19302-32-0

Basic information

• Product Name: Benzenemethanamine, a-methyl-N-(1-methylethyl)-, (S)-
• Synonyms: (S)-N-(1-phenylethyl)-1-methylethylamine;S(-)-N-isopropyl-α-methylbenzylamine;S-N-isopropyl-α-methylbenzylamine;(S)-N-(isopropyl)-α-phenylethylamine;(-)-N-isopropyl-(1S)-1-phenylethylamine
• CAS NO: 19302-32-0
• Molecular Formula: C11H17N
• Molecular Weight: 163.263
• Mol File: 19302-32-0.mol

Chemical Properties

• CAS DataBase Reference: Benzenemethanamine, a-methyl-N-(1-methylethyl)-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanamine, a-methyl-N-(1-methylethyl)-, (S)-(19302-32-0)
• EPA Substance Registry System: Benzenemethanamine, a-methyl-N-(1-methylethyl)-, (S)-(19302-32-0)

Safety Data

• Hazardous Substances Data: 19302-32-0(Hazardous Substances Data)

Upstream product

• 75-30-9 2-iodo-propane 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 132273-96-2 (1S,1'R)-N-isopropyl-N-2'-hydroxy-1'-phenylethyl-1-phenylethylamine 
• 67-64-1 acetone 
• 618-36-0 rac-methylbenzylamine 
• 75-26-3 isopropyl bromide 
• 75815-80-4 (1S)-N-(1-methylethylidene)-1-phenylethylamine 
• 112211-92-4 (R)-N-(2-Hydroxy-1-phenylethyl)-N-isopropylamine 
• 132273-89-3 (2R,4R)-N-isopropyl-2-methyl-4-phenyl-1,3-oxazolidine 
• 108-18-9 diisopropylamine 
• 947503-92-6 N-(1-phenylethylidene)-2-propanamine 
• 98-86-2 acetophenone 
• 2627-86-3 (-)-α-methylbenzylamine 

Downstream Products

• 92973-56-3 S-(-)-N-methyl-N-isopropyl-α-phenylethylamine 
• 361459-12-3 (S)-2-[N-(1-phenylethyl)-N-isopropylamino]carbonylacetic acid 
• 832096-95-4 (+/-)-N-[1-(2-iodophenyl)-ethyl]-N-isopropyl acetamide 
• 832096-89-6 N-[(1S)-1-(2-iodophenyl)ethyl]-N-isopropyl-2-chloroquinoline-3-carboxamide 
• 89218-01-9 [(E)-2-(Diphenyl-phosphinoyl)-vinyl]-isopropyl-(1-phenyl-ethyl)-amine 

Relevant articles and documents

Design of new axially chiral NADH mimics. Mechanistic investigation of the enantioselective hydride transfer

This paper reports the design of a new axially chiral NADH model which relies on the configurational control around the C3-C=O chiral axis by means of a chiral relay installed on the cyclic structure. The conformational and configurational control of the

USEFUL CHIRAL LACTONES DERIVED FROM CIS-BICYCLOOCTAN-3,7-DIONE VIA ASYMMETRIC DEPROTONATION

The monoketal derived from cis-bicyclooctane-3,7-dione was deprotonated using chiral lithium amide bases and the enolates were trapped as either enol acetates or trimethylsilyl enol ethers.Oxidative cleavage of the enol derivatives provided useful

Continuous Flow Chiral Amine Racemization Applied to Continuously Recirculating Dynamic Diastereomeric Crystallizations

A new, dynamic diastereomeric crystallization method has been developed, in which the mother liquors are continuously separated, racemized over a fixed-bed catalyst, and recirculated to the crystallizer in a resolution-racemization-recycle (R3) process. S

Enantioselective reduction of: N -alkyl ketimines with frustrated Lewis pair catalysis using chiral borenium ions

Enantioselective reduction of ketimines was demonstrated using chiral N-heterocyclic carbene (NHC)-stabilised borenium ions in frustrated Lewis pair catalysis. High levels of enantioselectivity were achieved for substrates featuring secondary N-alkyl substituents. Comparative reactivity and mechanistic studies identify key determinants required to achieve useful enantioselectivity and represent a step forward in the further development of enantioselective FLP methodologies.

