9-Propyl phenanthrene

Michaelides, M.R. Hong, Y. DiDomenico, S., Jr. Asin, K.E. Britton, D.R. Lin, C.W. Williams, M. Shiosaki, K. (1995) (5aR,llbS)-4,5,5a,6,7,llb-hexahydro-2-propyl-3-thia-5-azacyclopent-l-ena[c]-phenanthrene-9, 10-diol (A-86929) a potent and selective dopamine Di agonist that maintains behavioral efficacy following repeated administration and characterization of its diacetyl prodrug (ABT-431). J. Med. Chem. 38, 3445-3447. 

Propound modification of the structure, with migration of the basic side-chain and reversion to a fully aromatic phenanthrene derivative, occurs when thebaine [i] [1] or codeinone [n] [2] is heated with dilute hydrochloric acid, the product being the phenolic secondary amine thebenine [in], Triacetylthebenine is produced when -codeinone [iv] is heated with acetic anhydride [3], and thebenine-8-methyl ether (methebenine), 8-ethyl ether (ethebenine), and 8-propyl ether (prothe-benine) can be prepared by heating thebaine or codeinone with hydrochloric acid and methyl, ethyl, and propyl alcohol respectively [2, 4]. Methebenine, which can be hydrolysed to thebenine by hot 20 per cent, hydrochloric acid [4], is also obtained by the action of stannous chloride and acetic anhydride on thebaine [5]. 

Abweichcnd hiervon zieht die Photoaddition von Methanol an Xeoa bietinsaure-mcthylester einen Dehydrierungsschritt nach sich2 nnd liefert l,4a-Dimelhyl-7-[2-methoxy-propyl-(2) -l-methoxycarbonyl-1,2,3,4,4a,4b, 5,6,10,10a-decahydro-phenanthren ... 

The first reaction was found by Levy and Szwarc to be predominant when methyl radicals attacked isooctane. The second reaction is predominant, however, for aromatic hydrocarbons. The free radicals formed in the above two reactions will react with each other, with other free radicals, or with impurities. The affinity of the methyl radical to attack an aromatic increases in the following order benzene, diphenyl ether, pyridine, diphenyl, benzophenone, naphthalene, quinoline, phenanthrene, pyrene, and anthracene. The ability of free alkyl radicals to interact with isopropylbenzene and cyclohexene decreases in the following order methyl, ethyl, propyl, butyl, isopropyl, sec-butyl, and tertiary butyl. 

O.lO-Dioxy-O.lO-diithyl-O.lO-dlhydro-antiiracen 6,1030,1503. 9.l0-Dioxy-9.l0-diithyl-9.l0 Iihydro-phenanthren 6,1030. 9-Ow-9-[a-oxy. - thyl,propyl]-fluoren 6 1503. 

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