J.-W. Yuan et al. / Tetrahedron 72 (2016) 3084e3091
3089
JPeC¼5.2 Hz). 31P NMR (CDCl3)
d
: 15.1. 19F NMR (CDCl3)
d
: ꢁ110.2.
JHeH¼8.8 Hz, 2H), 4.79e4.71 (m, 2H), 3.75 (s, 3H), 1.36 (d,
HRMS (ESI) m/z: 407.1421 [MþH]þ (calcd for C21H25FO5Pþ
JHeH¼6.2 Hz, 6H), 1.32 (d, JHeH¼6.2 Hz, 6H). 13C NMR (CDCl3)
d:
407.1418).
165.3 (d, JPeC¼12.5 Hz), 150.5, 148.5 (d, JPeC¼6.7 Hz), 131.6, 129.5,
126.2 (d, JPeC¼1.3 Hz), 126.1, 121.6 (d, JPeC¼181.7 Hz), 121.3, 114.2,
71.6 (d, JPeC¼5.6 Hz), 55.3, 24.0 (d, JPeC¼4.0 Hz), 23.7 (d,
4.2.3. (E)-Phenyl 3-(4-chlorophenyl)-2-(diisopropoxyphosphoryl)ac-
rylate (3c). 97.1 mg (yield 92%); Brownish yellow crystal, mp
JPeC¼5.3 Hz). 31P NMR (CDCl3)
d: 12.0. HRMS (ESI) m/z: 419.1620
60e61 ꢀC. IR (KBr)
n
(cmꢁ1): 2979, 2933 (eCH3), 1745 (C]O), 1591,
[MþH]þ (calcd for C22H28O6Pþ 419.1618).
1491 (Are), 1254 (P]O), 1173 (PeO). 1H NMR (CDCl3)
d: 7.75 (d,
JPeH¼23.7 Hz, 1H), 7.49 (d, JHeH¼8.5 Hz, 2H), 7.41e7.38 (m, 4H),
4.2.8. (E)-Methyl 2-(diisopropoxyphosphoryl)-3-phenylacrylate
(3h). 71.7 mg (yield 88%); Light yellow viscous liquid. IR (KBr)
7.27e7.23 (m,1H), 7.06 (d, JHeH¼8.5 Hz, 2H), 4.85e4.77 (m, 2H),1.41
(d, JHeH¼6.2 Hz, 6H), 1.38 (d, JHeH¼6.2 Hz, 6H). 13C NMR (CDCl3)
d:
n
(cmꢁ1): 2979, 2937 (eCH3), 1728 (C]O), 1612, 1375 (Are), 1254
(P]O), 1047 (PeO). 1H NMR (CDCl3)
d: 7.61 (d, JPeH¼24.0 Hz, 1H),
164.7 (d, JPeC¼12.2 Hz), 150.3, 147.1 (d, JPeC¼6.6 Hz), 136.7, 132.1 (d,
JPeC¼19.9 Hz), 130.6, 129.6, 129.0, 126.2, 125.8 (d, JPeC¼179.9 Hz),
121.1, 72.0 (d, JPeC¼5.5 Hz), 24.0 (d, JPeC¼3.8 Hz), 23.8 (d,
7.37e7.32 (m, 5H), 4.76e4.66 (m, 2H), 3.74 (s, 3H), 1.34 (d,
JHeH¼6.2 Hz, 6H), 1.30 (d, JHeH¼6.2 Hz, 6H). 13C NMR (CDCl3)
d:
JPeC¼5.2 Hz). 31P NMR (CDCl3)
d: 10.5. HRMS (ESI) m/z: 423.1125
167.0 (d, JPeC¼12.4 Hz), 147.7 (d, JPeC¼6.4 Hz), 133.7 (d,
JPeC¼19.8 Hz), 130.3, 129.0, 128.7, 125.4 (d, JPeC¼179.4 Hz), 71.6 (d,
JPeC¼5.3 Hz), 52.3, 24.0 (d, JPeC¼3.7 Hz), 23.6 (d, JPeC¼6.4 Hz). 31P
[MþH]þ (calcd for C21H25ClO5Pþ 423.1123).
