Organic & Biomolecular Chemistry
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(E)-4-(m-tolyl)but-3-en-2-one (3c; 53 mg, 66%). Yellow liquid;
7.42 (m, 2H), 7.41–7.33 (m, 2H), 6.73 (d, J = 16.3 Hz, 1H), 2.40
1H NMR (400 MHz, CDCl3) δ 7.51 (d, J = 16.3 Hz, 1H), 7.37 (d, 60 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 197.9, 141.6, 136.3,
J = 7.1 Hz, 2H), 7.31 (t, J = 7.9 Hz, 1H), 7.23 (d, J = 7.4 Hz, 1H),
6.73 (d, J = 16.3 Hz, 1H), 2.40 (s, 6H). 13C NMR (101 MHz,
CDCl3) δ 198.4, 143.6, 138.6, 134.4, 131.4, 128.9 (d, J = 5.2 Hz),
127.0, 125.5, 27.5, 21.3. IR (νmax, cm-1): 2923, 1667, 1610, 1256,
135.0, 130.3 (d, J = 13.2 Hz), 128.2, 128.0, 126.4, 27.V8ie.wIRArt(icνlme aOxnline
DOI: 10.1039/C6OB01198E
cm-1): 2924, 1669, 1612, 1564, 1257, 973, 779, 681. Anal Calcd
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for C10H9ClO: C, 66.49; H, 5.02. Found: C, 66.59; H, 4.99.
(E)-4-(4-chlorophenyl)but-3-en-2-one (3k; 46 mg, 51%). Light
1
974, 777, 690. Anal Calcd for C11H12O: C, 82.46; H, 7.55. Found: 65 yellow solid; H NMR (400 MHz, CDCl3) δ 7.53-7.45 (m, 3H),
C, 82.66; H, 7.61.
7.39 (d, J = 8.5 Hz, 2H), 6.71 (d, J = 16.3 Hz, 1H), 2.40 (s, 3H).
13C NMR (101 MHz, CDCl3) δ 198.0, 141.9, 136.4, 132.9, 129.3
(d, J = 12.2 Hz), 127.5, 27.7. IR (νmax, cm-1): 2924, 1668, 1609,
1490, 1256, 1089, 975, 808. Anal Calcd for C10H9ClO: C, 66.49;
(E)-4-(p-tolyl)but-3-en-2-one (3d; 42mg, 53%). Yellow liquid;
10 1H NMR (400 MHz, CDCl3) δ 7.51 (d, J = 16.3 Hz, 1H), 7.46 (d,
J = 8.1 Hz, 2H), 7.22 (d, J = 8.0 Hz, 2H), 6.70 (d, J = 16.3 Hz,
1H), 2.40 (s, 3H), 2.39 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 70 H, 5.02. Found: C, 66.72; H, 5.13.
198.45, 143.51, 141.02, 131.68, 129.72, 128.27, 126.27, 27.43,
21.49. IR (νmax, cm-1): 2923, 1664, 1610, 1357, 1256, 1180, 975,
15 801. Anal Calcd for C11H12O: C, 82.46; H, 7.55. Found: C, 82.62;
H, 7.60.
(E)-4-(2-bromophenyl)but-3-en-2-one (3l; 94 mg, 84%).
Yellow oil; H NMR (400 MHz, CDCl3) δ 7.91 (d, J = 16.3 Hz,
1
1H), 7.64 (dt, J = 8.0, 1.6 Hz, 2H), 7.36 (t, J = 7.6 Hz, 1H), 7.26
(td, J = 7.6, 1.6 Hz, 1H), 6.64 (d, J = 16.3 Hz, 1H), 2.44 (s, 3H).
(E)-4-(4-methoxyphenyl)but-3-en-2-one (3e; 65 mg, 74%). 75 13C NMR (101 MHz, CDCl3) δ 198.3, 141.9, 134.5, 133.5, 131.4,
Yellow solid; 1H NMR (400 MHz, CDCl3) δ 7.53 – 7.47 (m, 3H),
6.96 – 6.92 (m, 2H), 6.63 (d, J = 16.2 Hz, 1H), 3.86 (s, 3H), 2.38
20 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 198.4, 161.6, 143.2,
130.0, 127.1, 125.0, 114.4, 55.4, 27.4. IR (νmax, cm-1): 2960, 1735,
129.9, 127.8 (d, J = 7.2 Hz), 125.6, 27.2. IR (νmax, cm-1): 2923,
1669, 1606, 1465, 1256, 1025, 971, 749. Anal Calcd for
C10H9BrO: C, 53.36; H, 4.03. Found: C, 53.47; H, 4.08.
