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Organic & Biomolecular Chemistry
(1S*,2R*)-5,8-Dimethoxy-2-methyl-1,2-dihydronaphthalen-1-ol J = 10.0 Hz, 1H), 6.81 (d, J = 8.8 Hz, 1H), 6.73 (d, J = 9.2 Hz,
(3a). Prepared according to general procedure I. A colorless oil 1H), 6.12 (dd, J = 5.6, 10.0 Hz, 1H), 5.17 (bs, 1H), 3.91 (d, J =
liquid (27.3 mg, 62%). Rf = 0.20 on silica gel (ethyl acetate– 5.2 Hz, 1H), 3.84 (s, 3H), 3.72 (s, 3H), 2.44 (s 1H). 13C NMR
petroleum ether = 1 : 10, v/v). IR (film, cm−1) 3466(br), 3034(s), (100 MHz, CDCl3) δ 151.3, 149.5, 140.0, 128.5(2C), 128.2, 128.0
2954(s), 2929(s), 2835(s), 1596(s), 1481(s), 1367(m), 1307(m), (2C), 126.8, 123.2, 122.4, 120.4, 111.3, 110.6, 67.4, 56.2, 55.9,
1257(s), 1116(s), 1087(s), 958(s), 910(s), 798(s), 765(s), 717(s). 48.1. HRMS (EI+) calcd for C18H18O3 [M+]: 282.1256. Found:
1H NMR (400 MHz, CDCl3) δ 6.88 (dd, J = 9.7, 2.8 Hz, 1H), 282.1252.
6.80–6.73 (m, 2H), 5.74 (d, J = 9.7 Hz, 1H), 4.89 (d, J = 4.4 Hz,
(1S*,2S*)-5,8-Dimethoxy-2-(4-methoxyphenyl)-1,2-dihydro-
1H), 3.83 (s, 3H), 3.79 (s, 3H), 2.54 (m, 1H), 1.69 (d, J = 8.8 Hz, naphthalen-1-ol (3f). Prepared according to general pro-
1H), 1.35 (d, J = 7.5 Hz, 3H). 13C NMR (100 MHz, CDCl3) cedure I. A colorless oil liquid (25.6 mg, 41%). Rf = 0.18 on
δ 150.5, 149.5, 132.0, 125.7, 122.4, 120.5, 111.1, 110.4, 64.3, silica gel (ethyl acetate–petroleum ether = 1 : 10, v/v). IR (film,
56.1(2C), 34.6, 15.2; HRMS (APCI) calcd for [C13H16O3 + Na]+: cm−1) 3460(br), 2997(m), 2927(s), 2852(s), 1722(m), 1668(m),
243.0997. Found: 243.0992.
1604(s), 1483(s), 1460(s), 1365(w), 1255(s), 1180(s), 1095(s),
(1S*,2R*)-5,8-Dimethoxy-2-pentyl-1,2-dihydronaphthalen-1-ol 958(m), 864(m), 829(s), 800(s), 721(s), 540(m). 1H NMR
(3b). Prepared according to general procedure I. A colorless oil (400 MHz, CDCl3) δ 7.13–7.02 (m, 3H), 6.83–6.67 (m, 4H), 6.11
liquid (25.4 mg, 46%). Rf = 0.20 on silica gel (ethyl acetate– (dd, J = 9.6, 5.6 Hz, 1H), 5.12 (s, 1H), 3.98 (s, 1H), 3.84 (s, 3H),
petroleum ether = 1 : 10, v/v). 1H NMR (400 MHz, CDCl3) δ 6.89 3.75 (s, 6H), 1.63(s, 1H). 13C NMR (100 MHz, CDCl3) δ 158.4,
(d, J = 10.0 Hz, 1H), 6.82–6.73 (m, 2H), 5.81 (d, J = 9.6 Hz, 1H), 151.3, 149.5, 131.8, 129.0, 128.5, 123.2, 122.4, 120.2, 113.9,
4.99 (s, 1H), 3.85 (s, 3H), 3.81 (s, 3H), 2.35 (s, 1H), 1.90–1.81 111.3, 110.5, 67.6, 56.2, 55.9, 55.2, 47.3. HRMS (EI+) calcd for
(m, 1H), 1.63–1.56 (m, 3H), 1.40–1.33 (m, 4H), 0.96–0.84 (m, C19H20O4 [M+]: 312.1362. Found: 312.1359.
