77486-09-0

Basic information

• Product Name: Acetic acid, [oxido(phenylmethyl)imino]-, methyl ester, (2Z)-
• CAS NO: 77486-09-0
• Molecular Formula: C10H11NO3
• Molecular Weight: 193.202
• Mol File: 77486-09-0.mol

Chemical Properties

• CAS DataBase Reference: Acetic acid, [oxido(phenylmethyl)imino]-, methyl ester, (2Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid, [oxido(phenylmethyl)imino]-, methyl ester, (2Z)-(77486-09-0)
• EPA Substance Registry System: Acetic acid, [oxido(phenylmethyl)imino]-, methyl ester, (2Z)-(77486-09-0)

Safety Data

• Hazardous Substances Data: 77486-09-0(Hazardous Substances Data)

Upstream product

• 109745-70-2 methyl glyoxylate methyl hemi-acetal 
• 622-30-0 N-benzyl hydroxylalmine 
• 53386-64-4 methyl 2-(benzylamino)acetate 
• 100-46-9 benzylamine 
• 77486-09-0 (Z)-N-benzyl-α-methoxycarbonylmethanimine N-oxide 
• 29601-98-7 N-benzylhydroxylamine hydrochloride 
• 922-68-9 Methyl glyoxylate 

Downstream Products

• 119680-68-1 methyl N-benzyl-5-<<(benzyloxycarbonyl)amino>methyl>isoxazolidine-3-carboxylate 
• 1340600-95-4 C₁₄H₁₀⁽²⁾H₇NO₄ 
• 1340600-97-6 C₁₄H₁₆⁽²⁾HNO₄ 
• 1316673-94-5 N-benzylidene-1-(tert-butoxy)-2-methoxy-2-oxoethanamine N-oxide 
• 1316673-35-4 N-benzylidene-2-methoxy-2-oxo-1-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)ethanamine N-oxide 
• 1316673-88-7 N-benzylidene-2-methoxy-2-oxo-1-(4,4,5,5-tetramethyl-2-(pent-4-en-1-yl)-1,3-dioxolan-2-yl)ethanamine N-oxide 
• 1316673-90-1 N-benzylidene-1-methoxy-1-oxo-3-(2,2,3,3-tetramethyl-1,4-dioxaspiro[4.4]nonan-6-yl)propan-2-amine N-oxide 
• 1316673-54-7 N-benzylidene-2-methoxy-1-(1-methoxycyclopentyl)-2-oxoethanamine N-oxide 
• 1316673-55-8 N-benzylidene-3-(cyclopentyloxy)-1-methoxy-1-oxopropan-2-amine N-oxide 
• 1316673-73-0 N-benzylidene-1-methoxy-3-(methyl(phenyl)amino)-1-oxopropan-2-amine N-oxide 

Relevant articles and documents

Dynamics in Catalytic Asymmetric Diastereoconvergent (3 + 2) Cycloadditions with Isomerizable Nitrones and α-Keto Ester Enolates

Reaction design in asymmetric catalysis has traditionally been predicated on a structurally robust scaffold in both substrates and catalysts, to reduce the number of possible diastereomeric transition states. Herein, we present the stereochemical dynamics in the Ni(II)-catalyzed diastereoconvergent (3 + 2) cycloadditions of isomerizable nitrile-conjugated nitrones with α-keto ester enolates. Even in the presence of multiple equilibrating species, the catalytic protocol displays a wide substrate scope to access a range of CN-containing building blocks bearing adjacent stereocenters with high enantio- and diastereoselectivities. Our computational investigations suggest that the enantioselectivity is governed in the deprotonation process to form (Z)-Ni-enolates, while the unique syn addition is mainly controlled by weak noncovalent bonding interactions between the nitrone and ligand.

Catalytic migratory oxidative coupling of nitrones

A Cu(I)-catalyzed migratory oxidative coupling between nitrones and heterocycles or a methylamine is described. Selective C-C bond-formation proceeds through cleavage of two C(sp3)-H bonds concomitant with C=N double bond-migration. The reaction provides an alternating nitrone moiety, allowing for further synthetically useful transformations. Radical clock studies suggest that the nucleophilic addition of nitrones to an oxidatively generated carbocation is a key step.

Studies on tandem transesterification and intramolecular cycloaddition of nitrones. 1. Sequential bicyclization of α-methoxycarbonylnitrones with allyl alcohols

Treatment of α-methoxycarbonylnitrones with 5 equiv. of allyl alcohols in the presence of 1 equiv. of titanium tetraisopropoxide causes tandem transesterification, E,Z-isomerization of the nitrone moieties, and intramolecular cycloaddition to afford bicyclized compounds in one step. To reduce amounts of allyl alcohol, combined use of a catalytic amount of titanium tetraisopropoxide and molecular sieves 4A was found to be a more improved catalytic system. It was also found that reactions of (Z)-allyl alcohols with α-methoxycarbonylnitrone are more facile than those of (E)-allyl alcohols. This aspect was extended to geometry differentiated cycloaddition.

NOVEL E-Z EQUILIBRIUM OF N-ALKYL-α-ALKOXYCARBONYLNITRONE IN SOLUTION

Four N-alkyl-α-alkoxycarbonylnitrone were prepared and their NMR specra in C6D6, CDCl3, or CD3SOCD3 were measured.From the analyses of the spectra, it was found that the nitrones exhibited a facile equilibrium in all solvents used and E/Z ratio in equilibrium depended largely on the polarity of the solvent.