37577-22-3

Usage

Uses

Used in Medicinal Chemistry:
(R)-1-(3-TRIFLUOROMETHYLPHENYL)-2-AMINOPROPANE is used as a pharmacological agent for its potential role in the development of new drugs, given its unique structure and properties that may contribute to novel therapeutic effects.
Used in Synthesis of Biologically Active Molecules:
In the field of organic chemistry, (R)-1-(3-TRIFLUOROMETHYLPHENYL)-2-AMINOPROPANE serves as a building block for the synthesis of other biologically active molecules, leveraging its distinct chemical features to create compounds with specific biological activities.
Used in Research and Development:
(R)-1-(3-TRIFLUOROMETHYLPHENYL)-2-AMINOPROPANE is utilized as a valuable tool in scientific research and development, particularly in disciplines that require the exploration of new chemical entities with unique structural features and potential applications in various fields such as pharmaceuticals, materials science, and beyond.

InChI:InChI=1/C10H12F3N/c1-7(14)5-8-3-2-4-9(6-8)10(11,12)13/h2-4,6-7H,5,14H2,1H3/t7-/m1/s1

Upstream product

• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 21906-39-8 3-(trifluoromethyl)phenylacetone 
• 154140-24-6 2-chloro-1-<3-(trifluoromethyl)phenyl>propane 
• 135561-78-3 (R)-1-(3’-trifluoromethylphenyl)-2-propanol 
• 135561-77-2 (R)-2-azido-1-<3-(trifluoromethyl)phenyl>propane 

Relevant academic research and scientific papers

METHOD FOR TREATING EPILEPSY

In certain embodiments, the present disclosure is directed to methods and uses for treating a mammal having an epileptic seizure disorder or being at risk for having an epileptic seizure disorder, comprising administering certain herein disclosed isolated fenfluramine enantiomers that are surprisingly effective as anti-epilepsy drugs (AEDs), despite having lower anti-seizure potency than fenfluramine racemate, by virtue of also being less cardiotoxic than fenfluramine racemate. Preferred embodiments contemplate treatment of Dravet syndrome; other preferred embodiments contemplate treatment of other epileptic seizure disorders.

Amine dehydrogenases: Efficient biocatalysts for the reductive amination of carbonyl compounds

Amines constitute the major targets for the production of a plethora of chemical compounds that have applications in the pharmaceutical, agrochemical and bulk chemical industries. However, the asymmetric synthesis of α-chiral amines with elevated catalytic efficiency and atom economy is still a very challenging synthetic problem. Here, we investigated the biocatalytic reductive amination of carbonyl compounds employing a rising class of enzymes for amine synthesis: amine dehydrogenases (AmDHs). The three AmDHs from this study-operating in tandem with a formate dehydrogenase from Candida boidinii (Cb-FDH) for the recycling of the nicotinamide coenzyme-performed the efficient amination of a range of diverse aromatic and aliphatic ketones and aldehydes with up to quantitative conversion and elevated turnover numbers (TONs). Moreover, the reductive amination of prochiral ketones proceeded with perfect stereoselectivity, always affording the (R)-configured amines with more than 99% enantiomeric excess. The most suitable amine dehydrogenase, the optimised catalyst loading and the required reaction time were determined for each substrate. The biocatalytic reductive amination with this dual-enzyme system (AmDH-Cb-FDH) possesses elevated atom efficiency as it utilizes the ammonium formate buffer as the source of both nitrogen and reducing equivalents. Inorganic carbonate is the sole by-product.

Syntheses of (S)-fenfluramine from (R) or (S)-1-propan-2-ol

(R) and (S)-1-propan-2-ol 3 are useful intermediates in the synthesis of fenfluramine (S)-1.They can be obtained from optically active propylene oxide (R) or (S)-7.The alcohol (R)-3 was transformed in two steps into (S)-fenfluramine using the action of ethylamine on a sulfonate (R)-4.We describe a new one-pot synthesis for (S)-fenfluramine from the azide (S)-5, which was obtained from the alcohol (R)-3 in two steps.We also propose an original and rapid procedure to transform the alcohol (S)-3 into (S)-fenfluramine via the chloride (R)-14 and the azide (S)-5, without preliminary inversion of the alcohol.All of these reactions have been achieved without any loss of chirality.Keywords - 1-propan-2-ol / fenfluramine / asymmetric synthesis / chiral methyloxirane / nucleophilic substitution