), 1.45 (m, 2H), 0.85 (t, J = 7.4 Hz, 3H); 13C-NMR (75 MHz, CDCl3)
δ
172.2, 137.9, 135.6,
1
29.1, 128.2, 41.2, 38.6, 31.4, 22.8, 21.0, 11.3.
1
3
-Phenyl-N-propylpropanamide (2a) (derived from 1f) [34]: white solid (76.5 mg, 80%). H-NMR (300
MHz, CDCl3) δ 7.32–7.24 (m, 2H), 7.23–7.15 (m, 3H), 5.50 (s, 1H), 3.16 (td, J = 6.9, 6.5 Hz, 2H), 2.96 (t,
13
J = 7.7 Hz, 2H), 2.46 (t, J = 7.7 Hz, 2H), 1.44 (m, 2H), 0.84 (t, J = 7.4 Hz, 3H); C-NMR (75 MHz, CDCl3)
δ 172.1, 141.0, 128.6, 128.4, 126.3, 41.3, 38.6, 31.9, 22.9, 11.3.
1
4
7
(
-Cyclohexyl-N-propylbenzamide (2g): white solid (99.4 mg, 81%). H-NMR (300 MHz, CDCl )
δ
3
.73–7.66 (m, 2H), 7.26–7.21 (m, 2H), 6.32 (s, 1H), 3.39 (td, J = 7.4, 6.5 Hz, 2H), 2.53 (m, 1H), 1.94–1.73
m, 5H), 1.61 (m, 2H), 1.43 – 1.22 (m, 5H), 0.96 (t, J = 7.4 Hz, 3H); 1 C-NMR (75 MHz, CDCl )
3
δ
167.6,
3
+
151.6, 132.4, 127.0 (
×
2), 44.5, 41.7, 34.3, 26.8, 26.1, 23.0, 11.5; HRMS (FTMS-ESI) m/z: [M + 1] calc for
C H NO 246.1852, found 246.1849.
16
23
1
1
-Phenyl-N-propylcyclopentane-1-carboxamide (2h): white solid (113.4 mg, 98%). H-NMR (300 MHz,
CDCl3) 7.38–7.21 (m, 5H), 5.22 (s, 1H), 3.09 (td, J = 7.0, 5.9 Hz, 2H), 2.52–2.41 (m, 2H), 2.06–1.96 (m,
H), 1.89–1.75 (m, 2H), 1.75–1.60 (m, 2H), 1.36 (m, 2H), 0.75 (t, J = 7.4 Hz, 3H); 13C-NMR (75 MHz,
δ
2
CDCl ) δ 176.4, 144.4, 128.6, 126.8 (× 2), 59.3, 41.4, 36.9, 24.0, 22.7, 11.1.
3
1
(
3r,5r,7r)-N-Propyladamantane-1-carboxamide (2i): colorless oil (109.6 mg, 99%). H-NMR (300 MHz,
CDCl3) δ 5.63 (s, 1H), 3.21 (td, J = 6.7, 6.3 Hz, 2H), 2.08–2.01 (m, 3H), 1.88–1.82 (m, 6H), 1.76–1.68 (m,
6
2
H), 1.51 (m,2H), 0.91 (t, J = 7.4 Hz, 3H); 13C-NMR (75 MHz, CDCl3)
3.0, 11.4.
δ
177.7, 41.0, 40.7, 39.4, 36.6, 28.3,
1
2
-(4-Isobutylphenyl)-N-propylpropanamide (2j): colorless oil (74.2 mg, 60%). H-NMR (300 MHz,
CDCl3)
δ
7.22–7.16 (m, 2H), 7.14–7.08 (m, 2H), 5.41 (s, 1H), 3.53 (q, J = 7.2 Hz, 1H), 3.14 (td, J = 7.1,
5
6
4
.9 Hz, 2H), 2.45 (d, J = 7.2 Hz, 2H), 1.84 (m, 1H), 1.51 (d, J = 7.2 Hz, 3H), 1.41 (m, 2H), 0.90 (d, J = 6.6 Hz
,
H), 0.80 (t, J = 7.4 Hz, 3H); 13C-NMR (75 MHz, CDCl3)
δ
174.5, 140.7, 138.8, 129.6, 127.4, 46.8, 45.1,
1.3, 30.2, 22.8, 22.4, 18.5, 11.2.
N-Propylpent-4-enamide (2k): colorless oil (66.4 mg, 94%). 1H-NMR (300 MHz, CDCl3)
J = 8.7 Hz, 1H), 5.69 (s, 1H), 5.04 (dd, J = 18.9, 13.6 Hz, 2H), 3.22 (d, J = 6.8 Hz, 2H), 2.33 (dt, J = 35.4,
.5 Hz, 4H), 1.52 (dd, J = 14.5, 7.3 Hz, 2H), 0.92 (t, J = 7.2 Hz, 3H); 13C-NMR (75 MHz, CDCl3)
172.3,
37.2, 115.5, 41.3 36.0, 29.8, 22.9, 11.4.
δ 5.82 (t,
7
δ
1