1- and 2-cinnamoyloxyacetonaphthones
overlapping signals. This is due to the presence of two naphthyl
rings in the structure of these compounds as shown in the
table. The protons showed chemical shift values in the range
(s), 1136 (vs), 1063 (m), 1022 (w), 996 (m), 919 (w), 865 (w), 817
(s), 764 (vs) cm−1; elemental analysis: calcd for C21H16O3: C: 79.73,
H:5.10, found: C:79.97, H:4.91.
1
of δ = 8.08–7.44 ppm. The methylene H signal was observed
at δ = 4.23 ppm as a singlet followed by the methyl signal at
2.δ = 40 ppm.
(E)-2-Acetylnaphthalen-1-yl-3-(4-chlorophenyl)acrylate (2)
UV (CHCl3): 327 (sh),280 nm; IR (KBr): 3423 (w), 3354 (w), 3086 (w),
3007 (w), 1730 (vs) 1715 (vs), 1682 (vs), 1621 (s), 1590 (s), 1489 (s),
1466 (s), 1404 (s), 1350 (m), 1325 (m), 1276 (m), 1212 (s), 1196 (m),
1150 (m), 1073 (m), 1008 (w), 988 (m), 923 (w), 828 (w), 754 (vs)
cm−1; elemental analysis: calcd for C21H15ClO3: C: 71.90, H: 4.31,
Cl: 10.11; found : C: 72.13, H: 4.24.
In summary, we have synthesized cinnamoyloxy-substituted
acetonaphthones and examined their structure with a number
of analytical techniques. The chemical shifts associated with
naphthyl protons varied marginally. In contrast, substitution of
the phenyl ring in the cinnamoyl moiety resulted in significant
changes in chemical shifts corresponding to the electron donat-
ing/withdrawing groups attached to the ring. The trifluoromethyl-
substituted compound showed the highest influence for the
trans-double bond protons (H15) compared to other substituted
groups on the phenyl ring. Introduction of a thiophene ring in
the structure shifted the trans-double bond 1H signal to lower
frequency (δ = 6.55 ppm) compared to the phenyl-substituted
compounds.
(E)-2-Acetylnaphthalen-1-yl-3-(4-bromophenyl)acrylate(3)
UV (CHCl3): 322 (sh), 290 nm; IR (KBr): 3441 (w), 3086 (w), 3066
(w),3010 (w), 1730 (vs), 1715 (vs), 1682 (vs), 1594 (s), 1508 (m),
1489 (s), 1465 (s), 1403 (s), 1387 (w), 1349 (m), 1325 (m), 1276 (m),
1232 (s), 1196 (m), 1150 (m), 1073 (m), 1009 (w), 923 (w), 828 (w),
755 (vs), 729 (m) cm−1; elemental analysis: calcd for C21H15BrO3:
C: 63.81, H: 3.83, found: C: 63.70, H: 3.73.
Experimental
(E)-2-Acetylnaphthalen-1-yl-3-(4-methoxyphenyl)acrylate(4)
All the chemicals were obtained from Aldrich Sigma and were
used without further purification. NMR spectra were recorded in
dimethyl sulfoxide and the chemical shifts are reported relative
to residual DMSO-d6 at δ = 2.54 ppm. For the NMR, samples
were prepared by dissolving approximately 10 mg of compound
in 0.5 ml of DMSO-d6. The NMR data was acquired on a Bruker
UV (CHCl3): 315, 295 (sh)nm; IR (KBr): 3442 (w), 3361 (w),3020 (s),
2973 (vw), 1731 (vs), 1683 (vs), 1631 (vs), 1603 (vs), 1574 (m), 1514
(s), 1465 (m), 1424 (m), 1360 (w), 1216 (m), 1172 (s), 1122 (vs), 1065
(m), 1028 (m), 984 (m), 828 (s), 754 (vs) cm−1
.
1
(E)-2-Acetylnaphthalen-1-yl-3-(2-(trifluoromethyl)phenyl)acrylate
(5)
900 MHz NMR spectrometer equipped with a cryoprobe. The H
NMR spectra were acquired with a sw = 10 ppm with a 90◦ pulse of
9 µs,numberofpoints=64 K,acquisitiontime=3.6 sand32scans.
The carbon spectra were acquired with a sweep width of 230 ppm.
