149437-76-3

Usage

Chemical Properties

Off-White Solid

Uses

4-Fluorophenyl-5’-oxobutyric Acid (cas# 149437-76-3) is a compound useful in organic synthesis.

Upstream product

• 108-55-4 glutaric anhydride, 
• 462-06-6 fluorobenzene 
• 53715-97-2 5,5'-oxybis(5-oxopentanoic acid) 
• 352-13-6 4-flourophenylmagnesium bromide 

Downstream Products

• 1056188-47-6 C₁₆H₁₉FO₄ 
• 793673-93-5 (-)-6-(4-fluorophenyl)tetrahydro-2H-pyran-2-one 
• 189028-93-1 (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione 
• 852148-48-2 (4S)-4-benzyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-1,3-oxazolidin-2-one 
• 914777-32-5 6-(4-fluorophenyl)-3,4-dihydro-2H-pyran-2-one 
• 914777-33-6 1,9-bis(4-fluorophenyl)nonane-1,5,9-trione 
• 1235493-23-8 5-(2-(tert-butoxycarbonyl)hydrazono)-5-(4-fluorophenyl)pentanoic acid 
• 1242183-65-8 3-(6-(4-fluorophenyl)-4-(furan-2-yl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)propanoic acid 
• 924909-70-6 1-(4-fluoro-phenyl)-5-morpholin-4-yl-pentane-1,5-dione 
• 1187468-22-9 (S)-2-(4-fluorophenyl)piperidine 
• 1187468-21-8 (R)-2-(4-fluorophenyl)piperidine 
• 189028-95-3 (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one 
• 1394905-64-6 (S)-6-(4-fluorophenyl)piperidin-2-one 
• 1017158-54-1 C₁₁H₁₃FO₃ 

Relevant academic research and scientific papers

Chromatography-free stereoselective synthesis of (R)-3-benzylpiperidine

The present study describes aza-Michael addition reactions of 4-aroylpent-4-enoic acids with (R)-phenylglycinol. Subsequent spontaneous lactamization yielded the corresponding piperidin-2-ones, which can selectively crystallize in very high diastereomeric purity. These are useful intermediates in the stereoselective syntheses of diverse 3-benzylpiperidines, as herein demonstrated by a chromatography-free and straightforward Gram-scale synthesis of (R)-3-benzylpiperidine hydrochloride.

Method for synthesizing 4-(4-fluorobenzoyl) butyric acid and analogues thereof in continuous flow microreactor

The invention relates to a method for synthesizing 4-(4-fluorobenzoyl) butyric acid and analogues thereof in a continuous flow microreactor, which comprises the following steps: (1) uniformly mixing a compound 1 and a compound 2 to obtain a homogeneous phase solution A; (2) uniformly mixing aluminum trichloride, a compound 1 and an organic solvent to obtain a homogeneous phase solution B; (3) diluting concentrated hydrochloric acid with water to prepare a solution C; and (4) transferring the homogeneous phase solution A and the homogeneous phase solution B into a first micro-reaction module for a Friedel-Crafts acylation reaction, after the reaction is finished, transferring the obtained reaction solution and the solution C into a second micro-reaction module for quenching reaction, and then performing liquid separation, washing and vacuum concentration to obtain a target compound 3; wherein the specific synthesis route is as follows. By adopting the method disclosed by the invention, the target product can be continuously and rapidly synthesized, aluminum trichloride is not needed for treatment, the reaction condition is mild, the reaction time is short, and the yield is high and reaches 90% or above.

Iridium-Catalyzed Asymmetric Hydrogenation of ?- A nd ?-Ketoacids for Enantioselective Synthesis of ?- A nd ?-Lactones

A highly efficient asymmetric hydrogenation of ?- A nd ?-ketoacids was developed by using a chiral spiro iridium catalyst (S)-1a, affording the optically active ?- A nd ?-hydroxy acids/lactones in high yields with excellent enantioselectivities (up to >99% ee) and turnover numbers (TON up to 100000). This protocol provides an efficient and practical method for enantioselective synthesis of Ezetimibe.

INHIBITORS OF APOL1 AND METHODS OF USING SAME

The disclosure provides at least one entity chosen from compounds of formula (I), solid state forms of the same, compositions comprising the same, and methods of using the same, including use in treating focal segmental glomerulosclerosis (FSGS) and/or non-diabetic kidney disease (NDKD).

