JOURNAL OF CHEMICAL RESEARCH 2013 549
2-(2-Hydroxy-4-(4-propylphenyl)but-3-yn-2-yl)phenol (1p): Brown
oil; H NMR (500 MHz, CDCl3) δ 8.38 (s, 1H), 7.55 (dd, J = 7.8,
1,4-Bis(2-chlorophenyl)buta-1,3-diyne (3l):16 White solid, m.p.
138–140 °C (lit. 138–140 °C);16 1H NMR (500 MHz, CDCl3) δ 7.58
(dd, J = 7.7, 1.6 Hz, 2H), 7.42 (dd, J = 8.1, 1.0 Hz, 2H), 7.33–7.29 (m,
2H), 7.25–7.21 (m, 2H).
1
1.5 Hz, 1H), 7.40 (d, J = 8.1 Hz, 2H), 7.23–7.19 (m, 1H), 7.15 (d,
J = 8.1 Hz, 2H), 6.92–6.86 (m, 2H), 3.23 (s, 1H), 2.59 (t, 2H), 1.93 (s,
3H), 1.66–1.61 (m, 2H), 0.93 (t, J = 7.3 Hz, 3H). 13C NMR (125 MHz,
CDCl3) δ 154.85, 143.91, 131.72, 129.67, 128.59, 128.10, 127.02,
119.84, 119.10, 117.81, 89.86, 86.76, 73.18, 37.95, 31.38, 24.33,
13.73. HRMS (ESI): m/z calcd for C19H20O2Na [M + Na]: 303.1361;
found: 303.1360.
1,4-Bis(4-bromophenyl)buta-1,3-diyne (3m):17 Pale yellow solid,
1
m.p. 138–140 °C (lit. 140–141 °C); H NMR (500 MHz, CDCl3)
δ 7.48 (d, J = 8.6 Hz, 4H), 7.38 (d, J = 8.6 Hz, 4H).
1,4-Bis(4-propylphenyl)buta-1,3-diyne (3p):18 White solid, m.p.
1
108–109 °C (lit. 107–108 °C); H NMR (500 MHz, CDCl3) δ 7.43
(d, J = 8.2 Hz, 4H), 7.14 (d, J = 8.1 Hz, 4H), 2.59 (t, J = 8.0 Hz, 4H),
1.67–1.59 (m, 4H), 0.93 (t, J = 7.3 Hz, 6H).
2-(4-(4-Chlorophenyl)-2-hydroxybut-3-yn-2-yl)phenol (1q):Yellow
1
oil; H NMR (500 MHz, CDCl3) δ 8.54 (s, 1H), 7.53 (dd, J = 7.7,
1.6 Hz, 1H), 7.420–7.40 (m, 2H), 7.34–7.31 (m, 2H), 7.25–7.21 (m,
1H), 6.95–6.90 (m, 2H), 3.98 (s, 1H), 1.96 (s, 3H). 13C NMR
(125 MHz, CDCl3) δ 154.61, 134.88, 132.98, 129.68, 128.68, 127.91,
126.79, 120.47, 119.95, 117.76, 91.56, 85.08, 72.75, 31.21. HRMS
(ESI): m/z calcd for C16H13ClO2Na [M + Na]: 295.0502; found:
295.0499.
Received 24 April 2013; accepted 24 June 2013
Paper 1301911 doi: 10.3184/174751913X13739011239995
Published online: 6 September 2013
References
2-(1-Hydroxy-3-phenyl-1-(p-tolyl)prop-2-yn-1-yl)phenol (1r): Pale
1
2
3
4
5
6
7
8
9
R. Shintani, K. Takatsu, T. Katoh, T. Nishimura and T. Hayashi, Angew.
Chem. Int. Ed., 2008, 47, 1447.
A. Horita, H. Tsurugi, A. Funayama, T. Satoh and M. Miura, Org. Lett.,
2007, 9, 2231.
T. Nishimura, H. Araki, Y. Maeda and S. Uemura, Org. Lett., 2003, 5,
2997.
T. Nishimura, T. Katoh, K. Takatsu, R. Shintani and T. Hayashi, J. Am.
Chem. Soc., 2007, 129, 14158.
A. Funayama, T. Satoh and M. Miura, J. Am. Chem. Soc., 2005, 127,
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T. Sugiishi, A. Kimura and H. Nakamura, J. Am. Chem. Soc., 2010, 132,
5332
D. Susanti, F. Koh, J.A. Kusuma, P. Kothandaraman and P.W.H. Chan,
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H. Harkat, A.L. Blanc, J.-M. Weibel and P. Pale, J. Org. Chem., 2008, 73,
1620.
