Molecules 2017, 22, 39
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n-Butyl 3-(phenylsulfonyl)propanoate (3ac): pale yellow oil; 1H-NMR:
δ
7.89 (m, 2H), 7.63 (m, 3H), 4.03 (m,
2H), 3.45 (t, 2H, J = 7.5 Hz), 2.73 (t, 2H, J = 7.5 Hz), 1.56 (m, 2H), 1.33 (m, 2H), 0.90 (m, 3H); 13C-NMR:
δ
169.7, 138.3, 133.8, 129.2, 127.9, 64.9, 51.2, 30.2, 27.6, 18.8, 13.4; HRMS (ESI): Calcd. for: C13H19O4S
[M + H]+: 271.0999; found: 271.0998.
◦
t-Butyl 3-(phenylsulfonyl)propanoate (3ad): yellow solid, m.p. 46~48 C; 1H-NMR:
3H), 3.37 (t, 2H, J = 7.8 Hz), 2.65 (t, 2H, J = 7.8 Hz), 1.38 (s, 9H); 13C-NMR:
169.2, 138.7, 134.0, 129.5,
128.2, 82.0, 51.7, 29.0, 28.1; HRMS (ESI): Calcd. for: C13H19O4S [M + Na]+: 293.0818; found: 293.0819.
δ 7.91 (m, 2H),7.62 (m,
δ
Benzyl 3-(phenylsulfonyl)propanoate (3ae): pale yellow solid, m.p. 61~63 ◦C; 1H-NMR:
7.89 (m, 2H),
7.59 (m, 3H), 7.32 (m, 5H), 5.05 (s, 2H), 3.43 (t, 2H, J = 7.8 Hz), 2.73 (t, 2H, J = 7.8 Hz); 13C-NMR:
δ
δ
169.7, 138.3, 135.1, 134.0, 139.4, 128.6, 128.4, 128.3, 128.1, 67.0, 51.3, 27.8; HRMS (ESI): Calcd. for:
C16H16NaO4S [M + Na]+: 327.0662; found: 327.0666.
1
3-(Phenylsulfonyl)propanenitrile (3af) [19]: H-NMR:
δ
7.94 (m, 2H), 7.69 (m, 3H), 7.32 (m, 5H), 3.40 (t,
2H, J = 7.6 Hz), 2.82 (t, 2H, J = 7.6 Hz); 13C-NMR:
δ 137.5, 134.8, 129.8, 128.3, 116.1, 51.1, 12.1; HRMS
(ESI): Calcd. for: C9H9NNaO2S [M + Na]+: 218.0246; found: 218.0249.
1
Methyl 3-tosylpropanoate (3ba) [20]: H-NMR: δ 7.72 (d, 2H, J = 8.2 Hz), 7.31 (d, 2H, J = 8.2 Hz), 3.57 (s,
3H), 3.35 (t, 2H, J = 7.5 Hz), 2.67 (t, 2H, J = 7.5 Hz), 2.39 (s, 3H); 13C-NMR:
δ 170.4, 145, 135.4, 129.9,
128.1, 52.1, 51.4, 27.6, 21.5; HRMS (ESI): Calcd. for: C11H15O4S [M + H]+: 243.0686; found: 243.0690.
1
Ethyl 3-tosylpropanoate (3bb) [20]: H-NMR:
δ
7.74 (d, 2H, J = 7.8 Hz), 7.32 (d, 2H, J = 7.8 Hz), 4.03 (q,
2H, J = 7.1 Hz), 3.36 (t, 2H, J = 7.6 Hz), 2.66 (t, 2H, J = 7.6 Hz), 2.40 (s, 3H), 1.17 (t, 2H, J = 7.1 Hz), 0.90
(m, 3H); 13C-NMR:
170.0, 145.0, 135.5, 130.0, 128.1, 61.3, 51.5, 27.9, 21.6, 14.0; HRMS (ESI): Calcd. for:
C12H17O4S [M + H]+: 257.0842; found: 257.0844.
δ
1
Methyl 3-((4-methoxyphenyl)sulfonyl)propanoate (3ca) [20]: H-NMR:
2H, J = 9.0 Hz), 3.89 (s, 3H), 3.64 (s, 3H), 3.41 (t, 2H, J = 7.1 Hz), 2.74 (t, 2H, J = 7.1 Hz); 13C-NMR:
170.4, 163.9, 130.3, 129.8, 114.5, 55.7, 52.2, 51.6, 27.7; HRMS (ESI): Calcd. for: C11H15O5S [M + H]+:
259.0635; found: 259.0637.
δ 7.83 (d, 2H, J = 9.0 Hz), 7.04 (d,
δ
1
Methyl 3-((4-chlorophenyl)sulfonyl)propanoate (3da) [21]: H-NMR:
δ 7.78 (d, 2H, J = 8.5 Hz), 7.49 (d, 2H,
J = 8.5 Hz), 3.55 (s, 3H), 3.38 (t, 2H, J = 7.6 Hz), 2.67 (t, 2H, J = 7.6 Hz); 13C-NMR:
δ 170.1, 140.5, 136.8,
129.6, 52.2, 51.3, 27.4; HRMS (ESI): Calcd. for: C10H11ClNaO4S [M + Na]+: 284.9959; found: 284.9962.
Methyl 3-((4-(trifluoromethyl)phenyl)sulfonyl)propanoate (3ea): white solid, m.p. 120~122 ◦C; 1H-NMR:
δ
8.06 (d, 2H, J = 8.2 Hz), 7.85 (d, 2H, J = 8.6 Hz), 3.64 (s, 3H), 3.47 (t, 2H, J = 7.5 Hz), 2.77 (t, 2H,
J = 7.5 Hz); 13C-NMR:
δ 170.2, 142.0, 135.7, 128.9, 127.0, 126.6, 52.4, 51.4, 27.4; HRMS (ESI): Calcd. for:
C11H11F3NaO4S [M + Na]+: 319.0222; found: 319.0226.
Methyl 3-((4-cyanophenyl)sulfonyl)propanoate (3fa): pale yellow solid, m.p. 119~122 ◦C; 1H-NMR:
δ
8.03
(m, 2H), 7.87 (m, 2H), 3.64 (s, 3H), 3.46 (t, 2H, J = 7.5 Hz), 2.77 (t, 2H, J = 7.5 Hz); 13C-NMR:
δ 17.02, 142.8,
133.3, 129.1, 118.0, 117.1, 52.6, 51.5, 27.4; HRMS (ESI): Calcd. for: C11H12NO4S [M + H]+: 254.0482;
found: 254.0486.
1
1,2-Bis(phenylsulfonyl)ethane (3ag) [22]: H-NMR:
13C-NMR: δ 138.0, 134.6, 129.7, 128.1, 49.5.
δ 7.88 (m, 4H), 7.70 (m, 2H), 7.60 (m, 6H), 3.45 (s, 4H);
1-Methoxy-4-((2-(phenylsulfonyl)ethyl)sulfonyl)benzene (3cg): white solid, m.p. 150~152 ◦C; 1H-NMR:
7.87 (d, 2H, J = 7.6 Hz), 7.78 (d, 2H, J = 8.8 Hz, 7.70 (t, 1H, J = 7.4 Hz ), 7.58 (t, 2H, J = 7.7 Hz ), 3.88
(s, 3H), 3.42 (m, 4H); 13C-NMR:
164.4, 138.1, 134.6, 130.4, 129.8, 129.4, 128.1, 114.5, 55.9, 49.8; HRMS
(ESI): Calcd. for: C15H17O5S2 [M + H]+: 341.0512; found: 341.0515.
δ
δ