4- Hydroxy-3-phenyl-2-heptanone

Favorskii reported the conversion of 3-hydroxy-4-heptanone to 4-hy-droxy-3-heptanone, as well as analogous transformations of 2-hydroxy-3-pentanone and 2-hydroxy-4,4-dimethyl-3-pentanone. These reactions were carried out at elevated temperatures, in ethanol solutions containing a small proportion of sulfuric acid. At the same time, Favorskii reported the isomerization of 2-hydroxypropiophenone to l-hydroxy-l-phenyl-2-pro-panone under the conditions of yeast fermentation—a claim which the evidence given hardly justified and which von Auwers and Mauss disputed. However, Temnikova reported that this conversion does take place in both acid and alkaline media, and the list of what appear to be... 

Four diarylheptanoids were isolated from the methanol ic extract of the rhizomes of 4. officinarum and identified on the basis of their spectral data and by chemical correlations as l,7-diphenylhept-4-en-3-one (40), 7-(4"-hydroxy-3"-methoxyphenyl)-l-phenylhept-4-en-3-one (41), 1,7-dipheny 1-5-hydroxy-3-heptanone (43) and 5-hydroxy-7-(4"-hydroxy-3"-methoxyphenyl)-l-phenyl-3-heptanone (44) [38]. From the chloroform-soluble fraction of the methanolic extract of the rhizomes of A. officinarum, three new diarylheptanoids, 5-methoxy-7-(4"-hydroxy-3"-methoxyphenyl)-l-phenyl-3-heptanone (46), 5-hydroxy-7-(4"-hydroxyphenyl)- -phenyl-3-heptanone (45) and 7-(4"-hydroxy-3"-methoxyphenyl)- -phenyl-3,5-heptanedione (49) were isolated together with 41, 43 and 44 [39]. Compound 44 was the major constituent of the chloroform-soluble fraction. Compounds 41, 43-46 and 49 showed inhibitory effect against PG synthetase and IC50 values of the compounds were reported [39]. In addition to compounds 43, 44 and 52, three new diarylheptanoids, 42,47 and 48 were isolated from the rhizomes of A. officinarum and the structures were elucidated on the basis of the spectroscopic data [40]. The configuration of C-5 of 43 and 52 was determined to be R and that of hexahydrocurcumin was S [40]. 

DIRECTED ALDOL CONDENSATIONS threo-4-HYDROXY-3-PHENYL-2-HEPTANONE, 54, 49 DIRECTED LITHIATION OF AROMATIC COMPOUNDS (2-DIMETHYL-AMINO- 5-METHYLPHENYL) DI-PHENYLCARBINOL, 53, 56 DIRECT IODINATION OF POLYALKYL-BENZENES IODODURENE, 51, 94 Disiamylborane, 53, 79 Disodium hydroxylaminedisulfo-nate, 52, 83... 

Carbonyl alkylation and condensation reactions are always of great value in synthesis, and the formation of o-ANIS ALDEHYDE via 4,4-dimethyl-2-oxazoline, 2,2-DIMETHYL-3-PHENYLPROPION-ALDEHYDE via alkylation of the magnesio-enamine salt and threo-4-HYDROXY-3-PHENYL-2-HEPTANONE via a directed aldol... 

DIRECTED ALDOL CONDENSATIONS THREO-4-HYDROXY-3-PHENYL-2-HEPTANONE... 

The present procedures illustrate general methods for the use of preformed lithium enolates5 as reactants in the aldol condensation6 and for the quenching of alkali metal enolates in acetic anhydride to form enol acetates with the same structure and stereochemistry as the starting metal enolate.7 The aldol product, [Pg.55]

Hydroxy-1 -(3, 4 -dihydroxyphenyl)-7-phenyl-3-heptanone (phenylpropane ketone) Alpinia officinarum (Zingiberaceae) [rhizome] 5-LOX (18nM)... 

Directed aldol condensation. House et al. have published a detailed procedure for the aldol condensation of the lithium enolate of phenylacetone with n-butyraldehyde in the presence of zinc chloride to give fhreo-4-hydroxy-3-phenyl-2-heptanone. Ether or ether-dimethoxyethane mixtures are the most suitable... 

Figure 2. Structures of diarylheptanoids isolated from Alpinia officinarum. AO-1 (5-hydroxy-7-(4 -hydroxy-3 -methoxyphenyl)- l-phenyl-3-heptanone), AO-2(5-methoxy-7-(4 -hydroxy-3 -methoxyphenyl)-l-phenyl-3-heptanone), AO-3 (7-(4 -hydroxyphenyl)-l-phenylhept-4-en-3-one), AO-4 (7-(4 -hydroxy-3"-methoxyphenyl)- l-phenylhept-4-en-3-one), AO-5 (1,7-diphenylhept-4-en-3-one).

---