388 J. Chin. Chem. Soc., Vol. 51, No. 2, 2004
Huang and Wang
5.01 (dd, J = 17.0 Hz, 2.0 Hz, 1H, CH2=CHCH3CHAr), 5.04
(dd, J = 10.3 Hz, 2.0 Hz, 1H, CH2=CHCH3CHAr), 5.11 (dd, J
= 11.0 Hz, 1.5 Hz, 1H, CH2=CHAr), 5.44 (dd, J = 17.5 Hz, 1.5
Hz, 1H, CH2=CHAr), 6.15 (ddd, J = 17.0 Hz, 10.3 Hz, 5.0 Hz,
1H, CH2=CHCH3CHAr), 6.77 (d, J = 8.5 Hz, 1H, ArH), 7.03
(dd, J = 17.5 Hz, 11.0 Hz, 1H, CH2=CHAr), 7.18 (d, J = 8.5 Hz,
1H, ArH); 13C NMR (CDCl3, 125 MHz) d 15.56 (OCH2CH3),
18.80 (CH2=CHCHCH3), 34.90 (CH2=CHCH3CHAr), 55.62
(OCH3), 68.79 (OCH2CH3), 110.18, 112.83, 113.45, 122.36,
130.85, 135.93, 136.73, 142.82, 145.91, 152.53; EI-MS (70
eV) m/z (rel. intensity, %) 232 (M+, 45.35), 203 (47.03), 175
(34.06), 171 (29.38), 157 (91.16), 145 (27.65), 144 (25.66),
143 (100), 129 (56.41), 128 (56.06), 115 (64.87); HRMS
calcd for C15H20O2: 232.1463. Found: 232.1463.
(CH3CH=CHCH2Ar), 55.80, 55.85 (each, OCH3), 108.28,
112.52, 113.11, 126.04, 128.57, 129.65, 130.85, 134.09,
147.38, 148.76; EI-MS (70 eV) m/z (rel. intensity, %) 218
(M+, 88.71), 203 (90.21), 189 (100), 188 (68.90), 176
(46.40), 174 (43.09), 172 (40.73), 128 (47.51), 115 (60.36);
HRMS calcd for C14H18O2: 218.1307. Found: 218.1307.
2-(2-Butenyl)-5-ethoxy-4-methoxy-1-vinylbenzene (8b)
Pure 8b (1.03 g, 81%) was obtained as pale yellow liq-
1
uid, Rf 0.63 (EA/n-hexane = 1/7); H NMR (CDCl3, 500
MHz) d 1.46 (t, J = 7.0 Hz, 3H, OCH2CH3), 1.66 (dd, J = 6.5
Hz, 1.5 Hz, 3H, CH3CH=CHCH2Ar), 3.32 (d, J = 6.5 Hz, 2H,
CH3CH=CHCH2Ar), 3.86 (s, 3H, OCH3), 4.12 (q, J = 7.0 Hz,
2H, OCH2CH3), 5.18 (dd, J = 11.0 Hz, 1.5 Hz, 1H, CH2=CHAr),
5.41 (dq, J = 14.0 Hz, 6.5 Hz, 1H, CH3CH=CHCH2Ar), 5.52
(dd, J = 17.5 Hz, 1.5 Hz, 1H, CH2=CHAr), 5.56 (dtd, J = 14.0
Hz, 6.5 Hz, 1.5 Hz, 1H, CH3CH=CHCH2Ar), 6.64, 7.04 (each
s, 1H, ArH), 6.90 (dd, J = 17.5 Hz, 11.0 Hz, 1H, CH2=CHAr);
13C NMR (CDCl3, 125 MHz) d 14.83 (OCH2CH3), 17.86
(CH3CH=CHCH2Ar), 35.84 (CH3CH=CHCH2Ar), 55.91
(OCH3), 64.40 (OCH2CH3), 109.98, 112.79, 113.06, 126.07,
128.60, 129.71, 130.92, 134.16, 146.70, 149.15; EI-MS (70
eV) m/z (rel. intensity, %) 232 (M+, 63.50), 203 (39.19), 190
(38.13), 189 (81.99), 175 (100), 174 (37.40), 160 (33.04),
143 (32.32), 131 (33.48), 129 (43.16), 128 (49.94), 115
(50.74), 91 (33.62); HRMS calcd for C15H20O2: 232.1463.
Found: 232.1463.
