I
M.-Y. Chang, N.-C. Hsueh
Paper
Synthesis
3-Butoxy-2-methoxy-6-phenylnaphthalene (4c)
HRMS (ESI-TOF): m/z [M + H]+ calcd for C26H23O2: 367.1698; found:
367.1699.
Yield: 150 mg (98%); colorless solid; mp 115–117 °C (hexanes/EtOAc).
IR (CHCl3): 2957, 1542, 1305, 1218 cm–1
.
2-Methoxy-6-phenyl-3-(2-phenylallyloxy)naphthalene (4f-1)
1H NMR (400 MHz, CDCl3): δ = 7.93 (d, J = 1.2 Hz, 1 H), 7.78–7.74 (m, 3
H), 7.63 (dd, J = 1.2, 8.4 Hz, 1 H), 7.52–7.49 (m, 2 H), 7.41–7.37 (m, 1
H), 7.22 (s, 1 H), 7.17 (s, 1 H), 4.19 (t, J = 6.8 Hz, 2 H), 4.02 (s, 3 H),
2.00–1.93 (m, 2 H), 1.65–1.55 (m, 2 H), 1.07 (d, J = 7.2 Hz, 3 H).
13C NMR (100 MHz, CDCl3): δ = 149.9, 149.3, 141.4, 136.8, 129.4,
128.7 (2 ×), 128.3, 127.2 (2 ×), 126.9, 126.7, 124.2, 123.6, 107.6, 106.2,
68.4, 55.8, 31.0, 19.2, 13.9.
Yield: 18 mg (10%); colorless solid; mp 139–141 °C (hexanes/EtOAc).
IR (CHCl3): 2966, 1536, 1324, 1231 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 7.87 (d, J = 1.6 Hz, 1 H), 7.77 (d, J = 8.4
Hz, 1 H), 7.71–7.69 (m, 2 H), 7.62 (dd, J = 1.6, 8.4 Hz, 1 H), 7.56–7.53
(m, 2 H), 7.49–7.45 (m, 2 H), 7.42–7.32 (m, 4 H), 7.25 (s, 1 H), 7.17 (s,
1 H), 5.64 (d, J = 0.8 Hz, 1 H), 5.56 (d, J = 1.2 Hz, 1 H), 5.12 (s, 2 H), 4.00
(s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 150.1, 148.8, 142.4, 141.4, 138.5,
136.9, 129.3, 128.8 (2 ×), 128.7, 128.5 (2 ×), 128.0, 127.2 (2 ×), 127.0,
126.8, 126.1 (2 ×), 124.4, 124.0, 114.6, 109.1, 106.5, 70.5, 55.9.
HRMS (ESI-TOF): m/z [M + H]+ calcd for C21H23O2: 307.1698; found:
307.1698.
X-Ray Crystallographic Data12
HRMS (ESI-TOF): m/z [M + H]+ calcd for C26H23O2: 367.1698; found:
367.1698.
Single crystal was grown by slow diffusion of EtOAc into a solution of
compound 4c in CH2Cl2 to yield a colorless prism. The compound
crystallized in the triclinic crystal system, space group P-1, a =
7.5311(6) Å, b = 9.3406(7) Å, c = 12.0799(9) Å, V = 823.02(11) Å3, Z = 2,
dcalcd = 1.236 g/cm3, F(000) = 328, 2θ range 2.243–26.771°, R indices
(all data): R1 = 0.0405, wR2 = 0.1010.
3-Methoxy-7-phenyl-1-(1-phenylallyl)naphthalen-2-ol (4g)
Yield: 157 mg (86%); colorless gum.
IR (CHCl3): 3452, 2960, 1534, 1319, 1231 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 7.98 (d, J = 1.6 Hz, 1 H), 7.76 (d, J = 8.4
Hz, 1 H), 7.55 (dd, J = 1.6, 8.4 Hz, 1 H), 7.46–7.20 (m, 10 H), 7.13 (s, 1
H), 6.78–6.69 (m, 1 H), 6.25 (s, 1 H), 5.89 (d, J = 8.0 Hz, 1 H), 5.31 (dt,
J = 1.6, 7.6 Hz, 1 H), 5.28 (d, J = 0.8 Hz, 1 H), 4.05 (s, 3 H).
3-Cyclopentyloxy-2-methoxy-6-phenylnaphthalene (4d)
Yield: 149 mg (94%); colorless solid; mp 118–120 °C (hexanes/EtOAc).
IR (CHCl3): 2953, 1544, 1302, 1219 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 7.89 (d, J = 1.2 Hz, 1 H), 7.75 (d, J = 8.4
Hz, 1 H), 7.73–7.70 (m, 2 H), 7.60 (dd, J = 2.0, 8.4 Hz, 1 H), 7.50–7.46
(m, 2 H), 7.38–7.34 (m, 1 H), 7.18 (s, 1 H), 7.15 (s, 1 H), 4.97–4.92 (m,
1 H), 3.99 (s, 3 H), 2.13–1.84 (m, 6 H), 1.72–1.62 (m, 2 H).
13C NMR (100 MHz, CDCl3): δ = 150.5, 148.5, 141.5, 136.8, 129.5,
128.7 (2 ×), 128.2, 127.2 (2 ×), 126.9, 126.7, 124.3, 123.6, 109.4, 106.3,
80.2, 55.9, 32.8 (2 ×), 24.3 (2 ×).