NMR (CDCl3)
d
: 11.3. HRMS (ESI) m/z: 327.1358 [MþH]þ (calcd for
4.2.4.(E)-Phenyl 2-(diisopropoxyphosphoryl)-3-(4-nitrophenyl)acry-
late (3d). 92.0 mg (yield 85%); Reddish-brown viscous liquid. IR
C16H24O5Pþ 327.1356).
(KBr)
n
(cmꢁ1): 2981, 2930 (eCH3), 1747 (C]O), 1591, 1523 (Are),
1255 (P]O), 1176 (PeO). 1H NMR (CDCl3)
d: 8.27 (d, JPeH¼8.7 Hz,
4.2.9. (E)-Diethyl (3-oxo-1-phenylbut-1-en-2-yl)phosphonate (3i).
36.7 mg (yield 52%); Brownish yellow viscous liquid. IR (KBr)
2H), 7.85 (d, JHeH¼23.5 Hz, 1H), 7.69 (d, JHeH¼8.7 Hz, 2H), 7.40 (d,
JHeH¼7.7 Hz, 2H), 7.27 (d, JHeH¼9.2 Hz, 1H), 7.02 (d, JHeH¼7.6 Hz,
1H), 4.88e4.80 (m, 2H), 1.43 (d, JHeH¼6.2 Hz, 6H), 1.40 (d,
n
(cmꢁ1): 2985, 2908 (eCH3, eCH2), 1701 (C]O), 1606, 1448 (Are),
1252 (P]O), 1051 (PeO). 1H NMR (CDCl3)
d: 7.57 (d, JPeH¼25.6 Hz,
JHeH¼6.2 Hz, 6H). 13C NMR (CDCl3)
: 164.0 (d, JPeC¼11.7 Hz), 150.1,
d
1H), 7.41e7.30 (m, 5H), 4.23e4.16 (m, 4H), 2.27 (s, 3H), 1.37 (t,
148.5, 145.7 (d, JPeC¼6.6 Hz), 140.0 (d, JPeC¼19.8 Hz), 129.8 (d,
JPeC¼1.5 Hz), 129.7 (d, JPeC¼178.6 Hz), 129.7, 126.5, 123.9, 120.9,
JHeH¼7.0 Hz, 6H). 13C NMR (CDCl3)
: 203.2 (d, JPeC¼8.5 Hz),145.0 (d,
d
72.4 (d, JPeC¼5.8 Hz), 24.1 (d, JPeC¼4.1 Hz), 23.8 (d, JPeC¼5.1 Hz). 31
P
JPeC¼5.8 Hz), 133.9 (d, JPeC¼169.7 Hz), 133.6 (d, JPeC¼21.3 Hz), 130.3,
129.2 (d, JPeC¼1.0 Hz), 128.9, 62.7 (d, JPeC¼5.7 Hz), 31.1 (d,
NMR (CDCl3)
d
: 9.1. HRMS (ESI) m/z: 434.1365 [MþH]þ (calcd for
JPeC¼2.0 Hz), 16.2 (d, JPeC¼6.5 Hz). 31P NMR (CDCl3)
d: 13.9. HRMS
C
21H25NO7Pþ 434.1363).
(ESI) m/z: 283.1095 [MþH]þ (calcd for C14H20O4Pþ 283.1094).
4.2.5. (E)-Phenyl 2-(diisopropoxyphosphoryl)-3-(p-tolyl)acrylate(3e).
72.4 mg (yield 72%); Brown yellow viscous liquid. IR (KBr)
(cmꢁ1):
2979, 2935 (eCH3), 1747 (C]O), 1589, 1489 (Are), 1255 (P]O), 1176
(PeO). 1H NMR (CDCl3)
n
4.2.10. (E)-Diisopropyl (1-nitro-2-phenylvinyl)phosphonate (3j).
