6
Y. OUESLATI ET AL.
4.2.4. Methyl 2-((6-oxocyclohex-1-enyl)methylsulfanyl)acetate (2d) [51,62]
1
Yield = 72%; colorless oil; H NMR (300 MHz, CDCl3) δ 6.96 (t, J = 4.1 Hz, 1H), 3.74
(s, 3H), 3.40 (d, J = 0.9 Hz, 2H), 3.19 (s, 2H), 2.49–2.42 (m, 4H), 2.08–1.95 (m, 2H); 13
C
NMR (75 MHz, CDCl3) δ 198.0, 170.8, 147.7, 135.1, 52.3, 38.2, 32.9, 30.4, 25.9, 22.9; MS
(m/z) (relative intensity): 214 (C10H14O3S, M+, 15), 182 (29), 155 (17), 141 (100), 109 (13),
79 (38), 53 (24).
4.2.5. 2-((4-Chlorophenylsulfanyl)methyl)cyclohex-2-enone (2e) [51,62]
1
Yield = 85%; yellow oil; H NMR (300 MHz, CDCl3) δ 7.34–7.13 (m, 4H), 6.76 (t,
J = 3.5 Hz, 1H), 3.66 (d, J = 1.0 Hz, 2H), 2.49–2.39 (m, 2H), 2.36–2.25 (m, 2H), 2.05–1.88
(m, 2H); 13C NMR (75 MHz, CDCl3) δ 197.9, 147.7, 134.9, 134.7, 132.3, 131.5, 128.8, 38.2,
32.8, 25.9, 22.8; MS (m/z) (relative intensity): 252 (C13H13ClOS, M+, 94), 144 (82), 109
(41), 108 (44), 81 (100), 79 (76), 53 (73).
4.2.6. 2-((Pyrimidin-2-ylsulfanyl)methyl)cyclohex-2-enone (2f)
Yield = 60%; yellow solid; mp = 90–92°C; 1H NMR (300 MHz, CDCl3) δ 8.33 (d,
J = 4.9 Hz, 2H), 7.01 (t, J = 4.0 Hz, 1H), 6.83 (t, J = 4.9 Hz, 1H), 3.80 (d, J = 1.1 Hz, 2H),
2.38–2.12 (m, 4H), 1.84–1.78 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 197.9, 171.9, 157.0,
147.8, 135.4, 116.4, 38.0, 28.7, 25.9, 22.7; MS (m/z) (relative intensity): 220 (C11H12N2OS,
M+, 79), 192 (22), 187 (100), 163 (51), 131 (33), 112 (32), 79 (46), 53 (61); HRMS (ESI):
calcd for C11H13N2OS [M + H]+ 221.07486, found 221.07594.
4.2.7. 2-(1-(Propylsulfanyl)ethyl)cyclohex-2-enone (2g) [51,62]
Yield = 94%; yellow oil; IR: 1670 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.03 (t, J = 4.2 Hz,
1H), 4.04 (qd, J = 7.0, 0.6 Hz, 1H), 2.54–2.33 (m, 6H), 2.08–1.92 (m, 2H), 1.67–1.48 (m,
2H), 1.35 (d, J = 7.1 Hz, 3H), 0.96 (t, J = 7.3 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ
197.8, 145.2, 141.7, 38.5, 35.7, 33.6, 26.0, 22.8, 22.7, 21.4, 13.6; HRMS (ESI): calcd for
C11H18OSNa [M + Na]+ 221.0976, found 221.0971.
4.2.8. 2-(1-(Isopropylsulfanyl)ethyl)cyclohex-2-enone (2h)
1
Yield = 88%; colorless oil; H NMR (300 MHz, CDCl3) δ 7.03 (t, J = 4.1 Hz, 1H), 4.10
(q, J = 7.0 Hz, 1H), 2.89–2.81 (m, 1H), 2.50–2.35 (m, 4H), 2.04–1.92 (m, 2H), 1.33 (d,
J = 7.0 Hz, 3H), 1.25–1.21 (m, 6H); 13C NMR (75 MHz, CDCl3) δ 197.4, 145.0, 142.8,
38.6, 35.2, 35.10, 26.2, 23.8, 23.5, 22.9, 22.2; MS (m/z) (relative intensity): 198 (C11H18OS,
M+, 37), 155 (99), 124 (100), 96 (30), 79 (25), 67 (39), 55 (25); HRMS (ESI): calcd for
C11H19OS [M + H]+ 199.11566, found 199.11642.
4.2.9. 2-(1-(Benzylsulfanyl)ethyl)cyclohex-2-enone (2i)
1
Yield = 89%; yellow oil; H NMR (300 MHz, CDCl3) δ 7.28–7.16 (m, 5H), 6.92 (t,
J = 4.2 Hz, 1H), 3.98 (q, J = 7.0 Hz, 1H), 3.66 (s, 2H), 2.38–2.27 (m, 4H), 1.94–1.84 (m,
2H), 1.29 (d, J = 7.1 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 197.3, 145.0, 141.7, 138.6,
128.9, 128.4, 126.8, 38.6, 36.8, 36.6, 26.0, 22.7, 21.3; MS (m/z) (relative intensity): 246
(C15H18OS, M+, 6), 155 (100), 123 (45), 91 (58), 77 (19), 65 (23), 55 (18); HRMS (ESI):
calcd for C15H19OS [M + H]+ 247.11566, found 247.12180.