66644-69-7

Usage

InChI:InChI=1/C11H12O4/c1-3-15-11(13)10(12)8-6-4-5-7-9(8)14-2/h4-7H,3H2,1-2H3

Upstream product

• 95-92-1 oxalic acid diethyl ester 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 4755-77-5 Ethyl oxalyl chloride 
• 100-66-3 methoxybenzene 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 623-49-4 ethyl cyanoformate 
• 578-57-4 2-bromoanisole 
• 75716-82-4 imidazol-1-yl-oxo-acetic acid ethyl ester 
• 41024-43-5 ethyl α-hydroxy-α-(o-methoxyphenyl)acetate 
• 16750-63-3 2-methoxyphenylmagnesium bromide 
• 7035-03-2 2-methoxy-benzeneacetonitrile 
• 142682-69-7 ethyl 2-(2-methoxyphenyl)acetimidate hydrochloride 
• 139507-52-1 monoethoxyoxalic acid N-methoxy-N-methylamide 
• 6957-89-7 Ethyl dichloro-(ethoxy)-acetate 

Downstream Products

• 41024-43-5 ethyl α-hydroxy-α-(o-methoxyphenyl)acetate 
• 85905-77-7 (2-Methoxy-phenyl)-triethylsilanyloxy-acetic acid ethyl ester 
• 85905-81-3 (Dibutyl-ethyl-silanyloxy)-(2-methoxy-phenyl)-acetic acid ethyl ester 
• 85905-85-7 (2-Methoxy-phenyl)-triisobutylsilanyloxy-acetic acid ethyl ester 
• 131391-97-4 (E)-2,3-Bis-(2-methoxy-phenyl)-acrylic acid ethyl ester 
• 131391-96-3 (E)-2,3-Bis-(2-methoxy-phenyl)-acrylic acid tert-butyl ester 
• 13130-21-7 3-(2-hydroxyphenyl)-2H-chromen-2-one 
• 1196988-56-3 C₁₁H₁₄O₄ 
• 352030-18-3 C₁₆H₁₄ClNO₃ 
• 27993-89-1 3-(2-methoxy-phenyl)-1H-quinoxalin-2-one 
• 1255772-30-5 3-(2-methoxyphenyl)-2H-benzo[b][1,4]oxazin-2-one 
• 1247201-08-6 ethyl 2-hydroxy-2-(o-methoxyphenyl)propanoate 
• 65709-27-5 2-(2-Methoxyphenyl)piperazine 

Relevant academic research and scientific papers

MAXI-K POTASSIUM CHANNEL OPENERS FOR THE TREATMENT OF FRAGILE X ASSOCIATED DISORDERS

The present invention relates to the compounds of formula (I) and pharmaceutical compositions containing these compounds. The compounds provided herein can act as maxi-K potassium channel openers, which makes them suitable for use in therapy, particularly in the treatment or prevention of fragile X associated disorders, such as fragile X syndrome.

Selective Acylation of Aryl- A nd Heteroarylmagnesium Reagents with Esters in Continuous Flow

A selective acylation of readily accessible organomagnesium reagents with commercially available esters proceeds at convenient temperatures and short residence times in continuous flow. Flow conditions allow us to prevent premature collapse of the hemiacetal intermediates despite noncryogenic conditions, thus furnishing ketones in good yields. Throughout, the coordinating ability of the ester and/or Grignard was crucial for the reaction outcome. This was leveraged by the obtention of several bisaryl ketones using 2-hydroxy ester derivatives as substrates.

PROCESSES FOR PREPARING ACC INHIBITORS AND SOLID FORMS THEREOF

The present disclosure provides solid forms, including a salt or co-crystal, of Compound I which exhibits Acetyl-CoA carboxylase ("ACC") inhibitory activity and may be useful in treating ACC mediated diseases. Also provided herein are processes or steps f

Discovery of novel 2-(3-phenylpiperazin-1-yl)-pyrimidin-4-ones as glycogen synthase kinase-3β inhibitors

We herein describe the results of further evolution of glycogen synthase kinase (GSK)-3β inhibitors from our promising compounds containing a 2-phenylmorpholine moiety. Transformation of the morpholine moiety into a piperazine moiety resulted in potent GSK-3β inhibitors. SAR studies focused on the phenyl moiety revealed that a 4-fluoro-2-methoxy group afforded potent inhibitory activity toward GSK-3β. Based on docking studies, new hydrogen bonding between the nitrogen atom of the piperazine moiety and the oxygen atom of the main chain of Gln185 has been indicated, which may contribute to increased activity compared with that of the corresponding phenylmorpholine analogues. Effect of the stereochemistry of the phenylpiperazine moiety is also discussed.

