325-89-3

Basic information

• Product Name: 3-Amino-3-(4-fluorophenyl)propanoic acid
• Synonyms: 3-AMINO-3-(4-FLUOROPHENYL)PROPANOIC ACID;3-AMINO-3-(4-FLUOROPHENYL)PROPIONIC ACID;3-(4-FLUOROPHENYL)-BETA-ALANINE;DL-3-AMINO-3-(4-FLUORO-PHENYL)-PROPIONIC ACID;DL-BETA-(P-FLUOROPHENYL)ALANINE;RARECHEM AK HC T330;TIMTEC-BB SBB003727;3-AMINO-(4-FLUOROPHENYL)PROPIONIC ACID,&
• CAS NO: 325-89-3
• Molecular Formula: C₉H₁₀FNO₂
• Molecular Weight: 183.18
• EINECS: -0
• Product Categories: C9;Carbonyl Compounds;Carboxylic Acids;B-Amino
• Mol File: 325-89-3.mol

Chemical Properties

• Melting Point: 224-228 °C (dec.)(lit.)
• Boiling Point: 308.8 °C at 760 mmHg
• Flash Point: 140.6 °C
• Appearance: /
• Density: 1.289 g/cm³
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 3.66±0.10(Predicted)
• BRN: 3258498
• CAS DataBase Reference: 3-Amino-3-(4-fluorophenyl)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-3-(4-fluorophenyl)propanoic acid(325-89-3)
• EPA Substance Registry System: 3-Amino-3-(4-fluorophenyl)propanoic acid(325-89-3)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 325-89-3(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Upstream product

• 79-20-9 acetic acid methyl ester 
• 459-57-4 4-fluorobenzaldehyde 
• 141-82-2 malonic acid 

Downstream Products

• 612532-52-2 3-amino-3-(4-fluorophenyl)propan-1-ol 
• 151911-23-8 (R)-β-amino-β-(4-fluorophenyl)propionic acid 
• 151911-33-0 (S)-β-amino-β-(4-fluorophenyl)propionic acid 
• 151911-29-4 (S)-β-(N-phenylacetylamino)-β-(4-fluorophenyl)propionic acid 
• 181519-32-4 3-amino-3-(4-fluorophenyl)propionic acid methyl ester 
• 1257211-79-2 (R)-1-[3-benzamido-3-(4-fluorophenyl)propanamido]-3-methylbutylboronic acid 
• 1269634-21-0 methyl 3-benzamido-3-(4-fluorophenyl)propanoate 
• 1647-94-5 3-benzamido-3-(4-fluorophenyl)propanoic acid 
• 190190-83-1 2-ethoxycarbonyl(4-fluorophenyl)ethylammonium chloride 
• 284493-72-7 3-((tert-butoxycarbonyl)amino)-3-(4-fluorophenyl)propanoic acid 
• 1132-68-9 L-4-fluorophenylalanine 
• 459-32-5 (E)-4-fluorocinnamic acid 
• 1609344-56-0 rac-tert-butyl [2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-(4-fluorophenyl)ethyl]carbamate 
• 354148-17-7 rac-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-(4-fluorophenyl)propanoic acid 

Relevant articles and documents

Anticoagulated small-molecule compound, application thereof and drug including compound

The invention relates to an anticoagulated small-molecule compound, application thereof and a drug including the compound. A structural formula of the anticoagulated small-molecule compound is shown in the description, and the anticoagulated small-molecul

Synthesis, molecular docking and biological evaluation of novel phthaloyl derivatives of 3-amino-3-aryl propionic acids as inhibitors of Trypanosoma cruzi trans-sialidase

In the last two decades, trans-sialidase of Trypanosoma cruzi (TcTS) has been an important pharmacological target for developing new anti-Chagas agents. In a continuous effort to discover new potential TcTS inhibitors, 3-amino-3-arylpropionic acid derivatives (series A) and novel phthaloyl derivatives (series B, C and D) were synthesized and molecular docking, TcTS enzyme inhibition and determination of trypanocidal activity were carried out. From four series obtained, compound D-11 had the highest binding affinity value (?11.1 kcal/mol) compared to reference DANA (?7.8 kcal/mol), a natural ligand for TS enzyme. Furthermore, the 3D and 2D interactions analysis of compound D-11 showed a hydrogen bond, π-π stacking, π-anion, hydrophobic and Van der Waals forces with all important amino acid residues (Arg35, Arg245, Arg314, Tyr119, Trp312, Tyr342, Glu230 and Asp59) on the active site of TcTS. Additionally, D-11 showed the highest TcTS enzyme inhibition (86.9% ± 5) by high-performance ion exchange chromatography (HPAEC). Finally, D-11 showed better trypanocidal activity than the reference drugs nifurtimox and benznidazole with an equal % lysis (63 ± 4 and 65 ± 2 at 10 μg/mL) and LC50 value (52.70 ± 2.70 μM and 46.19 ± 2.36 μM) on NINOA and INC-5 strains, respectively. Therefore, D-11 is a small-molecule with potent TcTS inhibition and a strong trypanocidal effect that could help in the development of new anti-Chagas agents.