1
orange solid, m.p. 136–137 °C; H NMR (500 MHz, DMSO) δ 9.16
(s, 1H), 7.50–7.38 (m, 7H), 7.33 (d, J = 1.8 Hz, 1H), 7.21 (s, 1H), 7.13
(d, J = 8.0 Hz, 2H), 6.93 (dd, J = 8.1, 1.5 Hz, 1H), 6.63 (d, J = 8.1 Hz,
1H), 2.27 (s, 3H), 2.22 (s, 3H). 13C NMR (125 MHz, DMSO) δ 152.28,
142.08, 136.28, 131.24, 129.61, 129.07, 128.66, 128.57, 128.26,
127.30, 126.95, 126.03, 122.37, 116.33, 92.55, 84.97, 73.08, 20.57,
20.38. HRMS (ESI): m/z calcd for C23H20O2Na [M + Na]: 351.1361;
found: 351.1360.
(2R)-1,2,4-Triphenylbut-3-yne-1,2-diol (1s): White solid, m.p.
156–158 °C; 1H NMR (500 MHz, DMSO) δ 7.55 (d, J = 7.1 Hz, 2H),
7.45–7.37 (m, 5H), 7.32–7.18 (m, 8H), 6.20 (s, 1H), 5.54 (d, J =
4.7 Hz, 1H), 4.73 (d, J = 4.6 Hz, 1H). 13C NMR (125 MHz, DMSO)
δ 143.16, 141.27, 131.18, 128.67, 128.49, 127.11, 127.06, 127.00,
126.96, 126.54, 122.62, 92.34, 85.68, 79.84, 75.56. HRMS (ESI): m/z
calcd for C22H18O2Na [M + Na]: 337.1204; found: 337.1203.
1,4-Diphenylbuta-1,3-diyne (3a):13 White solid, m.p. 86–88 °C
G.S. Kumar, C.U. Maheswari, R.A. Kumar, M.L. Kantam and K.R. Reddy,
Angew. Chem. Int. Ed., 2011, 50, 11748.
10 G. Egglinton and W. McRae, Adv. Org. Chem., 1963, 4, 225.
11 H. Harkat, A.L. Blanc, J.–M. Weibel and P. Pale, J. Org. Chem., 2008, 73,
1620.
12 M.I. Antczak, F. Cai and J.M. Ready, Org. Lett., 2011, 13, 184.
13 S. Adimurthy, C.C. Malakar and U. Beifuss, J. Org. Chem., 2009, 74,
5648.
14 X. Meng, C.B. Li, B.C. Han, T.S. Wang and B.H. Chen, Tetrahedron.,
2010, 66, 4029.
15 M. Eugen, U. Dominik and M. Thomas J.J., Eur. J. Org. Chem., 2011,
238.
1
(lit. 86–87 °C); H NMR (500 MHz, CDCl3) δ 7.57–7.50 (m, 4H),
7.40–7.31 (m, 6H).
1,4-Di-p-tolylbuta-1,3-diyne (3i):13 White solid, m.p. 182–184 °C
(lit. 186–187 °C); 1H NMR (500 MHz, CDCl3) δ 7.42 (d, J = 8.1 Hz,
4H), 7.14 (d, J = 7.9 Hz, 4H), 2.36 (s, 6H).
1,4-Bis(4-methoxyphenyl)buta-1,3-diyne (3j):13 White solid, m.p.
1
138–140 °C (lit. 140–141 °C); H NMR (500 MHz, CDCl3) δ 7.46
(d, J = 8.8 Hz, 4H), 6.85 (d, J = 8.8 Hz, 4H), 3.82 (s, 6H).
1,4-Bis(4-chlorophenyl)buta-1,3-diyne (3k):14 White solid, m.p.
257–259 °C (lit. 253 °C);15 1H NMR (500 MHz, CDCl3) δ 7.45 (d,
J = 8.4 Hz, 4H), 7.32 (d, J = 8.5 Hz, 4H).
16 T.M. Wu, S.H. Huang and F.Y. Tsai, Appl. Organomet. Chem., 2011, 25,
395.
17 V. Kumar, A. Chipeleme and K. Chibale, Eur. J. Org. Chem., 2008, 43.
18 K. Yin, C.J. Li, J. Li and X.S. Jia, Green Chem., 2011, 13, 591.