176.0838, with an isotope distribution pattern that is the same
as the calculated one.
δ 8.25 (d, 2H, J ) 8.7 Hz), 7.71 (d, 1H, J ) 16.2 Hz), 7.69 (d,
2H, J ) 8.7 Hz), 6.57 (d, 1H, J ) 16.2 Hz), 4.30 (q, 2H, J ) 7.2
Hz), 1.35 (t, 3H, J ) 7.2 Hz). 13C NMR (75 MHz, CDCl3): δ 165.9,
148.3, 141.5, 140.5, 128.5, 124.0, 122.5, 60.9, 14.1. HRMS-EI
([M]+): calcd for C11H11NO4 221.0688, found 221.0687, with an
isotope distribution pattern that is the same as the calculated
one.
Eth yl (E)-3-(2-m eth ylp h en yl)-2-p r op en oa te10 was synthe-
sized from 2-methylbenzaldehyde (b). 1H NMR (300 MHz,
CDCl3): δ 7.97 (d, 1H, J ) 15.6 Hz), 7.53 (d, 1H, J ) 7.2 Hz),
7.20 (m, 3H), 6.35 (d, 1H, J ) 15.6 Hz), 4.26 (q, 2H, J ) 7.2 Hz),
2.42 (s, 3H), 1.33 (t, 3H, J ) 7.2 Hz). 13C NMR (75 MHz,
CDCl3): δ 167.3, 142.5, 137.8, 133.7, 131.0, 130.2, 126.6, 126.5,
119.5, 60.7, 20.0, 14.6. HRMS-EI ([M]+): calcd for C12H14O2
190.0994, found 190.0990, with an isotope distribution pattern
that is the same as the calculated one.
Eth yl (E)-3-(4-ch lor op h en yl)-2-p r op en oa te9 was synthe-
sized from 4-chlorobenzaldehyde (j). 1H NMR (300 MHz,
CDCl3): δ 7.62 (d, 1H, J ) 16.2 Hz), 7.44 (d, 2H, J ) 8.4 Hz),
7.34 (d, 2H, J ) 8.4 Hz), 6.40 (d, 1H, J ) 16.2 Hz), 4.26 (q, 2H,
Eth yl (E)-3-(2,6-d im eth ylp h en yl)-2-pr op en oa te11 was syn-
thesized from 2,6-dimethylbenzaldehyde (c). 1H NMR (300 MHz,
CDCl3): δ 7.84 (d, 1H, J ) 16.2 Hz), 7.06 (m, 3H), 6.06 (d, 1H,
J ) 16.2 Hz), 4.27 (q, 2H, J ) 7.2 Hz), 2.34 (s, 6H), 1.34 (t, 3H,
J ) 7.2 Hz). 13C NMR (75 MHz, CDCl3): δ 166.7, 143.2, 126.5,
133.9, 128.2, 128.1, 123.8, 60.4, 21.0, 14.2. HRMS-EI ([M]+):
calcd for C13H16O2 204.1150, found 204.1152, with an isotope
distribution pattern that is the same as the calculated one.
Eth yl (E)-3,3-d ip h en yla cr yla te12 was synthesized from
diphenylacetaldehyde (d ). 1H NMR (300 MHz, CDCl3): δ 7.42
(dd, 1H, J ) 15.6, 7.2 Hz), 7.23 (m, 10H), 5.73 (d, 1H, J ) 15.6
Hz), 4.86 (d, 1H, J ) 7.2 Hz), 4.17 (q, 2H, J ) 7.2 Hz), 1.24 (t,
3H, J ) 7.2 Hz). 13C NMR (75 MHz, CDCl3): δ 166.4, 149.8,
141.4, 128.6, 128.5, 126.8, 122.9, 60.3, 53.3, 14.1. HRMS-EI
([M]+): calcd for C18H18O2 266.1307, found 266.1300, with an
isotope distribution pattern that is the same as the calculated
one.
J
) 7.2 Hz), 1.33 (t, 3H, J ) 7.2 Hz). 13C NMR (75 MHz,
CDCl3): δ 166.6, 143.0, 136.0, 132.8, 129.1, 128.6, 118.7, 60.5,
14.2. HRMS-EI ([M]+): calcd for C11H11ClO2 210.0448, found
210.0448, with an isotope distribution pattern that is the same
as the calculated one.
Eth yl (E)-3-(4-tr iflu or om eth ylp h en yl)-2-p r op en oa te9 was
synthesized from 4-trifluorotolualdehyde (k ). 1H NMR (300 MHz,
CDCl3): δ 7.69 (d, 1H, J ) 16.2 Hz), 7.62 (s, 4H), 6.51 (d, 1H, J
) 16.2 Hz), 4.28 (q, 2H, J ) 6.9 Hz), 1.34 (t, 3H, J ) 6.9 Hz).