The 90◦ pulse width was 12 µs, number of points = 128 K, acquisi-
tion time = 1.5 s, number of scans = 128. The COSY spectra were
run using similar parameters as stated for 1H NMR spectra and the
number of indirect increment in indirect dimension (td1) was set
at 256 and the size was 4 K. The TOCSY spectra had similar parame-
ters as described above with a mixing time of 80 ms. For the HSQC,
the 1H spectral parameters were used. Additionally, the sweep
width for the carbon dimension was 160 ppm, number of point =
2 K, number of scans = 4 and 128 increments, the 1JCH coupling
constant set to 145 Hz. The HMBC spectrum was also set with 1H
parameters and the carbon sweep width used was 230 ppm, num-
ber of scans = 8, multibond coupling set at 8.0 Hz. The raw data
was usually multiplied by an exponential or shifted sine squared
UV (CHCl3): 320 (sh), 286 nm; IR: (KBr): 3430, (vs) 3065 (w), 3028
(w), 2922 (vw), 1733 (vs), 1707 (vs), 1690 (vs), 1634 (m), 1594 (m),
1505 (m), 1466 (m), 1447 (m), 1428 (m), 1411 (m), 1381 (m), 1352
(w), 1312 (vs), 1273 (vs), 1235 (s), 1209 (w), 1136 (vs), 1062 (m),
1095 (s), 977 (m), 920 (vw), 865 (w), 817 (m), 764 (vs), 741 (vs)
cm−1; elemental analysis: calcd for C22H15F3O3: :68.75, H: 3.93, F:
14.83, Found: C: 68.57, H:4.01.
1-Acetylnaphthalen-2-yl-cinnamate (6)
UV (CHCl3): 333 (sh), 286 nm; IR: 3442 (vw), 3404 (vw), 3075 (s),
2924 (vw), 1732 (vs), 1637 (s), 1579 (s), 1511 (m), 1464 (m), 1433
(m), 1417 (m), 1387 (m), 1354 (s), 1306 (s), 1276 (m), 1211 (vs),
1144 (vs), 1076 (w), 1018 (m), 996 (vs), 925, (w) 866 (s), 849 (s), 826
(s), 765 (vs), 742 (vs) cm−1; elemental analysis: calcd for C21H16O3:
C: 79.73, H:5.10, found: C: 79.88, H:4.86.
1
function before performing the Fourier transform. The H signal
splittingpatternsweredesignatedasfollows:s,singlet;d,doublets;
t, triplets and m, multiplets. UV/Vis spectra were obtained from a
Lambda UV spectrometer using either methanol or chloroform as
solvent. Infrared spectra were taken as KBr disc on a Lambda FTIR
spectrometer. The infrared frequencies are designated as follows:
vw, very weak; w, weak; m, medium; s, strong and vs, very strong.
Elemental analysis was performed at the elemental analysis facility
of the School of Molecular Biosciences, University of Queensland.
(E)-1-Acetylnaphthalen-2-yl-3-(4-chlorophenyl)acrylate (7)
UV (CHCl3); 310, 281 nm; IR (KBr): 3443 (m), 3067 (w), 2919 (w),
1730 (vs), 1708 (vs), 1630 (m), 1589 (w), 1490 (w), 1403 (w), 1384
(vw), 1302 (s), 1217 (s), 1134 (s), 1117 (s), 1084 (m), 986 (s), 967 (m),
866 (w), 819 (vs), 765 (s), 743 (s) cm−1
.
(E)-1-acetylnaphthalen-2-yl-3-(4-bromophenyl)acrylate (8)
Physical constants of compounds
UV (CHCl3): 330 (sh),303; IR (KBr): 3456 (m), 3065 (w), 2919 (vw),
1732 (vs), 1708 (vs), 1637 (m), 1583 (w), 1487 (w), 1403 (m), 1352
(s), 1306 (s), 1273 (vw), 1218 (s), 1135 (s), 1119 (s), 1105 (m), 1072
(w), 1009 (w), 988 (s), 869 (m), 848(m0, 817 (vs), 768 (s), 743 (vs)
cm−1; elemental analysis: calcd for C21H15BrO3, C: 63.81, H: 3.83,
found: C: 64.15, H: 3.74
(E)-2-Acetylnaphthalen-1-yl-3-phenylacrylate (1)
UV (CHCl3): 332 (sh), 283 nm; IR(KBr): 3429 (w), 3065 (w), 3028 (w),
2922 (w), 1732 (vs), 1706 (vs), 1634 (vs), 1594 (s), 1505 (m), 1447
(m), 1428 (w), 1411 (w), 1382 (m), 1353 (w), 1303 (m), 1235 (s), 1209
c
Magn. Reson. Chem. 2010, 48, 804–810
Copyright ꢀ 2010 John Wiley & Sons, Ltd.
wileyonlinelibrary.com/journal/mrc