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Volume 2010
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Short Note

1-(2,5-Dimethyl-3-thienyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one

by
Abdullah M. Asiri
1,2,* and
Salman A. Khan
1
1
Chemistry Department, Faculty of Science, King Abdul Aziz University, P.O. Box 80203, Jeddah, Saudi Arabia Chemistry Department, Faculty of Science, King Abdul Aziz University, P.O. Box 80203, Jeddah, Saudi Arabia Chemistry Department, Faculty of Science, King Abdul Aziz University, P.O. Box 80203, Jeddah, Saudi Arabia
2
The Center of Excellence for Advanced Materials Research, King Abdul Aziz University, Jeddah, P.O. Box 80203, Saudi Arabia
*
Author to whom correspondence should be addressed.
Molbank 2010, 2010(3), M692; https://doi.org/10.3390/M692
Submission received: 3 June 2010 / Accepted: 4 August 2010 / Published: 5 August 2010
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Abstract

:
The title compound, 1-(2,5-dimethyl-3-thienyl)-3-(2,4,5-trimethoxy­phenyl)prop-2-en-1-one (3) was synthesized in high yield by an aldol condensation reaction of 3-acetyl-2,5-dimethythiophene and 2,4,5-trimethoxybenzaldehyde in methanolic NaOH at room temperature. Its structure was fully characterized by elemental analysis, IR, 1H NMR, 13C NMR and EI-MS spectral data.

Graphical Abstract

α,β-Unsaturated ketones are biogenic precursors [1] of flavonoids in higher plants, they are also known as chalcones. They display a wide variety of pharmacological properties, including antitumor [2], antibacterial [3], antiviral [4], anti-inflammatory [5], antiulcerative [6] and hepatoprotective activities [7]. Chemically, they consist of either aromatic groups or alkyl groups with an unsaturated chain. Cyclizations of chalcones give pyrazolines, thiazines, or pyrimidines which can show dramatically increased biological activity. On the basis of these aspects, in this paper we are reporting a novel chalcone from 3-acetyl-2,5-dimethythiophene and 2,4,5-trimethoxybenzaldehyde.
A solution of 3-acetyl-2,5-dimethythiophene (0.38 g, 0.0025 mol) and 2,4,5-trimethoxybenzaldehyde (0.49 g, 0.0025 mol) in ethanolic solution of NaOH (6 g in 10 mL of ethanol) was stirred for 16 h at room temperature. The solution was poured onto ice-cold water of pH ~ 2 (pH adjusted by HCl). The separated solid was filtered off, washed several times with a saturated solution of NaHCO3 and left to dry. The residual was recrystallized from methanol/chloroform.
Light-yellow solid: yield: 72%; m.p. 107–108 °C
EI-MS m/z (rel. int.%): 334 (61) [M + 1]+
IR (KBr) vmax cm-1: 3016 (Ar-H), 2924 (C-H), 1642 (C=O), 1572(C=C)
1H NMR (600 MHz, CDCl3)(δ/ppm): 8.01 (d, C=CH, J = 15.6 Hz), 7.26 (s, 1H, CHaromatic), 7.20 (d, C=CH, J = 15.6Hz), 7.08 (s, CHaromatic), 6.51 (s, 1H, 4-CH thiophene), 3.94 (s, OCH3), 3.73 (s, OCH3), 3.62 (s, OCH3), 2.44 (s, 3H, CH3), 2.17 (s, 3H, CH3).
13CNMR (150 MHz, CDCl3) δ: 187.22, 154.44, 152.18, 146.21, 143.11, 138.89, 137.16, 135.08, 126.06, 123.10, 115.45, 111.06, 96.70, 56.49, 56.35, 56.04, 15.80, 15.08.
Anal. calc. for C18H20SO4: C, 65.04, H, 6.06; Found: C, 64.98, H, 5.97.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

The authors would like to thank the deanship of scientific research for the financial support of this work via Grant No. (3-045/430).

References

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Molbank 2010 m692 g001 550
Figure 1. Synthesis of compound 3.
Figure 1. Synthesis of compound 3.
Molbank 2010 m692 g001

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MDPI and ACS Style

Asiri, A.M.; Khan, S.A. 1-(2,5-Dimethyl-3-thienyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one. Molbank 2010, 2010, M692. https://doi.org/10.3390/M692

AMA Style

Asiri AM, Khan SA. 1-(2,5-Dimethyl-3-thienyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one. Molbank. 2010; 2010(3):M692. https://doi.org/10.3390/M692

Chicago/Turabian Style

Asiri, Abdullah M., and Salman A. Khan. 2010. "1-(2,5-Dimethyl-3-thienyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one" Molbank 2010, no. 3: M692. https://doi.org/10.3390/M692

APA Style

Asiri, A. M., & Khan, S. A. (2010). 1-(2,5-Dimethyl-3-thienyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one. Molbank, 2010(3), M692. https://doi.org/10.3390/M692

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