924-44-7 | Ethyl glyoxalate, 50% in toluene

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Description

• Catalog Number: AB46112
• Chemical Name: Ethyl glyoxalate, 50% in toluene
• CAS Number: 924-44-7
• Molecular Formula: C4H6O3
• Molecular Weight: 102.0886
• MDL Number: MFCD00044009
• SMILES: CCOC(=O)C=O
• NSC Number: 49206

Computed Properties

• Complexity: 77
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 7
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• XLogP3: 0.4

Literature

• Applications of ortho-phenylisonitrile and ortho-N-Boc aniline for the two-step preparation of novel bis-heterocyclic chemotypes.

  Molecular diversity 20120801

• Base-catalyzed direct conversion of dipyrromethanes to 1,9-dicarbinols: a [2 + 2] approach for porphyrins.

  Organic letters 20120406

• 3-aminopiperidine-based peptide analogues as the first selective noncovalent inhibitors of the bacterial cysteine protease IdeS.

  Journal of medicinal chemistry 20120322

• Copper-catalyzed [5+1] annulation of 2-ethynylanilines with an N,O-acetal leading to construction of quinoline derivatives.

  Organic letters 20120203

• Total synthesis of (±)-streptonigrin: de novo construction of a pentasubstituted pyridine using ring-closing metathesis.

  Journal of the American Chemical Society 20111019

• A three-component reaction forming naphthyridones--synthesis of lophocladine analogs.

  Organic letters 20111007

• A straightforward one-pot multicomponent synthesis of polysubstituted pyrroles.

  Chemical communications (Cambridge, England) 20110621

• Enantioselective organocatalytic Michael-Wittig-Michael-Michael reaction: dichotomous construction of pentasubstituted cyclopentanecarbaldehydes and pentasubstituted cyclohexanecarbaldehydes.

  Organic letters 20110318

• 4-(Piperidin-1-yl)-4H-benzo[b]tetra-zolo[1,5-d][1,4]diazepin-5(6H)-one.

  Acta crystallographica. Section E, Structure reports online 20110101

• Kinetics and products of gas-phase reactions of ozone with methyl methacrylate, methyl acrylate, and ethyl acrylate.

  The journal of physical chemistry. A 20100819

• Polymeric ethyl glyoxylate in an asymmetric aldol reaction catalyzed by diarylprolinol.

  Organic letters 20100702

• A straightforward three-component synthesis of alpha-amino esters containing a phenylalanine or a phenylglycine scaffold.

  The Journal of organic chemistry 20100416

• Lewis Acid catalyzed three-component hetero-Diels-alder (povarov) reaction of N-arylimines with strained norbornene-derived dienophiles.

  The Journal of organic chemistry 20100205

• Catalytic asymmetric three-component Mannich-type reaction of alkenyl trichloroacetates.

  Organic letters 20091119

• Synthesis of (S)- and (R)-5-oxo-piperazine-2-carboxylic acid and its application to peptidomimetics.

  The Journal of organic chemistry 20091106

• Highly efficient asymmetric synthesis of 3-indolyl(hydroxy)acetates via Friedel-Crafts alkylation of indoles.

  The Journal of organic chemistry 20090904

• Asymmetric petasis reactions catalyzed by chiral biphenols.

  Journal of the American Chemical Society 20080604

• Organocatalytic synthesis of beta-alkylaspartates via beta-lactone ring opening.

  The Journal of organic chemistry 20071012

• Enol esters: versatile substrates for Mannich-type multicomponent reactions.

  Organic letters 20071011

• Highly enantioselective carbonyl-ene reactions catalyzed by a hindered silyl-salen-cobalt complex.

  Organic letters 20070927

• Enantioselective reductive coupling of 1,3-enynes to glyoxalates mediated by hydrogen: asymmetric synthesis of beta,gamma-unsaturated alpha-hydroxy esters.

  Organic letters 20070913

• The first organocatalytic carbonyl-ene reaction: isomerisation-free C-C bond formations catalysed by H-bonding thio-ureas.

  Beilstein journal of organic chemistry 20070101

• A rapid divergent synthesis of highly substituted delta-lactones.

  Organic letters 20061012

• Synthesis of novel keto-ACE analogues as domain-selective angiotensin I-converting enzyme inhibitors.

  Bioorganic & medicinal chemistry letters 20060901

• Alpha-hydroxy esters via enantioselective hydrogen-mediated C-C coupling: regiocontrolled reactions of silyl-substituted 1,3-diynes.

  Organic letters 20060817

• 2-Methyl-(1Z,3E)-butadiene-1,3,4-tricarboxylic acid, 'isoprenetricarboxylic acid'.

  The Journal of organic chemistry 20050902

• Domino coupling relay approach to polycyclic pyrrole-2-carboxylates.

  Journal of the American Chemical Society 20050810

• Self-supported heterogeneous titanium catalysts for enantioselective carbonyl-ene and sulfoxidation reactions.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20050704

• Diastereoselective reductive imino-aldol reaction of alpha-imino esters promoted by titanium tetraiodide: synthesis of alpha,beta-diamino esters.

  Organic & biomolecular chemistry 20050621

• Synthetic studies toward ecteinascidin 743.

  The Journal of organic chemistry 20050527

• Synthesis of the C11-C29 fragment of amphidinolide F.

  Organic letters 20041014

• New taxane derivatives: synthesis of baccatin[14,1-d]furan-2-one nucleus and its condensation with the norstatine side chain.

  The Journal of organic chemistry 20041001

• Highly diastereo- and enantioselective reactions of enecarbamates with ethyl glyoxylate to give optically active syn and anti alpha-alkyl-beta-hydroxy imines and ketones.

  Angewandte Chemie (International ed. in English) 20040621

• The Direct catalytic asymmetric cross-Mannich reaction: a highly enantioselective route to 3-amino alcohols and alpha-amino acid derivatives.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20040419

• Highly enantioselective Friedel-Crafts reaction of aromatic amines with ethyl glyoxylate catalyzed by chiral titanium(IV) complexes: practical synthesis of aminomandelic acid derivatives.

  The Journal of organic chemistry 20040109

• Solid-phase synthesis of 1-substituted tetrahydroisoquinoline derivatives employing BOC-protected tetrahydroisoquinoline carboxylic acids.

  Journal of combinatorial chemistry 20040101

• Polymer-supported bisBINOL ligands for the immobilization of multicomponent asymmetric catalysts.

  Organic letters 20030724

• A convenient and scalable synthesis of ethyl N-[(2-Boc-amino)ethyl]glycinate and its hydrochloride. Key intermediates for peptide nucleic acid synthesis.

  The Journal of organic chemistry 20030221

• C(2)-symmetric Sc(III)-complexes as chiral Lewis acids. Catalytic enantioselective aldol additions to glyoxylate esters.

  Organic letters 20021003

• On the intermediates in chiral bis(oxazoline)copper(II)-catalyzed enantioselective reactions--experimental and theoretical investigations.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20020415

• Cycloaddition reaction of 2-azadienes derived from beta-amino acids with electron-rich and electron-deficient alkenes and carbonyl compounds. Synthesis of pyridine and 1,3-oxazine derivatives.

  The Journal of organic chemistry 20020405