Cyclohexylpropionic acid

C12H20O2, Mr 196.29, bpo.nkPa. 91 °C, has not yet been found in nature. It is a colorless liquid with a sweet-fruity odor, reminiscent of pineapples. The ester is prepared by esterification of 3-cyclohexylpropionic acid (obtained by hydrogenation of cinnamic acid) with allyl alcohol. It is used in perfumery to obtain fruity top notes as well as pineapple and chamomile nuances. 

The diazotization/fluorodediazoniation of a-amino acids takes place with retention of configuration. Thus, when (S )-2-amino-3-cyclohexylpropionic acid (1) is treated with excess sodium nitrite in hydrogen fluoride/pyridine, (5 )-2-fluoro-3-cyclohexylpropionic acid (2) is obtained without any racemization.82... 

Cyclohexylpropionic acid was deprotonated with 2.2 equivalent of lithium diisopropylamide and the resulting dianion was condensed with trifluoroacetaldehyde which was generated in situ from its ethyl hemiacetal. The P-hydroxy acid 1 was isolated as a racemic mixture of two diastereomers. Silylation with tert-butyldimethylsilyl triflate was followed by ester hydrolysis to give the acid 2. A Curtius rearrangement with diphenylphosphoryl azide in the presence of benzyl alcohol afforded the protected P-amino alcohol 3 which was used in the preparation of the trifluoromethyl alcohol I. Oxidation using the Dess-Martin periodinane reagent (9) yielded the trifluoromethyl ketone II as a mixture of diastereomers. The signal for the carbonyl carbon in the 13C-NMR spectrum of this ketone appeared at 94.5 ppm and this is consistent with the hydrated form of the trifluoromethyl ketone. 

Synonyms Allyl-3-cyclohexanepropionate Allyl cyclohexylpropionate 3-Allylcyclohexyl propionate Allyl 3-cyclohexylpropionate Allyl hexahydrophenylpropionate Cyclohexylpropionic acid allyl ester 2-Propenyl 3-cyclohexanepropanoate Empirical C12H20O2... 

Cyclohexylpropionic acid allyl ester. See Allyl cyclohexanepropionate 1-Cyclohexyl-2-pyrrolidinone N-Cyclohexylpyrrolidinone N-Cyclohexyl-2-pyrrolidinone 1-Cyclohexyl-2-pyrrolidone. See N-Cyclohexyl pyrrolidone N-Cyclohexyl pyrrolidone CAS 6837-24-7 EINECS/ELINCS 229-919-7 Synonyms 1-Cyclohexyl-2-pyrrolidinone N-Cyclohexylpyrrolidinone N-Cyclohexyl-2-pyrrolidinone 1-Cyclohexyl-2-pyrrolidone 2-Pyrrolidinone, 1-cyclohexyl-Empi heal C10H17NO... 

Carboxylic acids. Vinylcyclohexane refluxed 18 hrs. with n-propylmagnesium bromide and some titanium tetrachloride, then treated with GO2, and hydrolyzed -cyclohexylpropionic acid. Y 51%. F. e., also preferential reaction, s. H. L. Finkbeiner and G. D. Cooper, J. Org. Chem. 26, 4779 (1961) 27, 1493, 3395 (1962). 

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