148600-15-1Relevant articles and documents
A novel general method for preparation of α-fluoro-α-arylcarboxylic acid. Direct fluorination of silyl ketene acetals with Selectfluor
Zhang, Fei,Song, Jake Z.
, p. 7641 - 7644 (2006)
The reaction of an α-arylcarboxylic acid with TBSCl and LiHMDS in THF yielded bis-silyl ketene acetal, which was directly fluorinated with inexpensive Selectfluor to produce the corresponding α-fluoro-α-arylcarboxylic acid in high yield. Application of the methodology to the synthesis of α-fluorocarboxylic ester from the corresponding carboxylic ester is also described.
Electrochemical carboxylation of α,α-difluorotoluene derivatives and its application to the synthesis of α-fluorinated nonsteroidal anti-inflammatory drugs
Yamauchi, Yusuke,Fukuhara, Tsuyoshi,Hara, Shoji,Senboku, Hisanori
, p. 428 - 442 (2008/09/16)
Electrochemical carboxylation of α,α-difluorotoluene derivatives resulted in an efficient fixation of carbon dioxide to give the corresponding α-fluorophenylacetic acids in good yields, and this reaction was successfully applied to the synthesis of α-fluorinated nonsteroidal anti-inflammatory drugs (NSAIDs). Georg Thieme Verlag Stuttgart.
Effect of fluorine substitution of α-and β-hydrogen atoms in ethyl phenylacetate and phenylpropionate on their stereoselective hydrolysis by cultured cancer cells
Yamazaki, Yoshimitsu,Yusa, Shiro,Kageyama, Yu-Ichi,Tsue, Hirohito,Hirao, Ken-Ichi,Okuno, Hiroaki
, p. 167 - 171 (2007/10/03)
(±)-Ethyl 2-fluoro-2-phenylacetate was stereoselectively hydrolyzed by cultured cells of several rat cancer cell lines to give the carboxylic acid rich in the R enantiomer. The stereoselectivity increased for (±)-ethyl 2-fluoro-2-phenylpropionate (2b) with all present cell lines and for (±)-ethyl 2-phenyl-3,3,3-trifluoropropionate (3b) with rat hepatoma McA-RH7777 cell line. The stereoselectivity was different for the different cell lines, as McA-RH7777 cells preferred (R)-2b in contrast with the preference towards (S)-2b by other cells such as ras oncogene-transformed rat liver Anr4 cells. These stereoselectivities were different from those for non-fluorinated (±)-ethyl 2-phenylpropionate. Thus fluorine atoms are recognized by ester hydrolases of cancer cells, and fluorine substitution on the acyl group will be useful for making ester-type anticancer prodrugs more specific to cancer cells.
