104942-85-0

Basic information

• Product Name: (R)-(+)-N-1-phenylethyl-N-trimethylsilylmethylamine
• Synonyms: (R)-(+)-N-1-phenylethyl-N-trimethylsilylmethylamine
• CAS NO: 104942-85-0
• Molecular Weight: 207.391
• Mol File: 104942-85-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 242.2±15.0 °C(Predicted)
• Density: 0.887±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (R)-(+)-N-1-phenylethyl-N-trimethylsilylmethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-N-1-phenylethyl-N-trimethylsilylmethylamine(104942-85-0)
• EPA Substance Registry System: (R)-(+)-N-1-phenylethyl-N-trimethylsilylmethylamine(104942-85-0)

Safety Data

• Hazardous Substances Data: 104942-85-0(Hazardous Substances Data)

Usage

General Description

(R)-(+)-N-1-phenylethyl-N-trimethylsilylmethylamine is a chemical compound with the molecular formula C13H21NSi. It is a chiral amine that is commonly used as a reagent in organic synthesis. The compound contains a phenyl group and a trimethylsilylmethyl group attached to a nitrogen atom, which makes it a versatile building block for the synthesis of various organic molecules. It is often used in asymmetric catalysis and as a chiral auxiliary in the preparation of pharmaceuticals and other biologically active molecules. The compound is also known for its ability to facilitate the stereoselective synthesis of complex organic compounds.

Upstream product

• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 2344-80-1 Chloromethyltrimethylsilane 

Downstream Products

• 133407-38-2 (R)-N-(1-phenylethyl)-N-(methoxymethyl)-N-(trimethylsilylmethyl)amine 
• 134139-07-4 (R)-(+)-N-1-phenylethyl-N-(butoxymethyl)trimethylsilylmethylamine 
• 134139-14-3 (3S,4R)-3-butoxycarbonyl-1-<(R)-1-phenylethyl>-1-azoniabicyclo<2.2.1>heptane bromide 
• 134139-14-3 (3R,4S)-3-butoxycarbonyl-1-<(R)-1-phenylethyl>-1-azoniabicyclo<2.2.1>heptane bromide 
• 134139-13-2 (3S,4R)-3-propoxycarbonyl-1-<(R)-1-phenylethyl>-1-azoniabicyclo<2.2.1>heptane bromide 
• 134139-20-1 (3R,4S)-3-propoxycarbonyl-1-<(R)-1-phenylethyl>-1-azoniabicyclo<2.2.1>heptane bromide 
• 133407-40-6 (3S,4R)-3-ethoxycarbonyl-1-<(R)-1-phenylethyl>-1-azoniabicyclo<2.2.1>heptane bromide 
• 135821-85-1 (3R,4S)-3-ethoxycarbonyl-1-<(R)-1-phenylethyl>-1-azoniabicyclo<2.2.1>heptane bromide 
• 133407-39-3 (3aS,7aR)-2-<(R)-1-phenylethyl>-perhydropyrano<3,4-c>pyrrol-4-one 
• 134234-14-3 (3aR,7aS)-2-<(R)-1-phenylethyl>-perhydropyrano<3,4-c>pyrrol-4-one 
• 133407-39-3 2-<(R)-1-phenylethyl>-perhydropyrano<3,4-c>pyrrol-4-one 

Relevant articles and documents

Non-stabilized azomethine ylides in [3 + 2] cycloadditions. Pyrrolidinylfuranones from (5S)-5-menthyloxy-4-vinylfuran-2(5H)-one

Upon sonication with lithium fluoride in acetonitrile N-benzyl-N-methoxymethyl(trimethylsilylmethyl)amines 9a-c undergo chemoselective 1,3-dipolar cycloaddition with 4-vinylfuranones 2 and 6 to afford pyrrolidinylfuranones 10, 11a-c and 12a-c. The stereochemistry is assigned by X-ray analyses and proton NMR data comparison of related oxiranylfuranone 13.

Single and double diastereoselection in azomethine ylide cycloaddition reactions with unsaturated chiral bicyclic lactams

Double diastereoselectivity data were analyzed to provide insight into the structural features that influence π-facial selectivity in 1,3-dipolar cycloadditions of chiral and achiral azomethine ylides to chiral, unsaturated bicyclic lactams. Three major steric contributions to the differences in stability (ΔΔG(≠)) between competing cycloaddition transition states were identified. The first major set of steric interactions involve that between the dipoles and the substituents on the left hemisphere (R2) and concave faces of the bicyclic lactams. This effectively hindered both α- and β-approaches in the nonextended transition states. The second major steric interaction was provided by the nonbonded interactions (i) between the R1 angular substituent on the bicyclic lactam and the π-system of the dipole. This interaction was shown to be very significant, causing reversal in π-facial attack of chiral and achiral dipoles when the angular substituent is changed from phenyl or methyl to hydrogen. The high diastereoselectivity observed now opens a route to highly substituted chiral, nonracemic pyrrolidines.