13C NMR (75 MHz, CDCl3): δ 166.3, 142.6, 137.8, 132.0, 129.6,
128.1, 125.7, 120.8, 60.7, 14.2. HRMS-EI ([M]+): calcd for
C12H11O2F3 244.0711, found 244.0718, with an isotope distribu-
tion pattern that is the same as the calculated one.
Eth yl (E)-3-(4-m eth oxyp h en yl)-2-p r op en oa te9 was syn-
thesized from 4-methoxybenzaldehyde (l). 1H NMR (300 MHz,
CDCl3): δ 7.64 (d, 1H, J ) 15.9 Hz), 7.46 (d, 2H, J ) 9.0 Hz),
6.88 (d, 2H, J ) 9.0 Hz), 6.30 (d, 1H, J ) 15.9 Hz), 4.24 (q, 2H,
J ) 7.2 Hz), 3.81 (s, 3H), 1.32 (t, 3H, J ) 7.2 Hz). 13C NMR (75
MHz, CDCl3): δ 167.2, 161.2, 144.1, 129.5, 127.0, 115.6, 114.1,
60.2, 55.2, 14.2. HRMS-EI ([M]+): calcd for C12H14O3 206.0943,
found 206.0950, with an isotope distribution pattern that is the
same as the calculated one.
Eth yl (E)-3-(4-d im eth ya m in op h en yl)-2-p r op en oa te16 was
synthesized from 4-dimethylaminobenzaldehyde (m ). 1H NMR
(300 MHz, CDCl3): δ 7.62 (d, 1H, J ) 15.6 Hz), 7.40 (d, 2H, J )
9.0 Hz), 6.64 (d, 2H, J ) 9.0 Hz), 6.21 (d, 1H, J ) 15.6 Hz), 4.23
(q, 2H, J ) 6.9 Hz), 2.98 (s, 6H), 1.32 (t, 3H, J ) 6.9 Hz). 13C
NMR (75 MHz, CDCl3): δ 167.8, 151.6, 145.0, 129.6, 122.1, 112.4,
111.6, 59.9, 40.0, 14.3. HRMS-EI ([M]+): calcd for C13H17NO2
219.1259, found 219.1255, with an isotope distribution pattern
that is the same as the calculated one.
Eth yl (E)-3-(4-a cetylp h en yl)-2-p r op en oa te16 was synthe-
sized from 4-acetylbenzaldehyde (n ). 1H NMR (300 MHz,
CDCl3): δ 7.96 (d, 2H, J ) 7.8 Hz), 7.69 (d, 1H, J ) 16.2 Hz),
7.6 (d, 2H, J ) 7.8 Hz), 6.52 (d, 1H, J ) 16.2 Hz), 4.28 (q, 2H,
J ) 7.2 Hz), 2.61 (s, 3H), 1.35 (t, 3H, J ) 7.2 Hz). 13C NMR (75
MHz, CDCl3): δ 197.1, 166.3, 142.8, 138.6, 137.8, 128.7, 128.0,
120.6, 60.6, 26.5, 14.1. HRMS-EI ([M]+): calcd for C13H14O3
218.0943, found 218.0943, with an isotope distribution pattern
that is the same as the calculated one.
Eth yl (E)-3-cycloh exyl-2-p r op en oa te13 was synthesized
from cyclohexanecarboxaldehyde (e). 1H NMR (300 MHz,
CDCl3): δ 6.92 (dd, 1H, J ) 15.9, 7.2 Hz), 5.76 (d, 1H, J ) 15.9
Hz), 4.18 (q, 2H, J ) 7.2 Hz), 2.14 (m, 1H), 1.75 (m, 5H), 1.29 (t,
3H, J ) 7.2 Hz), 1.16 (m, 5H). 13C NMR (75 MHz, CDCl3): δ
167.1, 154.2, 118.8, 60.1, 40.3, 31.6, 25.9, 25.7, 14.2. HRMS-EI
([M]+): calcd for C11H18O2 182.1307, found 182.1307, with an
isotope distribution pattern that is the same as the calculated
one.
Eth yl (E,E)-5-p h en ylp en ta -2,4-d ien oa te9 was synthesized
from trans-cinnamaldehyde (f). 1H NMR (300 MHz, CDCl3): δ
7.5-6.8 (m, 8H), 5.99 (d, 1H, J ) 15.0 Hz), 4.22 (q, 2H, J ) 7.2
Hz), 1.31 (t, 3H, J ) 7.2 Hz). 13C NMR (75 MHz, CDCl3): δ 167.0,
144.5, 140.3, 135.9, 128.9, 128.7, 127.1, 126.1, 121.2, 60.2, 14.2.
