The Journal of Organic Chemistry
Page 16 of 22
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2.3 Hz, 1H), 6.02 (d, J = 2.3 Hz, 1H), 4.07 (d, J = 7.4 Hz, 1H), 3.91 (d, J = 7.5 Hz, 1H),
13
3.87 (s, 3H), 1.15 (s, 9H), 1.13 (s, 9H) ppm; C NMR (75 MHz, CDCl ) δ 192.7, 185.6,
3
163.9, 149.9, 149.6, 138.7, 137.9, 135.4, 130.5, 129.1, 128.5, 127.6, 114.0, 55.5, 40.6,
40.1, 39.9, 35.1, 29.3 ppm; IR (KBr) 2960, 2903, 1647, 1621, 1601, 1511, 1481, 1233,
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+
754, 704 cm ; HRMS (ESI) calcd for [C30
H
34
O
3
+H] 443.2581, found 443.2580.
5
,7-di-tert-butyl-1-(3-methoxybenzoyl)-2-phenylspiro[2.5]octa-4,7-dien-6-one
o
1
(
4ag). 40.2 mg, Yield 91%; White solid, m.p. 144–146 C; H NMR (300 MHz, CDCl
3
)
δ 7.52 – 7.19 (m, 8H), 7.13 (d, J = 7.3 Hz, 1H), 6.59 (s, 1H), 6.04 (s, 1H), 4.08 (d, J =
1
3
7
.3 Hz, 1H), 3.93 (d, J = 7.4 Hz, 1H), 3.82 (s, 3H), 1.16 (s, 9H), 1.13 (s, 9H) ppm; C
NMR (75 MHz, CDCl ) δ 194.5, 185.6, 159.9, 150.1, 149.9, 138.8, 138.5, 137.7, 135.2,
29.8, 129.1, 128.6, 127.7, 120.7, 120.1, 112.3, 55.4, 41.1, 40.4, 40.0, 35.2, 29.2 ppm;
IR (KBr) 3056, 2957, 2861, 1665, 1644, 1619, 1603, 1581, 1484, 878, 771, 742, 695
3
1
-1
+
cm ; HRMS (ESI) calcd for [C30
H
34
O
3
+H] 443.2581, found 443.2577.
1
-(benzo[d][1,3]dioxole-5-carbonyl)-5,7-di-tert-butyl-2-phenylspiro[2.5]octa-
o
1
4
,7-dien-6-one (4ah). 45.0 mg, Yield 99%; White solid, m.p. 181–183 C; H NMR
300 MHz, CDCl ) δ 7.44 (dd, J = 8.2, 1.6 Hz, 1H), 7.39 – 7.36 (m, 1H), 7.35 – 7.21
m, 5H), 6.85 (d, J = 8.1 Hz, 1H), 6.59 (d, J = 2.6 Hz, 1H), 6.04 (s, 2H), 6.02 (d, J =
(
(
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2
9
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.6 Hz, 1H), 4.06 (d, J = 7.4 Hz, 1H), 3.88 (d, J = 7.5 Hz, 1H), 1.17 (s, 9H), 1.13 (s,
13
H) ppm; C NMR (75 MHz, CDCl
3
) δ 192.3, 185.6, 152.2, 150.0, 149.7, 148.4, 138.6,
37.8, 135.3, 132.3, 129.1, 128.6, 127.7, 124.7, 108.1, 107.9, 102.0, 40.6, 40.2, 39.9,
5.1, 29.3, 29.3 ppm; IR (KBr) 2961, 2909, 1665, 1644, 1618, 1506, 1491, 1455, 1434,
-1
O
+Na]+
253, 1098, 1040, 868, 743, 696 cm ; HRMS (ESI) calcd for [C30
H
32
4
79.2193, found 479.2195.
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-(2-naphthoyl)-5,7-di-tert-butyl-2-phenylspiro[2.5]octa-4,7-dien-6-one (4ai).
o
1
2
8.1 mg, Yield 61%; White solid, m.p. 139–141 C; H NMR (300 MHz, CDCl ) δ 8.29
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(s, 1H), 7.92 (dt, J = 16.9, 8.0 Hz, 4H), 7.57 (dt, J = 15.1, 6.5 Hz, 2H), 7.42 – 7.27 (m,
5
H), 6.64 (d, J = 2.4 Hz, 1H), 6.12 (d, J = 2.4 Hz, 1H), 4.15 (d, J = 7.5 Hz, 1H), 4.08
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(
d, J = 7.5 Hz, 1H), 1.19 (s, 9H), 1.12 (s, 9H) ppm; C NMR (75 MHz, CDCl
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) δ 194.5,
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85.6, 150.2, 149.9, 138.5, 137.8, 135.7, 135.3, 134.8, 132.4, 130.2, 129.6, 129.2, 128.8,
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