Beilstein J. Org. Chem. 2012, 8, 192–200.
HRMS–ESI (m/z): [M + H]+ calcd for C24H22NO, 340.1696; 3-(3,4-Dihydro-2H-pyran-5-yl)-2-methylisoindolin-1-one
found, 340.1699.
(3k): Colorless solid, mp 94–97 °C; 1H NMR (400 MHz,
CDCl3) δ 1.20–1.27 (m, 1H), 1.40–1.47 (m, 1H), 1.71–1.79 (m,
2-Benzyl-3-cyclohexenylisoindolin-1-one (3d): Colorless 2H), 3.00 (s, 3H), 3.92–4.04 (m, 2H), 4.65 (s, 1H), 6.79 (s, 1H),
solid, mp 109–112 °C; 1H NMR (400 MHz, CDCl3) 7.36 (d, J = 7.2 Hz, 1H), 7.44 (t, J = 7.2 Hz, 1H), 7.53 (t, J =
δ 1.15–1.19 (m, 1H), 1.38–1.43 (m, 3H), 1.50–1.59 (m, 2H), 7.2 Hz, 1H), 7.81 (d, J = 7.2 Hz, 1H) ppm; 13C NMR (100
2.13 (t, J = 2.4 Hz, 2H), 4.06 (d, J = 14.8 Hz, 1H), 4.71 (s, 1H), MHz, CDCl3) δ 17.0, 21.5, 26.6, 65.2, 66.0, 108.2, 122.2,
5.19 (d, J = 14.8 Hz, 1H), 5.93 (s, 1H), 7.26–7.30 (m, 5H), 123.0, 128.1, 131.3, 132.7, 144.2, 144.6, 168.2 (CO) ppm;
7.41–7.50 (m, 3H), 7.87 (d, J = 7.2 Hz, 1H) ppm; 13C NMR MS m/z (% relative intensity): 229 (100), 200 (47), 186 (35),
(100 MHz, CDCl3) δ 21.8, 22.0, 22.2, 25.4, 43.9, 66.7, 122.4, 172 (54), 146 (51), 128 (20), 115 (17), 91 (24); HRMS–ESI
123.4, 127.3, 128.1, 128.4 (4C), 130.2, 131.4, 132.3, 133.4, (m/z): [M + H]+ calcd for C14H16NO2, 230.1176; found,
137.4, 144.4, 168.3 (CO) ppm; MS m/z (% relative intensity): 230.1175.
303 (64), 222 (27), 199 (70), 183 (6), 170 (12), 157 (15), 129
(27), 91 (100), 40 (37); HRMS–ESI (m/z): [M + H]+ calcd for (E)-1-Benzyl-5-(2-phenylethenyl)-1H-pyrrol-2(5H)-one (6a):
C21H22NO, 304.1696; found, 304.1691.
Colorless syrup; 1H NMR (400 MHz, CDCl3) δ 4.08 (d, J =
14.8 Hz, 1H), 4.54 (d, J = 9.2 Hz, 1H), 5.12 (d, J = 14.8 Hz,
(E)-2-Benzyl-3-(hex-2-enyl)isoindolin-1-one (4b): Colorless 1H), 5.69 (dd, J = 9.2 Hz, 15.6 Hz, 1H), 6.26 (dd, J = 1.6 Hz,
syrup; 1H NMR (400 MHz, CDCl3) δ 0.74 (t, J = 7.2 Hz, 3H), 5.6 Hz, 1H), 6.59 (d, J = 15.6 Hz, 1H), 6.96 (dd, J = 1.6 Hz,
1.25–1.87 (m, 2H), 1.79–1.86 (m, 2H), 2.55–2.70 (m, 2H), 4.17 6.0 Hz, 1H), 7.23–7.35 (m, 8H), 7.40 (dd, J = 1.6 Hz, 8.0 Hz,
(d, J = 15.2 Hz, 1H), 4.39 (dd, J = 4.0 Hz, 5.6 Hz, 1H), 2H) ppm; 13C NMR (100 MHz, CDCl3) δ 42.4, 64.8, 126.1,
4.91–4.98 (m, 1H), 5.36–5.42 (m, 1H), 5.42 (d, J = 15.2 Hz, 126.6, 127.4, 128.0, 128.2, 128.6 (2C), 128.7 (2C), 128.7 (2C),
1H), 7.28–7.32 (m, 5H), 7.37 (d, J = 7.2 Hz, 1H), 7.43–7.53 (m, 128.9 (2C), 135.7, 137.6, 146.6, 170.9 (CO) ppm; MS m/z
2H), 7.88 (d, J = 7.6 Hz, 1H) ppm; 13C NMR (100 MHz, (% relative intensity): 275 (22), 190 (11), 189 (100), 184 (30),
CDCl3) δ 13.4, 22.3, 34.1, 34.5, 43.9, 58.4, 122.4 (2C), 123.7, 161 (29), 160 (39), 132 (37), 119 (22), 104 (48), 91 (21);
127.5, 128.0, 128.1 (2C), 128.7 (2C), 131.2, 132.4, 135.4, HRMS–ESI (m/z): [M + H]+ calcd for C19H18NO, 276.1383;
137.2, 145.1, 168.5 (CO) ppm; MS m/z (% relative intensity): found, 276.1385.
305 (4), 223 (18), 222 (100), 186 (6), 172 (6), 132 (8), 104 (5),
91 (89); HRMS–ESI (m/z): [M + H]+ calcd for C21H24NO,
Supporting Information
306.1853; found, 306.1851.
Supporting Information File 1
Characterization data of the title compounds, 1H NMR and
13C NMR spectra.
3-(2,2-Diphenylethenyl)-2-methylisoindolin-1-one (3h):
Colorless solid, mp 146–148 °C; 1H NMR (400 MHz, CDCl3)
δ 3.08 (s, 3H), 5.01 (d, J = 10.0 Hz, 1H), 5.71 (d, J = 10.0 Hz,
1H), 7.25–7.27 (m, 5H), 7.38–7.46 (m, 5H), 7.47–7.52 (m, 3H),
7.83 (d, J = 7.6 Hz, 1H) ppm; 13C NMR (100 MHz, CDCl3)
δ 27.5, 61.3, 122.8, 123.4, 124.3, 127.2 (2C), 127.9, 128.1,
128.3 (3C), 128.8 (2C), 129.5 (2C), 131.3, 132.3, 138.5, 140.4,
144.5, 148.1, 168.0 (CO) ppm; MS m/z (% relative intensity):
325 (28), 310 (15), 294 (9), 265 (5), 248 (11), 220 (18), 188
(10), 178 (11), 165 (13), 149 (37), 91 (30), 57 (63), 43 (100);
HRMS–ESI (m/z): [M + H]+ calcd for C23H20NO, 326.1540;
found, 326.1545.
Supporting Information File 2
X-ray data for compound 3h.
Acknowledgements
This work was financially supported by the National Natural
Crystal data for 3h (recrystallized from ethanol): Science Foundation of China (20872056).
C23H19NO, Mr = 325.39. Monoclinic, a = 17.373(11) Å, b =
References
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