Chao Chen et al.
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5.13 (s, 1H), 3.86–3.76 (m, 2H), 3.68–3.59 (m, 2H), 1.25 (t, J = 7.0
Hz, 6H). 13C NMR (100 MHz, CDCl3, TMS, ppm): δ 192.73, 150.35,
138.04, 131.11, 123.40, 103.77, 64.18, 15.21. MS (EI, 70 eV) m/z
(%) 253 (9) [M+], 105 (100); Known compound.[10a] (CAS NO.:
95480-19-6)
1H NMR (400 MHz, CDCl3, TMS, ppm): δ 7.81 (d, J = 4.1 Hz, 1H),
7.11 (d, J = 4.1 Hz, 1H), 5.02 (s, 1H), 3.81–3.72 (m, 2H), 3.69–3.60
(m, 2H), 1.27 (t, J = 7.1 Hz, 6H). 13C NMR (100 MHz, CDCl3, TMS,
ppm): δ 185.69, 139.35, 134.15, 130.04, 122.88, 101.29, 62.36,
14.11; MS (EI, 70 eV) m/z (%) 292 (14) [M+], 111 (100); HRMS (EI):
m/z calcd: 291.9769; Found 291.9765.
2,2-Diethoxy-1-(naphthalen-2-yl)ethan-1-one (2j): Oil; IR (KBr
film): 3070, 2979, 2931, 2888, 1688, 1598, 1579, 1449, 1395, 1285,
1-(Benzo[b]thiophen-2-yl)-2,2-diethoxyethan-1-one (2p): Oil;
IR (KBr film): 3062, 2976, 2927, 1675, 1595, 1556, 1511, 1287,
1
1229, 1116, 1062 cm-1. H NMR (400 MHz, CDCl3, TMS, ppm): δ
1
8.79 (s, 1H), 8.15 (d, J = 7.1 Hz, 1H), 7.99 (d, J = 8.0 Hz, 1H), 7.87 (t,
J = 8.1 Hz, 2H), 7.60 (t, J = 7.4 Hz, 1H), 7.54 (t, J = 7.4, 1H), 5.42 (s,
1H), 3.85–3.76 (m, 2H), 3.75–3.66 (m, 2H), 1.27 (t, J = 7.1 Hz, 6H).
13C NMR (100 MHz, CDCl3, TMS, ppm): δ 194.09, 135.81, 132.43,
132.04, 131.04, 129.94, 128.69, 128.13, 127.74, 126.61, 124.92,
102.41, 63.18, 15.27. MS (EI, 70 eV) m/z (%) 258 (18) [M+], 155
(100); Known compound.[10a] (CAS NO.: 930278-31-2)
(E)-1,1-Diethoxy-4-phenylbut-3-en-2-one (2k): Oil; IR (KBr
film): 3062, 3028, 2978, 2930, 2883, 1697, 1609, 1491, 1449, 1331,
1322, 1168, 1063, 904, 868, 759, 690, 563, 485 cm-1. 1H NMR (400
MHz, CDCl3, TMS, ppm): δ 7.79 (d, J = 16.1 Hz, 1H), 7.60 (dd, J1 =
1249, 1113, 1063 cm-1. H NMR (400 MHz, CDCl3, TMS, ppm): δ
8.36 (s, 1H), 7.91 (d, J = 7.9 Hz, 1H), 7.87 (d, J = 8.0 Hz, 1H),
7.49–7.43 (m, 1H), 7.40 (t, J = 7.5 Hz, 1H), 5.21 (s, 1H), 3.85–3.78
(m, 2H), 3.74–3.66 (m, 2H), 1.29 (t, J = 7.1 Hz, 6H). 13C NMR (100
MHz, CDCl3, TMS, ppm): δ 189.40, 142.69, 139.30, 139.10, 132.34,
127.65, 126.40, 124.94, 122.83, 102.60, 63.42, 15.23; MS (EI, 70
eV) m/z (%) 264 (12) [M+], 161 (100); HRMS (EI): m/z calcd:
264.0820; Found 264.0816.
