Y. Nie et al. / Tetrahedron 75 (2019) 130563
5
125.5, 43.8, 21.2, 19.9. HRMS (ESI): calcd. for C12H14O (M þ H)þ
d
9.78 (t, J ¼ 1.2 Hz, 1H), 7.59 (d, J ¼ 8.0 Hz, 2H), 7.37 (d, J ¼ 8.0 Hz,
2H), 6.50 (d, J ¼ 11.6 Hz, 1H), 5.72 (dt, J ¼ 11.6, 7.2 Hz, 1H), 2.70e2.54
(m, 4H). 13C NMR (101 MHz, Chloroform-d)
201.2, 140.6, 132.2,
175.1117; found 175.1120.
d
4.2.3. (Z)-5-(2-bromophenyl)pent-4-enal (2c)
129.1, 128.9, 128.9 (q, J ¼ 32.6 Hz), 125.2 (q, J ¼ 3.7 Hz), 124.2 (q,
J ¼ 272.7 Hz), 43.7, 21.2. HRMS (ESI): calcd. for C12H11F3O (M þ H)þ
229.0835; found 229.0841.
Yellow oil (80 mg, 84% yield). 1H NMR (500 MHz, Chloroform-d)
d
9.74 (s, 1H), 7.58 (d, J ¼ 8.0 Hz, 1H), 7.32e7.23 (m, 2H), 7.12 (td,
J ¼ 8.5, 2.5 Hz, 1H), 6.51 (d, J ¼ 11.5 Hz, 1H), 5.73 (dt, J ¼ 11.0, 7.5 Hz,
1H), 2.58e2.53 (m, 2H), 2.52e2.47 (m, 2H). 13C NMR (126 MHz,
4.2.11. (Z)-5-(4-methoxyphenyl)pent-4-enal (2k)
Yellow oil (53 mg, 70% yield). 1H NMR (400 MHz, Chloroform-d)
Chloroform-d)
d 201.5, 137.1, 132.7, 131.1, 130.4, 130.0, 128.6, 127.0,
43.5, 21.1. HRMS (ESI): calcd. for C11H11BrO (M þ H)þ 239.0066;
d
9.76 (s, 1H), 7.20 (d, J ¼ 8.4 Hz, 2H), 6.87 (d, J ¼ 8.4 Hz, 2H), 6.41 (d,
found 239.0072.
J ¼ 11.6 Hz, 1H), 5.50 (dt, J ¼ 11.6, 6.8 Hz, 1H), 3.80 (s, 3H), 2.71e2.61
(m, 2H), 2.56 (t, J ¼ 7.2 Hz, 2H). 13C NMR (126 MHz, Chloroform-d)
4.2.4. (Z)-5-(3-chlorophenyl)pent-4-enal (2d)
d
201.9, 129.9, 129.8, 128.5, 113.7, 55.3, 44.0, 21.3. HRMS (ESI): calcd.
Yellow oil (47 mg, 61% yield). 1H NMR (400 MHz, Chloroform-d)
for C12H14O2 (M þ H)þ 191.1067; found 191.1071.
d
9.77 (s, 1H), 7.30e7.19 (m, 3H), 7.14 (d, J ¼ 7.2 Hz, 1H), 6.41 (d,
J ¼ 11.6 Hz, 1H), 5.65 (dt, J ¼ 11.6, 6.8 Hz, 1H), 2.70e2.51 (m, 4H). 13
C
4.2.12. (Z)-5-(4-(trifluoromethoxy)phenyl)pent-4-enal (2l)
Yellow oil (79 mg, 81% yield). 1H NMR (400 MHz, Chloroform-d)
NMR (101 MHz, Chloroform-d)
d 201.4, 138.9, 134.1, 131.4, 129.5,
129.1, 128.7, 126.9, 126.8, 43.7, 21.2. HRMS (ESI): calcd. for C11H11ClO
d
9.78 (s, 1H), 7.28 (d, J ¼ 8.8 Hz, 2H), 7.18 (d, J ¼ 8.4 Hz, 2H), 6.45 (d,
(M þ H)þ 195.0571; found 195.0579.