3-Benzyloxy-4-methoxy-2-(1-methyl-2-propenyl)-1-vinyl-
benzene (7f)
Pure 7f (1.33 g, 82%) was obtained as pale yellow liq-
uid; Rf 0.77 (EA/n-hexane = 1/7); 1H NMR (CDCl3, 400 MHz) d
1.35 (d, J = 7.2 Hz, 3H, CH2=CHCH3CHAr), 3.86 (s, 3H, OCH3),
4.24 (m, 1H, CH2=CHCH3CHAr), 4.95 (s, 2H, OCH2C6H5), 4.98
(dd, J = 17.2 Hz, 1.2 Hz, 1H, CH2=CHCH3CHAr), 5.02 (dd, J =
10.6 Hz, 1.2 Hz, 1H, CH2=CHCH3CHAr), 5.11 (dd, J = 11.0
Hz, 1.5 Hz, 1H, CH2=CHAr), 5.44 (dd, J = 17.5 Hz, 1.5 Hz,
1H, CH2=CHAr), 6.56 (ddd, J = 17.2 Hz, 10.6 Hz, 5.0 Hz,
1H, CH2=CHCH3CHAr), 6.80 (d, J = 8.8 Hz, 1H, ArH),
7.03 (dd, J = 17.5 Hz, 11.0 Hz, 1H, CH2=CHAr), 7.21 (d, J
= 8.8 Hz, 1H, ArH), 7.31-7.47 (m, 5H, OCH2C6H5); 13C
NMR (CDCl3, 125 MHz) d 18.80 (CH2=CHCH3CHAr),
34.93 (CH2=CHCH3CHAr), 55.68 (OCH3), 74.74 (OCH2C6H5),
110.38, 112.94, 113.51, 122.72, 127.77, 128.07, 128.33,
130.97, 135.92, 136.89, 137.86, 142.74, 145.58; EI-MS (70
eV) m/z (rel. intensity, %) 294 (M+, 4.10), 203 (25.11), 175
(8.12), 171 (9.23), 161 (10.90), 157 (11.91), 145 (7.54), 143
(14.90), 129 (8.78), 128 (14.74), 115 (17.14), 91 (98.20);
HRMS calcd for C20H22O2: 294.1620. Found: 294.1620.
5-Benzyloxy-2-(2-butenyl)-4-methoxy-1-vinylbenzene (8c)
Pure 8c (1.26 g, 78%) was obtained as pale yellow liq-
1
uid; Rf 0.66 (EA/n-hexane = 1/7); H NMR (CDCl3, 500
MHz) d 1.66 (dd, J = 6.5 Hz, 1.5 Hz, 3H, CH3CH=CHCH2Ar),
3.31 (d, J = 6.5 Hz, 2H, CH3CH=CHCH2Ar), 3.88 (s, 3H,
OCH3), 5.14 (dd, J = 11.0 Hz, 1.5 Hz, 1H, CH2=CHAr), 5.15
(s, 2H, OCH2C6H5), 5.41 (dq, J = 15.1 Hz, 6.5 Hz, 1H,
CH3CH=CHCH2Ar), 5.41 (dd, J = 17.5 Hz, 1.5 Hz 1H,
CH2=CHAr), 5.54 (dtd, J = 15.1 Hz, 6.5 Hz, 1.5 Hz, 1H,
CH3CH=CHCH2Ar), 6.66, 7.06 (each s, 1H, ArH), 6.86
(dd, J = 17.5 Hz, 11.0 Hz, 1H, CH2=CHAr), 7.31-7.46 (m,
5H, OCH2C6H5); 13C NMR (CDCl3, 125 MHz) d 17.88
(CH3CH=CHCH2Ar), 35.87 (CH3CH=CHCH2Ar), 56.00
(OCH3), 71.30 (OCH2C6H5), 111.44, 113.11, 113.21,
126.151, 127.40, 127.80, 128.50, 128.66, 129.64, 131.54,
133.99, 137.32, 146.63, 149.54; EI-MS (70 eV) m/z (rel. in-
tensity, %) 294 (M+, 17.26), 203 (39.72), 175 (16.19), 143
(19.72), 133 (9.30), 1129 (9.80), 128 (21.41), 117 (9.24), 115
(15.52); HRMS calcd for C20H22O2: 294.1620. Found:
294.1620.
2-(2-Butenyl)-4,5-dimethoxy-1-vinylbenzene (8a)
Pure 8a (0.92 g, 77%) was obtained as pale yellow liq-
1
uid, Rf 0.54 (EA/n-hexane = 1/7); H NMR (CDCl3, 500
MHz) d 1.66 (dd, J = 6.5 Hz, 1.5 Hz, 3H, CH3CH=CHCH2Ar),
3.32 (d, J = 6.8 Hz, 2H, CH3CH=CHCH2Ar), 3.87, 3.89 (each
s, 3H, OCH3), 5.19 (dd, J = 11.0 Hz, 1.5 Hz, 1H, CH2=CH2Ar),
5.41 (dq, J = 14.0 Hz, 6.5 Hz, 1H, CH3CH=CHCH2Ar), 5.54
(dd, J = 17.5 Hz, 1.5 Hz, 1H, CH2=CH2Ar), 5.55 (dtd, J = 14.0
Hz, 6.8 Hz, 1.5 Hz, 1H, CH3CH=CHCH2Ar), 6.64, 7.03 (each
s, 1H, ArH), 6.91 (dd, J = 17.5 Hz, 11.0 Hz, 1H, CH2=CHAr);
13C NMR (CDCl3, 125 MHz) d 17.81 (CH3), 35.78