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(s, 3H); 13C NMR (100 MHz, CDCl3) d 184.3, 151.9, 139.0, 131.7, 128.5; HRMS (ESI-TOF) calcd for [C9H8O + Na]+ 155.0467, found
129.6, 127.6, 122.9, 119.5, 13.0.
155.0473.
Dec-1-en-3-one (4d). Isolated yield of 4d, (44.7 mg, 58%).
1H-Imidazole-4-carbaldehyde (2t). Isolated yield of 2t, (24.5
mg, 51%). Pale yellow solid, mp 174–176 ꢀC; 1H NMR (400 MHz, Colorless oil; IR (CHCl3, cmꢂ1): n 2980, 2929, 2857, 1703, 1684,
CD3OD) d 9.77 (s, 1H), 7.93 (s, 1H), 7.90 (s, 1H); 13C NMR 1616, 1466, 1402, 1478, 1263, 1184, 1081, 985, 962, 911; 1H NMR
(100 MHz, CD3OD) d 183.4, 138.8, 134.9, 129.5.
(400 MHz, CDCl3/TMS) d 6.35 (dd, J ¼ 17.7, 10.5 Hz, 1H), 6.21
Dibenzo[b,d]furan-4-carbaldehyde (2u). Isolated yield of 2u, (dd, J ¼ 17.6, 1.2 Hz, 1H), 5.81 (dd, J ¼ 10.5 Hz, 1H), 2.57 (t, J ¼
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ꢀ
(71.6 mg, 73%). White solid, mp 94–96 C; H NMR (400 MHz, 7.5 Hz, 2H), 1.61–1.57 (m, 2H), 1.32–1.26 (m, 8H), 0.88 (t, J ¼ 6.9
CDCl3/TMS) d 10.6 (s, 1H), 8.21 (dd, J ¼ 7.6, 1.2 Hz, 1H), 8.01– Hz, 3H); 13C NMR (100 MHz, CDCl3) d 200.8, 136.4, 127.6, 39.5,
7.95 (m, 2H), 7.70 (d, J ¼ 8.1 Hz, 1H), 7.54 (td, J ¼ 7.8, 1.1 Hz, 31.5, 29.0, 28.9, 23.8, 22.4, 13.9; HRMS (ESI-TOF) calcd for
1H), 7.49 (t, J ¼ 7.5 Hz, 1H), 7.42 (t, J ¼ 7.5 Hz, 1H); 13C NMR [C10H18O + Na]+ 177.1250, found 177.1245.
(100 MHz, CDCl3) d 188.4, 156.6, 155.9, 128.1, 127.5, 126.6,
126.0, 123.5, 122.9, 122.8, 121.2, 120.8, 112.1.
2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-enone (4e). Isolated
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yield of 4e, (35.3 mg, 47%). Colorless oil; H NMR (500 MHz,
Acetophenone (2v). Isolated yield of 2v, (60 mg, quant.). CDCl3/TMS) d 6.75–6.74 (m, 1H), 4.76 (d, J ¼ 19.8 Hz, 2H), 2.71–
Colorless oil; 1H NMR (400 MHz, CDCl3/TMS) d 7.97–7.92 2.63 (m, 1H), 2.59–2.54 (m, 1H), 2.46–2.07 (m, 3H), 1.77 (d, J ¼
(m, 2H), 7.57–7.51 (m, 1H), 7.48–7.41 (m, 2H), 2.59 (s, 3H); 13C 1.2 Hz, 3H), 1.73 (s, 3H); 13C NMR (100 MHz, CDCl3) d 199.8,
NMR (100 MHz, CDCl3) d 198.1, 137.0, 133.0, 128.5, 128.2, 26.5. 146.7, 144.7, 135.4, 110.4, 43.1, 42.4, 31.2, 20.5, 15.7.
Benzophenone (2w). Isolated yield of 2w, (91.1 mg, quant.).
Cyclohex-2-en-1-one (4f). Isolated yield of 4f, (32.7 mg, 68%).
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White solid, mp 47–49 ꢀC; H NMR (400 MHz, CDCl3/TMS) d Colorless oil; 1H NMR (500 MHz, CDCl3/TMS) d 6.98 (td, J ¼
7.81 (d, J ¼ 7.0 Hz, 4H), 7.61–7.57 (m, 2H), 7.49 (t, J ¼ 7.8 Hz, 10.1, 4.2 Hz, 1H), 6.00 (td, J ¼ 10.1, 2.0 Hz, 1H), 2.43–2.39 (m,
4H); 13C NMR (100 MHz, CDCl3) d 196.7, 137.5, 132.4, 130.0, 2H), 2.36–2.32 (m, 2H), 2.04–1.98 (m, 2H); 13C NMR (100 MHz,
128.2.
