Methoxy acetophenone

Acetophenone, 4 methoxy 2 (p-methoxyphenyl)-, 40,16 30 Acetoxy-5 androstene 170-car-boxylic acid, 42, 4 30-Acetoxyetienic acid, 42, 4 3/8-Acetoxy-S pregnen-20 one, conversion to 3/3-acetoxyetienic acid, 42, 5... 

Neurokinines comprise of a group of peptides involved in nerve transmission. The nonpeptidic neurokinin antagonist talnetant has been evaluated for its effect on irritable bowel syndrome (IBS) and urinary incontinence as well as depression and schizophrenia. The quinoline portion of this compound has been prepared through a Pfitzinger condensation of isatin with methoxy acetophenone. Methoxy ether cleavage and amide... 

Another example of enhanced sensitivity to substituent effects in the gas phase can be seen in a comparison of the gas-phase basicity for a series of substituted acetophenones and methyl benzoates. It was foimd that scnsitivtiy of the free energy to substituent changes was about four times that in solution, as measured by the comparison of A( for each substituent. The gas-phase data for both series were correlated by the Yukawa-Tsuno equation. For both series, the p value was about 12. However, the parameter r" ", which reflects the contribution of extra resonance effects, was greater in the acetophenone series than in the methyl benzoate series. This can be attributed to the substantial resonance stabilization provided by the methoxy group in the esters, which diminishes the extent of conjugation with the substituents. 

Besides acetophenone, this reaction was also applied to p-methoxy-and p-bromoacetophenone, but in all cases yields are low. 

Eupe and Majewski attempted to determine by experiment the influence of the relative positions of osmophores on each other in the same molecule. In the case of the three methyl tri-azo-benzoates no great difference in the type of odour exists, only a difference in the strengths, the para compound being the strongest and the ortho the weakest. Of the three methoxy-acetophenones, as another example, the meta isomer is almost odourless in comparison with the ortho and para. 

Alkoxy-substituted allylaluminum reagents diethyl[(Z)-3-methoxy-2-propenyl]- and -[(Z)-3-(l-methoxy-l-methylethyl)-2-propenyl]aluminum have been prepared by treatment of the corresponding alkoxyallyllithiums with diethylaluminum chloride in tetrahydrofuran at — 78 =C4. These reagents provide the syn-diastereomer with 9-11 1 selectivity in reactions with aldehydes at — 78 °C. The reaction of diethyir(Z)-3-methoxy-2-propenyl]a]uminum and acetophenone provided the iy -diastereomer with 4 1 selectivity. 

Mit Natrium-bis-[2-methoxy-athoxy]-dihydrido-aluminat konnen in sieden-dem Xylol Hydroxy-benzaldehyde und -acetophenone innerhalb weniger Stunden zu Al-kyl-phenolen reduziert werden (Vorschrift S. 171) z.B.2 ... 

C,4H,ftN202S 84711-26-2) see Etomidate /V-ethoxycarbonyl-3-methoxy-8,14-didehydroinorphinan (C2(tH25N03i 58025-69-7) see Butorphanol 2 -e(hoxycarbonylmethoxy-4 -(3-methyl-2-butenyloxy)-acetophenone... 

The boron trifluoride etherate catalysed formation of oxazoles has been used in synthesis. Doyle has successfully employed the reaction in the synthesis of annuloline 20, a disubstituted oxazole isolated from the roots of the annual rye grass. Thus, l-diazo-4 -methoxy-acetophenone 19 was reacted with 3,4-dimethoxycinnamonitrile in the presence of boron trifluoride etherate to yield the natural product 20 in 48% yield (Scheme 11).<80JOC3657>... 

It is interesting to note that among initiators studied, a benzyl ketal type initiator (2,2-dimethoxy-2-phenyl acetophenone) is more active than other initiators of acetophenone type. 2,2-Dimethoxy-2-phenyl acetophenone is more active than BME, probably due to the presence of the extra methoxy group on the -carbon, which gives a more active phenyldimethoxy methyl radical (and it further cleaves to give an even more active methyl radical) than the phenylmethoxy methyl radical from BME (4). It is known that the phenylmethoxy methyl radical dimerizes easily and thus loses some of its role as a radical in a... 

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