References and Notes
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Physical and spectral data for selected
new compounds are reported below: Compound 4a (C21H28O3SSe):
oil; [α]D
¹8.0
-40.9
(c = 1.38, CHCl3). ¹H
NMR (400 MHz): δ = 7.35 (dd, 1 H, J = 1.4, 7.7 Hz), 7.15-7.25
(m, 6 H), 7.10 (dd, 1 H, J = 1.2,
7.5 Hz), 6.95 (dt, 1 H, J = 1.4,
7.5 Hz), 4.84 (d, 1 H, J = 2.9
Hz), 4.36 (d, 1 H, J = 9.1 Hz),
4.19 (q, 1 H, J = 6.9 Hz), 3.60
(dd, 1 H, J = 2.9, 9.1 Hz),
3.58 (s, 3 H), 3.56 (s, 3 H), 3.17 (s, 3 H), 1.87 (s, 3 H), 1.35
(d, 3 H, J = 6.9 Hz). ¹³C NMR
(100.62 MHz): δ = 145.9, 139.5, 136.1, 132.6,
128.6 (2 × CHAr), 128.2, 128.1 (2 × CH),
127.7, 127.3, 126.3, 105.7, 84.8, 57.7, 57.02, 57.01, 56.4, 43.7,
21.4, 13.9. GC-MS: m/z (%) = 442 (5), 440
(20) [M+], 438 (10), 436 (4),
231 (100), 215 (2), 183 (71), 121 (72), 91 (19), 75 (69). Compound 4b (C21H27O3ClSSe):
oil. ¹H NMR (400 MHz):
δ = 7.35
(d, 1 H, J = 7.3 Hz), 7.15-7.20
(m, 2 H), 7.05-7.13 (m, 3 H), 6.95-7.00 (m, 2
H), 4.85 (d, 1 H, J = 2.6 Hz),
4.33 (d, 1 H, J = 9.4 Hz), 4.10
(q, 1 H, J = 6.9 Hz), 3.60 (s,
3 H), 3.59 (s, 3 H), 3.58 (dd, 1 H, J = 2.6,
9.4 Hz), 3.15 (s, 3 H), 1.90 (s, 3 H), 1.41 (d, 3 H, J = 6.9 Hz). ¹³C
NMR (100.62 MHz): δ = 145.2, 137.6, 135.6, 133.5,
132.0, 129.5 (2 × CH), 127.7 (2 × CH), 127.2,
126.9, 125.9, 105.2, 83.9, 57.4, 56.6, 56.4, 56.3, 43.2, 20.6, 13.2.
GC-MS: m/z (%) = 476 (6), 474 (12) [M+],
472 (6), 470 (2), 231 (100), 215 (9), 183 (68), 155 (45), 135 (8),
91 (16), 75 (60). Compound 4c (C22H30O3SSe):
oil. ¹H NMR (400 MHz): d = 7.38 (dd,
1 H, J = 1.3, 7.8 Hz), 7.19
(dd, 1 H, J = 1.7, 7.8 Hz),
7.14 (ddd, 1 H, J = 1.3, 7.3,
7.8 Hz) 7.04-7.08 (m, 2 H), 6.94-6.98 (m, 3 H),
4.83 (d, 1 H, J = 2.9 Hz), 4.32
(d, 1 H, J = 9.2 Hz), 4.15 (q,
1 H, J = 6.9 Hz), 3.58 (s, 3
H), 3.57 (dd, 1 H, J = 2.9,
9.2 Hz), 3.56 (s, 3 H), 3.16 (s, 3 H), 2.28 (s, 3 H), 1.87 (s, 3
H), 1.34 (d, 3 H, J = 6.9 Hz). ¹³C
NMR (100.62 MHz): δ = 145.4, 137.3, 136.0, 135.8,
132.3, 128.4 (2 × CH), 128.0 (2 × CH), 127.1,
126.8, 125.8, 105.3, 84.2, 57.4, 56.9, 56.5, 56.1, 43.3, 21.1, 20.9,
13.4. GC-MS: m/z (%) = 454 (21) [M+],
452 (10), 231 (72), 229 (37), 215 (11), 183 (49), 135 (100), 105(6),
91 (14), 75 (52). Compound 4e (C25H30O3SSe):
oil. ¹H NMR (400 MHz): δ = 7.70-7.75
(m, 2 H), 7.69 (s, 1 H), 7.53 (d, 1 H, J = 8.5
Hz), 7.45-7.50 (m, 2 H), 7.33 (d, 1 H, J = 7.8
Hz), 7.19 (d, 1 H, J = 8.6 Hz),
7.00 (dd, 1 H, J = 7.6, 8.0
Hz), 6.92 (d, 1 H, J = 7.5 Hz),
6.80 (t, 1 H, J = 7.5 Hz), 4.93
(d, 1 H,
J = 2.5 Hz),
4.52 (d, 1 H, J = 9.6 Hz), 3.83
(q, 1 H, J = 6.9 Hz), 3.71 (dd,
1 H, J = 2.5, 9.6 Hz), 3.63
(s, 3 H), 3.62 (s, 3 H), 3.25 (s, 3 H), 1.78 (s, 3 H), 0.88 (d,
3 H, J = 6.9 Hz). ¹³C NMR
(100.62 MHz): δ = 145.5, 136.9, 136.1, 133.6,
133.1, 132.7, 128.5, 128.4, 128.3, 127.9, 127.8, 127.4, 127.1, 126.3,
126.0, 125.7, 105.8, 85.2, 57.9, 57.0, 56.7, 43.6, 30.7, 20.3, 13.6.
Compound 10 (C20H26O2SSe):
oil; [α]D
¹8.0 = 19.9 (c = 1.11, CHCl3). ¹H
NMR (400 MHz): δ = 7.40 (d, 1 H,
J = 8.0
Hz), 7.10-7.30 (m, 7 H), 7.00-7.05 (m, 1 H), 4.35
(d, 1 H, J = 9.5 Hz), 4.25-4.30
(m, 1 H), 4.03 (q, 1 H, J = 7.0 Hz),
3.72 (dd, 1 H, J = 4.5, 9.5
Hz), 3.18 (s, 3 H), 3.07 (d, 1 H, J = 9.1
Hz), 1.89 (s, 3 H), 1.41 (d, 3 H, J = 7.0
Hz), 1.38 (d, 3 H, J = 6.3 Hz). ¹³C
NMR (100.62 MHz): δ = 144.5, 139.3, 134.8, 132.0,
128.6, 127.91 (2 × CH), 127.88 (2 × CH), 127.4,
127.2, 125.9, 86.2, 67.4, 63.6, 56.9, 43.1, 21.1, 20.1, 13.0. GC-MS: m/z (%) = 410
(7) [M+], 408 (3), 231 (82),
229 (40), 215 (13), 194 (31), 183 (100), 181 (57), 147 (13), 121
(36), 105 (28), 91 (45), 77 (21), 51 (4).
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Kim JH.
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