E,E-1-(4-Bromophenyl)-5-(3-indolyl)-1,4-pentadien-3-one
by
Gang-Chun Sun
1, 
Rui-Yun Guo
2,
Jian-Qiang Qu
1,
Liu-Fang Wang
1,*,
Jun-Biao Chang
2,* and
Rong-Feng Chen
2 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.
Molecules 2000, 5(12), M191; https://doi.org/10.3390/M191
Submission received: 20 September 2000
/
Accepted: 30 November 2000
/
Published: 25 December 2000
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
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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MDPI and ACS Style
Sun, G.-C.; Guo, R.-Y.; Qu, J.-Q.; Wang, L.-F.; Chang, J.-B.; Chen, R.-F. E,E-1-(4-Bromophenyl)-5-(3-indolyl)-1,4-pentadien-3-one. Molecules 2000, 5, M191. https://doi.org/10.3390/M191
AMA Style
Sun G-C, Guo R-Y, Qu J-Q, Wang L-F, Chang J-B, Chen R-F. E,E-1-(4-Bromophenyl)-5-(3-indolyl)-1,4-pentadien-3-one. Molecules. 2000; 5(12):M191. https://doi.org/10.3390/M191
Chicago/Turabian StyleSun, Gang-Chun, Rui-Yun Guo, Jian-Qiang Qu, Liu-Fang Wang, Jun-Biao Chang, and Rong-Feng Chen. 2000. "E,E-1-(4-Bromophenyl)-5-(3-indolyl)-1,4-pentadien-3-one" Molecules 5, no. 12: M191. https://doi.org/10.3390/M191
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