F
M.-Y. Chang et al.
Paper
Synthesis
1H NMR (400 MHz, CDCl3): = 8.54 (s, 1 H), 8.20 (d, J = 15.6 Hz, 1 H),
8.11 (dd, J = 1.6, 8.4 Hz, 1 H), 7.99 (d, J = 8.0 Hz, 1 H), 7.94 (d, J = 8.8 Hz,
1 H), 7.90 (d, J = 8.0 Hz, 1 H), 7.63–7.55 (m, 3 H), 7.38 (d, J = 7.6 Hz, 1
H), 7.25 (t, J = 7.6 Hz, 1 H), 6.96 (d, J = 8.4 Hz, 1 H), 6.00-5.91 (m, 1 H),
5.02 (dq, J = 1.6, 10.0 Hz, 1 H), 4.98 (dq, J = 1.6, 16.8 Hz, 1 H), 4.60–
4.54 (m, 1 H), 3.62 (d, J = 6.0 Hz, 2 H), 1.36 (t, J = 6.0 Hz, 6 H).
13C{1H} NMR (100 MHz, CDCl3): = 190.4, 156.0, 142.9, 136.4, 135.54,
135.48, 135.4, 132.5, 130.0, 129.7, 129.5, 128.5, 128.3, 127.8, 127.1,
126.7, 124.5, 124.0, 118.7, 115.2, 114.7, 70.3, 30.0, 22.1 (2 ×).
3-(2-Allyl-3-benzyloxy-4-methoxyphenyl)-1-naphthalen-2-ylpro-
penone (1m)
Yield: 347 mg (80%); colorless gum.
1H NMR (400 MHz, CDCl3): = 8.54 (s, 1 H), 8.12–8.09 (m, 2 H), 7.99
(d, J = 8.0 Hz, 1 H), 7.94 (d, J = 8.8 Hz, 1 H), 7.90 (d, J = 8.0 Hz, 1 H), 7.64
(d, J = 8.8 Hz, 1 H), 7.61–7.55 (m, 3 H), 7.51 (d, J = 8.4 Hz, 2 H), 7.43–
7.33 (m, 3 H), 6.93 (d, J = 8.4 Hz, 1 H), 6.03–5.93 (m, 1 H), 5.07 (dq, J =
1.6, 10.0 Hz, 1 H), 5.02 (s, 2 H), 4.94 (dq, J = 1.6, 17.2 Hz, 1 H), 3.94 (s, 3
H), 3.66 (d, J = 5.6 Hz, 2 H).
13C{1H} NMR (100 MHz, CDCl3): = 190.3, 154.5, 146.1, 142.5, 137.5,
136.6, 135.6, 135.3, 134.5, 132.4, 129.8, 129.4, 128.4, 128.3 (2 ×),
128.2, 128.0 (2 ×), 127.9, 127.7, 127.5, 126.6, 124.5, 123.1, 121.7,
115.9, 110.4, 74.8, 55.7, 30.2.
HRMS (ESI-TOF): m/z [M + H]+ calcd for C25H25O2: 357.1855; found:
357.1861.
3-(2-Allyl-3-isopropoxy-4-methoxyphenyl)-1-naphthalen-2-yl-
propenone (1j)
HRMS (ESI-TOF): m/z [M + H]+ calcd for C30H27O3: 435.1960; found:
Yield: 294 mg (76%); colorless gum.
435.1968.
1H NMR (400 MHz, CDCl3): = 8.52 (d, J = 0.8 Hz, 1 H), 8.12–8.08 (m, 2
H), 7.98 (d, J = 8.0 Hz, 1 H), 7.93 (d, J = 8.8 Hz, 1 H), 7.89 (d, J = 8.0 Hz,
1 H), 7.62–7.53 (m, 3 H), 7.50 (d, J = 15.2 Hz, 1 H), 6.87 (d, J = 8.8 Hz, 1
H), 6.00–5.90 (m, 1 H), 5.04 (dq, J = 1.6, 10.0 Hz, 1 H), 4.94 (dq, J = 1.6,
17.2 Hz, 1 H), 4.56–4.49 (m, 1 H), 3.89 (s, 3 H), 3.68 (dt, J = 1.6, 6.0 Hz,
2 H), 1.29 (d, J = 6.0 Hz, 6 H).
13C{1H} NMR (100 MHz, CDCl3): = 190.5, 154.6, 145.0, 143.1, 136.5,
135.7, 135.3, 134.7, 132.5, 129.8, 129.4, 128.4, 128.1, 127.7, 127.6,
126.6, 124.6, 122.4, 121.6, 115.9, 110.2, 74.8, 55.6, 30.5, 22.6 (2 ×).
