E,E-1-(4-Bromophenyl)-5-(3-indolyl)-1,4-pentadien-3-one

Gang-Chun Sun; Rui-Yun Guo; Jian-Qiang Qu; Liu-Fang Wang; Jun-Biao Chang; Rong-Feng Chen

doi:10.3390/M191

,

and

¹

National Key Laboratory of Applied Chemistry, Lanzhou University, Lanzhou 730000, P.R.China

²

Henan Institute of Chemistry, Zhengzhou 450002, P.R.China

^*

Authors to whom correspondence should be addressed.

Molecules2000, 5(12), M191;https://doi.org/10.3390/M191

This article belongs to the Section Molbank Section of Molecules, 1997-2001

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3-(1-Butenone-3)indole 1 was prepared by previously published method [1]. The solution of 1 (93mg, 0.5mmol), p-bromobenzaldehyde (93mg, 0.5mmol), sodium hydroxide (100mg) in a mixture of ethanol (2ml) and water (2ml) was stirred at room temperature for 24 hours. The precipitate was then filtered and washed with water for several times. The crude product was purified by recrystalisation from acetone to give a yellow powder of E,E-1-(4-bromophenyl)-5-(3-indolyl)-1,4-pentadien-3-one (106mg, 60%).

Mp: 259-260°C.

IR (KBr, cm^-1):3174.6 (N-H), 1643.2 (C=O), 1612.4 (C=C), 1569.9, 1515.9, 1488.9, 1434.9, 1346.2, 1195.8, 1130.2, 964.3, 848.6, 744.5.

UV-Vis (nm): 215.5, 311.5, 465.0.

¹H NMR (400 MHz, DMSO-d6): 7.14 (d, J=16Hz, 1H, 4-H); 7.19-7.27 (m, 2H, 5′-H, 6′-H); 7.47 (d, J=16Hz, 1H, 2-H); 7.47-7.52 (m, 1H, 7′-H); 7.63 (d, J=16Hz, 1H, 5-H), 7.66 (d, J=8.4Hz, 2H, 3″-H, 5″-H); 7.76 (d, J=8.4Hz, 2H,2″-H, 6″-H); 8.05 (d, J=16Hz, 1H, 1-H); 8.02 (d, J=2.8Hz, 1H, 2′-H); 8.05-8.09 (m, 1H, 4′-H), 11.88 (s, 1H, 1′-H).

MS m/z: 352 (M⁺).

Acknowledgement

This research was supported by the NSF of China (NO:29972009) and the NSF of Gansu Province (NO:ZS991-A23-059-Y).

Supplementary Materials

References

Xie, J.; Xie, L.; Gu, Z.; Liu, Y.; Wang, Z. Acta Pharmaceutica Sinica 1994, 23, 732–736.

Sample Availability: Available from the authors.

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