HRMS-EI ([M]+): calcd for C13H14O2 202.0994, found 202.0991,
with an isotope distribution pattern that is the same as the
calculated one.
Eth yl (E)-2-d ecen oa te14 was synthesized from octylaldehyde
(g). 1H NMR (300 MHz, CDCl3): δ 6.97 (dt, 1H, J ) 15.6, 7.2
Hz), 5.81 (d, 1H, J ) 15.6 Hz), 4.18 (q, 2H, J ) 7.2 Hz), 2.19 (m,
2H), 1.45 (m, 2H), 1.29 (m, 11H), 0.89 (t, 3H, J ) 6.9 Hz). 13C
NMR (75 MHz, CDCl3): δ 166.7, 149.4, 121.1, 60.0, 32.1, 31.7,
29.0, 28.0, 22.6, 14.2, 14.0. HRMS-EI ([M - OC2H5]+): calcd for
C10H17O 153.1279, found 153.1282, with an isotope distribution
pattern that is the same as the calculated one.
Eth yl (E)-3-(4-a cetoxyp h en yl)-2-p r op en oa te17 was syn-
thesized from methyl 4-formylbenzoate (o). 1H NMR (300 MHz,
CDCl3): δ 8.04 (d, 2H, J ) 8.1 Hz), 7.69 (d, 1H, J ) 15.9 Hz),
7.57 (d, 2H, J ) 8.1 Hz), 6.51 (d, 1H, J ) 15.9 Hz), 4.28 (q, 2H,
J ) 7.1 Hz), 3.92 (s, 3H), 1.34 (t, 3H, J ) 7.1 Hz). 13C NMR (75
MHz, CDCl3): δ 166.4, 166.3, 143.0, 138.6, 131.2, 130.0, 127.8,
120.6, 60.6, 52.1, 14.2. HRMS-EI ([M]+): calcd for C13H14O4
234.0892, found 234.0890, with an isotope distribution pattern
that is the same as the calculated one.
Eth yl (E)-3-(4-m eth ylp h en yl)-2-p r op en oa te9 was synthe-
sized from 4-methylbenzaldehyde (h ). 1H NMR (300 MHz,
CDCl3): δ 7.66 (d, 1H, J ) 15.6 Hz), 7.40 (d, 2H, J ) 7.8 Hz),
7.17 (d, 2H, J ) 7.8 Hz), 6.39 (d, 1H, J ) 15.6 Hz), 4.25 (q, 2H,
J ) 7.1 Hz), 2.35 (s, 3H), 1.32 (t, 3H, J ) 7.1 Hz). 13C NMR (75
MHz, CDCl3): δ 167.0, 144.5, 140.5, 131.6, 129.5, 127.9, 117.0,
60.3, 21.3, 14.2. HRMS-EI ([M]+): calcd for C12H14O2 190.0994,
found 190.0990, with an isotope distribution pattern that is the
same as the calculated one.
Eth yl (E)-3-(4-n itr op h en yl)-2-p r op en oa te15 was synthe-
sized from 4-nitrobenzaldehyde (i). 1H NMR (300 MHz, CDCl3):
Ack n ow led gm en t. We are grateful for financial
support of this work from the Department of Chemistry
of the University of Tennessee. We wish to acknowledge
Dr. Al Tuinman of UT Mass Spectroscopy Center for
assistance with high-resolution mass spectroscopy.
(10) Liu, J .-M.; Young, J .-J .; Li, Y.-T.; Sha, C.-K. J . Org. Chem. 1986,
51, 1120.
(11) Li, X.; Wu, H.; Hruby, V. J . Tetrahedron: Asymmetry 1995, 6,
83.
(12) Gualtieri, F.; Teodori, E.; Bellucci, C.; Pesce, E.; Piacenza, G.
J . Med. Chem. 1985, 28, 1621.
J O0341158
(13) Barrett, A. G. M.; Doubleday: W. W.; Tustin, G. J . Tetrahedron
1996, 52, 15325.
(14) Ando, K. J . Org. Chem. 1997, 62, 1934.
(15) Qian, C.; Wang, L. Tetrahedron 2000, 56, 7193.
(16) Butt, G.; Topsom, R. D. Spectrochim. Acta 1982, 38(A), 649.
(17) Bozell, J . J .; Vogt, C. E. J . Am. Chem. Soc. 1988, 110, 2655.
J . Org. Chem, Vol. 68, No. 9, 2003 3717