56150-08-4

Basic information

• Product Name: diethyl α-benzyl α-hydroxymalonate
• Synonyms: diethyl α-benzyl α-hydroxymalonate
• CAS NO: 56150-08-4
• Molecular Weight: 266.294
• Mol File: 56150-08-4.mol

Chemical Properties

• CAS DataBase Reference: diethyl α-benzyl α-hydroxymalonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl α-benzyl α-hydroxymalonate(56150-08-4)
• EPA Substance Registry System: diethyl α-benzyl α-hydroxymalonate(56150-08-4)

Safety Data

• Hazardous Substances Data: 56150-08-4(Hazardous Substances Data)

Upstream product

• 607-81-8 diethyl 2-benzylmalonate 
• 6921-34-2 benzylmagnesium chloride 
• 609-09-6 Diethyl ketomalonate 

Relevant articles and documents

Discovery of benzimidazole oxazolidinediones as novel and selective nonsteroidal mineralocorticoid receptor antagonists

Elaboration of the oxazolidinedione series led to replacement of the exocyclic amides with substituted benzimidazoles. The structure-activity relationship (SAR) exploration resulted in the discovery of potent and selective nonsteroidal mineralocorticoid receptor (MR) antagonists with significantly improved microsomal stability and pharmacokinetic (PK) profile relative to the HTS hit 1a. One compound 2p possessed comparable efficacy as spironolactone (SPL) at 100 mg/kg (p.o.) in the rat natriuresis model. As such, this series was validated as a lead series for further optimization.

Mineralocorticoid receptor antagonists: Identification of heterocyclic amide replacements in the oxazolidinedione series

Novel potent and selective mineralocorticoid receptor antagonists were identified, utilizing heterocyclic amide replacements in the oxazolidinedione series. Structure-activity relationship (SAR) efforts focused on improving lipophilic ligand efficiency (LLE) while maintaining nuclear hormone receptor selectivity and reasonable pharmacokinetic profiles.

I2-catalyzed direct α-hydroxylation of β-dicarbonyl compounds with atmospheric oxygen under photoirradiation

An I2-catalyzed hydroxylation of β-dicarbonyl moieties using air as the oxidant under photoirradiation has been developed for the easy preparation of α-hydroxy-β-dicarbonyl compounds. The transformation was completed with only 1 mol % of I2. With α-unsubstituted malonates, the hydroxylated dimerization product was afforded as the predominant product along with a minor product, α,α-dihydroxyl malonate.

Discovery of novel oxazolidinedione derivatives as potent and selective mineralocorticoid receptor antagonists

Novel oxazolidinedione analogs were discovered as potent and selective mineralocorticoid receptor (MR) antagonists. Structure-activity relationship (SAR) studies were focused on improving the potency and microsomal stability. Selected compounds demonstrat

MINERALOCORTICOID RECEPTOR ANTAGONISTS

The present invention is directed to compounds of the Formula (I) as well as pharmaceutically acceptable salts thereof, that are potentially useful for treating aldosterone-mediated diseases. The invention furthermore relates to processes for preparing compounds of the Formula (I), to their possible use in the treatment of the above mentioned diseases and for preparing pharmaceuticals for this purpose, and to pharmaceutical compositions which comprise compounds of the Formula (I).

MINERALOCORTICOID RECEPTOR ANTAGONISTS

The present invention is directed to compounds of the Formula (I) as well as pharmaceutically acceptable salts thereof, that are aldosterone receptor antagonists which might be useful for treating aldosterone-mediated diseases. The invention furthermore r

MINERALOCORTICOID RECEPTOR ANTAGONISTS

The present invention is directed to compounds of the Formula (I) as well as pharmaceutically acceptable salts thereof, that are possible useful for treating aldosterone-mediated diseases. The invention furthermore relates to processes for preparing compounds of the Formula (I), to their possible use for the treatment of the above mentioned diseases and for preparing pharmaceuticals for this purpose, and to pharmaceutical compositions which comprise compounds of the Formula (I).

Pd/C-catalyzed direct α-oxygenation of 1,3-dicarbonyl compounds using molecular oxygen

A hydroxyl group was readily and directly introduced into the α-position of a variety of β-dicarbonyl compounds by heterogeneous Pd/C-catalyzed oxygenation using molecular oxygen. Georg Thieme Verlag Stuttgart.

Mild air-oxidation of 1,3-dicarbonyl compounds with cesium salts: Novel α-hydroxylation accompanied by partial hydrolysis of malonate derivatives

1,3-Dicarbonyl compounds (1) were efficiently oxygenated at the α-position with cesium salts, such as CsF or Cs2CO3 (0.1 Meq) in DMF at room temperature. Reaction of malonate derivatives (1a, b) with excess amount (2 Meq) of Cs2

Oxidation of 1,3-dicarbonyl compounds using (camphorylsulfonyl)oxaziridines

The oxidation of 1,3-dicarbonyl compounds with (camphorylsulfonyl)oxaziridines 2 was studied in both cyclic and acyclic systems. Two reaction pathways were identified: Enolate α-hydroxylation and a novel Baeyer-Villiger type oxidation. The Baeyer-Villiger oxidation product was observed only for the ketones and arises via rearrangement of an alkoxy epoxide. Synthetically useful ee's (82-95%) were observed only for enolates of β-ketoesters where the keto group is part of a 6-membered ring.