1
H NMR (CDCl ): δ = 7.91 (d, J = 7.0 Hz, 2H), 7.50 (dd, J = 7.0, 7.0 Hz, 1H), 7.42 (dd, J = 7.0 Hz, 2H),
3
1
3
6
1
2
.59 (s, 1H), 3.80-3.71 (m, 1H), 1.90 (s, 3H), 1.06 (d, J = 6.7 Hz, 6H); C NMR (CDCl
3
): δ = 191.5, 164.8,
-
1
39.3, 132.3, 128.4, 128.3, 120.9, 30.1, 20.7, 19.7; IR (neat): 2924, 1660, 1609, 1239 cm ; MS (ESI): m/z
+
+
11 [M+Na] ; HRMS (ESI): m/z calcd for C13H16ONa [M+Na] 211.1099. Found 211.0954.
(E)-4-Methyl-3-octen-2-one ((E)-7b)
1
3
H NMR (CDCl ): δ = 6.02 (s, 1H), 2.13 (s, 3H), 2.09-2.05 (m, 5H), 1.45-1.37 (m, 2H), 1.32-1.23 (m, 2H),
13
0
.87 (t, J = 7.3 Hz, 3H); C NMR (CDCl
3
): δ = 198.8, 158.9, 123.4, 40.9, 31.7, 29.6, 22.3, 19.2, 13.8; IR
-
1
+
(
neat): 3412, 2932, 1688, 1617 cm ; MS (ESI): m/z 163 [M+Na] ; HRMS (ESI): m/z calcd for C
9
H16ONa
+
[
M+Na] 163.1099. Found 163.1095.
(Z)-4-Methyl-3-octen-2-one ((Z)-7b)
1
H NMR (CDCl ): δ = 6.01 (s, 1H), 2.53 (t, J = 7.6 Hz, 2H ), 2.11 (s, 3H), 1.82 (d, J = 1.6 Hz, 3H), 1.42-1.27
3
13
(
m, 4H), 0.87 (t, J = 7.3 Hz, 3H); C NMR (CDCl
3
): δ = 198.2, 159.6, 123.9, 33.3, 31.7, 30.3, 25.3, 22.8,
-
1
+
1
3.9; IR (neat): 3413, 2959, 1688, 1616 cm ; MS (ESI): m/z 163 [M+Na] ; HRMS (ESI): m/z calcd for
+
C
9
H
16ONa [M+Na] 163.1099. Found 163.1096.
(E)-4,5-Dimethyl-3-hexen-2-one ((E)-7c)
1
3
H NMR (CDCl ): δ = 6.04 (s, 1H), 2.34-2.25 (m, 1H), 2.15 (s, 3H), 2.06 (s, 3H), 1.03 (d, J = 7.0 Hz, 6H);
13
-1
C NMR (CDCl
3
): δ = 199.3, 164.0, 121.4, 38.2, 31.8, 20.9, 16.8; IR (neat): 3413, 2965, 1686, 1616 cm ;
+
+
MS (ESI): m/z 149 [M+Na] ; HRMS (ESI): m/z calcd for C H14ONa [M+Na] 149.0942. Found 149.0944.
8
(Z)-4,5-Dimethyl-3-hexen-2-one ((Z)-7c)
1
3
H NMR (CDCl ): δ = 5.95 (s, 1H), 3.92-3.82 (m, 1H), 2.11 (s, 3H), 1.75 (s, 3H), 0.97 (d, J = 7.0 Hz, 6H);
13
-1
C NMR (CDCl
3
): δ = 198.3, 164.2, 123.5, 31.9, 29.1, 20.9, 19.3; IR (neat): 3412, 2966, 1688, 1612 cm ;
+
+
MS (ESI): m/z 149 [M+Na] ; HRMS (ESI): m/z calcd for C H14ONa [M+Na] 149.0942. Found 149.0945.
8
(E)- 5-Methyl-1-phenyl-4-nonen-3-one ((E)-7d)
1
H NMR (CDCl
7.6 Hz, 2H), 2.13-2.08 (m, 5H), 1.46-1.38 (m, 2H), 1.33-1.26 (m, 2H), 0.89 (t, J = 7.3 Hz, 3H); C NMR
CDCl ): δ = 199.9, 159.2, 141.4, 128.3, 128.3, 125.9, 122.8, 45.8, 40.9, 30.1, 29.6, 22.3, 19.3, 13.8; IR
3
): δ = 7.27-7.23 (m, 2H), 7.19-7.14 (m, 3H), 6.02 (s, 1H), 2.90 (t, J = 7.6 Hz, 2H), 2.73 (t, J
13
=
(
(
[
3
-1
+
neat): 2930, 1686, 1617 cm ; MS (ESI): m/z 253 [M+Na] ; HRMS (ESI): m/z calcd for C16H22ONa
+
M+Na] 253.1568. Found 253.1555.
(Z)- 5-Methyl-1-phenyl-4-nonen-3-one ((Z)-7d)
1
H NMR (CDCl
7.7 Hz, 2H), 2.57 (t, J = 7.7 Hz, 2H), 1.85 (s, 3H), 1.44-1.30 (m, 4H), 0.90 (t, J = 7.2 Hz, 3H); C NMR
CDCl ): δ = 199.3, 159.9, 141.4, 128.3, 128.2, 125.8, 123.4, 45.8, 33.5, 30.3, 30.0, 25.4, 22.9, 13.9; IR
3
): δ = 7.27-7.23 (m, 2H), 7.19-7.14 (m, 3H), 6.01 (s, 1H), 2.89 (t, J = 7.7 Hz, 2H), 2.71 (t, J
13
=
(
(
[
3
-1
+
neat): 2929, 1686, 1616 cm ; MS (ESI): m/z 253 [M+Na] ; HRMS (ESI): m/z calcd for C16H22ONa
+
M+Na] 253.1568. Found 253.1555.
(E)-4-Phenyl-3-hexen-2-one ((E)-7h)
1
H NMR (CDCl ): δ = 7.46-7.41 (m, 2H), 7.39-7.33 (m, 3H), 6.36 (s, 1H), 3.03 (q, J = 7.6 Hz, 2H), 2.26 (s,
3
1
3
3
2
H), 1.04 (t, J = 7.6 Hz, 3H); C NMR (CDCl
3
): δ = 198.4, 160.4, 141.3, 128.9, 128.5, 126.8, 124.1, 32.2,
-
1
+
4.4, 13.5; IR (neat): 2968, 1682, 1597 cm ; MS (ESI): m/z 197 [M+Na] ; HRMS (ESI): m/z calcd for
+
C
12
H
14ONa [M+Na] 197.0942. Found 197.0936.
(Z)-4-Phenyl-3-hexen-2-one ((Z)-7h)
S-12