9H-Fluoren-9-one (2x). Isolated yield of 2x, (90.1 mg, quant.).
CDCl3) d 199.8, 150.7, 129.9, 38.1, 25.6, 22.7.
3-Phenylpropiolaldehyde (4g). Isolated yield of 4g, (55.3 mg,
Yellow solid, mp 80–82 C; H NMR (400 MHz, CDCl3/TMS) d 85%). Colorless oil; IR (CHCl3, cmꢂ1): n 2926, 2855, 2738, 2240,
7.66 (d, J ¼ 7.4 Hz, 2H), 7.53–7.46 (m, 4H), 7.31–7.27 (m, 2H); 2189, 1660, 1596, 1489, 1444, 1388, 1283, 1260, 1178, 1160,
13C NMR (100 MHz, CDCl3) d 193.7, 144.3, 134.5, 134.0, 128.9, 1070, 1027, 1002, 978, 922, 688, 617; 1H NMR (400 MHz, CDCl3/
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ꢀ
124.1, 120.2.
TMS) d 9.41 (s, 1H), 7.59 (dd, J ¼ 8.3, 1.1 Hz, 2H), 7.51–7.46 (m,
1-(Benzo[d][1,3]dioxol-5-yl)butan-1-one (2y). Isolated yield of 1H), 7.39–7.37 (m, 2H); 13C NMR (100 MHz, CDCl3) d 176.8,
2y, (87.5 mg, 91%). Colorless oil; IR (CHCl3, cmꢂ1): n 3079, 2964, 133.2, 131.2, 128.7, 119.3, 95.1, 88.4; HRMS (ESI-TOF) calcd for
2928, 2906, 2873, 2784, 1674, 1605, 1504, 1488, 1443, 1359, [C9H6O + H]+ 131.0491, found 131.0494.
1303, 1248, 1141, 1114, 1089, 1039, 998, 935, 911, 807, 648, 620,
Oct-2-ynal (4h). Isolated yield of 4h, (40.3 mg, 65%). Color-
577; 1H NMR (400 MHz, CDCl3/TMS) d 7.56 (dd, J ¼ 8.2, 1.6 Hz, less oil; IR (CHCl3, cmꢂ1): n 3022, 2959, 2934, 2862, 2740, 2284,
1H), 7.44 (d, J ¼ 1.7 Hz, 1H), 6.84 (d, J ¼ 8.2 Hz, 1H), 6.03 (s, 2H), 2201, 1669, 1466, 1424, 1387, 1341, 1327, 1139, 1106, 1064,
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2.86 (t, J ¼ 7.3 Hz, 2H), 1.77–1.71 (m, 2H), 0.99 (t, J ¼ 7.4 Hz, 2H); 1028, 976, 929, 908, 882, 812, 668; H NMR (400 MHz, CDCl3/
13C NMR (100 MHz, CDCl3) d 198.1, 151.3, 147.9, 131.7, 123.9, TMS) d 9.18 (s, 1H), 2.41 (t, J ¼ 7.1 Hz, 2H), 1.62–1.57 (m, 2H),
107.54, 107.50, 101.6, 40.0, 17.7, 13.6; HRMS (ESI-TOF) calcd for 1.42–1.33 (m, 4H), 0.91 (t, J ¼ 7.1 Hz, 3H); 13C NMR (100 MHz,
[C11H12O3 + Na]+ 215.0679, found 215.0677.
CDCl3) d 177.3, 99.4, 81.6, 30.9, 27.2, 22.0, 19.0, 13.8.
1-(Benzo[d][1,3]dioxol-5-yl)-3-phenylprop-2-yn-1-one
Cinnamaldehyde (4a). Isolated yield of 4a, (57.5 mg, 87%).
(4i).
