(1R*,2S*)-3-Heptyl-2-(1-phenoxyvinyl)cyclopentanone (trans-
3de). Colourless oil; mmax(neat)/cm−1 1745; dH (300 MHz; CDCl3)
0.90 (3H, t, J = 6.9 Hz), 1.20–1.53 (12H, m), 1.70–1.83 (1H, m),
2.16–2.36 (2H, m), 2.37–2.55 (2H, m), 2.58 (1H, d, J = 11.1 Hz),
4.06 (1H, d, J = 2.1 Hz), 4.21 (1H, d, J = 2.1 Hz), 7.02–7.17 (3H,
m), 7.31–7.39 (2H, m); MS m/z (EI) 300 (M+); HRMS m/z (EI)
calcd for C20H28O2 300.2090 (M+), found 300.2069.
6.84 (2H, d, J = 8.4 Hz), 7.13 (2H, d, J = 8.4 Hz); dC (75 MHz;
CDCl3) 15.4, 19.5, 20.7, 27.4, 40.8, 118.4, 120.1, 130.3, 134.2,
151.9, 161.5, 208.1; MS m/z (EI) 216 (M+); HRMS m/z (EI) calcd
for C20H16O2 216.1150 (M+), found 216.1153.
2-[1-(4-Methylphenoxy)vinyl]cyclopentanone-3-spirocyclo-
hexane (exo-3bb). Colourless oil; mmax(neat)/cm−1 1740; dH
(300 MHz; CDCl3) 1.30–1.79 (11H, m), 2.17–2.27 (1H, m), 2.32
(3H, s), 2.33–2.39 (2H, m), 2.79 (1H, s), 4.05 (1H, d, J = 2.1 Hz),
4.13 (1H, d, J = 2.1 Hz), 6.93 (2H, d, J = 8.4 Hz), 7.13 (2H, d,
J = 8.4 Hz); dC (75 MHz; CDCl3) 20.8, 22.5, 22.7, 26.0, 31.5,
32.3, 36.2, 37.9, 43.7, 64.6, 91.9, 121.3, 121.3, 130.2, 130.2,
134.2, 152.5, 159.7, 218.6; MS m/z (EI) 284 (M+); HRMS m/z
(EI) calcd for C19H24O2 284.1776 (M+), found 284.1794.
(1R*,2S*)-3-Heptyl-2-[1-(4-chlorophenoxy)vinyl]cyclopenta-
none (trans-3df) and (E)-3-heptyl-2-[1-(4-chlorophenoxy)ethyl-
idene]cyclopentanone (endo-3df) (ratio of 68:32). Colourless oil;
mmax(neat)/cm−1 1742, 1700; dH (300 MHz; CDCl3) 0.86 (0.96H,
t, J = 6.9 Hz), 0.90 (2.04H, t, J = 6.9 Hz), 1.14–1.64 (12H, m),
1.70–1.81 (0.32H, m), 1.85–2.01 (0.32H, m), 2.22 (0.96H, s),
2.21–2.59 (3.36H, m), 3.10–3.21 (0.32H, m), 4.07 (0.68H, d,
J = 2.7 Hz), 4.24 (0.68H, d, J = 2.7 Hz), 6.85–6.91 (0.64H, m),
7.28–7.34 (0.64H, m), 7.27–7.33 (2.72H, m); MS m/z (EI) 334
(M+); HRMS m/z (EI) calcd for C20H27O2Cl 334.1700 (M+),
found 334.1701.
(1R*,2R*)-2-[1-(4-Methylphenoxy)vinyl]-3-phenylcyclo-
pentanone (trans-3cb). Colourless oil; mmax(neat)/cm−1 1740; dH
(300 MHz; CDCl3) 1.94–2.05 (1H, m), 2.27 (3H, s), 2.34–2.42
(2H, m), 2.49–2.57 (1H, m), 3.02 (1H, d, J = 12.0 Hz),
3.65–3.72 (1H, m), 3.89 (1H, dd, J = 2.5 and 1.0 Hz), 4.01 (1H,
d, J = 2.5 Hz), 6.83 (2H, d, J = 8.5 Hz), 7.09 (2H, dd, J = 8.5
and 1.0 Hz), 7.20–7.26 (1H, m), 7.33–7.35 (4H, m); dC (75 MHz;
CDCl3) 21.1, 29.6, 39.2, 46.8, 62.9, 92.2, 121.6, 121.6, 127.4,
127.8, 127.8, 129.2, 129.2, 130.6, 130.6, 134.8, 142.8, 153.3,
159.6, 214.7; MS m/z (EI) 292 (M+); HRMS m/z (EI) calcd for
C20H20O2 292.1464 (M+), found 292.1447.