(E)-4-(2-fluorophenyl)but-3-en-2-one (3m; 67 mg, 82%).
1681, 1597, 1510, 1244, 1172, 988, 817, 753. Anal Calcd for 80 Yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.69 (d, J = 16.5 Hz,
C11H12O2: C, 74.98; H, 6.86. Found: C, 75.10; H, 6.93.
1H), 7.58 (td, J = 7.6, 1.6 Hz, 1H), 7.42 – 7.36 (m, 1H), 7.23 –
7.16 (m, 1H), 7.15–7.09 (m, 1H), 6.80 (d, J = 16.5 Hz, 1H), 2.41
(s, 3H). 13C NMR (101 MHz, CDCl3) δ 198.4, 161.3 (d, J = 252.2
Hz), 135.6 (d, J = 3.5 Hz), 132.0 (d, J = 8.8 Hz), 129.2 (d, J = 5.4
(E)-4-(4-(dimethylamino)phenyl)but-3-en-2-one (3f; 67 mg,
1
25 71%). Orange solid; H NMR (400 MHz, CDCl3) δ 7.53 – 7.43
(m, 3H), 6.69 (d, J = 8.9 Hz, 2H), 6.57 (d, J = 16.1 Hz, 1H), 3.05
(s, 6H), 2.36 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 198.4, 152.0, 85 Hz), 128.7 (d, J = 2.7 Hz), 124.5 (d, J = 3.6 Hz), 116.2 (d, J =
144.3, 130.0, 122.4, 122.0, 111.9, 40.1, 27.2. IR (νmax, cm-1):
2923, 1660, 1594, 1523, 1253, 1166, 973, 810. Anal Calcd for
30 C12H15NO: C, 76.16; H, 7.99; N, 7.40. Found: C, 76.50; H, 8.16;
N, 7.18.
21.8 Hz), 27.5. 19F NMR (376 MHz, CDCl3) δ -114.8 (s). IR (νmax
cm-1): 2925, 1693, 1672, 1612, 1486, 1257, 1230, 978, 757. Anal
Calcd for C10H9FO: C, 73.16; H, 5.53. Found: C, 73.44; H, 5.67.
(E)-4-(4-bromophenyl)but-3-en-2-one (3n; 47 mg, 42%). Light
,
(E)-4-(2,4,6-trimethylphenyl)but-3-en-2-one (3g; 82 mg, 87%). 90 yellow solid; 1H NMR (400 MHz, CDCl3) δ 7.55 (dt, J = 8.8, 2.0
Yellow solid; 1H NMR (400 MHz, CDCl3) δ 7.71 (d, J = 16.6 Hz,
1H), 6.93 (s, 2H), 6.36 (d, J = 16.6 Hz, 1H), 2.41 (s, 3H), 2.36 (s,
35 6H), 2.31 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 198.5, 142.0,
138.5, 136.8, 132.4, 130.9, 129.2, 27.4, 21.1. IR (νmax, cm-1):
Hz, 2H), 7.46 (d, J = 16.4 Hz, 1H), 7.42 (dt, J = 8.8, 2.4 Hz, 2H),
6.72 (d, J = 16.3 Hz, 1H), 2.40 (s, 3H). 13C NMR (101 MHz,
CDCl3) δ 198.0, 141.9, 133.4, 132.2, 129.6, 127.6, 124.8, 27.7.
IR (νmax, cm-1): 2923, 1655, 1623, 1583, 1258, 1073, 1008, 976,
2921, 1668, 1608, 1250, 983, 853, 602. Anal Calcd for C13H16O: 95 805. Anal Calcd for C10H9BrO: C, 53.36; H, 4.03. Found: C,
C, 82.94; H, 8.57. Found: C, 83.08; H, 8.68.
53.58; H, 4.15.
(E)-4-(2-iodophenyl)but-3-en-2-one (3h; 92 mg, 68%). Yellow
40 solid; H NMR (400 MHz, CDCl3) δ 7.92 (dd, J = 8.0, 1.1 Hz,
(E)-4-(4-fluorophenyl)but-3-en-2-one (3o; 64 mg, 78%).