4H). 13C NMR (100 MHz, CDCl3) δ 150.5, 149.5, 130.8, 125.7,
(1S*,2R*)-6,7-Dimethoxy-2-methyl-1,2-dihydronaphthalen-1-ol
122.8, 120.6, 111.1, 110.4, 62.6, 56.2, 56.1, 39.8, 32.0, 29.6, (4a). Prepared according to general procedure I. A white solid
26.9, 22.7, 14.1. HRMS (EI+) calcd for C17H24O3 [M+]: 276.1725. (10.6 mg, 24%). Rf = 0.19 on silica gel (ethyl acetate–petroleum
Found: 276.1717.
ether = 1 : 5, v/v). 1H NMR (400 MHz, CDCl3) δ 6.96 (s, 1H),
(1S*,2R*)-2-Cyclohexyl-5,8-dimethoxy-1,2-dihydronaphtha- 6.73 (s, 1H), 6.59 (d, J = 9.0 Hz, 1H), 5.96 (dd, J = 3.2, 7.6 Hz,
len-1-ol (3c). Prepared according to general procedure I. A 1H), 4.75 (d, J = 7.2 Hz, 1H), 3.92 (s, 3H), 3.89 (s, 3H), 3.78 (s,
faint yellow solid (31.1 mg, 54%). Rf = 0.19 on silica gel (ethyl 1H), 2.01 (s, 1H). 1.33 (s, 3H). 13C NMR (100 MHz, CDCl3)
acetate–petroleum ether = 1 : 10, v/v). IR (film, cm−1) 3535(br), δ 150.5, 148.5, 128.7, 128.4, 127.7, 127.2, 110.2, 109.8, 74.4,
3045(m), 2995(m), 2926(s), 2846(s), 1597(s), 1487(s), 1444(s), 56.0, 55.9, 14.2. HRMS (EI+) calcd for C13H16O3 [M+]: 220.1099.
1261(s), 1076(s), 964(m), 887(m), 806(s), 711(s). 1H NMR Found: 220.1098.
(400 MHz, CDCl3) δ 6.92 (d, J = 9.9 Hz, 1H), 6.81–6.69 (m, 2H),
2,3-Dimethoxy-6-methylnaphthalene (4aa). Compound 4aa
6.00 (d, J = 9.8 Hz, 1H), 5.16 (d, J = 3.6 Hz, 1H), 3.95 (m, 1H), was the by-product of substrate 1c with methylmagnesium
3.83 (s, 3H), 3.80 (s, 3H), 2.21 (d, J = 12.0 Hz, 1H), 2.14 (d, J = bromide, 4aa was obtained as a white solid. Rf = 0.65 on silica
11.7 Hz, 1H), 2.04 (d, J = 8.9 Hz, 1H), 1.75 (m, 6H), 1.36–1.30 gel (ethyl acetate–petroleum ether = 1 : 5, v/v). m.p. 57–58 °C.
(m, 2H), 1.06–0.99 (m, 1H). 13C NMR (100 MHz, CDCl3) 1H NMR (400 MHz, CDCl3) δ 7.59 (d, J = 8.2 Hz, 1H), 7.47 (s,
δ 150.3, 149.5, 128.8, 125.9, 122.8, 121.0, 111.0, 110.4, 61.0, 1H), 7.18 (d, J = 8.1 Hz, 1H), 7.09 (s, 1H), 7.05 (s, 1H), 3.99 (s,
56.1, 56.0, 45.4, 36.5, 31.2, 31.1, 26.7, 26.4(2C). HRMS (EI+) 6H), 2.47 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 149.4, 148.8,
calcd for C18H24O3 [M+]: 288.1726. Found: 288.1724.
