C. CAO, B. LU AND G. CHEN
129.05, 129.60, 130.80, 133.25, 142.50, 156.33, 161.56, 166.42.
HRMS (ESI) Calcd for C17H18NO2, 268.1338; Found, 268.1332.
—
8.78(s, H). 13C NMR (CDCl3, 125 MHz) d: 14.36, 61.06, 120.65,
123.72, 126.05, 128.52, 129.94, 130.93, 134.30, 137.36, 148.65,
154.84, 158.68, 166.18. HRMS (ESI) Calcd for C16H15N2O4,
299.1032; Found, 299.1032.
p-NO PhCH NPhCO Et-p(6), m.p.: 177.0–178.3 8C(lit. 175–
—
2
2
179 8C[37]). 1H NMR(CDCl3, 500 MHz) d: 1.42(t, 3H, J ¼ 7.0 Hz),
4.40(q, 2H, J ¼ 7.0 Hz, J ¼ 14.5 Hz), 7.26(d, 2H, J ¼ 7.5 Hz), 8.11(t,
4H, J ¼ 8.5 Hz), 8.36(d, 2H, J ¼ 8.5 Hz), 8.55(s, H). 13C NMR (CDCl3,
125 MHz) d: 14.36, 61.08, 120.67, 124.09, 128.72, 129.68, 130.94,
141.04, 149.57, 154.89, 158.86, 166.16. HRMS (ESI) Calcd for
C16H15N2O4, 299.1032; Found, 299.1028.
m-MePhCH NPhCO Et-p(15), m.p.: 58.6–59.6 8C. 1H NMR
—
—
2
(CDCl3, 500 MHz) d: 1.41(t, 3H, J ¼ 7.5 Hz), 2.43(s, 3H), 4.39(q,
2H, J ¼ 7.0 Hz, J ¼ 14.0 Hz), 7.20(d, 2H, J ¼ 8.5 Hz), 7.36(m, 2H),
7.67(d, H, J ¼ 7.5 Hz), 7.77(s, H), 8.08(d, 2H, J ¼ 8.5 Hz), 8.41(s, H).
13C NMR (CDCl3, 125 MHz) d: 14.37, 21.30, 60.90, 120.63, 126.66,
127.61, 128.73, 129.16, 130.80, 132.75, 135.69, 138.66, 156.19,
161.92, 166.37. HRMS (ESI) Calcd for C17H18NO2, 268.1338; Found,
268.1327.
HPhCH NPhCO Et-p(7), m.p.: 47.6–48.2 8C(lit. 47 8C[38]).
—
—
2
1H NMR(CDCl3, 500 MHz) d:1.41(t, 3H, J ¼ 7.0 Hz), 4.40(q, 2H,
J ¼ 7.0 Hz, J ¼ 14.5 Hz), 7.21(d, 2H, J ¼ 8.5 Hz), 7.50(m, 3H), 7.91(d,
2H, J ¼ 7.5 Hz), 8.09(d, 2H, J ¼ 8.5 Hz), 8.44(s, H). 13C NMR (CDCl3,
125 MHz) d: 14.37, 60.93, 120.64, 127.66, 128.86, 129.03, 130.81,
131.89, 135.72, 158.10, 161.67, 166.36. HRMS (ESI) Calcd for
C16H16NO2, 254.1181; Found, 254.1183.
Acknowledgements
The work was supported by the Nature Science Foundation of
China (20772028).
p-Me NPhCH NPhCO Et-p(8), m.p.: 116.5–117.0 8C. 1H NMR
—
—
2
2
(CDCl3, 500 MHz) d: 1.40(t, 3H, J ¼ 7.0 Hz), 3.07(s, 6H), 4.37(q, 2H,
J ¼ 7.5 Hz, J ¼ 14.5 Hz), 6.73(d, 2H, J ¼ 9.0 Hz), 7.19(d, 2H, J ¼
8.0 Hz), 7.78(d, 2H, J ¼ 8.0 Hz), 8.05(d, 2H, J ¼ 9.0 Hz), 8.30 (s, H). 13
C
REFERENCES
NMR (CDCl3, 125 MHz) d: 14.39, 40.15, 60.77, 111.47, 120.79,
123.85, 126.69, 130.74, 130.79, 152.73, 157.08, 161.30, 166.57.
HRMS (ESI) Calcd for C18H21N2O2, 297.1603; Found, 297.1592.
¨
[1] H. Neuvonen, K. Neuvonen, F. Fu¨lop, J. Org. Chem. 2006, 71, 3141.
[2] H. Neuvonen, K. Neuvonen, A. Koch, E. Kleinpeter, J. Phys. Chem. A
2005, 109, 6279.