1,1'-(1,4-Phenylene)bis(2,2-diethoxyethan-1-one) (2q): Oil; IR
(KBr film): 2979, 2929, 2886, 1699, 1449, 1381, 1325, 1282, 1229,
1
1122, 1061 cm-1. H NMR (400 MHz, CDCl3, TMS, ppm): δ 8.21 (s,
6.8 Hz, J2 = 2.8 Hz, 2H), 7.43–7.36 (m, 3H), 7.11 (d, J = 16.1 Hz, 1H), 4H), 5.22 (s, 2H), 3.81–3.71 (m, 4H), 3.68–3.59 (m, 4H), 1.24 (t, J =
4.82 (s, 1H), 3.78–3.70 (m, 2H), 3.67–3.59 (m, 2H), 1.27 (t, J = 7.1
Hz, 6H). 13C NMR (100 MHz, CDCl3, TMS, ppm): δ 194.27, 144.84,
134.59, 130.72, 128.88, 128.63, 120.68, 102.42, 63.07, 15.20. MS
7.1 Hz, 12H). 13C NMR (100 MHz, CDCl3, TMS, ppm): δ 193.73,
137.02, 129.66, 102.76, 63.52, 15.22. MS (EI, 70 eV) m/z (%) 338
(8) [M+], 133 (100); Anal. Calcd for C18H26O6: C, 63.89; H, 7.74.
(EI, 70 eV) m/z (%) 234 (15) [M+], 103 (100); Known compound.[15b] Found: C, 63.76; H, 7.80. Known compound. (CAS NO.:
(CAS NO.: 29097-26-5)
66186-68-3)
2,2-Dimethoxy-1-phenylethan-1-one (2r): Oil; IR (KBr film):
1-(2,3-Dihydrobenzofuran-5-yl)-2,2-diethoxyethan-1-one (2l):
Oil; IR (KBr film): 2975, 2923, 1682, 1603, 1489, 1444, 1372, 1293,
2942, 2835, 1681, 1598, 1450, 1282, 1191, 775, 694 cm-1. 1H NMR
(400 MHz, CDCl3, TMS, ppm): δ 8.09 (d, J = 7.4 Hz, 2H), 7.55 (t, J =
7.4 Hz, 1H), 7.43 (t, J = 7.6 Hz, 2H), 5.20 (s, 1H), 3.45 (s, 6H). 13C
NMR (100 MHz, CDCl3, TMS, ppm): δ 193.37, 133.77, 133.59,
129.47, 128.42, 103.29, 54.52. MS (EI, 70 eV) m/z (%) 180 (17)
[M+], 105 (100); Known compound.[9a] (CAS NO.: 6956-56-5)
1-Phenyl-2,2-dipropoxyethan-1-one (2s): Oil; 1H NMR (400
MHz, CDCl3, TMS, ppm): δ 8.14 (d, J = 7.6 Hz, 2H), 7.54 (t, J = 7.3
Hz, 1H), 7.42 (t, J = 7.3 Hz, 2H), 5.22 (s, 1H), 3.65 (q, J = 7.5 Hz, 2H),
3.52 (q, J = 7.3 Hz, 2H), 1.62 (q, J = 6.5 Hz, 4H), 0.89 (t, J = 7.2 Hz,
6H). 13C NMR (100 MHz, CDCl3, TMS, ppm): δ 194.07, 133.72,
133.38, 129.76, 128.26, 103.01, 69.43, 22.91, 10.54. MS (EI, 70 eV)
m/z (%) 236 (12) [M+], 105 (100); Anal. Calcd for C14H20O3: C,
71.16; H, 8.53. Found: C, 71.08; H, 8.60. Known compound. (CAS
NO.: 54149-75-6)
1246, 1099, 1062 cm-1. H NMR (400 MHz, CDCl3, TMS, ppm): δ
1
8.05–8.03 (m, 2H), 6.80 (d, J = 8.9 Hz, 1H), 5.23 (s, 1H), 4.65 (t, J =
8.8 Hz, 2H), 3.77–3.70 (m, 2H), 3.67–3.60 (m, 2H), 3.24 (t, J = 8.8
Hz, 2H), 1.24 (t, J = 7.1 Hz, 6H). 13C NMR (100 MHz, CDCl3, TMS,
ppm): δ 192.54, 164.74, 131.96, 127.42, 127.08, 126.92, 109.07,
102.61, 72.27, 63.08, 28.98, 15.26. Anal. Calcd for C14H18O4: C,
67.18; H, 7.25. Found: C, 67.29; H, 7.20. MS (EI, 70 eV) m/z (%)
250 (13) [M+], 147 (100); Known compound. (CAS NO.:
