cas 459-31-4, 3-(4-FLUOROPHENYL)PROPIONIC ACID

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Photoredox Activation of Formate Salts: Hydrocarboxylation of Alkenes via Carboxyl Group Transfer
A photoredox activation mode of formate salts for carboxylation was developed. Using a formate salt as the reductant, carbonyl source, and hydrogen atom transfer reagent, a wide range of alkenes can be converted into acid products via a carboxyl group tra
Huang, Yan,Hou, Jing,Zhan, Le-Wu,Zhang, Qian,Tang, Wan-Ying,Li, Bin-Dong
p. 15004 - 15012
(2021/12/14)

Three-component Castagnoli-Cushman reaction with ammonium acetate delivers 2-unsubstituted isoquinol-1-ones as potent inhibitors of poly(ADP-ribose) polymerase (PARP)
An earlier described three-component variant of the Castagnoli-Cushman reaction employing homophthalic anhydrides, carbonyl compound and ammonium acetate was applied towards the preparation of 1-oxo-3,4-dihydroisoquinoline-4-carboxamides with variable substituent in position 3. These compounds displayed inhibitory activity towards poly(ADP-ribose) polymerase (PARP), a clinically validated cancer target. The most potent compound (PARP1/2 IC50 = 22/4.0 nM) displayed the highest selectivity towards PARP2 in the series (selectivity index = 5.5), more advantageous ADME prameters compared to the clinically used PARP inhibitor Olaparib.
Safrygin, Alexander,Zhmurov, Petr,Dar’in, Dmitry,Silonov, Sergey,Kasatkina, Mariia,Zonis, Yulia,Gureev, Maxim,Krasavin, Mikhail
p. 1916 - 1921
(2021/09/03)

Method for synthesizing phenylpropionic acid compounds through heterogeneous palladium metal catalysis
The invention discloses a method for synthesizing phenylpropionic acid compounds by heterogeneous catalysis. The method comprises the following steps: sequentially adding Pd@POL, toluene, styrene, formic acid and acetic anhydride into a reaction flask, stirring the reaction mixture at 80 DEG C to react, cooling the reaction solution to room temperature after the reaction is finished, diluting with dichloromethane, and transferring the solution into a separating funnel, washing with a sodium hydroxide solution, acidifying the water layer with a hydrochloric acid aqueous solution, extracting with dichloromethane, merging organic phases, drying with anhydrous sodium sulfate, and carrying out vacuum concentration to obtain the phenylpropionic acid compound. The method can remove heavy metal residues, is green and environment-friendly, is simple to operate and easy to implement, and the prepared phenylpropionic acid compound has a good application prospect.
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Paragraph 0040-0046

(2021/04/21)

Synthesis method of succinic acid derivative or 3 -arylpropionic acid (by machine translation)
The invention discloses a synthesis method of a succinic acid derivative or 3 -arylpropionic acid, which comprises the following steps: adding a base in a drying reaction tube and CO removing CO. 2 The reaction is carried out under the irradiation of visible light, the reaction is carried out under visible light irradiation, and then separation and purification are carried out to obtain the butanedioic acid derivative or 3 -arylpropionic acid product; the base comprises sodium tert-butoxide, potassium tert-butoxide, lithium tert-butyl alcohol and 4 - potassium carbonate; and the reaction substrate comprises an acrylate compound or an aryl vinyl compound. CO can be induced by visible light. 2 The scheme provided by the invention is mild in reaction condition and wide in reaction 3 - substrate selectivity, and the reaction substrate is wide in selectivity, the raw materials are cheap and easily available, and the method has a good industrial application prospect. (by machine translation)
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Paragraph 0101-0114; 0115; 0122

(2020/10/30)

