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894
M. BELLASSOUED ET AL.
Hz), 6.71–7.55 (m, 4H, Ar). 13C NMR (250 MHz, CDCl3) δ = 25.3, 56.0, 114.0, 127.2,
− −1
1
1
29.1, 132.3, 142.3, 160.3, 193.2. IR (neat): 1679 cm (C O), 1618 cm (C C). Anal.
Calc for C11H12O2: C, 75.00; H, 6.81. Found: C, 75.18; H, 6.48.
1
(
E)-4-(Pyridin-3-yl) but-3-en-2-one (4g). H NMR (250 MHz, CDCl3) δ = 2.39
(
s, 3H, CH3), 5.58 (d, 1H, J = 16.24 Hz), 6.01 (d, 1H, J = 16.24 Hz), 6.8–7.75 (m, 4H, Ar).
1
3
−1
C NMR (250 MHz, CDCl3) δ = 29.4, 127.5, 129.9, 143.8, 196.8. IR (neat): 1668 cm
−1
(
C O), 1614 cm (C C). Anal. Calc for C9H9NO: C, 73.47; H, 6.12. Found: C, 73.97;
H, 6.22.
1
(
Z)-4-(Pyridin-3-yl) but-3-en-2-one (4g). H NMR (250 MHz, CDCl3) δ = 2.24
(
s, 3H, CH3), 5.47 (d, 1H, J = 12.3 Hz), 6.02 (d, 1H, J = 12.3 Hz), 7.07–8.10 (m, 4H, Ar).
1
3
−1
C NMR (250 MHz, CDCl3) δ = 31.2, 126.9, 130.1, 144.2, 198.1. IR (neat): 1674 cm
−1
(
C O), 1621 cm (C C). Anal. Calc for C9H9NO: C, 73.47; H, 6.12. Found: C, 73.26;
H, 6.15.
1
(
E)-4-(Furan-2-yl) but-3-en-2-one (4h). H NMR (250 MHz, CDCl3) δ = 2.26
(
s, 3H, CH3), 6.42 (d, 1H, J = 15.9 Hz), 7.33 (d, 1H, J = 15.9 Hz), 6.2–7.4 (m, 3H, Ar).
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3
C NMR (250 MHz, CDCl3) δ = 28.2, 112.9, 113.0, 124.6, 129.8, 143.2, 145.4, 198.2. IR
− −1
1
(
neat): 1690 cm (C O), 1610 cm (C C). Anal. Calc for C8H8O2: C, 70.59; H, 5.88.
Found: C, 70.18; H, 5.68.
1
(
Z)-4-(Furan-2-yl) but-3-en-2-one (4h). H NMR (250 MHz, CDCl3) δ = 2.15
(
s, 3H, CH3), 6.01 (d, 1H, J = 12.7 Hz), 6.85 (d, 1H, J = 12.7 Hz), 7.05–7.40 (m, 3H, Ar).
1
3
C NMR (250 MHz, CDCl3) δ = 31.6, 110.6, 114.1, 123.5, 129.6, 144.9, 151.2, 198.2. IR
−1 −1
(
neat): 1681 cm (C O), 1619 cm (C C). Anal. Calc for C8H8O2: C, 70.59; H, 5.88.
Found: C, 70.71; H, 5.67.
E)-4-(Thiophen-2-yl) but-3-en-2-one (4i). H NMR (250 MHz, CDCl3) δ =
.29 (s, 3H, CH3), 6.47 (d, 1H, J = 15.9 Hz), 6.5–7.5 (m, 3H, Ar), 7.61 (d, 1H, J = 15.9
1
(
2
13
Hz). C NMR (250 MHz, CDCl3) δ = 29.1, 127.0, 129.9, 130.1, 132.8, 134.8, 137.7,
−1
−1
1
95.8. IR (neat): 1664 cm (C O), 1595 cm (C C). Anal. Calc for C8H8SO: C, 63.16;
H, 5.26. Found: C, 63.25; H, 5.15.
1
(
Z)-4-(Thiophen-2-yl) but-3-en-2-one (4i). H NMR (250 MHz, CDCl3) δ =
2
3
1
.16 (s, 3H, CH3), 6.07 (d, 1H, J = 12.2 Hz), 6.60 (d, 1H, J = 12.2 Hz), 6.90–7.45 (m,
13
H, Ar). C NMR (250 MHz, CDCl3) δ = 23.6, 126.9, 129.6, 129.9, 130.1, 133.8, 138.2,
−1
−1
85.7. IR (neat): 1670 cm (C O), 1610 cm (C C). Anal. Calc for C8H8SO: C, 63.16;
H, 5.26. Found: C, 63.55; H, 5.33.
1
(
3E, 5E)-6-Phenylhexa-3, 5-dien-2-one (4j). H NMR (250 MHz, CDCl3) δ =
2
1
.26 (s, 3H, CH3), 6.01 (d, 1H, J = 15.3 Hz), 6.28 (dd, 1H, J = 15.3, 10.2 Hz), 6.31 (d,
13
H, J = 15.3 Hz), 6.42 (dd, 1H, J = 15.3, 10.2 Hz), 7.25–7.48 (m, 5H, Ar). C NMR (250
MHz, CDCl3) δ = 31.2, 130.1, 132.4, 134.3, 137.8, 139.5, 139.7, 143.2, 194.3. IR (neat):
−1
−1
1
674 cm (C O), 1612 cm (C C). Anal. Calc for C12H12O: C, 83.72; H, 6.97. Found:
C, 83.31; H, 6.78.
1
(
3Z, 5E)-6-Phenylhexa-3,5-dien-2-one (4j). H NMR (250 MHz, CDCl3) δ =
2
1
.21 (s, 3H, CH3), 6.11 (d, 1H, J = 11.6 Hz), 6.15 (dd, 1H, J = 11.6, 7.2 Hz), 6.40 (d,
13
H, J = 15.8 Hz), 6.42 (dd, 1H J = 15.8, 7.2 Hz), 7.01–7.41 (m, 5H, Ar). C NMR (250
MHz, CDCl3) δ = 28.1, 128.9, 130.8, 132.5, 136.1, 138.7, 139.1, 144.9, 190.1. IR (neat):
−1
−1
1
670 cm (C O), 1619 cm (C C). Anal. Calc for C12H12O: C, 83.72; H, 6.97. Found:
C, 83.47; H, 6.67.
E)-Hex-3-en-2-one (4k). H NMR (250 MHz, CDCl3) δ = 0.89 (t, 3H, CH3),
.97 (m, 2H, CH2), 2.35 (s, 3H, COCH3), 5.97 (d, 1H, J = 16.16 Hz), 6.63 (dt, 1H,
1
(
1