1 -phenyl-4- tetralin

The use of co-(2-bromophenyl)alkyl-2-oxazolines (13) in base-promoted ring-closure reactions provides a good access to 1-phenyl-indane and 1-phenyl-tetralin derivatives (14) that contain easily manipulated oxazoline moieties. Satisfactory isolated yields of cyclized products 14 are obtained with lithium diisopropylamide (LDA) in THF at room temperature under irradiation with UV light, even when quaternary centers are formed (Scheme 10.39) [55]. The yield of 14 (n= 1, R= Ph) increases to 75% when the reaction proceeds under laboratory light for 48 h at room temperature. 

Early studies from the Pfizer laboratories had revealed that compounds from a series of mzn.s-l-amino-4-phenyl-tetralins possessed potent norepinephrine (NE) uptake blocking activity. The activity was highly specific for the (1/ , 4S)-enantiomer and was confined to the trans derivatives. The corresponding (IS, 4/ )-enantiomer was much less active and the diastereomeric cis racemates were inactive at blocking NE uptake. It was subsequently shown that many compounds from the diastereomeric cis senes were unexpectedly potent and selective inhibitors of serotonin (5-HT) uptake, thus differentiating these compounds from the trans compounds. One of these compounds, sertraline (5), was originally discovered as a racemic mixture. Resolution showed that the (+)-enantiomer was several times more selective for 5-HT uptake blocking activity than the (-)-isomer. The (+)-enantiomer was subsequently shown to possess the in vivo behavioral effects expected of a potent and selective 5-HT blocker. Thus, as opposed to... 

Hernandin (15) is a new compound which belongs to the category of phenyl-tetralin-type lignans. Many studies have been reported on the syntheses of this type lignans (ref. 2, 47), and some of them were carried out in connection with the syntheses of steganacin (ref. 48) and deoxyschizandrin (ref. 49). A route via an itaconic acid derivative, obtained by Stobbe condensation of a benzophenone derivative with diethyl succinate, followed by cyclization (ref. 41a, 50) was first undertaken through the scheme outlined in Chart 10. 

Monoamine uptake inhibition in rat brain synaptosomes of corpus striatum (5-HT, DA) and hypothalamus (NE) by l-methylamino-4-phenyl tetralins [72]. 

Laoton der 6.7-Dhnethoxy.2.oxynieth]d. l-[3.4.dimethoxy-phenyl]-tetralin-oarbonB4ure-(3) 18 II 223. 

This highly hydroxylated phenyl-tetralin-type lignan acid is available from Thuja plicata. It is recovered in about 2% yield from the heartwood. Because it is one of the strongest known natural acids, plicatic acid (6) is readily separable from... 

Tetralin and 1-methylnaphthalene were reagent grade and were used after washing with sulfuric acid, alkali, and water and the subsequent distillation at 70°C under reduced pressure. Various additives and model compounds were reagent grade, and some of them were used after recrystallization. Phenyl naphthyl ether and phenyl 9-phenanthryl ether were synthesized by refluxing a mixture of aryl bromide, phenol, CU2O and X-collidine (12). 

TABLE IV EFFECT OF PHENOLS ON THE THERMAL DECOMPOSITION OF PHENYL BENZYL ETHER AT 320°C FOR 30 MIN (Phenyl benzyl ether 27 mmole, Tetralin 220 mmole, Additive 140 mmole)... 

The most surprising observation from low temperature reactions was the formation of adducts between good donor solvents (Tetralin, octahydrophenanthrene, tetrahydroquinoline) and acceptor radicals. The resulting adducts were not of a single predominant structure. In particular, several isomers of toluene-Tetralin were formed as well as di-Tetralin. Several of these reactions were done with D -Tetralin which permitted the firm identification of the Tetralin moiety in the adducts. GLC-MS studies indicated that the Tetralin may be bonded to phenyl, benzyl, benzyloxy- or phenoxy-groups, depending on the acceptor used. 

The linear co-oxidation dependence was observed for the following pairs of hydrocarbons (333 K, initiator AIBN) tetralin-ethylbenzene, phenylcyclopentane-ethylbenzene, phenyl-cyclohexane-ethylbenzene, tetralin-phenylcyclohexane, cyclohexene-2-butene, 2,3-dimethyl, and cyclohexene-pinane [8]. 

Z)-l -Nitro-l-alkene werden in Diethylether an En-amine addiert3- u. Die Additionsreak-tion verlauft weitgehend diastereo- und enantioselektiv. Durch saure Hydrolyse kann das Amin nach der Addition abgespaltcn werden und man erhalt ein Keton. So reagiert 2-Morpholino-3,4-dihydro-naphthalin mit (Z)-2-Nitro-l-phenyl-ethen zu l-(2-Nitro-l-phe-nyl-ethyl) -2-oxo-tetralin. 

Als Nebenprodukt wird 3-(2-Nitro-l-phenyl-ethyl)-2-oxo-tetralin (Schmp. 127-129°) erhalten. Produkt zu Nebenprodukt entstehen im Verhaltnis 4 1. 

Die intramolekulare Friedel-Crafts-Reaktion von anti- bzw. jy -2-Nitro-5-phenyl-3-phe-nylthio-pentan mit Zinn(IV)-chlorid fuhrt unter Erhalt der Konfiguration zu trans- bzw. cis-5-Methyl-6-phenylthio-tetralin in 76- bzw. 70%iger Ausbeute1 ... 

The addition of 1-lithiocyclopropyl phenyl sulfide to paraformaldehyde was the first step of an efficient synthesis of cyclobutanonc (8).169 The adduct 7 was rearranged with/Moluenesulfonic acid monohydrate in a mixture of tetralin and water while the liberated benzenethiol was trapped with mercury(II) chloride. 

Vacuum distillation of the benzyl derivative 77 gave a mixture of equal amounts of four products (Scheme 19) stilbene was also formed, again suggesting a radical mechanism.7 A dilute solution in boiling tetralin, however, gave only 76 (60%) and 78 (18%).13 In the case of 59 both a methyl and a phenyl group were observed to migrate.13... 

Tetralins — see also Naphthalenes, tetrahydro-thermochemistry, 2, 368 Tetralones Schmidt reaction azepine synthesis by, 7, 531 Tetramisole—see Imidazo[2,I-6]thiazoie, ( )-2,3,5,6-tetrahydro-6-phenyl-... 

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