141178-32-7

Basic information

• Product Name: (1-PHENYL-PROPYL)-CARBAMIC ACID METHYL ESTER
• Synonyms: (1-PHENYL-PROPYL)-CARBAMIC ACID METHYL ESTER;Methyl (1-phenylpropyl)carbaMate
• CAS NO: 141178-32-7
• Molecular Formula: C11H15NO2
• Molecular Weight: 193.2423
• Mol File: 141178-32-7.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1-PHENYL-PROPYL)-CARBAMIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (1-PHENYL-PROPYL)-CARBAMIC ACID METHYL ESTER(141178-32-7)
• EPA Substance Registry System: (1-PHENYL-PROPYL)-CARBAMIC ACID METHYL ESTER(141178-32-7)

Safety Data

• Hazardous Substances Data: 141178-32-7(Hazardous Substances Data)

Usage

General Description

(1-Phenyl-propyl)-carbamic acid methyl ester, also known as fenethylline, is a synthetic compound that acts as a central nervous system stimulant. It is a prodrug of amphetamine and theophylline, and has been used as a psychostimulant and anorectic agent. Its effects include increased alertness, improved mood, and decreased fatigue. However, due to its potential for abuse and addiction, fenethylline is a controlled substance in many countries and is not approved for medical use in most of the world. It has a high potential for misuse and dependence, and its use can lead to serious health consequences and legal ramifications.

Upstream product

• 2941-20-0 1-phenylpropylamine 
• 79-22-1 methyl chloroformate 
• 67-56-1 methanol 
• 90-26-6 2-phenylbutyramide 
• 21962-56-1 1-phenylpropyl isocyanate 
• 97-94-9 triethyl borane 
• 27593-61-9 benzylidene-carbamic acid methyl ester 
• 86766-76-9 Methyl N-(1-Phenyl-1-propenyl)carbamate 
• 93-55-0 1-phenyl-propan-1-one 

Relevant articles and documents

Computationally Aided Absolute Stereochemical Determination of Enantioenriched Amines

A simple and efficient protocol for sensing the absolute stereochemistry and enantiomeric excess of chiral monoamines is reported. Preparation of the sample requires a single-step reaction of the 1,1′-(bromomethylene)dinaphthalene (BDN) with the chiral amine. Analysis of the exciton coupled circular dichroism generated from the BDN-derivatized chiral amine sample, along with comparison to conformational analysis performed computationally, yields the absolute stereochemistry of the parent chiral monoamine.

Combined Theoretical and Experimental Studies Unravel Multiple Pathways to Convergent Asymmetric Hydrogenation of Enamides

We present a highly efficient convergent asymmetric hydrogenation of E/Z mixtures of enamides catalyzed by N,P-iridium complexes supported by mechanistic studies. It was found that reduction of the olefinic isomers (E and Z geometries) produces chiral amides with the same absolute configuration (enantioconvergent hydrogenation). This allowed the hydrogenation of a wide range of E/Z mixtures of trisubstituted enamides with excellent enantioselectivity (up to 99% ee). A detailed mechanistic study using deuterium labeling and kinetic experiments revealed two different pathways for the observed enantioconvergence. For α-aryl enamides, fast isomerization of the double bond takes place, and the overall process results in kinetic resolution of the two isomers. For α-alkyl enamides, no double bond isomerization is detected, and competition experiments suggested that substrate chelation is responsible for the enantioconvergent stereochemical outcome. DFT calculations were performed to predict the correct absolute configuration of the products and strengthen the proposed mechanism of the iridium-catalyzed isomerization pathway.

(Tosylimino)phenyl-λ3-iodane as a reagent for the synthesis of methyl carbamates via hofmann rearrangement of aromatic and aliphatic carboxamides

A new, mild procedure for the Hofmann rearrangement of aromatic and aliphatic carboxamides using (tosylimino)phenyl-λ3-iodane, PhINTs, as a reagent is reported. Because of the mild reaction conditions, this method is particularly useful for the Hofmann rearrangement of substituted benzamides, which usually afford complex reaction mixtures with other hypervalent iodine oxidants. The mild reaction conditions and high selectivity in the reaction of carboxamides with PhINTs allow the isolation of the initially formed labile isocyanates or their subsequent conversion to stable carbamates by treatment with alcohols.