1214
C. LI ET AL.
3-(4-Fluorophenyl)-1-phenylprop-2-yn-1-ol[17]
1
Colorless oil. H NMR (400 MHz, CDCl3): d ¼ 2.42 (s,1H), d ¼ 5.67 (s, 1H),
d ¼ 6.98–7.02 (m, 2H), d ¼ 7.326–7.068 (m, 5H), d ¼ 7.59–7.61 (d, J ¼ 7.2, 2H). 13C
NMR (100 MHz, CDCl3): d ¼ 65.1, 85.6, 88.4, 115.5, 115.7, 118.4, 118.5, 126.7,
128.5, 128.7, 133.6, 133.7, 140.6, 161.4, 163.9. MS (FAB): m=z (%) ¼ 226 [Mþ]. Anal.
calcd. for C15H11FO: C, 79.63; H, 4.90. Found: C, 79.88; H, 4.87.
3-(4-Methoxyphenyl)-1-phenylprop-2-yn-1-ol[13]
1
Colorless oil. H NMR (400 MHz, CDCl3): d ¼ 2.03 (s, 1H), d ¼ 3.80 (s, 3H),
d ¼ 5.67 (s, 1H), d ¼ 6.82–6.84 (d, J ¼ 8.4 Hz, 2H), d ¼ 7.34–7.41 (m, 5H), d ¼ 7.60–
7.62 (d, J ¼ 7.6 Hz, 2H). 13C NMR (100 MHz, CDCl3): d ¼ 55.2, 65.1, 86.6, 87.3,
113.9, 114.4, 126.7, 128.3, 128.6, 133.2, 140.8, 159.7. MS (FAB): m=z (%) ¼ 238
[Mþ]. Anal. calcd. for C16H14O2: C, 80.65; H, 5.92. Found: C, 80.90; H, 5.89.
1-(2-Bromophenyl)-3-(2-chlorophenyl)prop-2-yn-1-ol
1
Colorless oil. H NMR (300 MHz, CDCl3): d ¼ 2.71 (s, 1H), d ¼ 6.06 (s, 1H),
d ¼ 7.17–7.29 (m, 3H), d ¼ 7.36–7.41 (m, 2H), d ¼ 7.46–7.52 (dd, J ¼ 2.1, 7.5 Hz,
1H), d ¼ 7.57–7.60 (m, 1H), d ¼ 7.90–7.94 (dd, J ¼ 1.8, 7.8 Hz, 1H). 13C NMR
(75 MHz, CDCl3): d ¼ 64.7, 83.6, 92.7, 122.2, 122.9, 126.4, 127.9, 128.9, 129.2,
129.7, 130.1, 133.0, 133.5, 136.1, 139.1. MS (FAB): m=z (%) ¼ 320 [Mþ]. Anal. calcd.
for C15H10BrClO: C, 56.02; H, 3.13. Found: C, 56.28; H, 3.16.
1-(4-Chlorophenyl)-3-m-tolylprop-2-yn-1-ol
1
Colorless oil. H NMR (400 MHz, CDCl3): d ¼ 2.33 (s, 4H), d ¼ 5.66 (s, 1H),
d ¼ 7.14 (d, J ¼ 7.2 Hz, 1H), d ¼ 7.19 (t, J ¼ 7.2 Hz, 1H), d ¼ 7.25 (d, J ¼ 13.8 Hz,
2H), d ¼ 7.36 (m, 2H), d ¼ 7.54 (d, J ¼ 8.4 Hz, 2H). 13C NMR (100 MHz, CDCl3):
d ¼ 21.2, 64.4, 87.2, 87.9, 122.0, 128.1, 128.3, 128.7, 128.8, 129.7, 132.3, 134.2,
134.4, 138.1, 139.2. MS (FAB): m=z (%) ¼ 256 [Mþ]. Anal. calcd. for C16H13ClO:
C, 74.85; H, 5.10. Found: C, 75.12; H, 5.04.
1-(2-Bromophenyl)-3-(naphthalene-1-yl)prop-2-yn-1-ol
1
Colorless oil. H NMR (300 MHz, CDCl3): d ¼ 2.77 (s, 1H), d ¼ 6.16 (s, 1H),
d ¼ 7.18–7.24 (m, 1H), d ¼ 7.36–7.43 (m, 2H), d ¼ 7.47–7.52 (m, 4H), d ¼ 7.68–7.71
(d, J ¼ 7.5 Hz, 1H), d ¼ 7.81–7.84 (m, 2H), d ¼ 7.90–7.94 (d, J ¼ 1.5 Hz, d, J ¼ 8.1 Hz,
1H), d ¼ 8.29–8.32 (d, J ¼ 8.4 Hz, 1H). 13C NMR (75 MHz, CDCl3): d ¼ 64.9, 84.9,
92.5, 119.8, 122.7, 125.1, 126.0, 126.4, 126.9, 128.0, 128.3, 128.6, 129.1, 130.0,
130.8, 133.0, 133.1, 133.2, 139.6. MS (FAB): m=z (%) ¼ 336 [Mþ]. Anal. calcd. for
C19H13BrO: C, 67.67; H, 3.89. Found: C, 67.88; H, 3.84.
1-Phenyl-3-(pyridine-3-yl)prop-2-yn-1-ol[18]
1
Colorless oil. H NMR (400 MHz, CDCl3): d ¼ 2.44 (s, 1H), d ¼ 5.67 (s, 1H),
d ¼ 7.12–7.14 (d, J ¼ 7.9 Hz, 1H), d ¼ 7.17–7.23 (q, J ¼ 8.0 Hz, 1H), d ¼ 7.26–7.29