3-(2-Allyl-3,4-dimethoxyphenyl)-1-benzo[1,3]dioxol-5-ylprope-
none (1n)
Yield: 268 mg (76%); colorless gum.
1H NMR (400 MHz, CDCl3): = 7.98 (d, J = 15.6 Hz, 1 H), 7.60 (dd, J =
1.6, 8.4 Hz, 1 H), 7.48 (d, J = 8.4 Hz, 1 H), 7.47 (d, J = 8.4 Hz, 1 H), 7.29
(d, J = 15.6 Hz, 1 H), 6.84 (dt, J = 0.8, 8.8 Hz, 1 H), 6.83 (d, J = 8.8 Hz, 1
H), 6.01 (s, 2 H), 6.00–5.91 (m, 1 H), 5.02 (dq, J = 1.6, 10.0 Hz, 1 H),
4.91 (dq, J = 1.6, 17.2 Hz, 1 H), 3.88 (s, 3 H), 3.79 (s, 3 H), 3.60 (d, J = 6.0
Hz, 2 H).
HRMS (ESI-TOF): m/z [M + H]+ calcd for C26H27O3: 387.1960; found:
13C{1H} NMR (100 MHz, CDCl3): = 188.1, 154.3, 151.4, 148.1, 147.2,
141.8, 136.5, 134.0, 133.0, 127.4, 124.4, 122.7, 121.2, 115.7, 110.3,
108.3, 107.7, 101.7, 60.8, 55.6, 29.9.
387.1968.
3-(2-Allyl-3-butoxy-4-methoxyphenyl)-1-naphthalen-2-ylprope-
none (1k)
HRMS (ESI-TOF): m/z [M + H]+ calcd for C21H21O5: 353.1389; found:
Yield: 296 mg (74%); colorless gum.
353.1382.
1H NMR (400 MHz, CDCl3): = 8.50 (s, 1 H), 8.12–8.07 (m, 2 H), 7.92
(d, J = 7.6 Hz, 1 H), 7.86 (d, J = 8.8 Hz, 1 H), 7.81 (d, J = 7.6 Hz, 1 H),
7.58–7.47 (m, 4 H), 6.80 (d, J = 8.8 Hz, 1 H), 6.03–5.93 (m, 1 H), 5.05
(dq, J = 1.6, 10.0 Hz, 1 H), 4.95 (dq, J = 1.6, 16.8 Hz, 1 H), 3.92 (t, J = 6.4
Hz, 2 H), 3.82 (s, 3 H), 3.63 (d, J = 5.6 Hz, 2 H), 1.80–1.73 (m, 2 H),
1.56–1.47 (m, 2 H), 0.98 (t, J = 7.2 Hz, 3 H).
13C{1H} NMR (100 MHz, CDCl3): = 189.9, 154.4, 146.4, 142.4, 136.5,
135.4, 135.1, 134.1, 132.3, 129.6, 129.2, 128.2, 127.9, 127.5, 127.2,
126.4, 124.3, 122.6, 121.3, 115.5, 110.2, 72.8, 55.4, 32.1, 29.9, 18.9,
13.7.
3-(2-Allyl-3,4-dimethoxyphenyl)-1-(3-methoxyphenyl)prope-
none (1o)
Yield: 277 mg (82%); colorless gum.
