Polycyclic Musks. I. Acyl- and Dinitropolyalkyltetralin Derivatives

Abstract

and could not be obtained in a state of purity which was satisfactory for analysis. g., 0.20 mole) in 50 ml. of methanol absorbed 1715 ml. of hydrogen at 23" with 1 g. of 5% palladium-charcoal catalyst (theoretical absorption calculated for two ethylenic links and hydrogenolysis of one bromide atom is 1470 ml.). This represents 116% of theoretical. The isolation and oxidation of the saturated alcohol to yield 3-hexanone was carried out in the manner described for 2-chloro-l,5-hexadien-3-ol. 3-Hexanone was isolated as the 2,4-dinitrophenylhydrazone, m.p. 130-132°; lit.12 m.p. 132°. Admixture with an authentic sample produced no depression in melting point.Crude 2-bromo-l,5-hexadien-3-ol (71.5 g., 0.40 mole) in 100 ml. of dry ether was added dropwise to phosphorus tribromide Professor J. L. E. Erickson, Louisiana State University, for their assistance and encouragement. We thank Mr, Harry Saunders of our perfumer staff for his help in odor evaluation of new musks. Thanks are due the Air Reduction Chemical and Carbide Company for generous samples of 2,5-dimethyI-2,5-hexanediol during the early stages of our work.

Synthesis, anticancer activities and molecular modeling studies of novel indole retinoid derivatives

“…2,5-Dichloro-2,5-dimethyl hexane (1), was prepared in 55% yield by passing dry hydrogen chloride gas over 2,5-dimethyl-2,5-hexandiole [18,25]. Benzene was alkylated by compound 1 in dichloromethane catalyzed with aluminum chloride to produce 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (2), in 48% yield [26]. Then, 1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone (3) was obtained by acetylation of intermediate 2 with acetyl chloride using AlCl 3 as a catalyst [26,27].…”

“…Benzene was alkylated by compound 1 in dichloromethane catalyzed with aluminum chloride to produce 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (2), in 48% yield [26]. Then, 1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone (3) was obtained by acetylation of intermediate 2 with acetyl chloride using AlCl 3 as a catalyst [26,27]. On the other hand, the corresponding aldehydes 4(aee) were obtained by treating indole derivatives bearing substituent at position 5 with dimethylformamide, using phosphorus oxychloride as a catalyst according to literature method [28e31].…”

Molecular orbital approach to possible discrimination of musk odor intensity

“…Published descriptions 2–10 of molecular structures and odor intensities of 203 musk‐related molecules were used in this study. Odor intensities for molecules 1–170 were classified into the following four categories: strong, represented by grade 3; medium, grade 2; weak, grade 1; odorless, grade 0 (Table I).…”

“…Odor intensities for molecules 1–170 were classified into the following four categories: strong, represented by grade 3; medium, grade 2; weak, grade 1; odorless, grade 0 (Table I). Odor intensities described as very strong, strong, and fairly strong in the reports 2–10 are included in grade 3. We only obtained data on the presence and absence of musk odor instead of intensity levels, for molecules 171–203 6, 7, 9, 10.…”

“…Musk molecules are known to have a wide variety of chemical structures and are the most systematically studied in terms of their odor intensities in perfumery. To find the reactive sites of musk molecules, we investigated electronic localizations of 203 musk‐related molecules including all structural varieties 2–10. The relationship between electronic localizations and odor intensities was studied by discriminative function analysis and multiple regression analysis.…”