(1S*,2S*)-3-Heptyl-2-[1-(4-methoxyphenoxy)vinyl]cyclo-
pentanone (cis-3da). Colourless oil; mmax(neat)/cm−1 1740; dH
(300 MHz; CDCl3) 0.88 (3H, t, J = 6.9 Hz), 1.21–1.56 (11H,
m), 1.66–1.79 (1H, m), 1.87–2.03 (1H, m), 2.03–2.16 (1H, m),
2.20–2.50 (3H, m), 3.08 (1H, d, J = 9.0 Hz), 3.79 (3H, s), 3.95
(1H, d, J = 2.1 Hz), 4.14 (1H, d, J = 2.1 Hz), 8.83–8.88 (2H, m),
8.91–8.97 (2H, m); MS m/z (EI) 330 (M+); HRMS m/z (EI) calcd
for C21H30O2 330.2195 (M+), found 330.2198.
(1R*,2S*)-3-Heptyl-2-[1-(4-methylphenoxy)vinyl]cyclo-
pentanone (trans-3db). Colourless oil; mmax(neat)/cm−1 1740; dH
(300 MHz; CDCl3) 0.90 (3H, t, J = 6.9 Hz), 1.20–1.53 (12H, m),
1.70–1.82 (1H, m), 2.20–2.35 (2H, m), 2.32 (3H, s), 2.36–2.56
(2H, m), 2.57 (1H, d, J = 10.8 Hz), 4.03 (1H, d, J = 2.1 Hz),
4.17 (1H, d, J = 2.1 Hz), 6.91–6.96 (2H, m), 7.10–7.16 (2H, m);
dC (75 MHz; CDCl3) 14.0, 20.7, 22.5, 26.9, 27.3, 29.1, 29.6, 31.7,
34.6, 38.5, 40.5, 61.8, 91.3, 120.2, 121.3, 130.1, 130.2, 134.0,
152.8, 159.9, 216.7; MS m/z (EI) 314 (M+); HRMS m/z (EI)
calcd for C21H30O2 314.2246 (M+), found 314.2232.
(1S*,2S*)-3-Heptyl-2-[1-(2,4,6-trimethylphenoxy)vinyl]cyclo-
pentanone (cis-3dc). Colourless oil; mmax(neat)/cm−1 1745; dH
(300 MHz; CDCl3) 0.89 (3H, s), 1.20–1.60 (11H, m), 1.74–1.88
(2H, m), 2.01–2.15 (1H, m), 2.11 (6H, s), 2.24–2.53 (3H, m), 2.25
(3H, s), 3.10 (1H, d, J = 8.4 Hz), 3.74 (1H, d, J = 2.1 Hz), 4.02
(1H, d, J = 2.1 Hz), 6.83 (2H, s); MS m/z (EI) 342 (M+); HRMS
m/z (EI) calcd for C23H34O2 342.2559 (M+), found 342.2544.
(E )-3-Heptyl-2-[1-(4-methoxyphenoxy)ethylidene]cyclo-
pentanone (endo-3da). Colourless oil; mmax(neat)/cm−1 1700; dH
(300 MHz; CDCl3) 0.86 (3H, t, J = 6.9 Hz), 1.18–1.48 (11H,
m), 1.57–1.69 (1H, m), 1.70–1.80 (1H, m), 1.85–2.00 (1H, m),
2.20 (3H, s), 2.29 (1H, ddd, J = 18.0, 8.7 and 2.7 Hz), 2.46 (1H,
ddd, J = 18.0, 10.8 and 8.7 Hz), 3.15–3.25 (1H, m), 3.81 (3H,
s), 6.88 (4H, s); dC (75 MHz; CDCl3) 14.1, 15.3, 22.7, 24.5, 27.6,
29.3, 29.7, 31.9, 34.2, 38.5, 39.2, 55.7, 114.8, 114.8, 121.7, 121.7,
122.8, 147.5, 156.8, 162.3, 208.5; MS m/z (EI) 330 (M+); HRMS
m/z (EI) calcd for C21H30O3 330.2195 (M+), found 330.2200.
(1R*,2S*)-3-Heptyl-2-[1-(4-methoxyphenoxy)vinyl]cyclo-
pentanone (trans-3da). Colourless oil; mmax(neat)/cm−1 1750; dH
(300 MHz; CDCl3) 0.90 (3H, t, J = 6.9 Hz), 1.20–1.54 (12H, m),
1.69–1.81 (1H, m), 2.18–2.54 (4H, m), 2.56 (1H, d, J = 10.8 Hz),
3.79 (3H, s), 3.98 (1H, d, J = 2.1 Hz), 4.14 (1H, d, J = 2.1 Hz),
6.82–6.89 (2H, m), 6.94–7.00 (2H, m); dC (75 MHz; CDCl3) 14.1,
22.7, 27.0, 27.4, 29.2, 29.7, 31.9, 34.8, 38.6, 40.6, 55.6, 61.9,
91.0, 114.7, 114.8, 121.7, 122.6, 148.6, 156.7, 160.5, 216.8; MS
m/z (EI) 330 (M+); HRMS m/z (EI) calcd for C21H30O3 330.2195
(M+), found 330.2183.