[3] J. Qin, C. Dai, X. Gong, D. Liu, C. Chen, B. Wu, Chin. J. Chem. Phys. 1991,
4, 30.
[4] H. Neuvonen, K. Neuvonen, P. Pasanen, J. Org. Chem. 2004, 69,
3794.
[5] K. Neuvonen, F. Fu¨lo¨p, H. Neuvonen, A. Koch, E. Kleinpeter, K. Pihlaja,
J. Org. Chem. 2003, 68, 2151.
[6] S. T. Lin, C. C. Lee, D. W. Liang, Tetrahedron 2000, 56, 9619.
[7] H. Neuvonen, K. Neuvonen, A. Koch, E. Kleinpeter, J. Mol. Struct.
THEOCHEM 2007, 815, 95.
[8] A. Kawasaki, J. Chem. Soc., Perkin Trans. 2 1990, 223.
[9] H. Neuvonen, K. Neuvonen, A. Koch, E. Kleinpeter, P. Pasanen, J. Org.
Chem. 2002, 67, 6995.
p-MeOPhCH NPhCO Et-p(9), m.p.: 79.4–79.9 8C. 1H NMR
—
—
2
(CDCl3, 500 MHz) d:1.40(t, 3H, J ¼ 7 Hz), 3.88 (s, 3H), 4.38(q, 2H,
J ¼ 7.5 Hz, J ¼ 14.5 Hz), 6.99(d, 2H, J ¼ 9.0 Hz), 7.19(d, 2H, J ¼
8.5 Hz), 7.86(d, 2H, J ¼ 8.5 Hz), 8.07(d, 2H, J ¼ 8.5 Hz), 8.36 (s, H); 13
C
NMR(CDCl3, 125 MHz) d: 14.38, 55.47, 60.87, 114.26, 120.68,
127.33, 128.83, 130.80, 130.83, 156.45, 160.84, 162.61, 166.43.
HRMS (ESI) Calcd for C17H18NO3, 284.1287; Found, 284.1278.
m-MePhCH NPhOMe-p(10), m.p.: 40.0–41.8 8C. 1H NMR
—
—
(CDCl3, 500 MHz) d: 2.42(s, 3H), 3.83(s, 3H), 6.93(d, 2H, J ¼ 8.5 Hz),
, 7.26(m, 3H), 7.35(t, H, J ¼ 7.5 Hz), 7.64(d, H, J ¼ 8.0 Hz), 7.75(s, H),
8.45(s, H). 13C NMR (CDCl3, 125 MHz) d: 21.32, 55.46, 114.31,
122.16, 126.20, 128.59, 128.67, 131.92, 136.29, 138.47, 144.91,
158.14, 158.74. HRMS (ESI) Calcd for C15H16NO, 226.1232; Found,
226.1221.
¨
[10] K. Neuvonen, F. Fu¨lop, H. Neuvonen, A. Koch, E. Kleinpeter, K. Pihlaja,
J. Org. Chem. 2001, 66, 4132.
[11] H. Neuvonen, K. Neuvonen, J. Chem. Soc., Perkin Trans. 2 1999,
1497.
´
[12] H. Dahn, P. Pechy, V. V. Toan, Magn. Reson. Chem. 1997, 35, 589.
[13] K. Neuvonen, F. Fu¨lop, H. Neuvonen, M. Simeonov, K. Pihlaja, J. Phys.
1
—
m-ClPhCH NPhOMe-p(11), m.p.: 71.0–71.4 8C. H NMR(CDCl ,
—
3
¨
500 MHz) d: 3.84(s, 3H), 6.94(d, 2H, J ¼ 9.0 Hz), 7.25(d, 2H,
J ¼ 9.0 Hz), 7.41(m, 2H), 7.73(d, H, J ¼ 7.5 Hz), 7.92 (s, H), 8.43 (s,
H). 13C NMR(CDCl3, 125 MHz) d: 55.48, 114.37, 122.29, 126.89,
128.04, 129.94, 130.86, 134.88, 138.15, 144.15, 156.45, 158.54.
HRMS (ESI) Calcd for C14H13ClNO, 246.0686; Found, 246.0678.
Org. Chem. 1997, 10, 55.
[14] D. M. Pawar, A. A. Khalil, D. R. Hooks, K. Collins, T. Elliott, J. Stafford, L.
Smith, E. A. Noe, J. Am. Chem. Soc. 1998, 120, 2108.
[15] T. Tsuji, H. Takeuchi, T. Egawa, S. Konaka, J. Am. Chem. Soc. 2001, 123,
6381.