Copper(II)-Catalyzed Benzylic C(sp3)-H Aerobic Oxidation of (Hetero)Aryl Acetimidates: Synthesis of Aryl-α-ketoesters

A straightforward method is developed in this paper for the synthesis of α-ketoesters through copper-catalyzed aerobic oxidation of (hetero)aryl acetimidates using molecular oxygen as a sustainable oxidant. The reaction represents the first example of the direct synthesis of aryl-α-ketoesters from arylacetimidates through the aerobic oxidation of a benzylic C(sp3)-H (CO) bond in moderate to good yield. This transformation occurs under mild reaction conditions with a wide range of substrates and utilizes a readily available oxidant and catalyst. The synthetic utility of this transformation is demonstrated through scaled-up synthesis. A plausible reaction mechanism is also proposed.

New gas-phase domino processes leading to benzopyranones and benzofurans

A new domino approach to flavones by gas phase pyrolysis of β,γ-dioxophosphonium ylides containing a 2-methoxyphenyl group is frustrated by unexpected and novel decarbonylation of the intermediate flavon-3-yl radical leading to 2-phenylbenzofuran. Alternative approaches based on dioxolane protection of one carbonyl, or selective elimination in β,β′-dioxo or β-oxo-β′-thioxo ylides were not successful, but pyrolysis of a β-oxo-β′-phenylimino ylide did give the required domino reaction leading to a protected benzopyranone in moderate yield.

Asymmetric Hydrogenation of α-Substituted Acrylic Acids Catalyzed by a Ruthenocenyl Phosphino-oxazoline-Ruthenium Complex

Asymmetric hydrogenation of various α-substituted acrylic acids was carried out using RuPHOX-Ru as a chiral catalyst under 5 bar H2, affording the corresponding chiral α-substituted propanic acids in up to 99% yield and 99.9% ee. The reaction could be performed on a gram-scale with a relatively low catalyst loading (up to 5000 S/C), and the resulting product (97%, 99.3% ee) can be used as a key intermediate to construct bioactive chiral molecules. The asymmetric protocol was successfully applied to an asymmetric synthesis of dihydroartemisinic acid, a key intermediate required for the industrial synthesis of the antimalarial drug artemisinin.

Reactions of organolithiums with dialkyl oxalates. A flow microreactor approach to synthesis of functionalized α-keto esters

Reactions of functionalized aryllithiums with dialkyl oxalates were achieved using a flow microreactor to obtain α-keto esters with high selectivity by virtue of fast 1:1 micromixing.

Highly homogeneous stereocontrolled construction of quaternary hydroxyesters by addition of dimethylzinc to α-ketoesters promoted by chiral perhydrobenzoxazines and B(OEt)3

A highly efficient enantioselective addition of Me2Zn to α-ketoesters, assisted by a chiral perhydro-1,3-benzoxazine ligand, is described. This novel catalytic system offers homogeneous elevated enantioselectivities in the preparation of α-hydroxyesters that bear a quaternary stereocenter, with a minor dependence on electronic and steric effects when aromatic, heteroaromatic, or aliphatic α-ketoesters are employed. The catalyst can be recovered and reused without loss of activity.

Enantioselective enolate protonation in sulfamichael addition to r-substituted n-acryloyloxazolidin-2-ones with bifunctional organocatalyst

Organocatalytic conjugate addition of thiols to R-substituted N-acryloyloxazolidin-2-ones followed by asymmetric protonation has been studied in the presence of cinchona alkaloid derived thioureas. Both of the enantiomers are accessible with the same level of enantioselectivity using pseudoenantiomeric quinine/quinidine derived catalysts. The addition/protonation products have been converted to useful biologically active molecules. 2011 American Chemical Society.