1443309-74-7)
1-(Benzofuran-2-yl)-2,2-diethoxyethan-1-one (2m): Oil; IR
(KBr film): 2978, 2887, 1687, 1613, 1550, 1447, 1283, 1114, 1061
cm-1. 1H NMR (400 MHz, CDCl3, TMS, ppm): δ 7.86 (s, 1H), 7.73 (d,
J = 7.9 Hz, 1H), 7.60 (d, J = 8.4 Hz, 1H), 7.48 (t, J = 8.0 Hz, 1H), 7.31
(t, J = 7.5 Hz, 1H), 5.22 (s, 1H), 3.85–3.76 (m, 2H), 3.74–3.65 (m,
2H), 1.28 (t, J = 7.1 Hz, 6H). 13C NMR (100 MHz, CDCl3, TMS, ppm):
δ 185.15, 155.72, 149.56, 128.70, 126.96, 123.89, 123.65, 117.19,
2,2-Bis(octyloxy)-1-phenylethan-1-one (2t): Oil; IR (KBr film):
2924, 1693, 1600, 1468 cm-1. 1H NMR (400 MHz, CDCl3, TMS,
112.51, 101.78, 63.36, 15.17. MS (EI, 70 eV) m/z (%) 248 (17) [M+], ppm): δ 8.11 (d, J = 7.8 Hz, 2H), 7.48 (t, J = 7.1 Hz, 1H), 7.37 (t, J =
145 (100); Anal. Calcd for C14H16O4: C, 67.73; H, 6.50. Found: C,
67.65; H, 6.43.
7.5 Hz, 2H), 5.17 (s, 1H), 3.67–3.62 (m, 2H), 3.55–3.49 (m, 2H),
1.59–1.53 (m, 4H), 1.25–1.18 (m, 20H), 0.82 (t, J = 6.4 Hz, 6H). 13
NMR (100 MHz, CDCl3, TMS, ppm): δ 193.87, 133.70, 133.24,
C
2,2-Diethoxy-1-(thiophen-2-yl)ethan-1-one (2n): Oil; IR (KBr
film): 3102, 2979, 2931, 2884, 1667, 1516, 1479, 1413, 1356, 1388, 129.73, 128.15, 103.05, 67.72, 31.75, 29.60, 29.22, 29.19, 25.99,
1273, 1239, 1114, 1058 cm-1. 1H NMR (400 MHz, CDCl3, TMS,
ppm): δ 8.44 (d, J = 3.4 Hz, 1H), 7.66 (d, J = 5.5 Hz, 1H), 7.28 (dd, J1
= 5.0 Hz, J2 = 2.8 Hz, 1H), 5.09 (s, 1H), 3.80–3.70 (m, 2H),
3.69–3.60 (m, 2H), 1.25 (t, J = 7.1 Hz, 6H). 13C NMR (100 MHz,
CDCl3, TMS, ppm): δ 188.95, 137.95, 135.14, 127.99, 125.53,
102.85, 63.19, 15.24. MS (EI, 70 eV) m/z (%) 214 (10) [M+], 111
(100); Known compound.[10a] (CAS NO.: 114329-79-2)
22.60, 14.02. MS (EI, 70 eV) m/z (%) 376 (9) [M+], 105 (100); Anal.
Calcd for C24H40O3: C, 76.55; H, 10.71. Found: C, 76.46; H, 10.65.
Known compound. (CAS NO.: 161065-36-7)
1,4-Diphenylbut-2-ene-1,4-dione (5): Oil; IR (KBr film): 3068,
1676, 1661, 1488, 1390, 1342, 1199, 1020, 975, 710, 620 cm-1. 1H
NMR (400 MHz, CDCl3, TMS, ppm): δ 8.07 (d, J = 7.2 Hz, 4H), 8.03
(s, 2H), 7.64 (t, J = 7.4 Hz, 2H), 7.54 (t, J = 7.6 Hz, 4H). 13C NMR
(100 MHz, CDCl3, TMS, ppm): δ 188.77, 135.80, 134.05, 132.86,
1-(5-Bromothiophen-2-yl)-2,2-diethoxyethan-1-one (2o): Oil;
IR (KBr film): 2974, 2925, 1674, 1515, 1407, 1322, 1117, 1064 cm-1. 127.88, 127.86. MS (EI, 70 eV) m/z (%) 236 (15) [M+], 105 (100);
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Chin. J. Chem. 2019, 37, XXX-XXX
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