T. Zhang et al. / Tetrahedron 64 (2008) 2412e2418
2417
1
4i . H
3b
1
(
m, 2H, CH ), 4.70 (t, J¼6.3 Hz, 1H, CH), 5.13e5.19 (m, 2H,
4.4.2.9.
(300 MHz, CDCl , TMS) d 2.10 (br, 1H, OH), 2.36e2.43
1-Phenyl-1,5-hexadien-3-ol
NMR
2
vinyls), 5.73e5.82 (m, 1H, vinyl), 7.23 (d, 2H, J¼8.4 Hz,
3
1
3
ArH), 7.47 (d, 2H, J¼8.4 Hz, ArH); C NMR (75 MHz,
(m, 2H, CH ), 4.33 (dd, 1H, J¼6.6 Hz, CH), 5.12e5.20 (m,
2
CDCl , TMS) d 43.8, 72.5, 118.9, 121.2, 127.5, 131.4,
3
2H, vinyls), 5.77e5.89 (m, 1H, vinyl), 6.22 (dd, 1H,
J ¼16.2 Hz, J ¼6.6 Hz, vinyl), 6.58 (d, 1H, J¼16.2 Hz, vi-
1
33.9, 142.7.
1
2
1
nyl), 7.20e7.38 (m, 5H, ArH); C NMR (75 MHz, CDCl ,
3
3
1
3a 1
4
CDCl , TMS) d 2.01 (br, 1H, OH), 2.48e2.54 (m, 2H,
.4.2.2. 1-Phenyl-3-buten-1-ol 4b . H NMR (300 MHz,
TMS) d 41.9, 71.6, 118.3, 126.4, 127.6, 128.5, 130.2, 131.5,
134.0, 136.6.
3
CH ), 4.73 (t, 1H, J¼6.9 Hz, CH), 5.12e5.20 (m, 2H, vinyls),
2
1
3b 1
5
.76e5.82 (m, 1H, vinyl), 7.26e7.36 (m, 5H, ArH).
4.4.2.10. 1-(p-Chlorophenyl)-3-buten-1-ol 4j . H NMR
300 MHz, CDCl , TMS) d 2.37e2.47 (m, 3H), 4.66 (t, 1H,
(
3
1
3b
1
4
(
(
.4.2.3. 1-(p-Nitrophenyl)-3-buten-1-ol 4c . H NMR
300 MHz, CDCl , TMS) d 2.36 (br, 1H, OH), 2.40e2.61
J¼6.9 Hz, CH), 5.10e5.16 (m, 2H, vinyls), 5.68e5.82 (m, 1H,
13
vinyl), 7.23e7.31 (m, 4H, ArH); C NMR (75 MHz, CDCl ,
3
3
m, 2H, CH ), 4.85e4.89 (m, 1H, CH), 5.16e5.22 (m, 2H, vi-
2
TMS) d 43.7, 72.5, 118.6, 127.1, 128.4, 133.0, 133.9, 142.2.
nyls), 5.72e5.86 (m, 1H, vinyl), 7.52e7.55 (m, 2H, ArH),
1
.18e8.23 (m, 2H, ArH); C NMR (75 MHz, CDCl , TMS)
3
13a
1
8
d 43.9, 72.1, 119.6, 123.59, 123.61, 126.5, 133.2, 151.1.
4.4.2.11. 2-(1-Hydroxy-but-3-enyl)-phenol 4k . H NMR
(300 MHz, CDCl , TMS) d 2.56e2.66 (m, 2H, CH ), 2.85
3
3
2
(
br, 1H, OH), 4.85e4.90 (m, 1H, CH), 5.20e5.25 (m, 2H, vi-
1
3b
1
4
(
.4.2.4. 1-(p-Methylphenyl)-3-buten-1-ol 4d . H NMR
300 MHz, CDCl , TMS) d 2.33 (s, 3H, CH ), 2.37 (br, 1H,
nyls), 5.78e6.00 (m, 1H, vinyl), 6.81e6.89 (m, 2H, ArH),
6.97 (d, 1H, J¼10.8 Hz, ArH), 7.22 (t, 1H, J¼17.1 Hz,
ArH), 8.04 (br, 1H, OH).
3
3
OH), 2.46 (t, 2H, J¼6.6 Hz, CH ), 4.63 (t, 1H, J¼6.6 Hz,
2
CH), 5.01e5.15 (m, 2H, vinyls), 5.73e5.82 (m, 1H, vinyl),
1
.05e7.24 (m, 4H, ArH); C NMR (75 MHz, CDCl , TMS)
3
13d
1
7
d 21.3, 43.6, 73.2, 118.0, 122.8, 126.4, 128.1, 128.2, 134.5,
4.4.2.12. Phenyl-(1-phenyl-3-butenyl)-amine . H NMR
(300 MHz, CDCl , TMS) d 2.45e2.62 (m, 2H, CH ), 4.14
3
3
2
1
37.9, 143.8.
