247113-86-6

Basic information

• Product Name: FMOC-L-4-Trifluoromethylphe
• Synonyms: N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-L-(4-TRIFLUOROMETHYLPHENYL)ALANINE;RARECHEM BK PT 0141;(S)-2-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-3-(4-TRIFLUOROMETHYL-PHENYL)-PROPIONIC ACID;Fluorenylmethoxycarbonyl-L-4-trifluoromethylphenylalanine;FMOC-L-4-TRIFLUOROMETHYLPHE;FMOC-L-4-TRIFLUOROMETHYLPHENYLALANINE;FMOC-L-4-TRIFLUOROPHENYLALANINE;FMOC-PHE(4-CF 3)-OH
• CAS NO: 247113-86-6
• Molecular Formula: C25H20F3NO4
• Molecular Weight: 455.43
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Amino Acid Derivatives;a-amino
• Mol File: 247113-86-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 128-138°C
• Boiling Point: 619 °C at 760 mmHg
• Flash Point: 328.2 °C
• Appearance: Pale brown/Powder
• Density: 1.351 g/cm³
• Storage Temp.: 2-8°C
• PKA: 3.65±0.10(Predicted)
• CAS DataBase Reference: FMOC-L-4-Trifluoromethylphe(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-L-4-Trifluoromethylphe(247113-86-6)
• EPA Substance Registry System: FMOC-L-4-Trifluoromethylphe(247113-86-6)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 247113-86-6(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Upstream product

• 1121-86-4 1-Fluoro-3-iodobenzene 
• 6140-17-6 4-methylbenzotrifluoride 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 402-49-3 4-bromomethyltrifluoromethylbenzene 
• 114872-59-2 diethyl 2-acetamido-2-<<4-(trifluoromethyl)phenyl>methyl>malonate 

Downstream Products

• 1213773-26-2 O-W-F-F(4-CF₃)-F-H(1-Bzl)-NH₂ 
• 1213772-93-0 O-W-F(4-CF₃)-I-F-H(1-Bzl)-NH₂ 
• 1213773-57-9 O-W-F-I-F(4-CF₃)-H(1-Bzl)-NH₂ 

Relevant articles and documents

Discovery and Optimization of Chromeno[2,3-c]pyrrol-9(2H)-ones as Novel Selective and Orally Bioavailable Phosphodiesterase 5 Inhibitors for the Treatment of Pulmonary Arterial Hypertension

Phosphodiesterase 5 (PDE5) inhibitors have been used as clinical agents to treat erectile dysfunction and pulmonary arterial hypertension (PAH). Herein, we detail the discovery of a novel series of chromeno[2,3-c]pyrrol-9(2H)-one derivatives as selective and orally bioavailable inhibitors against phosphodiesterase 5. Medicinal chemistry optimization resulted in 2, which exhibits a desirable inhibitory potency of 5.6 nM with remarkable selectivity as well as excellent pharmacokinetic properties and an oral bioavailability of 63.4%. In addition, oral administration of 2 at a dose of 5.0 mg/kg caused better pharmacodynamics effects on both mPAP (mean pulmonary artery pressure) and RVHI (index of right ventricle hypertrophy) than sildenafil citrate at a dose of 10.0 mg/kg. These activities along with its reasonable druglike properties, such as human liver microsomal stability, cytochrome inhibition, hERG inhibition, and pharmacological safety, indicate that 2 is a potential candidate for the treatment of PAH.

LIGAND-CONTROLLED C(SP3)-H ARYLATION AND OLEFINATION IN SYNTHESIS OF UNNATURAL CHIRAL ALPHA AMINO ACIDS

The use of ligands to tune the reactivity and selectivity of transition metal-catalysts for C(-sp3)-H bond functionalization is a central challenge in synthetic organic chemistry. Herein, we report a rare example of catalyst-controlled C(sp3)-H arylation using pyridine and quinoline derivatives: the former promotes exclusive monoarylation, whereas the latter activates the catalyst further to achieve diarylation. Successive application of these ligands enables the sequential diarylation of a methyl group in an alanine derivative with two different aryl iodides, affording a wide range of β-Ar-p-Ar ' -cc-amino acids with excellent levels of diastereoselectivity (d.r. > 20:1). Both configurations of the β-chiral center can be accessed by choosing the order in which the aryl groups are installed. The use of a quinoline derivative as a ligand also enables C(sp3)-H olefination of a protected alanine.