13C NMR (100 MHz, CDCl3): δ = 147.0, 144.1, 143.2, 141.6, 138.4 (2 ×),
136.4, 128.7 (2 ×), 128.2 (2 ×), 128.0, 127.9, 127.6 (2 ×), 127.2 (2 ×),
126.8, 125.9, 123.0 (2 ×), 121.0, 117.2, 104.8, 55.9, 45.8.
HRMS (ESI-TOF): m/z [M + H]+ calcd for C26H23O2: 367.1698; found:
367.1698.
3-[6-(2-Methoxy-6-phenylnaphthalene)hexyloxy]-2-methoxy-6-
phenylnaphthalene (4h)
HRMS (ESI-TOF): m/z [M + H]+ calcd for C22H23O2: 319.1698; found:
319.1695.
Yield: 262 mg (90%); colorless solid; mp 197–199 °C (hexanes/EtOAc).
IR (CHCl3): 2968, 1536, 1318, 1215 cm–1
.
3-Benzyloxy-2-methoxy-6-phenylnaphthalene (4e)
1H NMR (400 MHz, CDCl3): δ = 7.88 (d, J = 2.0 Hz, 2 H), 7.75 (d, J = 8.4
Hz, 2 H), 7.71–7.68 (m, 4 H), 7.59 (dd, J = 2.0, 8.4 Hz, 2 H), 7.48–7.44
(m, 4 H), 7.37–7.33 (m, 2 H), 7.19 (s, 2 H), 7.14 (s, 2 H), 4.19 (t, J = 6.8
Hz, 4 H), 3.99 (s, 6 H), 2.05–1.99 (m, 4 H), 1.67–1.63 (m, 4 H).
13C NMR (100 MHz, CDCl3): δ = 150.0 (2 ×), 149.3 (2 ×), 141.4 (2 ×),
136.9 (2 ×), 129.5 (2 ×), 128.8 (4 ×), 128.3 (2 ×), 127.2 (4 ×), 127.0 (2 ×),
126.8 (2 ×), 124.3 (2 ×), 123.7 (2 ×), 107.8 (2 ×), 106.3 (2 ×), 68.7 (2 ×),
55.9 (2 ×), 29.0 (2 ×), 25.9 (2 ×).
Yield: 160 mg (94%); colorless solid; mp 147–149 °C (hexanes/EtOAc).
IR (CHCl3): 2961, 1543, 1302, 1222 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 7.85 (d, J = 1.6 Hz, 1 H), 7.76 (d, J = 8.4
Hz, 1 H), 7.70–7.68 (m, 2 H), 7.61 (dd, J = 1.6, 8.4 Hz, 1 H), 7.53–7.31
(m, 8 H), 7.23 (s, 1 H), 7.18 (s, 1 H), 5.31 (s, 2 H), 4.03 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 150.0, 148.9, 141.3, 136.9, 136.7,
129.3, 128.7 (2 ×), 128.6 (2 ×), 128.5, 127.9, 127.3 (2 ×), 127.2 (2 ×),
127.0, 126.7, 124.4, 123.9, 108.8, 106.4, 70.7, 55.9.
HRMS (ESI-TOF): m/z [M + H]+ calcd for C40H39O4: 583.2848; found:
HRMS (ESI-TOF): m/z [M + H]+ calcd for C24H21O2: 341.1542; found:
583.2846.
341.1544.
3-(6-Bromohexyloxy)-2-methoxy-6-phenylnaphthalene (4i)
3-Methoxy-7-phenyl-1-(2-phenylallyl)naphthalen-2-ol (4f)
Yield: 165 mg (80% ); colorless gum.
IR (CHCl3): 2960, 1546, 1310, 1217 cm–1
.
Yield: 154 mg (84%); colorless gum.
IR (CHCl3): 3431, 2963, 1530, 1312, 1225 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 7.88 (d, J = 1.6 Hz, 1 H), 7.75 (d, J = 8.4
Hz, 1 H), 7.71–7.69 (m, 2 H), 7.60 (dd, J = 2.0, 8.4 Hz, 1 H), 7.49–7.45
(m, 2 H), 7.38–7.34 (m, 1 H), 7.18 (s, 1 H), 7.15 (s, 1 H), 4.16 (t, J = 6.8
Hz, 2 H), 4.00 (s, 3 H), 3.44 (t, J = 6.8 Hz, 2 H), 1.98–1.91 (m, 4 H),
1.62–1.55 (m, 4 H).
1H NMR (400 MHz, CDCl3): δ = 7.97 (d, J = 1.6 Hz, 1 H), 7.78 (d, J = 8.8
Hz, 1 H), 7.68–7.59 (m, 5 H), 7.46–7.39 (m, 4 H), 7.36–7.32 (m, 2 H),
7.12 (s, 1 H), 6.16 (s, 1 H), 5.37 (d, J = 1.2 Hz, 1 H), 4.69 (d, J = 1.6 Hz, 1
H), 4.30 (t, J = 1.6 Hz, 2 H), 4.06 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 150.0, 149.3, 141.4, 136.9, 129.5,
128.8 (2 ×), 128.4, 127.2 (2 ×), 127.0, 126.8, 124.3, 123.8, 107.8, 106.3,
66.6, 55.9, 33.8, 32.7, 28.8, 28.0, 25.3.
13C NMR (100 MHz, CDCl3): δ = 147.0, 145.9, 143.9, 142.1, 141.7,
136.9, 129.2, 128.7 (2 ×), 128.3 (2 ×), 128.2, 127.6, 127.5, 127.3 (2 ×),
126.9, 126.1 (2 ×), 123.3, 121.8, 117.7, 113.1, 107.3, 55.9, 30.4.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2018, 50, A–L