(br, 1H, NH), 4.35e4.39 (m, 1H, CH), 5.11e5.20 (m, 2H, vi-
nyls), 5.70e5.80 (m, 1H, vinyl), 6.48 (d, 2H, J¼8.4 Hz, ArH),
6.63 (t, 1H, J¼7.2 Hz, ArH), 7.06 (t, 2H, J¼10.5 Hz, ArH),
1
3b
1
4
(
.4.2.5. 1-(o-Nitrophenyl)-3-buten-1-ol 4e . H NMR
300 MHz, CDCl , TMS) d 2.45e2.58 (m, 2H, CH), 2.89 (s,
1
3
7.22 (t, 1H, J¼7.2 Hz, ArH), 7.28e7.36 (m, 4H, ArH);
C
3
1
5
H, OH), 4.83e4.87 (m, 1H, CH), 5.13e5.19 (m, 2H, vinyls),
.72e5.83 (m, 1H, vinyl), 7.51 (t, 1H, J¼7.8 Hz, ArH), 7.69
NMR (75 MHz, CDCl , TMS) d 43.3, 57.1, 113.4, 117.3,
3
118.3, 126.2, 126.9, 128.5, 129.0, 134.6, 143.5, 147.3.
(
(
d, 1H, J¼7.8 Hz, ArH), 8.09 (d, 1H, J¼7.8 Hz, ArH), 2.89
3
1
s, 1H, ArH); C NMR (75 MHz, CDCl , TMS) d 43.7,
3
13e
1
4.4.2.13. 2-Hydroxy-pent-4-enoic acid ethyl ester . H NMR
(300 MHz, CDCl , TMS) d 1.30 (t, 3H, J¼6.6 Hz, CH ),
7
2.0, 119.3, 120.7, 122.3, 129.2, 132.0, 133.2, 145.9, 148.1.
3
3
2.42e2.49 (m, 1H, CH ), 2.54e2.61 (m, 1H, CH ), 2.88 (d,
2 2
13c 1
4
(
.4.2.6. 1-(m-Nitrophenyl)-3-buten-1-ol 4f . H
NMR
300 MHz, CDCl , TMS) d 2.43e2.59 (m, 2H, CH ), 2.89 (s,
1H, J¼6.0 Hz, OH), 4.21e4.29 (m, 3H), 5.13 (s, 1H, vinyl),
5.17 (d, 1H, J¼8.1 Hz, vinyl), 5.77e5.86 (m, 1H, vinyl);
3
2
1
3
1
5
1
H, OH), 4.85 (t, 1H, J¼6.0 Hz, CH), 5.12e5.18 (m, 2H, vinyls),
.71e5.85 (m, 1H, vinyl), 7.51 (t, 1H, J¼8.1 Hz, ArH), 7.69 (d,
H, J¼7.5 Hz, ArH), 8.08e8.11 (m, 1H, ArH), 8.21 (t, 1H,
C NMR (75 MHz, CDCl , TMS) d 14.2, 38.6, 61.7, 69.9,
3
118.7, 132.5, 174.4.
1
3
J¼2.1 Hz, ArH); C NMR (75 MHz, CDCl , TMS) d 43.6,
3
72.0, 119.2, 120.7, 122.2, 129.2, 131.9, 133.2, 145.9, 148.1.
Acknowledgements
1
3a
1
4
.4.2.7. 1-(p-Methoxyphenyl)-3-buten-1-ol 4g . H NMR
Financial support from the Shanghai Municipal Committee
of Science and Technology (04JC14083, 06XD14005), Chi-
nese Academy of Sciences (KGCX2-210-01), and the National
Natural Science Foundation of China (20472096, 20272069,
(
300 MHz, CDCl , TMS) d 2.32 (br, 1H, OH), 2.48 (t, 2H,
3
J¼6.6 Hz, CH ), 3.78 (s, 3H, CH ), 4.65 (t, 1H, J¼6.6 Hz,
2
3
CH), 5.08e5.19 (m, 2H, vinyls), 5.73e5.79 (m, 1H, vinyl),
6
.86 (d, 2H, J¼8.4 Hz, ArH), 7.25 (d, 2H, J¼8.4 Hz, ArH);
20772030, and 20732008) are greatly acknowledged. Mr. Jie
1
3
C NMR (75 MHz, CDCl , TMS) d 43.6, 55.1, 72.9, 113.7,
3
Sun and Huping Zhu are acknowledged for X-ray analysis.
Dr. Lixiong Shao is also acknowledged for discussion.
1
18.0, 127.0, 134.6, 136.0, 158.9.
1
3a
1
4
.4.2.8. 1-Pheny-5-hexen-3-ol 4h . H NMR (300 MHz,
CDCl , TMS) d 1.65 (d, 1H, J¼3.9 Hz, OH), 1.76e1.83 (m,
3
2
H, CH ), 2.16e2.36 (m, 2H, CH ), 2.67e2.84 (m, 2H,
2
Supplementary data
2
CH ), 3.68 (m, 1H, CH), 5.14 (d, 2H, J¼12.9 Hz, vinyls),
2
1
3
5.78e5.84 (m, 1H, vinyl), 7.16e7.32 (m, 5H, ArH);
NMR (75 MHz, CDCl , TMS) d 32.0, 38.4, 42.0, 69.9,
C
Supplementary data and representative spectra associated
3
1
18.3, 125.8, 128.37, 128.41, 134.6, 142.0.