Hydrogenation reaction method
The invention relates to a hydrogenation reaction method, and belongs to the technical field of organic synthesis. The hydrogenation reaction method provided by the invention comprises the following steps: carrying out a hydrogen transfer reaction on a hydrogen acceptor compound, pinacol borane and a catalyst in a solvent in the presence of proton hydrogen, so that the hydrogen acceptor compound is subjected to a hydrogenation reaction; the catalyst is one or more than two of a palladium catalyst, an iridium catalyst and a rhodium catalyst; the hydrogen acceptor compound comprises one or morethan two functional groups of carbon-carbon double bonds, carbon-carbon triple bonds, carbon-oxygen double bonds, carbon-nitrogen double bonds, nitrogen-nitrogen double bonds, nitryl, carbon-nitrogentriple bonds and epoxy. The method is mild in reaction condition, easy to operate, high in yield, short in reaction time, wide in substrate application range, suitable for carbon-carbon double bonds,carbon-carbon triple bonds, carbon-oxygen double bonds, carbon-nitrogen double bonds, nitrogen-nitrogen double bonds, nitryl, carbon-nitrogen triple bonds and epoxy functional groups, good in selectivity and high in reaction specificity.
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Paragraph 0034; 0049-0052

(2020/05/14)

Generalized Chemoselective Transfer Hydrogenation/Hydrodeuteration
A generalized, simple and efficient transfer hydrogenation of unsaturated bonds has been developed using HBPin and various proton reagents as hydrogen sources. The substrates, including alkenes, alkynes, aromatic heterocycles, aldehydes, ketones, imines, azo, nitro, epoxy and nitrile compounds, are all applied to this catalytic system. Various groups, which cannot survive under the Pd/C/H2 combination, are tolerated. The activity of the reactants was studied and the trends are as follows: styrene'diphenylmethanimine'benzaldehyde'azobenzene'nitrobenzene'quinoline'acetophenone'benzonitrile. Substrates bearing two or more different unsaturated bonds were also investigated and transfer hydrogenation occurred with excellent chemoselectivity. Nano-palladium catalyst in situ generated from Pd(OAc)2 and HBPin extremely improved the TH efficiency. Furthermore, chemoselective anti-Markovnikov hydrodeuteration of terminal aromatic olefins was achieved using D2O and HBPin via in situ HD generation and discrimination. (Figure presented.).
Wang, Yong,Cao, Xinyi,Zhao, Leyao,Pi, Chao,Ji, Jingfei,Cui, Xiuling,Wu, Yangjie
supporting information
p. 4119 - 4129
(2020/08/10)

Method for selective reduction α, β - unsaturated carbonyl compound carbon-carbon double bond (by machine translation)
The invention discloses a method for selectively reducing carbon-carbon double bonds in α and β - unsaturated carbonyl compounds, which comprises the following steps of adding α, β - unsaturated carbonyl compounds shown in formula (I) in an electrolysis system and reducing α and β - unsaturated carbonyl compounds with carbonyl-conjugated carbon-carbon double bonds through an electrochemical cathodic reduction reaction. Compared with the reported method, the method disclosed by the invention does not use a metal catalyst and an external oxidant; and the reaction raw material and the electrolyte are low in price, nontoxic and tasteless, simple and convenient in post-treatment. (by machine translation)
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Paragraph 0039-0042

(2020/06/17)

Site-Selective, Remote sp3 C?H Carboxylation Enabled by the Merger of Photoredox and Nickel Catalysis
A photoinduced carboxylation of alkyl halides with CO2 at remote sp3 C?H sites enabled by the merger of photoredox and Ni catalysis is described. This protocol features a predictable reactivity and site selectivity that can be modulated by the ligand backbone. Preliminary studies reinforce a rationale based on a dynamic displacement of the catalyst throughout the alkyl side chain.
Sahoo, Basudev,Bellotti, Peter,Juliá-Hernández, Francisco,Meng, Qing-Yuan,Crespi, Stefano,K?nig, Burkhard,Martin, Ruben
supporting information
p. 9001 - 9005
(2019/06/24)