133.7, 129.3, 127.1, 126.3, 126.1, 125.5, 106.1, 105.8, 55.8(2C),
(1S*,2R*)-2-Allyl-5,8-dimethoxy-1,2-dihydronaphthalen-1-ol 21.6. MS (ESI) calcd for [C13H14O2 + H]+: 203.11. Found:
(3d). Prepared according to general procedure I. A white solid 203.18. HRMS (EI+) calcd for C13H14O2 [M+]: 202.0994. Found:
(32.2 mg, 62%). Rf = 0.19 on silica gel (ethyl acetate–petroleum 202.0991.
ether = 1 : 10, v/v). 1H NMR (400 MHz, CDCl3) δ 6.92 (d, J =
(1S*,2S*)-6,7-Dimethoxy-2-phenyl-1,2-dihydronaphthalen-1-ol
9.6 Hz, 1H), 6.82–6.74 (m, 2H), 6.03–5.95 (m, 1H), 5.82 (d, J = (4e). Prepared according to general procedure I. A white solid
9.6 Hz, 1H), 5.22 (d, J = 17.2 Hz, 1H), 5.14 (d, J = 10.0 Hz, 1H), (15.2 mg, 27%). Rf = 0.20 on silica gel (ethyl acetate–petroleum
5.00 (s, 1H), 3.83 (s, 3H), 3.80 (s, 3H), 2.64–2.59 (m, 1H), ether = 1 : 5, v/v). 1H NMR (400 MHz, CDCl3) δ 7.34–7.21 (m,
2.49–2.41 (m, 2H), 2.05–1.98 (m, 1H); 13C NMR (100 MHz, 5H), 6.96 (s, 1H), 6.73 (s, 1H), 6.59 (d, J = 9.3 Hz, 1H), 5.95 (d,
CDCl3) δ 150.5, 149.5, 136.8, 129.6, 125.5, 122.7, 120.9, 116.8, J = 8.9 Hz, 1H), 4.75 (d, J = 4.9 Hz, 1H), 4.01 (s, 1H), 3.91 (s,
111.2, 110.5, 62.6, 56.2, 56.0, 39.7, 34.1. HRMS (APCI) calcd for 3H), 3.88 (s, 3H), 1.98 (s, 1H). 13C NMR (100 MHz, CDCl3)
[C15H18O3 − H2O + H]+: 229.1229. Found: 229.1236.
δ 148.5, 143.4, 140.8, 128.7(2C), 128.4(2C), 128.0, 127.7, 127.2,
(1S*,2S*)-5,8-Dimethoxy-2-phenyl-1,2-dihydronaphthalen-1-ol 127.1, 125.0, 110.2, 109.8, 82.6, 74.3, 56.0, 50.2. HRMS (EI+)
(3e). Prepared according to general procedure I. A colorless oil calcd for C18H18O3 [M+]: 282.1256. Found: 282.1253.
liquid (42.3 mg, 75%). Rf = 0.20 on silica gel (ethyl acetate–
2,3-Dimethoxy-6-phenylnaphthalene (4ee). Compound 4ee
petroleum ether = 1 : 10, v/v). IR (film, cm−1) 3442(br), 3024(s), was the by-product of substrate 1c with methylmagnesium
2997(s), 2935(s), 2835(s), 1595(s), 1485(s), 1456(s), 1440(s), bromide; 4ee was obtained as a white solid. Rf = 0.62 on silica
1348(s), 1305(s), 1257(s), 1099(s), 1002(s), 896(s), 856(s), 738(s), gel (ethyl acetate–petroleum ether
=
1 : 5, v/v). m.p.
702(s). 1H NMR (400 MHz, CDCl3) δ 7.27–7.13 (m, 5H), 7.11 (d, 117–118 °C. 1H NMR (400 MHz, CDCl3) δ 7.91 (s, 1H), 7.76 (dd,
2084 | Org. Biomol. Chem., 2014, 12, 2080–2086
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