Synthesis method of chiral methyl 5-(4-fluorophenyl)-5-hydroxyvalerate

The invention provides a synthesis method of chiral methyl 5-(4-fluorophenyl)-5-hydroxyvalerate. The method comprises the following steps: fluorobenzene and glutaric anhydride taken as raw materials undergo a Friedel-Crafts acylation reaction to synthesize 5-(4-fluorophenyl)-5-carbonylvaleric acid; the 5-(4-fluorophenyl)-5-carbonylvaleric acid undergoes a reduction reaction to synthesize 5-(4-fluorophenyl)-5-hydroxyvaleric acid; the 5-(4-fluorophenyl)-5-hydroxyvaleric acid undergoes a cyclization reaction to produce 6-(4-fluorophenyl)-tetrahydropyran-2-one; and the 6-(4-fluorophenyl)-tetrahydropyran-2-one undergoes an alcoholysis reaction to obtain the target compound, namely chiral methyl 5-(4-fluorophenyl)-5-hydroxyvalerate. The synthesis method avoids the problem that carbonyl and ester groups are easy to reduce at the same time, has the advantages of solution control of reaction conditions, high yield, mild reaction temperature, simplicity, easiness in implementation and low cost,and can realize industrial production.

Asymmetric hydrogenation reaction γ - or δ - ketonato compound (by machine translation)

The invention relates to the field, of organic chemistry, specifically γ - or δ - keto acid compound asymmetric hydrogenation reaction, reaction formula as follows : Wherein R is H,C. 1 - C6 An alkyl or halogen, is R 1 - 5 in number of substituents . wherein n is 1 or 2;Cat. is a chiral spiro pyrimidyl phosphine ligand iridium complex . and γ - or δ - keto acid compound is subjected to an internal esterification reaction to further prepare a lactone compound. (by machine translation)

Cooperative iodine and photoredox catalysis for direct oxidative lactonization of carboxylic acids

A new method for the formation of γ- and δ-lactones from carboxylic acids through direct conversion of benzylic C-H to C-O bonds is described. The reaction is conveniently induced by visible light and relies on a mild cooperative catalysis by the combination of molecular iodine and an organic dye.

Study on the HPLC-based separation of some ezetimibe stereoisomers and the underlying stereorecognition process

The enantioseparation of ezetimibe stereoisomers by high-performance liquid chromatography on different chiral stationary phases, ie, 3 polysaccharide-based chiral columns, was studied. It was observed that cellulose-based Chiralpak IC column exhibited the best resolving ability. After the optimization of mobile phase compositions in both normal and reversed phase modes, satisfactory separation could be obtained on Chiralpak IC column, especially in normal phase mode. The use of prohibited solvents as nonstandard mobile phase gave rise to better resolution than that of standard mobile phases (n-hexane/alcohol system). In addition, the presence of ethanol in nonstandard mobile phase has played an important role in enhancing chromatographic efficiency and resolution between ezetimibe stereoisomers. Various attempts were made to comprehensively compare the chiral recognition capabilities of immobilized versus coated polysaccharide-based chiral columns, amylose-based versus cellulose-based chiral stationary phases, reversed versus normal phase modes, and standard versus nonstandard mobile phases. Moreover, possible solute-mobile phase-stationary phase interactions were derived to explain how stationary and mobile phases affected the separation. Then the method validation with respect to selectivity, linearity, precision, accuracy, and robustness was carried out, which was demonstrated to be suitable and accurate for the quantitative determination of (RRS)-ezetimibe impurity in ezetimibe bulk drug.

Iridium/f-Amphol-catalyzed Efficient Asymmetric Hydrogenation of Benzo-fused Cyclic Ketones

Iridium/f-Amphol-catalyzed asymmetric hydrogenation of various benzo-fused five to seven-membered cyclic ketones was successfully developed, affording a series of chiral benzo-fused cyclic alcohols with excellent results (75%–99% yields, 93%–>99% ee, and TON up to 297 000). The enantioenriched products can be employed as key intermediates or motifs for the synthesis of some important biologically active compounds, such as rasagiline mesylate TVP-1012 used for the treatment of Parkinson's disease, the enantiomer of anticonvulsant drug eslicarbazepine acetate (BIA 2-093). (Figure presented.).

Ezetimibe intermediate, synthesis method of intermediate and synthesis method of ezetimibe

The invention provides an ezetimibe intermediate, a synthesis method of the intermediate and a synthesis method of ezetimibe. The method is short in synthetic route. The method includes the steps of making fluorobenzene as the initial raw material sequentially have acylation reaction with glutaric anhydride and 4(S)-4-phenyl oxazolidinone to generate a compound II, protecting carbonyl through 2,2-bis-substituted-1,3-propylene glycol to obtain a compound III, generating a compound V through the compound III and a compound IV under the catalysis of titanium tetrachloride, cyclizing the compound V to generate a compound VI, hydrolyzing the compound VI to obtain a compound VII, and reducing the compound VII through a borane chiral reducing agent and removing a benzyl protecting group in a hydrogenated mode to obtain the ezetimibe. The method is high in yield, little in side reaction and suitable for industrial mass production.