6510
K. Nobushige et al. / Tetrahedron 71 (2015) 6506e6512
4.10. (E)-1-(2-(Methylsulfonyl)phenyl)-1,2-diphenylethene
4.15. (E)-1-(Methylsulfonyl)-2-(1-phenylprop-1-en-2-yl)ben-
(3a)
zene (3f)
Mp 118e119 ꢀC (yellow powder), 53 mg (64%), isolated by
Mp 123e125 ꢀC (yellow powder),18 mg (26%), isolated bycolumn
column chromatography using hexane/ethyl acetate (3:1, v/v); 1H
chromatography using hexane/ethyl acetate (3:1, v/v); 1H NMR
NMR (400 MHz, CDCl3)
d
2.53 (s, 3H), 6.71 (s, 1H), 7.17e7.25 (m,
(400 MHz, CDCl3)
d
2.30 (d, J¼1.6 Hz, 3H), 3.13 (s, 3H), 6.42 (d,
10H), 7.46 (dd, J¼1.3, 7.5 Hz, 1H), 7.52 (dt, J¼1.4, 7.7 Hz, 1H), 7.64
J¼1.4 Hz,1H), 7.28e7.31 (m,1H), 7.37 (dd, J¼1.1, 7.5 Hz,1H), 7.40e7.41
(m, 4H), 7.49 (dt, J¼1.4, 7.7Hz,1H), 7.64 (dt, J¼1.4, 7.5Hz,1H), 8.12(dd,
(dt, J¼1.4, 7.5 Hz, 1H), 8.13 (dd, J¼1.2, 8.0 Hz, 1H); 13C NMR
(100 MHz, CDCl3)
d
21.9, 120.9, 123.3, 127.9, 128.0, 128.3, 128.5,
J¼1.1, 8.0 Hz,1H); 13C NMR (100 MHz, CDCl3)
d 21.5, 45.0,127.2,127.7,
128.8, 129.1, 129.4, 129.6, 131.1, 132.3, 134.1, 134.4, 144.1, 149.1;
HRMS (APCI) m/z calcd for C21H19O2S (MþHþ) 335.1100, found
335.1122.
128.4,129.0,129.2,130.1,130.7,133.6,136.8,138.2,138.5,145.9; HRMS
(APCI) m/z calcd for C16H17O2S (MþHþ) 273.0944, found 273.0951.
4.16. (E)-1-(5-Methyl-2-(methylsulfonyl)phenyl)-1,2-
4.11. (E)-1,2-Bis(4-chlorophenyl)-1-(2-(methylsulfonyl)phe-
diphenylethene (3g)
nyl)ethene (3b)
Mp 169e171 ꢀC (yellow powder), 50 mg (57%), isolated by col-
Mp 46e48 ꢀC (white powder), 77 mg (77%), isolated by column
umn chromatography using hexane/ethyl acetate (3:1, v/v); 1H NMR
chromatography using hexane/ethyl acetate (3:1, v/v); 1H NMR
(400 MHz, CDCl3) d 2.44, (s, 3H), 2.51 (s, 3H), 6.68 (s, 1H), 7.18e7.26
(400 MHz, CDCl3)
d
2.64 (s, 3H), 6.63 (s, 1H), 7.10 (d, J¼8.4 Hz, 2H),
(m, 11H), 7.31 (d, J¼8.1 Hz, 1H), 7.99 (d, J¼8.1 Hz, 1H); 13C NMR
7.15 (d, J¼8.7 Hz, 2H), 7.17e7.22 (m, 4H), 7.41 (dd, J¼1.3, 7.6 Hz, 1H),
(100 MHz, CDCl3) d 21.4, 44.4, 127.2, 127.7, 128.1, 128.2, 128.8, 129.4,
7.54 (dt, J¼1.4, 7.9 Hz,1H), 7.64 (dt, J¼1.4, 7.5 Hz, 1H), 8.12 (dd, J¼1.3,
130.2,130.9,131.2,133.6,136.3,136.7,139.1,140.1,144.1,144.3; HRMS
8.0 Hz, 1H); 13C NMR (100 MHz, CDCl3)
d
44.7, 128.5, 128.60, 128.63,
(APCI) m/z calcd for C22H21O2S (MþHþ) 349.1257, found 349.1266.
