Propiophenone - CAS 93-55-0
Catalog number: 93-55-0
Molecular Formula:
Molecular Weight:
Propiophenone is an aryl ketone. It is a colorless, sweet-smelling liquid that is insoluble in water, but miscible with organic solvents. It is a common chemical reagent.
> 95%
Clear Colourless Oil
1-Phenyl-1-propanone; 3-Phenyl-3-propanone; Ethyl Phenyl Ketone; NSC 16937; Phenyl Ethyl Ketone; Propionylbenzene;
1.3-Methyl-2-phenyl-1-substituted-indole derivatives as indomethacin analogs: design, synthesis and biological evaluation as potential anti-inflammatory and analgesic agents.
Abdellatif KR1, Lamie PF1, Omar HA2,3. J Enzyme Inhib Med Chem. 2016 Apr;31(2):318-24. doi: 10.3109/14756366.2015.1022174. Epub 2015 Mar 23.
In a new group of 3-methyl-2-phenyl-1-substituted-indole derivatives (10a-f), the indomethacin analogs were prepared via the Fisher indole synthesis reaction of propiophenone with appropriately substituted phenylhydrazine hydrochloride. This is followed by the insertion of the appropriate benzyl or benzoyl fragment. All the synthesized compounds were evaluated for their anti-inflammatory (in vitro and in vivo) and analgesic activities. The methanesulphonyl derivatives 10d, e and f showed the highest anti-inflammatory (in vitro and in vivo) and analgesic activities. In addition, molecular docking studies were performed on compounds 10a-f and the results were in agreement with that obtained from the in vitro COX inhibition assays. The significant anti-inflammatory and analgesic activities exhibited by 10d and 10e warrant continued preclinical development as potential anti-inflammatory and analgesic agents.
2.Hypervalent iodine-promoted α-fluorination of acetophenone derivatives with a triethylamine·HF complex.
Kitamura T1, Muta K, Muta K. J Org Chem. 2014 Jun 20;79(12):5842-6. doi: 10.1021/jo500691b. Epub 2014 May 30.
The direct fluorination reaction of acetophenone using iodosylarenes and TEA·5HF was conducted under mild conditions except for use of a HF reagent. The fluorination reaction was applied to acetophenone derivatives, acetonaphthones, benzyl phenyl ketone, propiophenone, butyrophenone, 1-indanone, and phenacyl chloride, giving selectively the corresponding α-fluoroketone derivatives in good yields.
3.Isolation and structural determination of non-racemic tertiary cathinone derivatives.
Zhou MJ1, Bouazzaoui S, Jones LE, Goodrich P, Bell SE, Sheldrake GN, Horton PN, Coles SJ, Fletcher NC. Org Biomol Chem. 2015 Oct 7;13(37):9629-36. doi: 10.1039/c5ob01306b.
The racemic tertiary cathinones N,N-dimethylcathinone (1), N,N-diethylcathinone (2) and 2-(1-pyrrolidinyl)-propiophenone (3) have been prepared in reasonable yield and characterized using NMR and mass spectroscopy. HPLC indicates that these compounds are isolated as the anticipated racemic mixture. These can then be co-crystallized with (+)-O,O′-di-p-toluoyl-D-tartaric, (+)-O,O′-dibenzoyl-D-tartaric and (−)-O,O′-dibenzoyl-L-tartaric acids giving the single enantiomers S and R respectively of 1, 2 and 3, in the presence of sodium hydroxide through a dynamic kinetic resolution. X-ray structural determination confirmed the enantioselectivity. The free amines could be obtained following basification and extraction. In methanol these are reasonably stable for the period of several hours, and their identity was confirmed by HPLC and CD spectroscopy.
4.Anxiolytic-like effect of Illicium verum fruit oil, trans-anethole and related compounds in mice.
Miyagawa M1, Satou T, Yukimune C, Ishibashi A, Seimiya H, Yamada H, Hasegawa T, Koike K. Phytother Res. 2014 Nov;28(11):1710-2. doi: 10.1002/ptr.5190. Epub 2014 Jun 11.
The fruit of Illicium verum Hook. f. (star anise) is used by many as a spice. The fragrance of I. verum fruit is characteristically anise-like. In this study, hexane-extracted I. verum fruit oil (IVO), trans-anethole as the main component, and related compounds (propiophenone, 4'-methoxy-propiophenone, trans-β-methylstyrene) were analyzed in order to clarify the emotional effect of inhaling the fragrance of I. verum fruit. As a result, although 4 μL/L air IVO did not exhibit an anxiolytic-like effect, 1 μL/L air trans-anethole exhibited a significant effect (p < 0.05). Moreover, the anxiolytic-like effect of 1 μL/L air trans-anethole was significantly greater than 1 μL/L air propiophenone and 1 μL/L air 4'-methoxy-propiophenone (p < 0.05). Thus, the anxiolytic-like effect of trans-anethole was confirmed, and it is proposed that the methoxyl group and 1-propenyl group in the para position of the benzene ring are necessary for the effect.
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