Preparation method of organic carboxylic acid
The invention discloses a preparation method of organic carboxylic acid. The preparation method comprises the following steps that catalysts, olefins, water and solvents are added into a reaction container; CO is introduced; heating reaction is performed; after the reaction completion, separation is performed to obtain organic carboxylic acid; the catalysts comprise transition metal catalysts, ligands and catalysis assistants; the catalysis assistants comprise Lewis acid salt. The preparation method has the advantages that the dependency on protonic acid in the prior art is avoided; the Lewisacid salt is used as the catalysis assistant, so that the corrosion of a reaction system on equipment can be effectively prevented; the requirements on equipment are lowered. The preparation method has excellent substrate practicability; the operation steps are simple and fast; the reaction conditions are mild and are easy to control; the raw materials are cheap and can be easily obtained; the product yield and the product purity are high; the preparation method is suitable for large-scale industrial production; the normal/iso ratio of reaction products can be regulated and controlled throughthe catalysis assistants; the defects of regulating and controlling the normal/iso ratio of the reaction products by traditional phosphine ligands are overcome; the reaction progress of the reaction is simplified; the cost is favorably reduced.
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Paragraph 0065-0067

(2019/10/15)

Cyclohexyl-Fused, Spirobiindane-Derived, Phosphine-Catalyzed Synthesis of Tricyclic ?3-Lactams and Kinetic Resolution of ?3-Substituted Allenoates
A C2-symmetric chiral phosphine catalyst, NUSIOC-Phos, which can be easily derived from cyclohexyl-fused spirobiindane, was introduced. A highly enantioselective domino process involving pyrrolidine-2,3-diones and γ-substituted allenoates catalyzed by NUSIOC-Phos has been disclosed. Diastereospecific tricyclic γ-lactams containing five contiguous stereogenic centers were obtained in high yields and with nearly perfect enantioselectivities. A kinetic resolution process of racemic γ-substituted allenoates was developed for the generation of optically enriched chiral allenoates.
Wu, Mingyue,Han, Zhaobin,Li, Kaizhi,Wu, Ji'En,Ding, Kuiling,Lu, Yixin
supporting information
p. 16362 - 16373
(2019/10/16)

Regioselectivity inversion tuned by iron(iii) salts in palladium-catalyzed carbonylations
Impactful regioselectivity control is crucial for cost-effective chemical synthesis. By using cheap and abundant iron(iii) salts, the hydroxycarbonylations of both aromatic and aliphatic alkenes were significantly enhanced in both reactivity and selectivity (iso/n or n/iso up to >99:1). Moreover, Pd-catalyzed carbonylation selectivity can be switched from branched to linear by using different Fe(iii) salts. In addition, similar results were obtained for the carbonylation of secondary alcohols.
Huang, Zijun,Cheng, Yazhe,Chen, Xipeng,Wang, Hui-Fang,Du, Chen-Xia,Li, Yuehui
supporting information
p. 3967 - 3970
(2018/04/23)

Ligand-Controlled Regioselective Hydrocarboxylation of Styrenes with CO2 by Combining Visible Light and Nickel Catalysis
The ligand-controlled Markovnikov and anti-Markovnikov hydrocarboxylation of styrenes with atmospheric pressure of CO2 at room temperature using dual visible-light-nickel catalysis has been developed. In the presence of neocuproine as ligand, the Markovnikov product is obtained exclusively, while employing 1,4-bis(diphenylphosphino)butane (dppb) as the ligand favors the formation of the anti-Markovnikov product. A range of functional groups and electron-poor, -neutral, as well as electron-rich styrene derivatives are tolerated by the reaction, providing the desired products in moderate to good yields. Preliminary mechanistic investigations indicate the generation of a nickel hydride (H-NiII) intermediate, which subsequently adds irreversibly to styrenes.
Meng, Qing-Yuan,Wang, Shun,Huff, Gregory S.,Konig, Burkhard
supporting information
p. 3198 - 3201
(2018/03/13)

Direct β-Selective Hydrocarboxylation of Styrenes with CO2 Enabled by Continuous Flow Photoredox Catalysis
The direct β-selective hydrocarboxylation of styrenes under atmospheric pressure of CO2 has been developed using photoredox catalysis in continuous flow. The scope of this methodology was demonstrated with a range of functionalized terminal styrenes, as well as α-substituted and β-substituted styrenes.
Seo, Hyowon,Liu, Aofei,Jamison, Timothy F.
supporting information
p. 13969 - 13972
(2017/10/17)

