1058
H. Liu et al.
General procedure for the one-pot synthesis
of 3,4-dihydronaphthalen-1(2H)-ones 3–9
144.88, 138.76, 137.80, 137.00, 136.50, 135.80, 135.20,
130.20, 129.88, 129.02, 128.60, 128.32 (2C), 127.70 (2C),
126.20, 125.78, 40.98 (O=C–CH2), 28.80 (C=C–CH2),
23.24 (3CH2) ppm; IR (NaCl, film): vꢀ = 1,672, 1,610,
To a mixture of 2-iodocyclohex-2-enone or 2-iodo-4,4-
dimethylcyclohex-2-enone (1.0 mmol), 34 mg AgOAc
(0.20 mmol), 58 mg Pd[(C6H5)3P]4 (0.05 mmol), and
200 mg DIPEA (1.5 mmol) in 10 cm3 DMF was added the
appropriate 1-alkyne (2.5 mmol) at room temperature
under nitrogen. The resultant mixture was stirred at 100 °C
for 12 h under nitrogen. TLC showed the starting material
disappeared. The mixture was diluted with 15 cm3
dichloromethane (DCM) and the solid was removed by
filtration, the filtrate was then concentrated in vacuo and
purified by flash chromatography (silica gel, EtOAc/hex-
anes, 1:1) providing the desired products 3–9.
1,550, 1,458, 1,430, 1,320 cm-1
.
3,4-Dihydro-5,7-bis(1-hydroxycyclohexyl)-4,4-
dimethylnaphthalen-1(2H)-one (8, C24H34O3)
Yield: 73%; m.p.: 98–100 °C (EtOAc); 1H NMR
8
(300 MHz, CDCl3): d = 8.10 (d, J = 2.1 Hz, 1H, C–H),
6
7.95 (d, J = 2.1 Hz, 1H, C–H), 2.63 (t, J = 6.6 Hz, 2H,
O=C–CH2), 2.25 (bs, 2H, 2 OH), 2.10–1.23 (m, 22H, 3CH2
and 2 cyclohexyl), 1.20 (s, 6H, 2 CH3) ppm; 13C NMR
(75 MHz, CDCl3): d = 198.27 (1C=O), 146.88 (CH=C–C),
146.10 (CH=C–C), 142.56 (CH=C–C), 135.04 (CH=C–C),
127.36 (CH=C–C), 123.12 (CH=C–C), 74.86 (C–OH),
73.98 (C–OH), 39.42 (O=C–CH2), 38.94 (2C), 38.08 (2C),
31.82 (2C, 2 CH3), 28.78 (C=C–CH2), 26.12, 25.68, 23.78
(3CH2), 22.30 (4C) ppm; IR (NaCl, film): vꢀ = 3,450,
3,4-Dihydro-5,7-bis(1-hydroxycyclohexyl)-
naphthalen-1(2H)-one (3)
Yield: 87%; light brown solid; m.p.: 175–176 °C
(EtOAc/hexanes) (174–176 °C [15]).
1,665, 1,600, 1,510, 1,450, 735 cm-1
.
3,4-Dihydro-5,7-bis(1-hydroxy-1-methylethyl)-
naphthalen-1(2H)-one (4)
3,4-Dihydro-5,7-bis(1-hydroxy-1-methylethyl)-4,4-
dimethylnaphthalen-1(2H)-one (9, C18H26O3)
1
Yield: 82%; light brown solid; m.p.: 109–111 °C
(EtOAc/hexanes) (108–110 °C [15]).
Yield: 65%; m.p.: 81–83 °C (EtOAc/hexanes); H NMR
8
(300 MHz, CDCl3): d = 7.96 (d, J = 2.1 Hz, 1H, C–H),
7.80 (d, J = 2.1 Hz, 1H, C–H), 2.53 (t, J = 6.0 Hz, 2H,
6
3,4-Dihydro-5,7-bis(1-hydroxyethyl)naphthalen-1(2H)-one
(5)
Yield: 83%; oil (brown gum [15]).
O=C–CH2), 2.13 (bs, 2H, 2 OH), 1.90 (t, J = 6.0 Hz, 2H,
3CH2), 1.61 (s, 6H, 2 CH3), 1.49 (s, 6H, 2 CH3), 1.37 (s,
6H, 2 CH3) ppm; 13C NMR (75 MHz, CDCl3): d = 198.20
(1C=O), 146.42 (CH=C–C), 145.38 (CH=C–C), 141.60
(CH=C–C), 126.75 (CH=C–C), 124.12 (CH=C–C), 123.24
(CH=C–C), 74.20 (C–OH), 72.52 (C–OH), 39.10 (O=C–
CH2), 31.64 (2C, 2 CH3), 31.56 (2C, 2 CH3), 30.18 (2C, 2
CH3), 28.46 (C=C–CH2), 23.46 (3CH2) ppm; IR (NaCl,
film): vꢀ = 3,405, 1,665, 1,618, 1,578, 1,460, 1,378, 1,205,
3,4-Dihydro-5,7-diisobutylnaphthalen-1(2H)-one
(6, C18H26O)
Yield: 68%; oil; 1H NMR (300 MHz, CDCl3): d = 7.90 (d,
J = 2.1 Hz, 1H, = C–H), 7.82 (d, J = 2.1 Hz, 1H, = C–
8
6
2
H), 3.18 (t, J = 6.0 Hz, 2H, CH2), 2.62 (d, J = 6.6 Hz,
2H, =C–CH2), 2.51 (d, J = 6.6 Hz, 2H, =C–CH2), 2.50 (t,
4
3
J = 6.0 Hz, 2H, CH2), 2.08 (m, 2H, CH2), 2.02 (m, 1H,
CH), 1.86 (m, 1H, CH), 1.12 (d, J = 6.6 Hz, 6H, 2 CH3),
1.00 (d, J = 6.6 Hz, 6H, 2 CH3) ppm; 13C NMR (75 MHz,
CDCl3): d = 198.82 (1C=O), 147.24 (CH=C–C), 144.88
(CH=C–C), 138.76 (CH=C–C), 128.32 (CH=C–C), 127.70
(CH=C–C), 122.90 (CH=C–C), 42.86 (CH=C–CH2), 40.98
(CH=C–CH2), 39.02 (O=C–2CH2), 31.10 (CH), 29.68
(CH), 28.80 (C=C–4CH2), 23.24 (CH2–3CH2–CH2), 22.64
(2C, 2 CH3), 22.13 (2C, 2 CH3) ppm; IR (NaCl, film):
920, 738 cm-1
.
Acknowledgments We are grateful to the NSF of Jiangsu Province
(Grant BK2008216) for financial support.
References
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7. Barlow JW, Walsh JJ (2010) Eur J Med Chem 45:25
vꢀ = 1,672, 1,600, 1,552, 1,455, 1,427, 1,353 cm-1
.
3,4-Dihydro-5,7-diphenylnaphthalen-1(2H)-one
(7, C22H18O)
Yield: 79%; m.p.: 226–228 °C (EtOH); 1H NMR
8
(300 MHz, CDCl3): d = 8.20 (d, J = 2.1 Hz, 1H, C–H),
7.93 (d, J = 2.1 Hz, 1H, C–H), 7.56–7.28 (m, 10 H, 2
C6H5), 3.10 (t, J = 6.0 Hz, 2H, O=C–CH2), 2.43
6
3
(t, J = 6.0 Hz, 2H, C=C–CH2), 2.08 (m, 2H, CH2) ppm;
13C NMR (75 MHz, CDCl3): d = 198.82 (C=O), 147.24,
123