[16] K. Neuvonen, F. Fu¨lo¨p, H. Neuvonen, K. Pihlajat, J. Org. Chem. 1994,
59, 5895.
m-NO PhCH NPhOMe-p(12), m.p.: 71.3–71.8 8C. 1H NMR
—
—
2
[17] K. B. Wiberg, J. Org. Chem. 2002, 67, 1613.
[18] K. B. Wiberg, J. Org. Chem. 2002, 67, 4787.
(CDCl3, 500 MHz) d: 3.86(s, 3H), 6.97(d, 2H, J ¼ 9.0 Hz), 7.30(d,
2H, J ¼ 9.0 Hz), 7.65(t, H, J ¼ 0.08 Hz), 8.24(d, H, J ¼ 5.5 Hz), 8.31(d,
H, J ¼ 8.0 Hz) 8.57 (s, H); 8.74(s, H). 13C NMR (CDCl3, 125 MHz) d:
55.51, 114.47, 122.49, 123.23, 125.18, 129.72, 133.83, 138.13,
143.49, 148.62, 154.76, 158.97. HRMS (ESI) Calcd for C14H13N2O3,
257.0926; Found, 257.0917.
´
´ ´
[19] I. Szatmari, T. A. Martinek, L. Lazar, A. Koch, E. Kleinpeter, K. Neuvonen,
¨
F. Fu¨lop, J. Org. Chem. 2004, 69, 3645.
¨
[20] K. Neuvonen, F. Fu¨lop, H. Neuvonen, A. Koch, E. Kleinpeter, K. Pihlaja,
J. Org. Chem. 2005, 70, 10670.
[21] N. Kuze, H. Fujiwara, H. Takeuchi, T. Egawa, S. Konaka, J. Phys. Chem. A
1999, 103, 3054.
m-ClPhCH NPhCO Et-p(13), m.p.: 89.2–91.3 8C. 1H NMR
—
—
2
[22] D. M. Shin, D. G. Whitten, J. Phys. Chem. 1988, 92, 2945.
[23] C. Cao, G. Chen, Z. Yin, J. Phys. Org. Chem. 2008, 21, 808.
[24] R. Wrzalik, K. Merkel, A. Kocot, J. Mol. Model. 2003, 9, 248.
[25] S. Miyajima, A. Nakazato, N. Sakoda, Liq. Cryst. 1995, 18, 651.
[26] R. Pin˜ol, M. B. Ros, J. L. Serrano, T. Sierra, M. R. De La Funte, Liq. Cryst.
2004, 31, 1293.
[27] N. Ajeetha, V. G. K. M. Pisipati, Z. Naturforsch., A: Phys. Sci. 2003, 58,
735.
[28] C. Hansch, A. Leo, R. W. Taft, Chem. Rev. 1991, 91, 165.
[29] Y. H. Cheng, X. Zhao, K. S. Song, L. Liu, Q. X. Guo, J. Org. Chem. 2002,
67, 6638.
(CDCl3, 500 MHz) d: 1.41(t, 3H, J ¼ 7.0 Hz), 4.39(q, 2H, J ¼ 7.0 Hz,
J ¼ 14.0 Hz), 7.21(d, 2H, J ¼ 8.5 Hz), 7.43(t, H, J ¼ 8.0 Hz), 7.49(d, H,
J ¼ 8.5 Hz), 7.76(d, H, J ¼ 7.5 Hz) ,7.95 (s, H), 8.10(d, 2H, J ¼ 8 Hz),
8.40(s, H). 13C NMR (CDCl3, 125 MHz) d: 14.37, 60.97, 120.60,
127.39, 128.04, 128.49, 130.09, 130.84, 131.75, 135.05, 137.44,
155.47, 160.00, 166.27. HRMS (ESI) Calcd for C16H15ClNO2,
288.0791; Found: 288.0780.
1
—
m-NO PhCH NPhCO Et-p(14), m.p.: 162.9–163.0 8C. H NMR
—
2
2
(CDCl3, 500 MHz) d: 1.42(t, 3H, J ¼ 7.0 Hz), 4.40(q, 2H, J ¼ 7.0 Hz,
J ¼ 14.5 Hz), 7.26(d, 2H, J ¼ 8.5 Hz), 7.70(t, H, J ¼ 8.0 Hz), 8.12(d, 2H,
J ¼ 8.5 Hz), 8.27(d, H, J ¼ 8.0 Hz), 8.38(d, H, J ¼ 8 Hz), 8.54 (s, H),
[30] L. Liu, Y. Fu, R. Liu, R. Q. Li, Q. X. Guo, J. Chem. Inf. Comput. Sci.
2004, 44, 652.
[31] K. S. Song, L. Liu, Q. X. Guo, J. Org. Chem. 2003, 68, 262.
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