Pd-Catalyzed β-C(sp3)?H Arylation of Propionic Acid and Related Aliphatic Acids
A generally applicable Pd-catalyzed protocol for the β-C(sp3)?H arylation of propionic acid and related α-branched aliphatic acids is reported. Enabled by the use of N-acetyl-β-alanine as ligand our protocol delivers a broad range of arylation products. Notably, the highly challenging substrate, propionic acid, which lacks any acceleration through the Thorpe–Ingold effect, can be employed as substrate with synthetically useful yields. Furthermore, the scalability and synthetic applicability of the protocol are demonstrated.
Ghosh, Kiron K.,van Gemmeren, Manuel
supporting information
p. 17697 - 17700
(2017/12/07)

Metal-Free Chemoselective Oxidative Dehomologation or Direct Oxidation of Alcohols: Implication for Biomass Conversion
A transition metal-free, chemoselective reaction was performed using the sodium tert-butoxide-oxygen (NaOtBu-O2) system, resulting in either oxidative dehomologation or direct oxidation of alcohols. In particular, the newly developed protocol may be used to predict the major product formed, which depends on alkyl chain length of the alcohols and reaction conditions. The rational mechanism of this transformation was also demonstrated by performing an 18O isotopic labelling experiment. This protocol presents a straightforward method for biomass conversion of a lignin model compound to phenol and benzoic acid.
Kim, Sun Min,Shin, Hun Yi,Kim, Dong Wan,Yang, Jung Woon
p. 241 - 245
(2016/02/27)

Minimizing Aryloxy Elimination in RhI-Catalyzed Asymmetric Hydrogenation of β-Aryloxyacrylic Acids using a Mixed-Ligand Strategy
The first example of efficient asymmetric hydrogenation of challenging β-aryloxyacrylic acids was realized using a RhI-complex based on the heterocombination of a readily available chiral monodentate secondary phosphine oxide (SPO) and an achiral monodentate phosphine ligand as the catalyst. Excellent enantioselectivities (92->99% ee) were achieved for a wide variety of chiral β-aryloxypropionic acids with minor aryloxy elimination in most cases. The resultant products were readily transformed into biologically active compounds through simple synthetic manipulations.
Li, Yang,Wang, Zheng,Ding, Kuiling
supporting information
p. 16387 - 16390
(2015/11/09)

Synthesis and antitumor activity evaluation of 2-arylisoquinoline-1,3(2H, 4H)-diones in vitro and in vivo
Six 2-(2-acylaminobenzothiazol-6-yl)isoquinoline-1,3(2H,4H)-diones (1a-1f) and five 2-arylisoquinoline-1,3(2H,4H)-diones (1g-1k) were synthesized by refluxing homophthalic anhydrides with 2-acylaminobenzothiazolyl-6-amine or substituted aniline in glacial acetic acid. The cytotoxic activities of 1a-1k were evaluated via MTT method against A431, A549, and PC3. Compound 1b relatively displayed a higher cytotoxic activity than the others. The antitumor effect of 1b were evaluated in established nude mice PANC-1 xenograft model. The results suggest that compound 1b could potentially inhibit tumor growth.
Kang, Bo-Rui,Wang, Juan,Li, Huan,Li, Yan,Mei, Qi-Bing,Zhang, San-Qi
p. 1340 - 1349
(2014/03/21)

Rhodium(I)-catalyzed 1,4-addition of arylboronic acids to acrylic acid in water: One-step preparation of 3-arylpropionic acids
A practical method for the one-step preparation of 3-arylpropionic acids through rhodium-catalyzed 1,4-addition of arylboronic acids to acrylic acid is reported. The method is applicable to a broad scope of aryl boronic acids and displays a wide functional group tolerance operating in water as the optimal reaction medium. Georg Thieme Verlag Stuttgart · New York.
Vautravers, Nicolas R.,Breit, Bernhard
supporting information; experimental part
p. 2517 - 2520
(2011/11/12)

1,4-Cyclohexadiene with Pd/C as a rapid, safe transfer hydrogenation system with microwave heating
A method for the rapid, safe hydrogenation of alkenes and deprotection of benzyl ethers and carboxybenzyl amides is described using catalytic transfer hydrogenation under microwave heating conditions. Commonly available Pd/C catalyst is extremely effective with 1,4-cyclohexadiene as the hydrogen transfer source. In general, the reactions are complete within five minutes at 100 °C.
Quinn, John F.,Razzano, Dana A.,Golden, Kathryn C.,Gregg, Brian T.
scheme or table
p. 6137 - 6140
(2009/04/05)