J ¼ 11.6 Hz, 1H), 5.65 (dt, J ¼ 11.2, 7.2 Hz, 1H), 2.71e2.50 (m, 4H). 13
C
NMR (101 MHz, Chloroform-d)
d 201.4, 135.8, 131.0, 130.0, 129.0,
4.2.5. (Z)-5-(3-nitrophenyl)pent-4-enal (2e)
120.8, 120.5 (q, J ¼ 258.0 Hz), 43.7, 21.2. HRMS (ESI): calcd. for
Yellow oil (67 mg, 82% yield). 1H NMR (400 MHz, Chloroform-d)
C
12H11F3O2 (M þ H)þ 245.0784; found 245.0779.
d
9.80 (s, 1H), 8.10 (d, J ¼ 8.8 Hz, 2H), 7.60 (d, J ¼ 7.6 Hz, 1H), 7.52 (t,
J ¼ 8.0 Hz, 1H), 6.52 (d, J ¼ 11.6 Hz, 1H), 5.86e5.71 (m, 1H),
2.71e2.57 (m, 4H). 13C NMR (101 MHz, Chloroform-d)
201.0, 148.3,
4.2.13. (Z)-5-(4-bromophenyl)pent-4-enal (2m)
d
Yellow oil (87 mg, 91% yield). 1H NMR (500 MHz, Chloroform-d)
138.7, 134.6, 133.0, 129.2, 128.1, 123.4, 121.7, 43.5, 21.1. HRMS (ESI):
d
9.76 (t, J ¼ 1.5 Hz, 1H), 7.45 (d, J ¼ 8.5 Hz, 2H), 7.13 (d, J ¼ 8.5 Hz,
2H), 6.39 (dt, J ¼ 11.5, 1.5 Hz, 1H), 5.63 (dt, J ¼ 11.5, 6.5 Hz, 1H),
2.65e2.54 (m, 4H). 13C NMR (126 MHz, Chloroform-d)
201.4,131.4,
calcd. for C11H11NO3 (M þ H)þ 206.0812; found 206.0817.
d
4.2.6. (Z)-5-(m-tolyl)pent-4-enal (2f)
130.9, 130.3, 129.2, 43.7, 21.2. HRMS (ESI): calcd. for C11H11BrO
Yellow oil (54 mg, 77% yield). 1H NMR (400 MHz, Chloroform-d)
(M þ H)þ 239.0066; found 239.0072.
d
9.75 (s, 1H), 7.27e7.17 (m, 1H), 7.11e7.00 (m, 3H), 6.45 (d,
J ¼ 11.6 Hz, 1H), 5.58 (dt, J ¼ 11.6, 7.2 Hz, 1H), 2.71e2.60 (m, 2H),
4.2.14. (Z)-5-(4-chlorophenyl)pent-4-enal (2n)
2.55 (t, J ¼ 7.6 Hz, 2H), 2.35 (s, 3H). 13C NMR (126 MHz, Chloroform-
Yellow ointment (48 mg, 63% yield). 1H NMR (400 MHz, Chlo-
d)
d 201.8, 137.0, 130.5, 129.9, 129.5, 128.2, 127.6, 125.7, 43.9, 21.5,
roform-d)
J ¼ 8.4 Hz, 2H), 6.42 (dt, J ¼ 11.6, 1.6 Hz, 1H), 5.62 (dt, J ¼ 11.6, 6.8 Hz,
1H), 2.70e2.50 (m, 4H). 13C NMR (101 MHz, Chloroform-d)
201.4,
d
9.77 (t, J ¼ 1.6 Hz, 1H), 7.30 (d, J ¼ 8.0 Hz, 2H), 7.19 (d,
21.4. HRMS (ESI): calcd. for C12H14O (M þ H)þ 175.1117; found
175.1121.
d
135.5, 131.1, 130.7, 130.0, 129.2, 128.4, 43.7, 21.2. HRMS (ESI): calcd.
4.2.7. (Z)-5-(3-methoxyphenyl)pent-4-enal (2g)
for C11H11ClO (M þ H)þ 195.0571; found 195.0574.
Yellow oil (62 mg, 82% yield). 1H NMR (400 MHz, Chloroform-d)
d
9.76 (t, J ¼ 1.6 Hz, 1H), 7.29e7.21 (m, 1H), 6.86 (d, J ¼ 7.6 Hz, 1H),
6.82e6.76 (m, 2H), 6.45 (dt, J ¼ 11.6, 1.6 Hz, 1H), 5.61 (dt, J ¼ 11.6,
7.2 Hz, 1H), 3.81 (s, 3H), 2.70e2.62 (m, 2H), 2.60e2.53 (m, 2H). 13
NMR (101 MHz, Chloroform-d) 201.7, 159.5, 138.5, 130.3, 130.3,
4.2.15. (Z)-5-(4-(tert-butyl)phenyl)pent-4-enal (2o)
Yellow oil (71 mg, 82% yield). 1H NMR (400 MHz, Chloroform-d)
C
d
9.77 (t, J ¼ 1.6 Hz, 1H), 7.36 (d, J ¼ 8.4 Hz, 2H), 7.21 (d, J ¼ 8.0 Hz,
d
2H), 6.45 (dt, J ¼ 11.6, 1.6 Hz, 1H), 5.56 (dt, J ¼ 11.6, 7.2 Hz, 1H),
129.3, 121.2, 114.4, 112.3, 55.2, 43.8, 21.4. HRMS (ESI): calcd. for
C
2.73e2.62 (m, 2H), 2.61e2.52 (m, 2H), 1.32 (s, 9H). 13C NMR
12H14O2 (M þ H)þ 191.1097; found 191.1091.