130.2,130.4,130.6,132.1,132.8,133.3,133.6,133.9, 134.8,137.1, 139.1,
139.6, 143.3; HRMS (APCI) m/z calcd for C21H17Cl2O2S (MþHþ)
403.0321, found 403.0321.
4.17. (E)-1-(5-methoxy-2-(methylsulfonyl)phenyl)-1,2-
diphenylethene (3h)
4.12. (E)-1-(2-(Methylsulfonyl)phenyl)-1,2-bis(4-
trifluoromethylphenyl)ethene (3c)
Mp 130e131 ꢀC (yellow powder), 53 mg (59%), isolated by col-
umn chromatography using hexane/ethyl acetate (3:1, v/v); 1H NMR
(400 MHz, CDCl3) d 2.43 (s, 3H), 3.89 (s, 3H), 6.70 (s, 1H), 6.95e6.99
Mp 50e52 ꢀC (white powder), 70 mg (59%), isolated by column
(m, 2H), 7.18e7.26 (m, 10H), 8.04 (d, J¼8.7 Hz, 1H); 13C NMR
chromatography using hexane/ethyl acetate (3:1, v/v); 1H NMR
(100 MHz, CDCl3) d 44.4, 55.6, 112.8, 118.5, 127.3, 127.8, 128.1, 128.2,
(400 MHz, CDCl3)
d
2.67 (s, 3H), 6.78 (s, 1H), 7.28 (d, J¼8.3 Hz, 2H),
129.4,130.9,131.0,131.1,132.6,136.6,138.8,140.0,146.3,163.1; HRMS
7.35 (d, J¼8.1 Hz, 2H), 7.43 (dd, J¼1.3, 7.6 Hz, 1H), 7.47e7.49 (m, 4H),
(APCI) m/z calcd for C22H21O3S (MþHþ) 365.1206, found 365.1223.
7.58 (dt, J¼1.4, 7.8 Hz, 1H), 7.68 (dt, J¼1.4, 7.5 Hz, 1H), 8.14 (dd,
J¼1.3, 7.9 Hz, 1H); 13C NMR (100 MHz, CDCl3)
d
44.9, 123.9 (q,
4.18. (E)-1-(5-Phenoxy-2-(methylsulfonyl)phenyl)-1,2-
diphenylethene (3i)
J¼270.6 Hz), 124.0 (q, J¼270.3 Hz), 125.2 (q, J¼3.7 Hz), 125.4 (q,
J¼3.6 Hz), 129.0, 129.5 (q, J¼32.2 Hz), 129.6, 130.0 (q, J¼32.5 Hz),
130.3, 131.0, 131.1, 132.6, 133.7, 139.2, 139.6, 141.0, 142.0, 142.6;
HRMS (APCI) m/z calcd for C23H17F6O2S (MþHþ) 471.0848, found
471.0850.
Mp 58e60 ꢀC, 44 mg (41%), isolated by column chromatography
using hexane/ethyl acetate (3:1, v/v); 1H NMR (400 MHz, CDCl3)
d
2.45 (s, 3H), 6.71 (s, 1H), 6.97 (dd, J¼8.8, 2.6 Hz, 1H), 7.08e7.12 (m,
3H), 7.17e7.18 (m, 5H), 7.21e7.26 (m, 6H), 7.42 (dd, J¼7.4, 6.6 Hz, 2H)
4.13. (E)-1-(2-(Methylsulfonyl)phenyl)-1,2-bis(4-
methylphenyl)ethene (3d)
8.03 (d, J¼8.8 Hz,1H); 13C NMR (100 MHz, CDCl3)
d 44.3,116.0,120.3,
121.7, 125.1, 127.4, 127.9, 128.1 (overlapped), 129.4, 130.2, 130.9,
131.4, 132.6, 132.8, 136.5, 138.7, 139.6, 146.6, 154.9, 161.7; HRMS
(APCI) m/z calcd for C27H23O3S (MþHþ) 427.1362, found 427.1380.