Diastereoselective desymmetrization of diarylphosphinous acid-borane amides under Birch reduction

Treatment of diarylphosphinous acid-borane amides possessing chiral amido functionality with an alkali metal solution in liquid ammonia induced a preferential dearomatization of one aryl substituent at phosphorus leading to the formation of non-equimolar amounts of diastereomers. Diastereoselectivity of dearomatization depends strongly on the structure of a chiral auxiliary.

Efficient, selective, and green: Catalyst tuning for highly enatioselective reactions of ethylene

Fine tuning of the biaryl and amino moieties of Feringa's phosphoramidite ligands yields structurally simpler, yet more efficient and selective, ligands for asymmetric hydrovinylation of vinylarenes and acylic 1,3-dienes. The enantioselectivities and yields observed in the formation of the 3-arylbutenes are among the highest for all asymmetric catalytic processes reported to date for the synthesis of intermediates for the widely used antiinflammatory 2-arylpropionic acids including naproxen, ibuprofen, fenoprofen, and flurbiprofen.

Synthesis and dynamics of atropisomeric (S)-N-(α-phenylethyl)benzamides

The synthesis of atropisomeric 2-substituted benzamides 2a-e, 3a-e, and 4a-e, and characterization by X-ray structure analysis of 2d, 2e, 3c, 3e, 4c, and 4e are reported. Dynamic 1H NMR spectroscopic studies of benzamides 2b-d, 3b-d, and 4b-d i

Preparation of axially chiral quinolinium salts related to NAD+ models: New investigations of these biomimetic models as 'chiral amide-transferring agents'

The general purpose of this work is to investigate the potential of biomimetic NAD+ models as 'nucleophile-transferring agents' with the ultimate motivation to develop new synthetic tools. This first report focuses on the preparation of an axially chiral quinolinium salt 8. A preliminary investigation of these NAD+ analogues as 'chiral amide-transferring agents' is reported herein. The synthesis of the desired quinolinium salt 8 was first attempted via a Friedlaender approach. Given the poor reproducibility of this first synthetic route, a second strategy making use of an intramolecular nickel-catalyzed coupling was developed with success, furnishing the quinolinium salt 8 in 12% overall yield. The potential of the quinolinium salt 8 as a 'chiral amide-transferring agent' was then investigated. Regioselective 1,4-addition of benzylamine and piperidine produced, respectively, adducts 18a and 18b with high diastereoselectivity (de >95%). The resulting 'chiral masked-amide' 18b was reacted with various activated aryl esters affording the corresponding atropisomeric amide 20 with modest atropenantioselectivity (ee = 2-20%).

Diastereoselective carbozincation of propargylic amines

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Enantioselective Deprotonation of Benzyl Phosphates by Homochiral Lithium Amide Bases - Configurational Stability of Benzyl Carbanions with a Dialkoxyphosphoryloxy Substituent and Their Rearrangement to Optically Active α-Hydroxy Phosphonates

Benzyl dialkyl phosphates are deprotonated enantioselectively by homochiral lithium amides of isopropyl(1-phenylethyl)amine or bis(1-phenylethyl)amine.The short-lived benzylic carbanions formed are virtually configurationally stable relative to the rearrangement to optically active phenylhydroxymethylphosphonates.The enantiomeric excesses are up to 50percent.The pro-(S) hydrogen is removed by amides having (S) configuration.Homochiral diethyl (S)-phenylmethyl phosphate is deprotonated by both LDA and n-BuLi with a high primary kinetic isotope effect (kH/D ca. 50) and isomerizes to the corresponding α-hydroxy phosphonate with an enantiomeric excess of up to 85percent. - Keywords: Phosphate-phosphonate rearrangement / Carbanions, benzylic, configurational stability of / Phosphonates / Lithium amides, homochiral