286392-28-7

Basic information

• Product Name: glycine methyl ester (4-trifluoromethylbenzaldehyde)imine
• Synonyms: glycine methyl ester (4-trifluoromethylbenzaldehyde)imine
• CAS NO: 286392-28-7
• Molecular Weight: 245.201
• Mol File: 286392-28-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: glycine methyl ester (4-trifluoromethylbenzaldehyde)imine(CAS DataBase Reference)
• NIST Chemistry Reference: glycine methyl ester (4-trifluoromethylbenzaldehyde)imine(286392-28-7)
• EPA Substance Registry System: glycine methyl ester (4-trifluoromethylbenzaldehyde)imine(286392-28-7)

Safety Data

• Hazardous Substances Data: 286392-28-7(Hazardous Substances Data)

Upstream product

• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 5680-79-5 glycine ethyl ester hydrochloride 

Downstream Products

• 1166397-81-4 trimethyl (2R,3S,4R,5S)-5-(4-trifluoromethylphenyl)pyrrolidine-2,3,4-tricarboxylate 
• 1241941-54-7 methyl 4-(2,2,2-trifluoroacetyl)-5-(4-(trifluoromethyl)phenyl)-1H-pyrrole-2-carboxylate 
• 1257079-55-2 methyl (1S,3R,3aS,6aR)-3-[4-(trifluoromethyl)phenyl]-octahydro-4-oxocyclopenta[c]pyrrole-carboxylate 
• 1309923-05-4 (2R,5R)-4,4-diethyl 2-methyl 3-(2,2-diphenylvinylidene)-5-(4-(trifluoromethyl)phenyl)pyrrolidine-2,4,4-tricarboxylate 
• 1352401-92-3 methyl (2'S,3R,5'S)-1'-acetyl-2-oxo-2'-[4-(trifluoromethyl)phenyl]-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylate 
• 1373444-81-5 trimethyl (2S,3R,4S,5R)-5-(4-(trifluoromethyl)phenyl)pyrrolidine-2,3,4-tricarboxylate 
• 1384291-19-3 (2R,3R,4S,5S)-4-ethyl 2-methyl 3-(trifluoromethyl)-5-(4-(trifluoromethyl)phenyl)pyrrolidine-2,4-dicarboxylate 
• 1417912-36-7 (2R,4S,5R)-dimethyl 4-fluoro-5-(4-(trifluoromethyl)-phenyl)pyrrolidine-2,4-dicarboxylate 
• 1431318-73-8 (1'S,2S,3'R,3a'S,7a'R)-methyl 5,7'-dioxo-1'-(4-(trifluoromethyl)phenyl)-1',2',3',3a',4,5,7',7a'-octahydro-3H-spiro[furan-2,4'-isoindole]-3'-carboxylate 
• 1574239-92-1 (1S,6R,7R,9S)-methyl 10-oxo-9-(4-(trifluoromethyl)phenyl)-8-azabicyclo[4.3.1]-deca-2,4-diene-7-carboxylate 

Relevant articles and documents

Asymmetric construction of 3-vinylidene-pyrrolidine derivatives containing allene moiety via Ag(i)/TF-BiphamPhos-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with diethyl 2-(3,3-diphenylpropa-1,2-dienylidene) malonate

Catalytic asymmetric 1,3-dipolar cycloaddition of various azomethine ylides with diethyl 2-(3,3-diphenylpropa-1,2-dienylidene)malonate has been developed successfully with good to excellent enantioselectivity for the effcient construction of 3-vinylidene-pyrrolidine derivatives containing a unique allene moiety.

Well-Designed Phosphine-Urea Ligand for Highly Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition of Methacrylonitrile: A Combined Experimental and Theoretical Study

A novel chiral phosphine-urea bifunctional ligand has been developed for Cu-catalyzed asymmetric 1,3-dipolar cycloaddition of iminoesters with methacrylonitrile, a long-standing challenging substrate in asymmetric catalysis. Distortion-interaction energy analysis based on density functional theory (DFT) calculations reveals that the distortion energy plays an important role in the observed enantioselectivity, which can be attributed to the steric effect between the phosphine ligand and the dipole reactant. DFT calculations also indicate that nucleophilic addition is the enantioselectivity-determining step and hydrogen bonding between the urea moiety and methacrylonitrile assists in control of the diastereo- and enantioselectivity. By a combination of metal catalysis and organocatalysis, excellent diastereo- and enantioselectivities (up to 99:1 diastereomeric ratio, 99% enantiomeric excess) as well as good yields are achieved. A wide range of substitution patterns of both iminoester and acrylonitrile is tolerated by this catalyst system, providing access to a series of highly substituted chiral cyanopyrrolidines with up to two quaternary stereogenic centers. The synthetic utility is demonstrated by enantioselective synthesis of antitumor agent ETP69 with a pivotal nitrile pharmacophore and an all-carbon quaternary stereogenic center.

Enantiodivergent Combination of Natural Product Scaffolds Enabled by Catalytic Enantioselective Cycloaddition

An efficient strategy has been established for the enantiodivergent synthesis of natural product inspired compounds embodying both tropane and pyrrolidine natural product fragments. This strategy includes the enantioselective kinetic resolution of racemic tropanes by means of a copper(I)-catalyzed [3+2] cycloaddition and allows the preparation of two enantiopure products in a one-pot reaction in high yield and with high diastereo- and enantioselectivity by using one chiral catalyst.