42.2 mg (yield 63%); Light yellow viscous liquid. IR (KBr)
2978, 2933 (eCH3), 1614, 1450 (Are), 1246 (P]O), 1105 (PeO). 1H
NMR (CDCl3) : 7.53e7.43 (m, 3H), 7.39e7.36 (m, 3H), 6.27 (t,
n
(cmꢁ1):
d
: 8.05 (d, JPeH¼22.8 Hz, 1H), 7.40 (d,
JHeH¼7.5 Hz, 1H), 7.30 (t, JHeH¼7.7 Hz, 3H), 7.23e7.20 (m, 2H), 7.17 (t,
JHeH¼7.5 Hz, 1H), 6.86 (d, JHeH¼8.6 Hz, 2H), 4.88e4.80 (m, 2H), 2.40
d
JHeH¼17.4 Hz,1H), 4.77e4.66 (m, 2H), 1.37 (d, JHeH¼6.2 Hz, 6H), 1.30
(s, 3H), 1.41 (t, JHeH¼6.4 Hz, 12H). 13C NMR (CDCl3)
d: 164.6 (d,
(d, JHeH¼6.2 Hz, 6H). 13C NMR (CDCl3)
: 147.7 (d, JPeC¼6.8 Hz),
d
JPeC¼13.8 Hz), 150.3, 149.0 (d, JPeC¼6.3 Hz), 137.0, 133.9 (d,
JPeC¼18.5 Hz), 130.2 (d, JPeC¼39.7 Hz),127.9 (d, JPeC¼1.9 Hz),127.1 (d,
JPeC¼180.6 Hz), 126.0 (d, JPeC¼8.3 Hz), 121.2, 71.8 (d, JPeC¼5.6 Hz),
135.0 (d, JPeC¼23.2 Hz), 130.0, 128.8, 127.6, 115.6 (d, JPeC¼190.9 Hz),
70.4 (d, JPeC¼5.6 Hz), 24.1 (d, JPeC¼4.2 Hz), 24.0 (d, JPeC¼4.5 Hz). 31
P
NMR (CDCl3)
d
: 17.5. HRMS (ESI) m/z: 269.1303 [MþH]þ (calcd for
24.0 (d, JPeC¼3.9 Hz), 23.8 (d, JPeC¼5.0 Hz), 19.9. 31P NMR (CDCl3)
d:
C
14H22O3Pþ 269.1301).
10.2. HRMS (ESI) m/z: 403.1670 [MþH]þ (calcd for C22H28O5Pþ
403.1669).
4.2.11. (E)-Phenyl 2-(dimethoxyphosphoryl)-3-phenylacrylate
(3l). 43.2 mg (yield 52%); Light yellow viscous liquid. IR (KBr)
4.2.6. (E)-Phenyl 2-(diisopropoxyphosphoryl)-3-(3-methoxyphenyl)
acrylate (3f). 78.4 mg (yield 75%); Brown yellow viscous liquid. IR
n
(cmꢁ1): 2954, 2918, 2850 (eCH3), 1743 (C]O), 1591, 1491, 1456
(Are), 1259 (P]O), 1178 (PeO). 1H NMR (CDCl3)
d: 7.82 (d,
(KBr)
n
(cmꢁ1): 2979, 2935 (eCH3), 1745 (C]O), 1589, 1489 (Are),
JPeH¼24.0 Hz, 1H), 7.56 (dd, JHeH¼6.6 Hz, JHeH¼1.8 Hz, 2H),
1255 (P]O), 1176 (PeO). 1H NMR (CDCl3)
d
: 7.77 (d, JPeH¼23.7 Hz,
7.44e7.36 (m, 5H), 7.23 (d, JHeH¼7.5 Hz, 1H), 7.06 (t, JHeH¼1.0 Hz,
1H), 7.37 (t, JHeH¼7.9 Hz, 2H), 7.33 (t, JHeH¼7.8 Hz, 1H), 7.23 (t,
JHeH¼7.4 Hz, 1H), 7.13 (d, JHeH¼7.6 Hz, 1H), 7.05 (d, JHeH¼8.3 Hz,
3H), 6.96 (dd, JHeH¼8.3 Hz, JHeH¼1.6 Hz, 1H), 4.85e4.77 (m, 2H),
3.77 (s, 3H), 1.41 (d, JHeH¼6.2 Hz, 6H), 1.38 (d, JHeH¼6.2 Hz, 6H).
