Phenyl propanoate

Certain of the monoalkylated ethyl phenylacetates have been further alkylated with alkyl and aralkyl halides to produce the corresponding disuhstituted phenylacetic esters.4 Ethyl 2-phenyl-propanoate has been alkylated by methyl iodide to give pure ethyl 2-methyl-2-pheny]propanoate in 81% yield. Similarly, the alkylations of ethyl 2-phenylhexanoate with methyl iodide, M-butyl bromide, and benzyl chloride gave the corresponding pure dialkylated products in 73%, 92%, and 72% yields, respectively. 

Heteroarylphenylalanines could be smoothly obtained via microwave-promoted Suzuki reaction of heteroaryl halides with 2-amino-3-[4-(dihy-droxyboryl)phenyl]propanoic acid (Scheme 28) [46]. Interestingly, the free amino acid could be used without any protection of the amine and carboxylic acid fimctionahty. When 4-(dihydroxyboryl)-L-phenylalanine was used as organometallic partner no racemization was observed. The carboxylate anion and free amino group seem to shield the a-C - H from deprotonation and thus hmit racemization. 

The following chemicals were obtained commercially (Sigma Chemical Co.) and bioassayed with C. album and Amaranthus retroflexus L. (seeds collected in North Carolina in 1980) following identification DL-3-hydroxybutyric acid (DL-3-hydroxy-butyric acid as a Na salt) and L-3-phenyllactic acid (L-2-hydroxy-3-phenyl-propanoic acid). 

Phenylalanine (Phe or F) (2-amino-3-phenyl-propanoic acid) is a neutral, aromatic amino acid with the formula HOOCCH(NH2)CH2C6H5. It is classified as nonpolar because of the hydrophobic nature of the benzyl side chain. Tyr and Phe play a significant role not only in protein structure but also as important precursors for thyroid and adrenocortical hormones as well as in the synthesis of neurotransmitters such as dopamine and noradrenaline. The genetic disorder phenylketonuria (PKU) is the inability to metabolize Phe. This is caused by a deficiency of phenylalanine hydroxylase with the result that there is an accumulation of Phe in body fluids. Individuals with this disorder are known as phenylketonurics and must abstain from consumption of Phe. A nonfood source of Phe is the artificial sweetener aspartame (L-aspartyl-L-phenylalanine methyl ester), which is metabolized by the body into several by-products including Phe. The side chain of Phe is immune from side reactions, but during catalytic hydrogenations the aromatic ring can be saturated and converted into a hexahydrophenylalanine residue. ... 

Oxidative degradation of (/ )-(1 -mcthyl-2-propcny jcyclohcxanc (sec p422) and comparison of the acid 10 thus obtained with an authentic sample prepared from (S)-2-phenyl-propanoic acid by hydrogenation U6. 

Ethyl 2-[(Diphenylniethylene)aminol-3- 4-[3-(trifluoromethyl)-3//-diazirin-3-yl]phenyl)propanoate... 

Several aryl-substituted ethylene oxides may be cited m connexion with epoxide hydration. For instance, a-methylstyreoe oxide Fives j. 2-dihydroxy-2-phenyl propano on careful treatment with cold dilute hydrochloric acid.4 9 The isomeric substance -methylstyrene oxide, which can exist in two geometric modifications, is reported to... 

Phenyl propanoate. Slowly add 196g (120 ml) of redistilled thionyl chloride to a mixture of 150 g (1.6 mol) of pure phenol and 132g (133 ml, 1.7 mol) of propanoic acid (Fig. 2.55 with the addition of a gas absorption device), warming to drive off all the sulphur dioxide and hydrogen chloride, and distilling 190g (79%) of phenyl propanoate, b.p. 202-212 °C (the pure substance boils at 211 °C), are obtained. 

Phenyl acetate Phenyl propanoate Phenyl butanoate Diphenyl oxalate Phenyl salicylate (salol)... 

Anisodamine (Ada C17H23N04 MW 305.16 g/mol CAS-No 55869-99-3 [(lS,3S,5S,7S)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-3-yl](2S)-3-hydroxy-2-phenyl-propanoate). 

Ipratropium (Ipra C20H30NO3 MW 332.22 g/mol CAS-No. 60205-81-4 [8-methyl-8-(l-methylethyl)-8-azoniabicyclo[3.2.1] octane-3-yl] 3-hydroxy-2-phenyl-propanoate). 

An impressive illustration of the influence of the medium on the photo-Fries reaction product distribution can be found in Sch. 5 where the products of photolysis of 1-naphthyl 2-methyl 2-phenyl propanoate in hexane solution and within NaY are compared. Remarkably, whereas in solution eight products are formed, within NaY zeolite a single product dominates the product mixture. Cations present within zeolites help to anchor the reactants, intermediates and products to the surfaces of the zeolite and... 

The standard 13C NMR spectrum of phenyl propanoate is shown here. Predict the appearance of the DEPT-90 and DEPT-135 spectra. 

Results of molecular modeling show that the proposed geometry of the H-bonded COOH HOOC-complex with (R,S)-2-(4-isobutyl-phe-nyl)-propanoic acid (known as ibuprofen) positions the remote CH2 group close to the active metal site, and consequently, this position should be preferentially oxidized. When racemic 2-(4-isobutyl-phenyl)-propanoic acid is brought in contact with the catalyst, the selectivity for oxidation at the remote benzylic position is greater than 98%. 

Nonracemic phenylserine derivatives can be prepared by the addition of ammonia to a,/ -di-halocarboxylic acid esters via aziridines59. Treatment of (li )-menthyl 2,3-dibromo-3-phenyl-propanoate (7) with methanolic ammonia proceeds stereoselectively to give a readily separable mixture of the diastereomeric and thermodynamically more stable (17 )-menthyl a s-3-phenyl-2-aziridinecarboxylates (8A and 8B) as crystalline solids59. 

A mmetric hydrogenation catalyzed by palladium deposited on simpler synthetic polypeptides, homopolymers of a-amino acids or their derivatives, was studied by Beamer, Belding and Pickling (5, (5). In the hydrogenation in ethanol of a-meth-ylcinnamic acid [ J] and of a-acetamidocinnamic acid [4] to give 2-methyl-3-phenyl-propanoic acid [5] and phenylalanine, respectively, the predominant optical antipodte was found much dependent on the secondary conformation of the polypeptide (Table 1). 

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