Biphenyl carboxylic acid

C12H10 92-52-4) see Bifonazole Fenbufen 4-biphenylacetonitrile (C14H11N J760i-77-7) see Felbinac [3aR-(3aa,4a,5p,6aa)]-[l,l -biphenyl]-4-carboxylic acid 4-formylhexahydro-2-oxo-2fl-cyclopenta[6]furan-5-yl ester (C2iH,80j 38754-71-1) see Latanoprost [3alt-[3aa,4a(l ,35 ),5p,6aa]]-[4,4 -biphenyl]-4-carb-oxylic acid hexahydro-4-(3-hydroxy-5-phenyl-l-pentenyl)-2-oxo-21/-cyclopenta[6]furan-5-yl ester (C3 H ,05 41639-73-0) see Latanoprost... 

C30H34O5 39865-76-4) see Unoprostone isopropyl [3ait-[3aa,4a( ),5p,6aa]]-[l,l -biphenyl]-4-carboxylic acid hexahydro-2-oxo-4-(3-oxo-l-octenyl)-2i/-cyclopen-ta[A]furan-5-yl ester... 

Monaca et al. (2003) examined the effect of the SSRI citalopram on REMS in 5-HTia and 5-HTib knockout mice. Citalopram suppressed REMS in wild-type and 5-HTib mice but not in 5-HT,A I mutants. The 5-HTja receptor antagonist WAY 100635 prevented the citalopram-induced inhibition of REMS in wild-type and 5-HTib knockout mice. However, pretreatment with the 5-HTib receptor antagonist GR 127935 [2 -methyl-4 -(5-methyl-(l,2,4)oxadiazol-3-yl)-biphenyl-4-carboxylic acid ((4-methoxy-piperazine-l-yl)-phenyl)amide] was ineffective in this respect. It was concluded that the action of citalopram on REMS in the mouse depends exclusively on the activation of 5-HT,A receptors. Notwithstanding this, there is unequivocal evidence showing that administration of selective 5-HTib receptor agonists suppresses REMS in the rat. 

Sodium in liquid ammonia and ethanol reduced benzoic acid to 1,4-dihy-drobenzoic acid. Reduction of p-toluic acid was more complicated and afforded a mixture of cis- and rranj-l,2,3,4-tetrahydro-p-toluic acid and cis-and tra j-l,4-dihydrotoluic acid. m-Methoxybenzoic acid yielded 1,2,3,4-tetrahydro-5-methoxybenzoic acid, and 3,4,5-trimethoxybenzoic acid gave l,4-dihydro-3,5-dimethoxybenzoic acid in 87% yield (after hydrogenolysis of the methoxy group para to carboxyl) [984. In the case of 4 -methoxy-biphenyl-4-carboxylic acid, sodium in isoamyl alcohol at 130° reduced completely only the ring with the carboxylic group, thus giving 92% yield of 4-(p-methoxyphenyl)cyclohexanecarboxylic acid [955]. 

Biphenyl-4-carboxylic acid [92-92-2] M 198.2, m 228°. Crystd from C6H6-pet ether or aq EtOH. 

Fig. 10.3 Chemical structures of low affinity NMDA antagonists used for the treatment of AD, AD, AIDS dementia, and migrane. Memantine (a) Amantadine (b) (R,S)-N-2-(4-(3-thienyl)phenyl)-2-propanesulfonamide (LY392098) (c) and (R)-4 -[l-fluoro-l-methyl-2-(propane-2-sulphonylamino)-ethyl]-biphenyl-4-carboxylic acid methylamide (LY503430) (d)...

The dicarboxylic acid was obtained in 65% yield with 79% selectivity. Fortunately, there are better ways (see Chap. 6) to make this compound without the use of toxic carbon tetrachloride. This method gives 100% selectivity at 71% conversion in the reaction of biphenyl-4-carboxylic acid to form the 4,4 -biphenyldicarboxylic acid. /3-Cyclodextrin accelerates the platinum-catalyzed addition of triethoxysilane to styrene.231 The reaction is 100% complete in 30 min at 50°C with the cyclodextrin, but only 45% complete without it. The Wacker reaction of 1-decene produces several ketones owing to double-bond isomerization. If the reaction is run in a dimethylcyclodextrin, isomerization is reduced by faster reoxidation of palladium(O).232 The product 2-decanone is obtained with 98-99% selectivity (5.57). 

A soln. of startg. oxime ester (prepared from biphenyl-4-carboxylic acid and benzophenone oxime) in carbon tetrachloride irradiated with a 400 W high-pressure Hg-lamp through a Pyrex filter under N2 at room temp, until reaction complete 4-chlorobiphenyl. Y 88%. This radical method is generally applicable to ar., hetar. (e.g. pyridyl, quinolyl, quinoxalyl), and aliphatic acids (prim., sec. and tert.). Ketone, amide, and hydroxyl groups remained unaffected. F.e.s. M. Hasebe, T. Tsuchiya, Tetrahedron Letters 29, 6287-90 (1988). 

The SM reactions in water [89-91] as the only reaction solvent or under solvent-free [92,93] conditions can be microwave-assisted with dramatical shortening of the reaction times from hours to minutes. For example, Leadbeater and coworkers [90] have described a preparation of biphenyl-4-carboxylic acid (306) in 97% yield from 4-bromobenzoic acid (307) and phenylboronic acid (260) by ligandless Pd(OAc)2-based method applying the microwave-heating for only 10 minutes. Scheme 37. 

The synthetic route to the 3-nitro- and 3-cyano-4- -alkoxybiphenyl-4 -carboxylic acids is shown in Fig. 37. The 4- -alkoxy-biphenyl-4 -carboxylic acids (the hexade-cyloxy and the octadecyloxy homologues in the case of the preparation of materials that exhibit cubic phases) are prepared as de-... 

Compare the p/f values of biphenyl-3 Carboxylic acid (4.14) and biphenyl-4-carboxylic acid (4.21) to that of benzoic acid (4.20), and explain the different effect of the phenyl group on the pA values. 

The optically active low molecular weight mesogens employed were either 4 -(2-methylhexyloxy)-biphenyl-4-carboxylic acid (6) or terephthal-ylidene-bis[4-(4 -methyIhexyloxy) janiline] (7). 

Preparatiom of 4 -cyano-biphenyl-4-carboxylic acid (I-phenyl-ethyl)-amide zni-uci... 

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