2H), 3.88 (d, JPeH¼4.6 Hz, 6H). 13C NMR (CDCl3)
d: 164.8 (d,
JPeC¼13.1 Hz, C]O), 150.3, 150.1 (d, JPeC¼6.0 Hz), 133.4 (d,
JPeC¼19.8 Hz), 130.9, 129.5, 129.4, 129.4, 128.8, 126.3, 122.6 (d,
JPeC¼180.2 Hz), 53.3 (d, JPeC¼5.2 Hz). 31P NMR (CDCl3)
d: 16.4.
13C NMR (CDCl3)
d: 165.0 (d, JPeC¼12.6 Hz), 159.7, 150.4, 148.2 (d,
HRMS (ESI) m/z: 333.0888 [MþH]þ (cald for C17H18O5Pþ
JPeC¼6.4 Hz), 135.0 (d, JPeC¼19.8 Hz), 129.8, 129.5, 126.2, 125.6 (d,
333.0886).
JPeC¼179.6 Hz), 121.6, 121.2, 116.5, 114.3, 71.9 (d, JPeC¼5.4 Hz), 55.3,
24.1 (d, JPeC¼3.9 Hz), 23.8 (d, JPeC¼5.2 Hz). 31P NMR (CDCl3)
d:
10.8. HRMS (ESI) m/z: 419.1622 [MþH]þ (calcd for C22H28O6Pþ
4.2.12. (E)-Phenyl 2-(diethoxyphosphoryl)-3-phenylacrylate
419.1618).
(3m). 56.7 mg (yield 63%); Light yellow viscous liquid. IR (KBr)
n
(cmꢁ1): 2952, 2924, 2850 (eCH3, eCH2), 1743 (C]O), 1483, 1458
4.2.7. (E)-Phenyl 2-(diisopropoxyphosphoryl)-3-(4-methoxyphenyl)
(Are), 1255 (P]O), 1176 (PeO). 1H NMR (CDCl3)
d: 7.81 (d,
acrylate (3g). 85.7 mg (yield 82%); Light yellow crystal, mp
JPeH¼23.8 Hz, 1H), 7.56 (dd, JHeH¼5.7 Hz, JHeH¼1.9 Hz, 2H),
100e101 ꢀC. IR (KBr)
n
(cmꢁ1): 2978, 2936 (eCH3), 1741 (C]O),
7.44e7.37 (m, 5H), 7.26 (d, JHeH¼6.8 Hz, 1H), 7.05 (dd, JHeH¼8.7 Hz,
1601, 1512 (Are), 1267 (P]O), 1171 (PeO). 1H NMR (CDCl3)
d
: 7.69
JHeH¼1.2 Hz, 2H), 4.29e4.21 (m, 4H), 1.40 (t, JPeH¼7.1 Hz, 6H). 13
C
(d, JPeH¼24.0 Hz,1H), 7.50 (d, JHeH¼8.8 Hz, 2H), 7.34 (t, JHeH¼7.8 Hz,
NMR (CDCl3)
d
: 164.9 (d, JPeC¼12.4 Hz, C]O), 150.3, 149.3 (d,
2H), 7.18 (t, JHeH¼7.4 Hz, 1H), 7.07 (t, JHeH¼7.7 Hz, 2H), 6.86 (d,
JPeC¼6.4 Hz), 133.5 (d, JPeC¼19.6 Hz), 130.7, 129.5, 129.4, 128.8,