Kinetic Resolution of Aromatic β-Amino Acids Using a Combination of Phenylalanine Ammonia Lyase and Aminomutase Biocatalysts

An enzymatic strategy for the preparation of (R)-β-arylalanines employing phenylalanine aminomutase and ammonia lyase (PAM and PAL) enzymes has been demonstrated. Candidate PAMs with the desired (S)-selectivity from Streptomyces maritimus (EncP) and Bacillus sp. (PabH) were identified via sequence analysis using a well-studied template sequence. The newly discovered PabH could be linked to the first ever proposed biosynthesis of pyloricidin-like secondary metabolites and was shown to display better β-lyase activity in many cases. In spite of this, a method combining the higher conversion of EncP with a strict α-lyase from Anabaena variabilis (AvPAL) was found to be more amenable, allowing kinetic resolution of five racemic substrates and a preparative-scale reaction with >98% (R) enantiomeric excess. This work represents an improved and enantiocomplementary method to existing biocatalytic strategies, allowing simple product separation and modular telescopic combination with a preceding chemical step using an achiral aldehyde as starting material. (Figure presented.).

1-PHENYLPYRROLIDIN-2-ONE DERIVATIVES AS PERK INHIBITORS

The invention is directed to substituted pyrrolidinone and imidazolidinone derivatives. Specifically, the invention is directed to compounds according to Formula I: (I) wherein R1, R2, R3, R4, R5, R6, R7, X and Y are as defined herein. The compounds of the invention are inhibitors of PERK and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases/injuries associated with activated unfolded protein response pathways, such as Alzheimer's disease, neuropathic pain, spinal cord injury, traumatic brain injury, ischemic stroke, stroke, Parkinson's disease, diabetes, metabolic syndrome, metabolic disorders, Huntington's disease, Creutzfeldt- Jakob Disease, fatal familial insomnia, Gerstmann-Str?ussler-Scheinker syndrome, and related prion diseases, amyotrophic lateral sclerosis, progressive supranuclear palsy, myocardial infarction, cardiovascular disease, inflammation, organ fibrosis, chronic and acute diseases of the liver, fatty liver disease, liver steatosis, liver fibrosis, chronic and acute diseases of the lung, lung fibrosis, chronic and acute diseases of the kidney, kidney fibrosis, chronic traumatic encephalopathy (CTE), neurodegeneration, dementias, frontotemporal dementias, tauopathies, Pick's disease, Neimann-Pick's disease, amyloidosis, cognitive impairment, atherosclerosis, ocular diseases, arrhythmias, in organ transplantation and in the transportation of organs for transplantation. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting PERK activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

From bead to flask: Synthesis of a complex β-amido-amide for probe-development studies

A concise synthesis of benzimidazole-substituted β-amido-amide LLW62 is presented. The original synthesis of compounds related to LLW62 was developed on Rink resin as part of a "one-bead, one-compound" combinatorial approach for on-bead screening purposes. The current synthesis is carried out in solution and is amenable to scale-up for follow-up studies on LLW62 and investigations of related structures. The key step involves the use of a β-amino acid-forming three-component reaction (3CR), the scope of which defines its role in the synthetic strategy.

Enantioselective acylation of β-phenylalanine acid and its derivatives catalyzed by penicillin G acylase from alcaligenes faecalis

This study developed a simple, efficient method for producing racemic β-phenylalanine acid (BPA) and its derivatives via the enantioselective acylation catalyzed by the penicillin G acylase from Alcaligenes faecalis (Af-PGA). When the reaction was run at 25°C and pH 10 in an aqueous medium containing phenylacetamide and BPA in a molar ratio of 2:1, 8 U/mL enzyme and 0.1 M BPA, the maximum BPA conversion efficiency at 40 min only reached 36.1%, which, however, increased to 42.9% as the pH value and the molar ratio of phenylacetamide to BPA were elevated to 11 and 3:1, respectively. Under the relatively optimum reaction conditions, the maximum conversion efficiencies of BPA derivatives all reached about 50% in a relatively short reaction time (45-90 min). The enantiomeric excess value of product (eep) and enantiomeric excess value of substrate (ees) were all above 98% and 95%, respectively. These results suggest that the method established in this study is practical, effective, and environmentally benign and may be applied to industrial production of enantiomerically pure BPA and its derivatives.

