868659-09-0

Basic information

• Product Name: C₁₂H₁₃NO₄
• Synonyms: C₁₂H₁₃NO₄
• CAS NO: 868659-09-0
• Molecular Weight: 235.24
• Mol File: 868659-09-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: C₁₂H₁₃NO₄(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₂H₁₃NO₄(868659-09-0)
• EPA Substance Registry System: C₁₂H₁₃NO₄(868659-09-0)

Safety Data

• Hazardous Substances Data: 868659-09-0(Hazardous Substances Data)

Upstream product

• 5680-79-5 glycine ethyl ester hydrochloride 
• 1571-08-0 methyl 4-formylbenzoate 

Relevant articles and documents

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.

Application of the Cu(i)/TEMPO/O2 catalytic system for aerobic oxidative dehydrogenative aromatization of pyrrolidines

A Cu(i)/TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy)-catalyzed aerobic oxidative dehydrogenative aromatization reaction of fully saturated pyrrolidines to synthesize multi-substituted pyrroles was developed for the first time. The use of a non-precious metal catalyst, green oxidant and environmentally friendly solvent made the reaction more sustainable.