65245-10-5

Usage

InChI:InChI=1/C10H10O4/c11-8(6-9(12)10(13)14)7-4-2-1-3-5-7/h1-5,9,12H,6H2,(H,13,14)

Upstream product

• 14274-07-8 methyl 3-benzoylacrylate 
• 98-86-2 acetophenone 
• 298-12-4 Glyoxilic acid 
• 7647-01-0 hydrogenchloride 
• 583-06-2 3-benzoylacrylic acid 
• 7664-93-9 sulfuric acid 
• 13505-41-4 4,4,4-trichloro-3-hydroxy-1-phenylbutan-1-one 
• 19522-28-2 (Z)-4-oxo-4-phenyl-but-2-enoic acid methyl ester 
• 14274-07-8 methyl trans-β-benzoylacrylate 
• 563-96-2 2,2-dihydroxyacetic acid 
• 53515-22-3 3-bromo-4-oxo-4-phenylbutanoic acid 
• 90798-09-7 α-chloro-β-benzoylpropionic acid 
• 7732-18-5 water 
• 108-31-6 maleic anhydride 

Downstream Products

• 70529-47-4 hydroxy-4 phenyl-6 pyridazinone-3 
• 583-06-2 3-benzoylacrylic acid 
• 144-62-7 oxalic acid 
• 98-86-2 acetophenone 
• 298-12-4 Glyoxilic acid 
• 2166-31-6 6-phenylpyridazin-3(2H)-one 
• 51841-95-3 6-phenyl-3(2H)-pyridazinethione 
• 244090-26-4 2-phenyl-5,6,7,8-tetrahydroquinoline-4-carboxylic acid 
• 244090-25-3 methyl 2-phenyl-5,6,7,8-tetrahydroquinoline-4-carboxylate 
• 14274-07-8 methyl trans-β-benzoylacrylate 
• 352547-72-9 2-hydroxy-4-oxo-4-phenyl-butyric acid methyl ester 
• 4437-14-3 (E)-5,5'-diphenyl-3,3'-bifuranylidene-2,2'-dione 
• 77953-17-4 4-oxo-2-phenacyl-4-phenyl-butyric acid 
• 13983-60-3 2-hydroxy-4-phenyl-4-butyrolactone 

Relevant academic research and scientific papers

Direct aldol reactions of glyoxylic acid monohydrate with ketones

The direct aldol reaction of various ketones with glyoxylic acid afforded the β-hydroxy carbonyl compounds in good yields and high regioselectivities.

Structure-activity relationship study of pyridazine derivatives as glutamate transporter EAAT2 activators

Excitatory amino acid transporter 2 (EAAT2) is the major glutamate transporter and functions to remove glutamate from synapses. A thiopyridazine derivative has been found to increase EAAT2 protein levels in astrocytes. A structure-activity relationship study revealed that several components of the molecule were required for activity, such as the thioether and pyridazine. Modification of the benzylthioether resulted in several derivatives (7-13, 7-15 and 7-17) that enhanced EAAT2 levels by >6-fold at concentrations 50 of 0.5 μM.

InCl3-Catalyzed direct aldol reactions of glyoxylic acid monohydrate and glyoxylates with various ketones: Scope and limitations

The direct aldol reactions of various ketones with glyoxylic acid and glyoxylates afforded the α-hydroxy acid and α-hydroxy esters in good yields and high regioselectivities.

Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists

Results from a medicinal chemistry approach aimed at replacing the quinoline ring system in the potent and selective human neurokinin-3 (hNK-3) receptor antagonists 1-4 of general formula I are discussed. The data give further insight upon the potential NK-3 pharmacophore. In particular, it is highlighted that both the benzene-condensed ring and the quinoline nitrogen are crucial determinants for optimal binding affinity to the hNK-3 receptor. Some novel compounds maintained part of the binding affinity to the receptor (5, 6, 10 and 13) and compound 5, featuring the naphthalene ring system, appears to be suitable for further modifications: it offers the option to introduce electron-withdrawing groups at position 2 and 4, conferring on the ring an overall electron-deficiency similar to that of the quinoline.

Clay montmorillonite K10 catalyzed aldol-type reaction of aldehydes with silyl enol ethers in water

An environmentally friendly method for the cross aldol reaction of silyl enol ethers and ketene silyl acetal with various aldehydes using montmorillonite K10 is described. Cheap and commercially available montmorillonite K10 can be used without the need of an ion exchange process under solvent-free conditions or in water. Hydrate of aldehydes such as glyoxylic acid can be used directly. Thermal treatment of K10 increased the catalytic activity. The catalytic activity was supposed due to the properties of the structure of K10 and its inherent Bronsted acidity.

Indium-trichloride catalyzed Mukaiyama-aldol reaction in water: Solubility, aggregation and internal pressure effect

Studies on the effects of water and the binding characteristic of InCl3, in the Mukaiyama-aldol reaction with an in depth mechanistic probe on the probable internal pressure and aggregation effects exerted in this media.

Indium trichloride catalysed Mukaiyama aldol reaction in water

In the presence of a catalytic amount of indium(III) chloride (InCl3) (20 mol%), aldehydes react smoothly with ketone trimethylsilyl enol ethers in water to afford the corresponding aldol adducts in good yields.

CONDENSATION OF α,γ-DIKETO (OR KETOSUCCINIC) ESTERS WITH GLYOXYLIC ACID

2-Hydroxy-4-keto acids may be conveniently prepared by elimination of the oxalyl moiety, catalyzed by Zn(2+), from 4-carboxy-2-hydroxybutenolides.These are obtained in good yield by the addition of α,γ-diketo esters to sodium glyoxylate.If the α,γ-diketo esters, or ketosuccinic esters, carry an alkyl substituent in the β position their addition to sodium glyoxylate proceeds with the simultaneous splitting of the oxalyl moiety.The corresponding 2-enoic(4-keto or 3-carboxy) acids are obtained in good yields.