Colorless oil; 1H NMR (500 MHz, CDCl3/TMS) d 9.71 (d, J ¼ 7.7 Isolated yield of 4i, (110 mg, 88%). Pale yellow solid, mp 92–
Hz, 1H), 7.57 (dd, J ¼ 7.0, 2.4 Hz, 2H), 7.49 (d, J ¼ 16.0 Hz, 1H), 93 C; IR (CHCl3, cmꢂ1): n 3018, 2904, 2785, 2208, 1732, 1630,
ꢀ
7.45–7.43 (m, 3H), 6.57 (dd, J ¼ 16.0, 7.7 Hz, 1H); 13C NMR (125 1600, 1504, 1485, 1447, 1373, 1359, 1251, 1140, 1107, 1097,
MHz, CDCl3) d 193.7, 152.8, 134.0, 131.3, 129.1, 128.6, 128.5.
1043, 1014, 997, 936, 908, 885, 822, 688, 668; 1H NMR (400 MHz,
(E)-Oct-2-enal (4b). Isolated yield of 4b, (55.5 mg, 88%). CDCl3/TMS) d 7.90 (dd, J ¼ 8.2, 1.6 Hz, 1H), 7.68–7.63 (m, 3H),
Colorless oil; IR (CHCl3, cmꢂ1): n 2956, 2930, 2862, 1688, 1635, 7.48–7.40 (m, 3H), 6.92 (d, J ¼ 8.2 Hz, 1H), 6.09 (s, 2H); 13C
1465, 1382, 1146, 1097, 976, 909, 650; 1H NMR (400 MHz, NMR (100 MHz, CDCl3) d 176.1, 152.8, 148.2, 132.9, 132.0,
CDCl3/TMS) d 9.50 (d, J ¼ 7.9 Hz, 1H), 6.89–6.81 (m, 1H), 6.15– 130.6, 128.6, 127.2, 120.1, 108.2, 108.0, 102.1, 92.3, 86.7;
6.08 (m, 1H), 2.36–2.30 (m, 2H), 1.55–1.47 (m, 2H), 1.36–1.25 HRMS (ESI-TOF) calcd for [C16H10O3 + Na]+ 273.0522, found
(m, 4H), 0.90 (t, J ¼ 6.9, 3H); 13C NMR (100 MHz, CDCl3) d 194.2, 273.0523.
159.1, 132.9, 32.7, 31.3, 27.5, 22.4, 13.9; HRMS (ESI-TOF) calcd
for [C8H14O + K]+ 165.0676, found 165.0681.
1-(Benzo[d][1,3]dioxol-5-yl)oct-2-yn-1-one (4j). Isolated yield
of 4j, (83.7 mg, 68%). Colorless oil; IR (CHCl3, cmꢂ1): n 3076,
1-Phenylprop-2-en-1-one (4c). Isolated yield of 4c, (50.9 mg, 2961, 2932, 2791, 2210, 1742, 1637, 1602, 1503, 1487, 1444,
77%). Colorless oil; IR (CHCl3, cmꢂ1): n 3065, 3020, 1733, 1672, 1359, 1319, 1275, 1260, 1226, 1157, 1116, 1077, 1038, 934, 913,
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1609, 1580, 1448, 1404, 1286, 1233, 1180, 1072, 994, 698; 1H 888, 853, 806, 677, 648; H NMR (400 MHz, CDCl3/TMS) d 7.79
NMR (400 MHz, CDCl3/TMS) d 7.95 (d, J ¼ 7.1 Hz, 2H), 7.58–7.56 (dd, J ¼ 8.2, 1.7 Hz, 1H), 7.55 (d, J ¼ 1.6 Hz, 1H), 6.87 (d, J ¼ 8.1
(m, 1H), 7.45 (t, J ¼ 7.1 Hz, 2H), 7.16 (dd, J ¼ 17.1, 10.6 Hz, 1H), Hz, 1H), 6.06 (s, 2H), 2.47 (t, J ¼ 7.2 Hz, 2H), 1.67 (q, J ¼ 7.3 Hz,
6.44 (dd, J ¼ 17.1, 1.6 Hz, 1H), 5.94 (dd, J ¼ 10.6, 1.7 Hz, 1H); 13
C
2H), 1.48–1.32 (m, 4H), 0.92 (t, J ¼ 7.2 Hz, 3H) ppm; 13C NMR
NMR (100 MHz, CDCl3) d 191.0, 137.2, 132.9, 132.3, 130.1, 128.6, (100 MHz, CDCl3) d 176.2, 152.5, 147.9, 131.9, 126.9, 108.1,
40566 | RSC Adv., 2014, 4, 40561–40568
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