1H NMR (400 MHz, CDCl3): = 8.00 (d, J = 15.2 Hz, 1 H), 7.55 (d, J = 7.6
Hz, 1 H), 7.51 (d, J = 2.4 Hz, 1 H), 7.49 (d, J = 8.8 Hz, 1 H), 7.36 (d, J = 8.0
Hz, 1 H), 7.32 (d, J = 15.6 Hz, 1 H), 7.07 (dd, J = 2.8, 8.0 Hz, 1 H), 6.82 (d,
J = 8.8 Hz, 1 H), 5.99–5.89 (m, 1 H), 5.01 (dq, J = 1.6, 10.0 Hz, 1 H), 4.91
(dq, J = 1.6, 17.2 Hz, 1 H), 3.86 (s, 3 H), 3.82 (s, 3 H), 3.78 (s, 3 H), 3.59
(d, J = 5.6 Hz, 2 H).
13C{1H} NMR (100 MHz, CDCl3): = 190.0, 159.6, 154.3, 147.1, 142.4,
139.6, 136.4, 134.0, 129.3, 127.2, 122.8, 121.5, 120.8, 118.8, 115.6,
112.7, 110.3, 60.7, 55.5, 55.2, 29.9.
HRMS (ESI-TOF): m/z [M + H]+ calcd for C27H29O3: 401.2117; found:
401.2123.
3-(2-Allyl-3-cyclopentyloxy-4-methoxyphenyl)-1-naphthalen-2-
ylpropenone (1l)
HRMS (ESI-TOF): m/z [M + H]+ calcd for C21H23O4: 339.1596; found:
339.1590.
Yield: 342 mg ( 83%); colorless gum.
1H NMR (400 MHz, CDCl3): = 8.52 (s, 1 H), 8.12–8.08 (m, 2 H), 7.98
(d, J = 8.0 Hz, 1 H), 7.93 (d, J = 8.8 Hz, 1 H), 7.89 (d, J = 8.0 Hz, 1 H),
7.61–7.53 (m, 3 H), 7.50 (d, J = 15.6 Hz, 1 H), 6.87 (d, J = 8.4 Hz, 1 H),
6.00–5.91 (m, 1 H), 5.04 (dq, J = 1.6, 10.0 Hz, 1 H), 4.93 (dq, J = 1.6,
17.2 Hz, 1 H), 4.88–4.84 (m, 1 H), 3.89 (s, 3 H), 3.64 (dd, J = 1.6, 6.0 Hz,
2 H), 1.93–1.79 (m, 4 H), 1.77–1.71 (m, 2 H), 1.63–1.58 (m, 2 H).
13C{1H} NMR (100 MHz, CDCl3): = 190.5, 154.4, 145.4, 143.1, 136.5,
135.7, 135.3, 134.5, 132.5, 129.8, 129.4, 128.4, 128.1, 127.7, 127.6,
126.6, 124.6, 122.3, 121.6, 115.8, 110.4, 84.6, 55.6, 32.8 (2 ×), 30.3,
23.6 (2 ×).
3-(2-Allyl-3,4-dimethoxyphenyl)-1-(4-methoxyphenyl)prope-
none (1p)
Yield: 260 mg (77%); colorless gum.
1H NMR (400 MHz, CDCl3): = 8.03–7.98 (m, 3 H), 7.52 (d, J = 8.4 Hz, 1
H), 7.37 (d, J = 15.2 Hz, 1 H), 6.97 (d, J = 9.2 Hz, 2 H), 6.86 (d, J = 8.4 Hz,
1 H), 6.02–5.93 (m, 1 H), 5.04 (dq, J = 1.6, 10.4 Hz, 1 H), 4.93 (dq, J =
1.6, 16.8 Hz, 1 H), 3.91 (s, 3 H), 3.88 (s, 3 H), 3.82 (s, 3 H), 3.63 (dt, J =
1.6, 5.6 Hz, 2 H).
13C{1H} NMR (100 MHz, CDCl3): = 188.8, 163.2, 154.3, 147.3, 141.7,
136.6, 134.1, 131.2, 130.7 (2 ×), 127.7, 122.9, 121.7, 115.8, 113.7 (2 ×),
110.4, 60.9, 55.7, 55.4, 30.1.
HRMS (ESI-TOF): m/z [M + H]+ calcd for C28H29O3: 413.2117; found:
413.2122.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2019, 51, A–K