THERAPEUTIC FLUOROETHYLCYANO GUANIDINES
Disclosed herein is compound having a formula as described herein. Therapeutic methods, compositions, and medicaments related thereto are also disclosed.
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Page/Page column 14

(2008/12/04)

N-UREIDOALKYL-AMINO COMPOUNDS AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
The present application describes modulators of chemokine receptors of formula (I), or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.
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Page/Page column 221

(2008/06/13)

HETEROCYCLIC COMPOUND HAVING HIV INTEGRASE INHIBITORY ACTIVITY
A heterocyclic compound of the formula (I): wherein B1 is -C(R2)= or -N=; R1' is H, etc.; one of R1 and R2 is -Z1-Z2-Z3-R5 wherein Z1 and Z3 are independently single bond, optionally substituted alkylene, etc.; Z2 is single bond, optionally substituted alkylene, etc.; R5 is optionally substituted aryl, optionally substituted heteroaryl, etc., and the other of R1 and R2 is H; -A1- is -C(-Y)=C(-RA)-C(-R3)=C(-R4)-, etc. wherein Y is OH, etc.; RA is -COR7 wherein R7 is OH, etc.; one of R3 and R4 is carboxy, etc., and the other of R1 and R2 is H, etc, a prodrug thereof, a pharmaceutically acceptable salt thereof, and a solvate thereof, having an antiviral activity, more particularly, an inhibitory activity against HIV integrase, and a pharmaceutical composition containing the same, especially an anti-HIV drug.
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Page/Page column 48

(2008/06/13)

NITROGEN-CONTAINING HETEROARYL COMPOUNDS HAVING HIV INTEGRASE INHIBITORY ACTIVITY
A compound of the formula (I): wherein Z4, Z5 and Z9 each is independently carbon atom or nitrogen atom; Y is hydroxy, mercapto or amino; RA is a group of the formula: (wherein C ring is nitrogen-containing heteroaryl) has an inhibitory activity against integrase.
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Page 111; 112

(2008/06/13)

Direct synthesis of 3-arylpropionic acids by tetraphosphine/palladium catalysed Heck reactions of aryl halides with acrolein ethylene acetal
Through the use of [PdCl(C3H5)]2/Cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as a catalyst, a range of aryl bromides undergoes Heck reaction with acrolein ethylene acetal. With this acetal, the selective formation of 3-arylpropionic acids/esters was observed. The functional group tolerance on the aryl halide is remarkable; substituents such as fluoro, methyl, methoxy, acetyl, formyl, benzoyl, nitro or nitrile are tolerated. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered aryl bromides. Graphical Abstract.
Lemhadri, Mhamed,Doucet, Henri,Santelli, Maurice
p. 11533 - 11540
(2007/10/03)

The effect of vinyl esters on the enantioselectivity of the lipase-catalysed transesterification of alcohols
The enantioselectivity of the lipase from Pseudomonas cepacia (PCL) in the transesterification of 2-phenyl-1-propanol 1 was studied using a series of vinyl 3-arylpropanoates as acyl donors. The most enantioselective transesterification reaction of the alcohol was attained by using vinyl 3-(p-iodophenyl)- or 3-(p-trifluoromethylphenyl)propanoates, with enantiomer ratios, E, of 116 and 138, respectively. Vinyl 3-phenylpropanoate was also effective for the resolution of 1 mediated by lipases from P. fluorescens and porcine pancreas and for the PCL-catalysed transesterification of several 2-phenyl-1-alkanols. The enantiomeric resolution of 1 was practically carried out by the first enantioselective transesterification using PCL and vinyl 3-(p-iodophenyl)propanoate to afford (R)-1 and then the enantioselective hydrolysis of the resultant ester to afford (S)-1.
Kawasaki, Masashi,Goto, Michimasa,Kawabata, Shigeki,Kometani, Tadashi
p. 585 - 596
(2007/10/03)