Mp 70e73 ꢀC (white powder), 42 mg (46%), isolated by column
chromatography using hexane/ethyl acetate (3:1, v/v); 1H NMR
(400 MHz, CDCl3)
d
2.30 (s, 6H), 2.61 (s, 3H), 6.63 (s, 1H), 7.00e7.03
4.19. (E)-1-(5-Chloro-2-(methylsulfonyl)phenyl)-1,2-
(m, 4H), 7.08e7.13 (m, 4H), 7.42 (dd, J¼1.2, 7.6 Hz, 1H), 7.49 (dt,
diphenylethene (3j)
J¼1.3, 7.9 Hz, 1H), 7.60 (dt, J¼1.4, 7.4 Hz, 1H), 8.12 (dd, J¼1.2, 8.0 Hz,
1H); 13C NMR (100 MHz, CDCl3)
d
21.3, 22.7, 44.3, 128.0, 128.85,
Mp 157e159 ꢀC (yellow powder), 35 mg (38%), isolated by col-
128.89, 129.3, 129.9, 130.7, 131.09, 133.0, 133.3, 133.9, 136.3, 137.1,
137.5, 138.9, 139.2, 144.6; HRMS (APCI) m/z calcd for C23H23O2S
(MþHþ) 363.1413, found 363.1414.
umn chromatography using hexane/ethyl acetate (3:1, v/v); 1H
NMR (400 MHz, CDCl3)
d 2.51 (s, 3H), 6.71 (s, 1H), 7.12e7.23 (m,
10H), 7.46 (d, J¼2.0 Hz, 1H), 7.49 (dd, J¼2.2, 8.5 Hz, 1H), 8.06 (d,
J¼8.5 Hz, 1H); 13C NMR (100 MHz, CDCl3)
d 44.2, 127.6, 128.1, 128.2,
4.14. (E)-1-(Methylsulfonyl)-2-(1-phenylhex-1-en-2-yl)ben-
zene (3e)
128.3,128.4,129.4,130.9,131.7,132.1,132.8,136.2,137.7, 138.4,138.7,
139.8, 145.9; HRMS (APCI) m/z calcd for C21H18ClO2S (MþHþ)
369.0711, found 369.0710.
Oil, 37 mg (47%), isolated by column chromatography using
hexane/ethyl acetate (3:1, v/v); 1H NMR (400 MHz, CDCl3)
d
0.80 (t,
4.20. (E)-1-(2-(Ethylsulfonyl)phenyl)-1,2-diphenylethene (3k)
J¼7.1 Hz, 3H), 1.25e1.33 (m, 4H), 2.79 (t, J¼7.3 Hz, 2H), 3.12 (s, 3H),
6.39 (s,1H), 7.29e7.30 (m,1H), 7.34 (dd, J¼1.3, 7.6 Hz,1H), 7.36e7.40
(m, 4H), 7.51 (dt, J¼1.4, 7.7 Hz, 1H), 7.62 (dt, J¼1.4, 7.5 Hz, 1H), 8.14
Mp 115e117 ꢀC (yellow powder), 45 mg (51%), isolated by column
chromatography using hexane/ethyl acetate (3:1, v/v); 1H NMR
(dd, J¼1.3, 8.0 Hz, 1H); 13C NMR (100 MHz, CDCl3)
d
13.8, 22.8, 30.3,
(400 MHz, CDCl3)
d
1.06 (t, J¼7.2Hz, 3H), 2.49 (q, J¼7.6Hz, 2H), 6.66 (s,
33.2, 44.9, 127.1, 127.7, 128.4, 128.8, 129.4, 130.0, 131.8, 133.1, 136.8,
138.6, 143.5, 144.2; HRMS (APCI) m/z calcd for C19H23O2S (MþHþ)
315.1413, found 315.1413.
1H), 7.18e7.21 (m, 10H), 7.47 (dd, J¼1.1, 7.6 Hz, 1H), 7.51 (dt, J¼1.3,
7.8 Hz, 1H), 7.63 (dt, J¼1.4, 7.5 Hz, 1H), 8.07 (dd, J¼1.1, 7.9 Hz, 1H); 13
C
NMR(100MHz,CDCl3)d7.2, 50.1,127.3,127.7,127.9,128.0,128.2,129.4,