Yellow oil. H NMR (400 MHz, CDCl3) δ 7.58–7.54 (m, 2H),
1
1
1H), 7.75 (d, J = 16.2 Hz, 1H), 7.59 (dd, J = 7.8, 1.5 Hz, 1H),
7.50 (d, J =16.3 Hz, 1H), 7.11 (t, J = 8.6 Hz, 2H), 6.67 (d, J =
7.39 (t, J = 7.6 Hz, 1H), 7.08 (td, J = 7.7, 1.6 Hz, 1H), 6.56 (d, J 100 16.3 Hz, 1H), 2.40 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 198.1,
= 16.2 Hz, 1H), 2.45 (s, 3H). 13C NMR (101 MHz, CDCl3) δ
198.2, 146.8, 140.0, 137.7, 131.45, 130.0, 128.7 (d, J = 5.1 Hz),
45 127.4 (d, J = 7.3 Hz), 101.6, 27.2. IR (νmax, cm-1): 2923, 1693,
1671, 1606, 1460, 1358, 1256, 1012, 971, 751. Anal Calcd for
C10H9IO: C, 44.14; H, 3.33. Found: C, 44.22; H, 3.35.
163.9 (d, J = 223.0 Hz), 142.0, 130.7 (d, J = 3.4 Hz), 130.1 (d, J
= 8.5 Hz), 126.9 (d, J = 2.4 Hz), 116.2 (d, J = 22.0 Hz), 27.6. 19
F
NMR (376 MHz, CDCl3) δ -109.2 (s). IR (νmax, cm-1): 2925, 1667,
1598, 1508, 1230, 1159, 976, 816. Anal Calcd for C10H9FO: C,
105 73.16; H, 5.53. Found: C, 73.38; H, 5.68.
(E)-4-(2-chlorophenyl)but-3-en-2-one (3i; 66mg, 73%). Yellow
solid. H NMR (400 MHz, CDCl3) δ 7.95 (d, J = 16.4 Hz, 1H),
(E)-4-(2-trifluoromethylphenyl)but-3-en-2-one (3p; 65 mg,
61%). Yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.90 (d, J = 16.2
Hz, 1H), 7.74 (d, J = 7.9 Hz, 2H), 7.60 (t, J = 7.8 Hz, 1H), 7.51 (t,
J = 7.6 Hz, 1H), 6.66 (d, J = 16.2 Hz, 1H), 2.43 (s, 3H). 13C NMR
1
50 7.65 (dd, J = 7.4, 2.1 Hz, 1H), 7.45 (dd, J = 7.7, 1.5 Hz, 1H), 7.35
(dd, J = 7.4, 1.9 Hz, 1H), 7.33 – 7.30 (m, 1H), 6.68 (d, J = 16.4
Hz, 1H), 2.44 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 198.3, 110 (101 MHz, CDCl3) δ 198.1, 138.9 (d, J = 1.9 Hz), 133.4, 132.2,
139.2 (d, J = 16.2 Hz), 135.1, 132.7, 131.3, 130.2 (d, J = 9.0 Hz),
129.6, 127.6 (d, J = 14.6 Hz), 127.2 (d, J = 5.0 Hz), 27.2. IR (νmax
55 cm-1): 2925, 1693, 1672, 1609, 1471, 1359, 1258, 974, 752. Anal
Calcd for C10H9ClO: C, 66.49; H, 5.02. Found: C, 66.76; H, 5.14.
131.2, 129.7, 128.9 (q, J =30.5 Hz), 127.8, 126.2 (q, J = 5.6 Hz),
124.0 (q, J = 275.0 Hz), 27.1. 19F NMR (376 MHz, CDCl3) δ -
58.9 (s). IR (νmax, cm-1): 2925, 1677, 1617, 1311, 1160, 1108,
1036, 975, 765, 657. Anal Calcd for C11H9F3O: C, 61.68; H, 4.24.
,
(E)-4-(3-chlorophenyl)but-3-en-2-one (3j; 65 mg, 72%). 115 Found: C, 61.94; H, 4.40.
Yellow liquid. 1H NMR (400 MHz, CDCl3) δ 7.54 (s, 1H), 7.48–
(E)-4-(4-trifluoromethylphenyl)but-3-en-2-one (3q; 70 mg,
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