Synthesis and in vitro evaluation of human FP-receptor selective prostaglandin analogues
The in vitro evaluation of a series of saturated prostaglandins revealed that compounds with omega chin aromatic rings retain nanomolar potency for the human prostaglandin F receptor (hFP receptor), exemplified by compound 8. In contrast, the double bonds are required for activity in the series with an acyclic omega chain as in PGF(2α). (C) 2000 Published by Elsevier Science Ltd.
DeLong, Mitchell A.,Amburgey, Jack,Taylor, Cynthia,Wos, John A.,Soper, David L.,Wang, Yili,Hicks, Renee
p. 1519 - 1522
(2007/10/03)

Bicyclic amide derivatives and their use as muscle relaxants
Novel compounds of formula (1) together with their salts and solvates have a number of uses in medicine, in particular as central muscle relaxants.
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(2008/06/13)

Bicyclic amide derivatives and their use as muscle relaxants
Novel compounds of formula (I) STR1 wherein R1, R2, R3 and R4 are each selected from hydrogen and fluoro and at least one and not more than two is fluoro; R5 is selected from hydrogen and C1 -C4 alkyl; R6 is selected from hydrogen, C1 -C4 ally and hydroxy; or R5 and R6 together with the ring carbon form a carbonyl group; R7 is selected from hydrogen and hydroxy, R8 and R9 are each selected from hydrogen, C1 -C4 alkyl and cyclo(C3 or C4) alkyl or together with the nitrogen form a morpholino group; and X is selected from a bond, methylene and --O-- and is always a bond or --O-- when any of R5, R6 and R7 is other than hydrogen and is always a bond when R5 and R6 together with the ring carbon form a carbonyl group; and their salts and solvates have a number of uses as central muscle relaxants. In particular, treatment of conditions associated with abnormally raised skeletal muscle tone. They are of special value in the relaxation of skeletal muscle in spastic, hypertonic and hyperkinetic conditions.
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(2008/06/13)

Carboxylic acid ionization constants by 19F NMR spectroscopy
The 19F NMR spectra of 26 simple fluorinated carboxylic acids were measured in aqueous solutions of pH 03-10.0. Analysis of the fluorine chemical shift dependence on pH allowed the determination of ionization constants from the titration curves
Boiadjiev, Stefan E.,Lightner, David A.
p. 751 - 757
(2007/10/03)

Amide derivatives and their therapeutic use
Novel carbocyclic amides together with their salts, solvates and physiologically active derivatives which have a number of uses in medicine, in particular as central muscle relaxants, and in the treatment or prophylaxis of anxiety, inflammation, arthritis and pain.
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(2008/06/13)

Novel N-substituted 3α-[bis(4'-fluorophenyl)methoxy]tropane analogues: Selective ligands for the dopamine transporter
A series of N-substituted 3α-[bis(4'-fluorophenyl)methoxy]tropane analogues has been prepared that function as dopamine uptake inhibitors. The N-methylated analogue of this series had a significantly higher affinity for the dopamine transporter than the p
Agoston, Gregory E.,Wu, Jae H.,Izenwasser, Sari,George, Clifford,Katz, Jonathan,Kline, Richard H.,Newman, Amy Hauck
p. 4329 - 4339
(2007/10/03)

Herbicidal isoquinolinoxy- or isoquinolinamino-phenoxy alkane carboxylic acid derivatives
The invention concerns novel compounds of the formula I STR1 The compounds are herbicides and in further embodiments the invention provides: processes for the preparation of compounds of formula I; intermediates useful in the preparation of compounds of formula I; compositions containing as active ingredient compounds of formula I; and processes for severely damaging or killing unwanted plants by applying to the plants or to the growth medium of the plants an effective amount of a compound of formula I.
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(2008/06/13)

Substituted oxiranecarboxylic acids, their use and medicaments containing them
Substituted oxiranecarboxylic acids of the formula STR1 wherein R1 denotes a hydrogen atom (--H), a halogen atom, a hydroxylroup, a lower alkyl group, a lower alkoxy group or a trifluoromethyl group, R2 has one of the meanings of Rs
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(2008/06/13)