Carica papaya lipase catalysed resolution of β-amino esters for the highly enantioselective synthesis of (S)-dapoxetine

An efficient synthesis of the (S)-3-amino-3-phenylpropanoic acid enantiomer has been achieved by Carica papaya lipase (CPL) catalysed enantioselective alcoholysis of the corresponding racemic N-protected 2,2,2-trifluoroethyl esters in an organic solvent. A high enantioselectivity (E > 200) was achieved by two strategies that involved engineering of the substrates and optimization of the reaction conditions. Based on the resolution of a series of amino acids, it was found that the structure of the substrate has a profound effect on the CPL-catalysed resolution. The enantioselectivity and reaction rate were significantly enhanced by switching the conventional methyl ester to an activated trifluoroethyl ester. When considering steric effects, the substituted phenyl and amino groups should not both be large for the CPL-catalysed resolution. The mechanism of the CPL-catalysed enantioselective alcoholoysis of the amino acids is discussed to delineate the substrate requirements for CPL-catalysed resolution. Finally, the reaction was scaled up, and the products were separated and obtained in good yields (≥ 80 %). The (S)-3-amino-3- phenylpropanoic acid obtained was used as a key chiral intermediate in the synthesis of (S)-dapoxetine with very high enantiomeric excess (> 99 %). A carica papaya lipase catalysed resolution of N-protected β-phenylalanine esters has been developed. High enantioselectivity was achieved by two strategies that involved engineering of the substrates and optimization of the reaction conditions. After 50 % conversion, the products were separated and used as key chiral intermediates for the synthesis of (S)-dapoxetine with > 99 % ee. Copyright

Kinetic resolution of aromatic β-amino acids by ω-transaminase

Racemic aromatic β-amino acids have been kinetically resolved into (R)-β-amino acids with high enantiomeric excess (>99%) by a novel ω-TA with ca. 50% conversion.

Stereoselective chemoenzymatic preparation of β-amino esters: Molecular modelling considerations in lipase-mediated processes and application to the synthesis of (S)-dapoxetine

A wide range of optically active 3-amino-3-arylpropanoic acid derivatives have been prepared by means of a stereoselective chemoenzymatic route. The key step is the kinetic resolution of the corresponding β-amino esters. Although the enzymatic acylations of the amino group with ethyl methoxyacetate showed synthetically useful enantioselectivities, the hydrolyses of the ester group catalyzed by lipase from Pseudomonas cepacia have been identified as the optimal processes concerning both activity and enantioselectivity. The enantiopreference of this lipase in these reactions has been explained, at the molecular level, by using a fragment-based approach in which the most favoured binding site for a phenyl ring and the most stable conformation of the 3-aminopropanoate core nicely match the (S)-configuration of the major products. The conversion and enantioselectivity values of the enzymatic reactions have been compared in order to understand the influence of the different substitution patterns present in the phenyl ring. This chemoenzymatic route has been successfully applied to the preparation of a valuable intermediate in the synthesis of (S)-dapoxetine, which has been chemically synthesised in excellent optical purity.

3-AMINO-3-ARYLPROPIONIC ACID n-ALKYL ESTERS, PROCESS FOR PRODUCTION THEREOF, AND PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE 3-AMINO-3-ARYLPROPIONIC ACIDS AND ESTERS OF THE ANTIPODES THERETO

The present invention is to provide an n-alkyl 3-amino-3-arylpropionate represented by the formula (I): wherein Ar1 represents an aryl group which may have a substituent(s), provided that a phenyl group and 4-methoxyphenyl group are excluded, R1 represents an n-propyl group or an n-butyl group, and a process for preparing the same, and its optically active compound and an optically active (S or R)-3-amino-3-arylpropionic acid represented by the formula (III-a): wherein Ar represents an aryl group which may have a substituent(s), and * represents an asymmetric carbon, and a process for preparing an optically active n-alkyl (R or S)-3-amino-3-arylpropionate represented by the formula (IV-a): wherein Ar and R1 have the same meanings as defined above, * represents an asymmetric carbon, provided that it has a reverse absolute configuration to the compound of the formula (III-a).