(126 MHz, Chloroform-d)
d 201.9, 149.8, 134.2, 130.2, 129.4, 128.5,
125.2, 44.0, 34.6, 31.3, 21.4. HRMS (ESI): calcd. for C15H20O (M þ H)þ
4.2.8. (Z)-5-(3-hydroxyphenyl)pent-4-enal (2h)
Yellow oil (43 mg, 61% yield). 1H NMR (400 MHz, Chloroform-d)
217.1587; found 217.1585.
d
9.75 (t, J ¼ 1.6 Hz, 1H), 7.19 (t, J ¼ 8.0 Hz, 1H), 6.83e6.69 (m, 3H),
4.2.16. (Z)-5-([1,10-biphenyl]-4-yl)pent-4-enal (2p)
6.41 (dt, J ¼ 11.6, 2.0 Hz, 1H), 6.34e6.04 (br, 1H), 5.58 (dt, J ¼ 11.6,
Yellow oil (63 mg, 66% yield). 1H NMR (400 MHz, Chloroform-d)
6.8 Hz, 1H), 2.70e2.61 (m, 2H), 2.61e2.53 (m, 2H). 13C NMR
d
9.77 (s, 1H), 7.58 (t, J ¼ 8.4 Hz, 4H), 7.43 (t, J ¼ 8.0 Hz, 2H), 7.34 (d,
(101 MHz, Chloroform-d)
d 202.6, 155.8, 138.6, 130.2, 130.1, 129.5,
J ¼ 8.0 Hz, 3H), 6.50 (d, J ¼ 12.0 Hz,1H), 5.63 (dt, J ¼ 11.6, 6.8 Hz, 1H),
121.1, 115.5, 114.0, 43.8, 21.4. HRMS (ESI): calcd. for C11H12O2
2.75e2.65 (m, 2H), 2.58 (t, J ¼ 7.2 Hz, 2H). 13C NMR (101 MHz,
(M þ H)þ 177.0910; found 177.0913.
Chloroform-d)
d 201.7, 140.7, 139.7, 136.1, 130.3, 139.0, 129.2, 128.8,
127.3, 127.0, 127.0, 43.9, 21.5. HRMS (ESI): calcd. for C17H16
O
4.2.9. (Z)-5-(p-tolyl)pent-4-enal (2i)
(M þ H)þ 237.1274; found 237.1279.
Yellow oil (45 mg, 64% yield). 1H NMR (500 MHz, Chloroform-d)
d
9.76 (t, J ¼ 1.5 Hz, 1H), 7.19e7.11 (m, 4H), 6.45 (dt, J ¼ 11.5, 2.0 Hz,
1H), 5.56 (dt, J ¼ 11.5, 7.0 Hz, 1H), 2.70e2.62 (m, 2H), 2.60e2.53 (m,
2H), 2.34 (s, 3H). 13C NMR (126 MHz, Chloroform-d)
201.9, 136.6,
4.2.17. (Z)-5-mesitylpent-4-enal (2q)
d
Yellow oil (77 mg, 95% yield). 1H NMR (500 MHz, Chloroform-d)
9.64 (s, 1H), 6.85 (s, 2H), 6.32 (d, J ¼ 11.0 Hz, 1H), 5.70 (dt, J ¼ 11.0,
134.2, 130.3, 129.3, 129.0, 128.6, 43.9, 21.4, 21.2. HRMS (ESI): calcd.
d
for C12H14O (M þ H)þ 175.1117; found 175.1114.
7.5 Hz, 1H), 2.41 (td, J ¼ 7.0, 1.5 Hz, 2H), 2.27 (s, 3H), 2.18e2.12 (m,
2H), 2.15 (s, 6H). 13C NMR (126 MHz, Chloroform-d)
d 201.9, 136.2,
4.2.10. (Z)-5-(4-(trifluoromethyl)phenyl)pent-4-enal (2j)
135.8, 133.1, 130.5, 129.2, 128.0, 43.2, 21.5, 21.0, 20.3. HRMS (ESI):
Yellow oil (84 mg, 92% yield). 1H NMR (400 MHz, Chloroform-d)
calcd. for C14H18O (M þ H)þ 203.1430; found 203.1436.