(E)-3-Heptyl-2-[1-(4-methylphenoxy)ethylidene]cyclopenta-
none (endo-3db). Colourless oil; mmax(neat)/cm−1 1700; dH
(300 MHz; CDCl3) 0.85 (3H, t, J = 6.9 Hz), 1.17–1.49 (11H,
m), 1.56–1.69 (1H, m), 1.70–1.80 (1H, m), 1.85–2.00 (1H, m),
2.21 (3H, s), 2.29 (1H, ddd, J = 18.3, 8.7 and 3.0 Hz), 2.34 (3H,
s), 2.46 (1H, ddd, J = 18.3, 10.8 and 8.7 Hz), 3.15–3.24 (1H,
m), 6.80–6.86 (2H, m), 7.10–7.16 (2H, m); dC (75 MHz; CDCl3)
14.0, 15.5, 20.7, 22.6, 24.5, 27.5, 29.3, 29.7, 31.8, 34.2, 38.5, 39.1,
120.3, 120.3, 123.5, 130.3, 130.3, 134.3, 151.8, 161.8, 208.4; MS
m/z (EI) 314 (M+); HRMS m/z (EI) calcd for C21H30O2 314.2246
(M+), found 314.2208.
(1R*,2S*)-3-Heptyl-2-[1-(2,4,6-trimethylphenoxy)vinyl]cyclo-
pentanone (trans-3dc). Colourless oil; mmax(neat)/cm−1 1745; dH
(300 MHz; CDCl3) 0.90 (3H, t, J = 6.9 Hz), 1.23–1.57 (12H, m),
1.76–1.88 (1H, m), 2.12 (6H, s), 2.25 (3H, s), 2.26–2.36 (2H, m),
2.37–2.49 (1H, m), 2.56 (1H, d, J = 10.8 Hz), 2.56–2.70 (1H, m),
3.72 (1H, d, J = 1.5 Hz), 3.99 (1H, d, J = 1.5 Hz), 6.83 (2H, s);
dC (75 MHz; CDCl3) 14.1, 15.9, 20.7, 22.7, 27.1, 27.3, 29.3, 29.7,
31.8, 34.7, 38.9, 40.7, 40.7, 61.6, 87.9, 129.3, 129.5, 129.5, 130.9,
134.5, 148.2, 156.5, 216.7; MS m/z (EI) 342 (M+); HRMS m/z
(EI) calcd for C23H34O2 342.2559 (M+), found 342.2575.
(E)-3-Heptyl-2-[1-(2,4,6-trimethoxyphenoxy)ethylidene]cyclo-
pentanone (endo-3dc). Colourless oil; mmax(neat)/cm−1 1700; dH
(300 MHz; CDCl3) 0.86 (3H, t, J = 6.9 Hz), 1.20–1.52 (11H, m),
1.66–1.82 (2H, m), 1.85–2.01 (1H, m), 2.07 (3H, s), 2.09 (3H,
s), 2.12 (3H, s), 2.27 (3H, s), 2.29 (1H, ddd, J = 18.3, 8.7 and
3.0 Hz), 2.47 (1H, ddd, J = 18.3, 11.4 and 8.7 Hz), 3.23–3.34
(1H, m), 6.86 (2H, d, J = 3.6 Hz); dC (75 MHz; CDCl3) 14.0,
14.2, 16.0, 16.4, 20.7, 22.7, 24.5, 27.7, 29.3, 29.9, 31.9, 33.9,
38.6, 39.5, 119.8, 129.5, 129.5, 129.5, 130.6, 135.1, 148.1, 163.5,
208.3; MS m/z (EI) 342 (M+); HRMS m/z (EI) calcd for C23H34O2
342.2559 (M+), found 342.2543.
(1R*,2S*)-3-Heptyl-2-[1-(2-methoxyphenoxy)vinyl]cyclo-
pentanone (trans-3dd). Colourless oil; mmax(neat)/cm−1 1740; dH
(300 MHz; CDCl3) 0.90 (3H, t, J = 6.9 Hz), 1.23–1.58 (12H, m),
1.75–1.88 (1H, m), 2.21–2.36 (2H, m), 2.37–2.50 (1H, m), 2.57
(1H, d, J = 10.8 Hz), 2.57–2.68 (1H, m), 3.81 (3H, s), 3.90 (1H,
d, J = 2.4 Hz), 4.09 (1H, d, J = 2.4 Hz), 6.88–6.98 (2H, m), 7.03–
7.16 (2H, m); dC (75 MHz; CDCl3) 14.1, 22.7, 27.1, 27.3, 29.3,
29.9, 31.9, 34.7, 38.8, 40.8, 56.0, 61.7, 89.7, 113.2, 121.2, 123.7,
125.9, 143.5, 152.0, 159.2, 216.7; MS m/z (EI) 330 (M+); HRMS
m/z (EI) calcd for C21H30O3 330.2195 (M+), found 330.2182.
O r g . B i o m o l . C h e m . , 2 0 0 4 , 2 , 3 0 9 9 – 3 1 0 7
3 1 0 5